id sid tid token lemma pos cord-003318-abs9rvjk 1 1 key key JJ cord-003318-abs9rvjk 1 2 : : : cord-003318-abs9rvjk 1 3 cord-003318-abs9rvjk cord-003318-abs9rvjk NN cord-003318-abs9rvjk 1 4 authors author NNS cord-003318-abs9rvjk 1 5 : : : cord-003318-abs9rvjk 1 6 Liu Liu NNP cord-003318-abs9rvjk 1 7 , , , cord-003318-abs9rvjk 1 8 Ming Ming NNP cord-003318-abs9rvjk 1 9 ; ; : cord-003318-abs9rvjk 1 10 Kong Kong NNP cord-003318-abs9rvjk 1 11 , , , cord-003318-abs9rvjk 1 12 Jian Jian NNP cord-003318-abs9rvjk 1 13 - - HYPH cord-003318-abs9rvjk 1 14 Qiang Qiang NNP cord-003318-abs9rvjk 2 1 title title NN cord-003318-abs9rvjk 2 2 : : : cord-003318-abs9rvjk 2 3 The the DT cord-003318-abs9rvjk 2 4 enzymatic enzymatic JJ cord-003318-abs9rvjk 2 5 biosynthesis biosynthesis NN cord-003318-abs9rvjk 2 6 of of IN cord-003318-abs9rvjk 2 7 acylated acylated JJ cord-003318-abs9rvjk 2 8 steroidal steroidal JJ cord-003318-abs9rvjk 2 9 glycosides glycoside NNS cord-003318-abs9rvjk 2 10 and and CC cord-003318-abs9rvjk 2 11 their -PRON- PRP$ cord-003318-abs9rvjk 2 12 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 2 13 activity activity NN cord-003318-abs9rvjk 2 14 date date NN cord-003318-abs9rvjk 2 15 : : : cord-003318-abs9rvjk 2 16 2018 2018 CD cord-003318-abs9rvjk 2 17 - - HYPH cord-003318-abs9rvjk 2 18 05 05 CD cord-003318-abs9rvjk 2 19 - - HYPH cord-003318-abs9rvjk 2 20 01 01 CD cord-003318-abs9rvjk 2 21 journal journal NN cord-003318-abs9rvjk 2 22 : : : cord-003318-abs9rvjk 2 23 Acta Acta NNP cord-003318-abs9rvjk 2 24 Pharm Pharm NNP cord-003318-abs9rvjk 2 25 Sin Sin NNP cord-003318-abs9rvjk 2 26 B B NNP cord-003318-abs9rvjk 2 27 DOI doi NN cord-003318-abs9rvjk 2 28 : : : cord-003318-abs9rvjk 2 29 10.1016/ 10.1016/ CD cord-003318-abs9rvjk 3 1 j.apsb.2018.04.006 j.apsb.2018.04.006 NNP cord-003318-abs9rvjk 3 2 sha sha NNP cord-003318-abs9rvjk 3 3 : : : cord-003318-abs9rvjk 4 1 5c08aea2dc326afc98c4359cf5f35951d13c09af 5c08aea2dc326afc98c4359cf5f35951d13c09af CD cord-003318-abs9rvjk 4 2 doc_id doc_id CD cord-003318-abs9rvjk 4 3 : : : cord-003318-abs9rvjk 4 4 3318 3318 CD cord-003318-abs9rvjk 4 5 cord_uid cord_uid NNS cord-003318-abs9rvjk 4 6 : : : cord-003318-abs9rvjk 5 1 abs9rvjk abs9rvjk NNP cord-003318-abs9rvjk 6 1 Herein herein RB cord-003318-abs9rvjk 6 2 we -PRON- PRP cord-003318-abs9rvjk 6 3 describe describe VBP cord-003318-abs9rvjk 6 4 the the DT cord-003318-abs9rvjk 6 5 discovery discovery NN cord-003318-abs9rvjk 6 6 and and CC cord-003318-abs9rvjk 6 7 functional functional JJ cord-003318-abs9rvjk 6 8 characterization characterization NN cord-003318-abs9rvjk 6 9 of of IN cord-003318-abs9rvjk 6 10 a a DT cord-003318-abs9rvjk 6 11 steroidal steroidal JJ cord-003318-abs9rvjk 6 12 glycosyltransferase glycosyltransferase NN cord-003318-abs9rvjk 6 13 ( ( -LRB- cord-003318-abs9rvjk 6 14 SGT SGT NNP cord-003318-abs9rvjk 6 15 ) ) -RRB- cord-003318-abs9rvjk 6 16 from from IN cord-003318-abs9rvjk 6 17 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 6 18 saundersiae saundersiae NN cord-003318-abs9rvjk 6 19 and and CC cord-003318-abs9rvjk 6 20 a a DT cord-003318-abs9rvjk 6 21 steroidal steroidal JJ cord-003318-abs9rvjk 6 22 glycoside glycoside NN cord-003318-abs9rvjk 6 23 acyltransferase acyltransferase NN cord-003318-abs9rvjk 6 24 ( ( -LRB- cord-003318-abs9rvjk 6 25 SGA SGA NNP cord-003318-abs9rvjk 6 26 ) ) -RRB- cord-003318-abs9rvjk 6 27 from from IN cord-003318-abs9rvjk 6 28 Escherichia Escherichia NNP cord-003318-abs9rvjk 6 29 coli coli NNS cord-003318-abs9rvjk 6 30 and and CC cord-003318-abs9rvjk 6 31 their -PRON- PRP$ cord-003318-abs9rvjk 6 32 application application NN cord-003318-abs9rvjk 6 33 in in IN cord-003318-abs9rvjk 6 34 the the DT cord-003318-abs9rvjk 6 35 biosynthesis biosynthesis NN cord-003318-abs9rvjk 6 36 of of IN cord-003318-abs9rvjk 6 37 acylated acylated JJ cord-003318-abs9rvjk 6 38 steroidal steroidal JJ cord-003318-abs9rvjk 6 39 glycosides glycoside NNS cord-003318-abs9rvjk 6 40 ( ( -LRB- cord-003318-abs9rvjk 6 41 ASGs ASGs NNP cord-003318-abs9rvjk 6 42 ) ) -RRB- cord-003318-abs9rvjk 6 43 . . . cord-003318-abs9rvjk 7 1 Initially initially RB cord-003318-abs9rvjk 7 2 , , , cord-003318-abs9rvjk 7 3 an an DT cord-003318-abs9rvjk 7 4 SGT SGT NNP cord-003318-abs9rvjk 7 5 gene gene NN cord-003318-abs9rvjk 7 6 , , , cord-003318-abs9rvjk 7 7 designated designate VBN cord-003318-abs9rvjk 7 8 as as IN cord-003318-abs9rvjk 7 9 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 7 10 , , , cord-003318-abs9rvjk 7 11 was be VBD cord-003318-abs9rvjk 7 12 isolated isolate VBN cord-003318-abs9rvjk 7 13 from from IN cord-003318-abs9rvjk 7 14 O. O. NNP cord-003318-abs9rvjk 7 15 saundersiae saundersiae NN cord-003318-abs9rvjk 7 16 . . . cord-003318-abs9rvjk 8 1 OsSGT1-containing ossgt1-containe VBG cord-003318-abs9rvjk 8 2 cell cell NN cord-003318-abs9rvjk 8 3 free free JJ cord-003318-abs9rvjk 8 4 extract extract NN cord-003318-abs9rvjk 8 5 was be VBD cord-003318-abs9rvjk 8 6 then then RB cord-003318-abs9rvjk 8 7 used use VBN cord-003318-abs9rvjk 8 8 as as IN cord-003318-abs9rvjk 8 9 the the DT cord-003318-abs9rvjk 8 10 biocatalyst biocatalyst NN cord-003318-abs9rvjk 8 11 to to TO cord-003318-abs9rvjk 8 12 react react VB cord-003318-abs9rvjk 8 13 with with IN cord-003318-abs9rvjk 8 14 49 49 CD cord-003318-abs9rvjk 8 15 structurally structurally RB cord-003318-abs9rvjk 8 16 diverse diverse JJ cord-003318-abs9rvjk 8 17 drug drug NN cord-003318-abs9rvjk 8 18 - - HYPH cord-003318-abs9rvjk 8 19 like like JJ cord-003318-abs9rvjk 8 20 compounds compound NNS cord-003318-abs9rvjk 8 21 . . . cord-003318-abs9rvjk 9 1 The the DT cord-003318-abs9rvjk 9 2 recombinant recombinant JJ cord-003318-abs9rvjk 9 3 OsSGT1 ossgt1 NN cord-003318-abs9rvjk 9 4 was be VBD cord-003318-abs9rvjk 9 5 shown show VBN cord-003318-abs9rvjk 9 6 to to TO cord-003318-abs9rvjk 9 7 be be VB cord-003318-abs9rvjk 9 8 active active JJ cord-003318-abs9rvjk 9 9 against against IN cord-003318-abs9rvjk 9 10 both both DT cord-003318-abs9rvjk 9 11 3β- 3β- CD cord-003318-abs9rvjk 9 12 and and CC cord-003318-abs9rvjk 9 13 17β 17β NNS cord-003318-abs9rvjk 9 14 - - : cord-003318-abs9rvjk 9 15 hydroxyl hydroxyl NN cord-003318-abs9rvjk 9 16 steroids steroid NNS cord-003318-abs9rvjk 9 17 . . . cord-003318-abs9rvjk 10 1 Unexpectedly unexpectedly RB cord-003318-abs9rvjk 10 2 , , , cord-003318-abs9rvjk 10 3 in in IN cord-003318-abs9rvjk 10 4 an an DT cord-003318-abs9rvjk 10 5 effort effort NN cord-003318-abs9rvjk 10 6 to to TO cord-003318-abs9rvjk 10 7 identify identify VB cord-003318-abs9rvjk 10 8 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 10 9 , , , cord-003318-abs9rvjk 10 10 we -PRON- PRP cord-003318-abs9rvjk 10 11 found find VBD cord-003318-abs9rvjk 10 12 the the DT cord-003318-abs9rvjk 10 13 bacteria bacteria NNS cord-003318-abs9rvjk 10 14 lacA laca ADD cord-003318-abs9rvjk 10 15 gene gene NN cord-003318-abs9rvjk 10 16 in in IN cord-003318-abs9rvjk 10 17 lac lac NNP cord-003318-abs9rvjk 10 18 operon operon NNP cord-003318-abs9rvjk 10 19 actually actually RB cord-003318-abs9rvjk 10 20 encoded encode VBD cord-003318-abs9rvjk 10 21 an an DT cord-003318-abs9rvjk 10 22 SGA SGA NNP cord-003318-abs9rvjk 10 23 , , , cord-003318-abs9rvjk 10 24 specifically specifically RB cord-003318-abs9rvjk 10 25 catalyzing catalyze VBG cord-003318-abs9rvjk 10 26 the the DT cord-003318-abs9rvjk 10 27 acetylations acetylation NNS cord-003318-abs9rvjk 10 28 of of IN cord-003318-abs9rvjk 10 29 sugar sugar NN cord-003318-abs9rvjk 10 30 moieties moiety NNS cord-003318-abs9rvjk 10 31 of of IN cord-003318-abs9rvjk 10 32 steroid steroid JJ cord-003318-abs9rvjk 10 33 17β 17β NNS cord-003318-abs9rvjk 10 34 - - HYPH cord-003318-abs9rvjk 10 35 glucosides glucoside NNS cord-003318-abs9rvjk 10 36 . . . cord-003318-abs9rvjk 11 1 Finally finally RB cord-003318-abs9rvjk 11 2 , , , cord-003318-abs9rvjk 11 3 a a DT cord-003318-abs9rvjk 11 4 novel novel JJ cord-003318-abs9rvjk 11 5 enzymatic enzymatic JJ cord-003318-abs9rvjk 11 6 two two CD cord-003318-abs9rvjk 11 7 - - HYPH cord-003318-abs9rvjk 11 8 step step NN cord-003318-abs9rvjk 11 9 synthesis synthesis NN cord-003318-abs9rvjk 11 10 of of IN cord-003318-abs9rvjk 11 11 two two CD cord-003318-abs9rvjk 11 12 ASGs asg NNS cord-003318-abs9rvjk 11 13 , , , cord-003318-abs9rvjk 11 14 acetylated acetylated NNP cord-003318-abs9rvjk 11 15 testosterone-17-O testosterone-17-O NNP cord-003318-abs9rvjk 11 16 - - HYPH cord-003318-abs9rvjk 11 17 β β NN cord-003318-abs9rvjk 11 18 - - HYPH cord-003318-abs9rvjk 11 19 glucosides glucosides NNP cord-003318-abs9rvjk 11 20 ( ( -LRB- cord-003318-abs9rvjk 11 21 AT-17β AT-17β NNP cord-003318-abs9rvjk 11 22 - - HYPH cord-003318-abs9rvjk 11 23 Gs Gs NNP cord-003318-abs9rvjk 11 24 ) ) -RRB- cord-003318-abs9rvjk 11 25 and and CC cord-003318-abs9rvjk 11 26 acetylated acetylated JJ cord-003318-abs9rvjk 11 27 estradiol-17-O estradiol-17-O NNS cord-003318-abs9rvjk 11 28 - - HYPH cord-003318-abs9rvjk 11 29 β β NN cord-003318-abs9rvjk 11 30 - - HYPH cord-003318-abs9rvjk 11 31 glucosides glucosides NNP cord-003318-abs9rvjk 11 32 ( ( -LRB- cord-003318-abs9rvjk 11 33 AE-17β AE-17β NNP cord-003318-abs9rvjk 11 34 - - HYPH cord-003318-abs9rvjk 11 35 Gs Gs NNP cord-003318-abs9rvjk 11 36 ) ) -RRB- cord-003318-abs9rvjk 11 37 , , , cord-003318-abs9rvjk 11 38 from from IN cord-003318-abs9rvjk 11 39 the the DT cord-003318-abs9rvjk 11 40 abundantly abundantly RB cord-003318-abs9rvjk 11 41 available available JJ cord-003318-abs9rvjk 11 42 free free JJ cord-003318-abs9rvjk 11 43 steroids steroid NNS cord-003318-abs9rvjk 11 44 using use VBG cord-003318-abs9rvjk 11 45 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 11 46 and and CC cord-003318-abs9rvjk 11 47 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 11 48 as as IN cord-003318-abs9rvjk 11 49 the the DT cord-003318-abs9rvjk 11 50 biocatalysts biocatalyst NNS cord-003318-abs9rvjk 11 51 was be VBD cord-003318-abs9rvjk 11 52 developed develop VBN cord-003318-abs9rvjk 11 53 . . . cord-003318-abs9rvjk 12 1 The the DT cord-003318-abs9rvjk 12 2 two two CD cord-003318-abs9rvjk 12 3 - - HYPH cord-003318-abs9rvjk 12 4 step step NN cord-003318-abs9rvjk 12 5 process process NN cord-003318-abs9rvjk 12 6 is be VBZ cord-003318-abs9rvjk 12 7 characterized characterize VBN cord-003318-abs9rvjk 12 8 by by IN cord-003318-abs9rvjk 12 9 EcSGA1-catalyzed EcSGA1-catalyzed NNP cord-003318-abs9rvjk 12 10 regioselective regioselective JJ cord-003318-abs9rvjk 12 11 acylations acylation NNS cord-003318-abs9rvjk 12 12 of of IN cord-003318-abs9rvjk 12 13 all all DT cord-003318-abs9rvjk 12 14 hydroxyl hydroxyl NN cord-003318-abs9rvjk 12 15 groups group NNS cord-003318-abs9rvjk 12 16 on on IN cord-003318-abs9rvjk 12 17 the the DT cord-003318-abs9rvjk 12 18 sugar sugar NN cord-003318-abs9rvjk 12 19 unit unit NN cord-003318-abs9rvjk 12 20 of of IN cord-003318-abs9rvjk 12 21 unprotected unprotected JJ cord-003318-abs9rvjk 12 22 steroidal steroidal JJ cord-003318-abs9rvjk 12 23 glycosides glycoside NNS cord-003318-abs9rvjk 12 24 ( ( -LRB- cord-003318-abs9rvjk 12 25 SGs SGs NNP cord-003318-abs9rvjk 12 26 ) ) -RRB- cord-003318-abs9rvjk 12 27 in in IN cord-003318-abs9rvjk 12 28 the the DT cord-003318-abs9rvjk 12 29 late late JJ cord-003318-abs9rvjk 12 30 stage stage NN cord-003318-abs9rvjk 12 31 , , , cord-003318-abs9rvjk 12 32 thereby thereby RB cord-003318-abs9rvjk 12 33 significantly significantly RB cord-003318-abs9rvjk 12 34 streamlining streamline VBG cord-003318-abs9rvjk 12 35 the the DT cord-003318-abs9rvjk 12 36 synthetic synthetic JJ cord-003318-abs9rvjk 12 37 route route NN cord-003318-abs9rvjk 12 38 towards towards IN cord-003318-abs9rvjk 12 39 ASGs asg NNS cord-003318-abs9rvjk 12 40 and and CC cord-003318-abs9rvjk 12 41 thus thus RB cord-003318-abs9rvjk 12 42 forming form VBG cord-003318-abs9rvjk 12 43 four four CD cord-003318-abs9rvjk 12 44 monoacylates monoacylate NNS cord-003318-abs9rvjk 12 45 . . . cord-003318-abs9rvjk 13 1 The the DT cord-003318-abs9rvjk 13 2 improved improved JJ cord-003318-abs9rvjk 13 3 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 13 4 activities activity NNS cord-003318-abs9rvjk 13 5 of of IN cord-003318-abs9rvjk 13 6 3′-acetylated 3′-acetylated CD cord-003318-abs9rvjk 13 7 testosterone17-O testosterone17-O NNP cord-003318-abs9rvjk 13 8 - - HYPH cord-003318-abs9rvjk 13 9 β β NN cord-003318-abs9rvjk 13 10 - - HYPH cord-003318-abs9rvjk 13 11 glucoside glucoside NN cord-003318-abs9rvjk 13 12 towards towards IN cord-003318-abs9rvjk 13 13 seven seven CD cord-003318-abs9rvjk 13 14 human human JJ cord-003318-abs9rvjk 13 15 tumor tumor NN cord-003318-abs9rvjk 13 16 cell cell NN cord-003318-abs9rvjk 13 17 lines line NNS cord-003318-abs9rvjk 13 18 were be VBD cord-003318-abs9rvjk 13 19 thus thus RB cord-003318-abs9rvjk 13 20 observable observable JJ cord-003318-abs9rvjk 13 21 . . . cord-003318-abs9rvjk 14 1 Steroidal steroidal JJ cord-003318-abs9rvjk 14 2 glycosides glycoside NNS cord-003318-abs9rvjk 14 3 ( ( -LRB- cord-003318-abs9rvjk 14 4 SGs SGs NNP cord-003318-abs9rvjk 14 5 ) ) -RRB- cord-003318-abs9rvjk 14 6 are be VBP cord-003318-abs9rvjk 14 7 characterized characterize VBN cord-003318-abs9rvjk 14 8 by by IN cord-003318-abs9rvjk 14 9 a a DT cord-003318-abs9rvjk 14 10 steroidal steroidal JJ cord-003318-abs9rvjk 14 11 skeleton skeleton NN cord-003318-abs9rvjk 14 12 glycosidically glycosidically RB cord-003318-abs9rvjk 14 13 linked link VBN cord-003318-abs9rvjk 14 14 to to IN cord-003318-abs9rvjk 14 15 sugar sugar NN cord-003318-abs9rvjk 14 16 moieties moiety NNS cord-003318-abs9rvjk 14 17 , , , cord-003318-abs9rvjk 14 18 which which WDT cord-003318-abs9rvjk 14 19 can can MD cord-003318-abs9rvjk 14 20 be be VB cord-003318-abs9rvjk 14 21 further further RB cord-003318-abs9rvjk 14 22 acylated acylate VBN cord-003318-abs9rvjk 14 23 with with IN cord-003318-abs9rvjk 14 24 aliphatic aliphatic JJ cord-003318-abs9rvjk 14 25 and and CC cord-003318-abs9rvjk 14 26 aromatic aromatic JJ cord-003318-abs9rvjk 14 27 acids acid NNS cord-003318-abs9rvjk 14 28 thus thus RB cord-003318-abs9rvjk 14 29 forming form VBG cord-003318-abs9rvjk 14 30 complex complex JJ cord-003318-abs9rvjk 14 31 acylated acylate VBN cord-003318-abs9rvjk 14 32 steroidal steroidal JJ cord-003318-abs9rvjk 14 33 glycosides glycoside NNS cord-003318-abs9rvjk 14 34 ( ( -LRB- cord-003318-abs9rvjk 14 35 ASGs asg NNS cord-003318-abs9rvjk 14 36 ) ) -RRB- cord-003318-abs9rvjk 14 37 1 1 CD cord-003318-abs9rvjk 14 38 . . . cord-003318-abs9rvjk 15 1 The the DT cord-003318-abs9rvjk 15 2 resulting result VBG cord-003318-abs9rvjk 15 3 steroidal steroidal JJ cord-003318-abs9rvjk 15 4 glycoside glycoside NN cord-003318-abs9rvjk 15 5 esters ester NNS cord-003318-abs9rvjk 15 6 ( ( -LRB- cord-003318-abs9rvjk 15 7 SGEs SGEs NNP cord-003318-abs9rvjk 15 8 ) ) -RRB- cord-003318-abs9rvjk 15 9 exhibit exhibit VBP cord-003318-abs9rvjk 15 10 a a DT cord-003318-abs9rvjk 15 11 wide wide JJ cord-003318-abs9rvjk 15 12 variety variety NN cord-003318-abs9rvjk 15 13 of of IN cord-003318-abs9rvjk 15 14 biological biological JJ cord-003318-abs9rvjk 15 15 activities activity NNS cord-003318-abs9rvjk 15 16 , , , cord-003318-abs9rvjk 15 17 like like IN cord-003318-abs9rvjk 15 18 cholesterol cholesterol NN cord-003318-abs9rvjk 15 19 - - HYPH cord-003318-abs9rvjk 15 20 lowering lower VBG cord-003318-abs9rvjk 15 21 effect effect NN cord-003318-abs9rvjk 15 22 2 2 CD cord-003318-abs9rvjk 15 23 , , , cord-003318-abs9rvjk 15 24 anti anti JJ cord-003318-abs9rvjk 15 25 - - JJ cord-003318-abs9rvjk 15 26 diabetic diabetic JJ cord-003318-abs9rvjk 15 27 properties property NNS cord-003318-abs9rvjk 15 28 3 3 CD cord-003318-abs9rvjk 15 29 , , , cord-003318-abs9rvjk 15 30 anti anti JJ cord-003318-abs9rvjk 15 31 - - JJ cord-003318-abs9rvjk 15 32 complementary complementary JJ cord-003318-abs9rvjk 15 33 activity activity NN cord-003318-abs9rvjk 15 34 4 4 CD cord-003318-abs9rvjk 15 35 , , , cord-003318-abs9rvjk 15 36 immunoregulatory immunoregulatory NNP cord-003318-abs9rvjk 15 37 functions functions NNP cord-003318-abs9rvjk 15 38 5 5 CD cord-003318-abs9rvjk 15 39 , , , cord-003318-abs9rvjk 15 40 6 6 CD cord-003318-abs9rvjk 15 41 and and CC cord-003318-abs9rvjk 15 42 anti anti JJ cord-003318-abs9rvjk 15 43 - - JJ cord-003318-abs9rvjk 15 44 cancer cancer JJ cord-003318-abs9rvjk 15 45 actions action NNS cord-003318-abs9rvjk 15 46 [ [ -LRB- cord-003318-abs9rvjk 15 47 7 7 CD cord-003318-abs9rvjk 15 48 ] ] -RRB- cord-003318-abs9rvjk 16 1 [ [ -LRB- cord-003318-abs9rvjk 16 2 8 8 CD cord-003318-abs9rvjk 16 3 ] ] -RRB- cord-003318-abs9rvjk 16 4 [ [ -LRB- cord-003318-abs9rvjk 16 5 9 9 CD cord-003318-abs9rvjk 16 6 ] ] -RRB- cord-003318-abs9rvjk 16 7 , , , cord-003318-abs9rvjk 16 8 which which WDT cord-003318-abs9rvjk 16 9 made make VBD cord-003318-abs9rvjk 16 10 ASGs asg NNS cord-003318-abs9rvjk 16 11 promising promising JJ cord-003318-abs9rvjk 16 12 compounds compound NNS cord-003318-abs9rvjk 16 13 with with IN cord-003318-abs9rvjk 16 14 pharmaceutical pharmaceutical JJ cord-003318-abs9rvjk 16 15 potential potential NN cord-003318-abs9rvjk 16 16 . . . cord-003318-abs9rvjk 17 1 Numerous numerous JJ cord-003318-abs9rvjk 17 2 methods method NNS cord-003318-abs9rvjk 17 3 , , , cord-003318-abs9rvjk 17 4 including include VBG cord-003318-abs9rvjk 17 5 direct direct JJ cord-003318-abs9rvjk 17 6 extraction extraction NN cord-003318-abs9rvjk 17 7 9 9 CD cord-003318-abs9rvjk 17 8 , , , cord-003318-abs9rvjk 17 9 chemical chemical NN cord-003318-abs9rvjk 17 10 synthesis synthesis NN cord-003318-abs9rvjk 17 11 10 10 CD cord-003318-abs9rvjk 17 12 , , , cord-003318-abs9rvjk 17 13 11 11 CD cord-003318-abs9rvjk 17 14 and and CC cord-003318-abs9rvjk 17 15 biosynthesis biosynthesis NN cord-003318-abs9rvjk 17 16 12 12 CD cord-003318-abs9rvjk 17 17 , , , cord-003318-abs9rvjk 17 18 have have VBP cord-003318-abs9rvjk 17 19 been be VBN cord-003318-abs9rvjk 17 20 developed develop VBN cord-003318-abs9rvjk 17 21 to to TO cord-003318-abs9rvjk 17 22 synthesize synthesize VB cord-003318-abs9rvjk 17 23 these these DT cord-003318-abs9rvjk 17 24 acylated acylate VBN cord-003318-abs9rvjk 17 25 steroidal steroidal JJ cord-003318-abs9rvjk 17 26 glycosides glycoside NNS cord-003318-abs9rvjk 17 27 . . . cord-003318-abs9rvjk 18 1 Direct direct JJ cord-003318-abs9rvjk 18 2 extraction extraction NN cord-003318-abs9rvjk 18 3 from from IN cord-003318-abs9rvjk 18 4 varied varied JJ cord-003318-abs9rvjk 18 5 organisms organism NNS cord-003318-abs9rvjk 18 6 is be VBZ cord-003318-abs9rvjk 18 7 one one CD cord-003318-abs9rvjk 18 8 of of IN cord-003318-abs9rvjk 18 9 the the DT cord-003318-abs9rvjk 18 10 main main JJ cord-003318-abs9rvjk 18 11 methods method NNS cord-003318-abs9rvjk 18 12 to to TO cord-003318-abs9rvjk 18 13 obtain obtain VB cord-003318-abs9rvjk 18 14 ASGs asg NNS cord-003318-abs9rvjk 18 15 [ [ -LRB- cord-003318-abs9rvjk 18 16 7 7 CD cord-003318-abs9rvjk 18 17 ] ] -RRB- cord-003318-abs9rvjk 18 18 [ [ -LRB- cord-003318-abs9rvjk 18 19 8 8 CD cord-003318-abs9rvjk 18 20 ] ] -RRB- cord-003318-abs9rvjk 18 21 [ [ -LRB- cord-003318-abs9rvjk 18 22 9 9 CD cord-003318-abs9rvjk 18 23 ] ] -RRB- cord-003318-abs9rvjk 18 24 . . . cord-003318-abs9rvjk 19 1 However however RB cord-003318-abs9rvjk 19 2 , , , cord-003318-abs9rvjk 19 3 the the DT cord-003318-abs9rvjk 19 4 content content NN cord-003318-abs9rvjk 19 5 of of IN cord-003318-abs9rvjk 19 6 ASGs asg NNS cord-003318-abs9rvjk 19 7 was be VBD cord-003318-abs9rvjk 19 8 usually usually RB cord-003318-abs9rvjk 19 9 low low JJ cord-003318-abs9rvjk 19 10 in in IN cord-003318-abs9rvjk 19 11 natural natural JJ cord-003318-abs9rvjk 19 12 sources source NNS cord-003318-abs9rvjk 19 13 [ [ -LRB- cord-003318-abs9rvjk 19 14 7 7 CD cord-003318-abs9rvjk 19 15 ] ] -RRB- cord-003318-abs9rvjk 19 16 [ [ -LRB- cord-003318-abs9rvjk 19 17 8 8 CD cord-003318-abs9rvjk 19 18 ] ] -RRB- cord-003318-abs9rvjk 19 19 [ [ -LRB- cord-003318-abs9rvjk 19 20 9 9 CD cord-003318-abs9rvjk 19 21 ] ] -RRB- cord-003318-abs9rvjk 19 22 . . . cord-003318-abs9rvjk 20 1 Moreover moreover RB cord-003318-abs9rvjk 20 2 , , , cord-003318-abs9rvjk 20 3 the the DT cord-003318-abs9rvjk 20 4 extraction extraction NN cord-003318-abs9rvjk 20 5 routes route NNS cord-003318-abs9rvjk 20 6 were be VBD cord-003318-abs9rvjk 20 7 highly highly RB cord-003318-abs9rvjk 20 8 time time NN cord-003318-abs9rvjk 20 9 - - HYPH cord-003318-abs9rvjk 20 10 consuming consume VBG cord-003318-abs9rvjk 20 11 and and CC cord-003318-abs9rvjk 20 12 required require VBD cord-003318-abs9rvjk 20 13 laborious laborious JJ cord-003318-abs9rvjk 20 14 purification purification NN cord-003318-abs9rvjk 20 15 procedures procedure NNS cord-003318-abs9rvjk 20 16 [ [ -LRB- cord-003318-abs9rvjk 20 17 7 7 CD cord-003318-abs9rvjk 20 18 ] ] -RRB- cord-003318-abs9rvjk 20 19 [ [ -LRB- cord-003318-abs9rvjk 20 20 8 8 CD cord-003318-abs9rvjk 20 21 ] ] -RRB- cord-003318-abs9rvjk 20 22 [ [ -LRB- cord-003318-abs9rvjk 20 23 9 9 CD cord-003318-abs9rvjk 20 24 ] ] -RRB- cord-003318-abs9rvjk 20 25 13 13 CD cord-003318-abs9rvjk 20 26 , , , cord-003318-abs9rvjk 20 27 resulting result VBG cord-003318-abs9rvjk 20 28 in in IN cord-003318-abs9rvjk 20 29 poor poor JJ cord-003318-abs9rvjk 20 30 yields yield NNS cord-003318-abs9rvjk 20 31 and/or and/or CC cord-003318-abs9rvjk 20 32 low low JJ cord-003318-abs9rvjk 20 33 purity purity NN cord-003318-abs9rvjk 20 34 of of IN cord-003318-abs9rvjk 20 35 the the DT cord-003318-abs9rvjk 20 36 final final JJ cord-003318-abs9rvjk 20 37 products product NNS cord-003318-abs9rvjk 20 38 . . . cord-003318-abs9rvjk 21 1 The the DT cord-003318-abs9rvjk 21 2 production production NN cord-003318-abs9rvjk 21 3 of of IN cord-003318-abs9rvjk 21 4 ASGs asg NNS cord-003318-abs9rvjk 21 5 was be VBD cord-003318-abs9rvjk 21 6 also also RB cord-003318-abs9rvjk 21 7 achieved achieve VBN cord-003318-abs9rvjk 21 8 by by IN cord-003318-abs9rvjk 21 9 chemical chemical NN cord-003318-abs9rvjk 21 10 synthesis synthesis NN cord-003318-abs9rvjk 21 11 previously previously RB cord-003318-abs9rvjk 21 12 [ [ -LRB- cord-003318-abs9rvjk 21 13 10 10 CD cord-003318-abs9rvjk 21 14 ] ] -RRB- cord-003318-abs9rvjk 22 1 [ [ -LRB- cord-003318-abs9rvjk 22 2 11 11 CD cord-003318-abs9rvjk 22 3 ] ] -RRB- cord-003318-abs9rvjk 22 4 [ [ -LRB- cord-003318-abs9rvjk 22 5 12 12 CD cord-003318-abs9rvjk 22 6 ] ] -RRB- cord-003318-abs9rvjk 22 7 [ [ -LRB- cord-003318-abs9rvjk 22 8 13 13 CD cord-003318-abs9rvjk 22 9 ] ] -RRB- cord-003318-abs9rvjk 23 1 [ [ -LRB- cord-003318-abs9rvjk 23 2 14 14 CD cord-003318-abs9rvjk 23 3 ] ] -RRB- cord-003318-abs9rvjk 23 4 . . . cord-003318-abs9rvjk 24 1 However however RB cord-003318-abs9rvjk 24 2 , , , cord-003318-abs9rvjk 24 3 these these DT cord-003318-abs9rvjk 24 4 efforts effort NNS cord-003318-abs9rvjk 24 5 often often RB cord-003318-abs9rvjk 24 6 encounter encounter VBP cord-003318-abs9rvjk 24 7 a a DT cord-003318-abs9rvjk 24 8 fundamental fundamental JJ cord-003318-abs9rvjk 24 9 challenge challenge NN cord-003318-abs9rvjk 24 10 , , , cord-003318-abs9rvjk 24 11 namely namely RB cord-003318-abs9rvjk 24 12 , , , cord-003318-abs9rvjk 24 13 regioselective regioselective NNP cord-003318-abs9rvjk 24 14 acylation acylation NN cord-003318-abs9rvjk 24 15 of of IN cord-003318-abs9rvjk 24 16 single single JJ cord-003318-abs9rvjk 24 17 hydroxyl hydroxyl NN cord-003318-abs9rvjk 24 18 group group NN cord-003318-abs9rvjk 24 19 of of IN cord-003318-abs9rvjk 24 20 unprotected unprotected JJ cord-003318-abs9rvjk 24 21 SGs SGs NNP cord-003318-abs9rvjk 24 22 in in IN cord-003318-abs9rvjk 24 23 the the DT cord-003318-abs9rvjk 24 24 late late JJ cord-003318-abs9rvjk 24 25 stage stage NN cord-003318-abs9rvjk 24 26 of of IN cord-003318-abs9rvjk 24 27 the the DT cord-003318-abs9rvjk 24 28 chemical chemical JJ cord-003318-abs9rvjk 24 29 synthesis synthesis NN cord-003318-abs9rvjk 24 30 of of IN cord-003318-abs9rvjk 24 31 ASGs ASGs NNPS cord-003318-abs9rvjk 24 32 . . . cord-003318-abs9rvjk 25 1 SGs SGs NNP cord-003318-abs9rvjk 25 2 generally generally RB cord-003318-abs9rvjk 25 3 possess possess VBP cord-003318-abs9rvjk 25 4 multiple multiple JJ cord-003318-abs9rvjk 25 5 hydroxyl hydroxyl NN cord-003318-abs9rvjk 25 6 groups group NNS cord-003318-abs9rvjk 25 7 with with IN cord-003318-abs9rvjk 25 8 similar similar JJ cord-003318-abs9rvjk 25 9 reactivity reactivity NN cord-003318-abs9rvjk 25 10 . . . cord-003318-abs9rvjk 26 1 Regioselective Regioselective NNP cord-003318-abs9rvjk 26 2 acylation acylation NN cord-003318-abs9rvjk 26 3 of of IN cord-003318-abs9rvjk 26 4 a a DT cord-003318-abs9rvjk 26 5 particular particular JJ cord-003318-abs9rvjk 26 6 one one CD cord-003318-abs9rvjk 26 7 of of IN cord-003318-abs9rvjk 26 8 multiple multiple JJ cord-003318-abs9rvjk 26 9 hydroxyl hydroxyl NN cord-003318-abs9rvjk 26 10 groups group NNS cord-003318-abs9rvjk 26 11 generally generally RB cord-003318-abs9rvjk 26 12 requires require VBZ cord-003318-abs9rvjk 26 13 multi multi JJ cord-003318-abs9rvjk 26 14 - - JJ cord-003318-abs9rvjk 26 15 step step JJ cord-003318-abs9rvjk 26 16 protection protection NN cord-003318-abs9rvjk 26 17 / / SYM cord-003318-abs9rvjk 26 18 deprotection deprotection NN cord-003318-abs9rvjk 26 19 procedures procedure NNS cord-003318-abs9rvjk 26 20 , , , cord-003318-abs9rvjk 26 21 which which WDT cord-003318-abs9rvjk 26 22 makes make VBZ cord-003318-abs9rvjk 26 23 the the DT cord-003318-abs9rvjk 26 24 synthetic synthetic JJ cord-003318-abs9rvjk 26 25 pathway pathway NN cord-003318-abs9rvjk 26 26 of of IN cord-003318-abs9rvjk 26 27 these these DT cord-003318-abs9rvjk 26 28 SGEs sge NNS cord-003318-abs9rvjk 26 29 costly costly JJ cord-003318-abs9rvjk 26 30 , , , cord-003318-abs9rvjk 26 31 wasteful wasteful JJ cord-003318-abs9rvjk 26 32 , , , cord-003318-abs9rvjk 26 33 long long JJ cord-003318-abs9rvjk 26 34 and and CC cord-003318-abs9rvjk 26 35 timeconsuming timeconsuming JJ cord-003318-abs9rvjk 26 36 , , , cord-003318-abs9rvjk 26 37 and and CC cord-003318-abs9rvjk 26 38 results result NNS cord-003318-abs9rvjk 26 39 in in IN cord-003318-abs9rvjk 26 40 low low JJ cord-003318-abs9rvjk 26 41 yield yield NN cord-003318-abs9rvjk 26 42 in in IN cord-003318-abs9rvjk 26 43 the the DT cord-003318-abs9rvjk 26 44 end end NN cord-003318-abs9rvjk 26 45 . . . cord-003318-abs9rvjk 27 1 The the DT cord-003318-abs9rvjk 27 2 biosynthesis biosynthesis NN cord-003318-abs9rvjk 27 3 of of IN cord-003318-abs9rvjk 27 4 ASGs asg NNS cord-003318-abs9rvjk 27 5 from from IN cord-003318-abs9rvjk 27 6 free free JJ cord-003318-abs9rvjk 27 7 steroids steroid NNS cord-003318-abs9rvjk 27 8 based base VBN cord-003318-abs9rvjk 27 9 on on IN cord-003318-abs9rvjk 27 10 enzymatic enzymatic JJ cord-003318-abs9rvjk 27 11 catalysis catalysis NN cord-003318-abs9rvjk 27 12 was be VBD cord-003318-abs9rvjk 27 13 deemed deem VBN cord-003318-abs9rvjk 27 14 to to TO cord-003318-abs9rvjk 27 15 reduce reduce VB cord-003318-abs9rvjk 27 16 the the DT cord-003318-abs9rvjk 27 17 number number NN cord-003318-abs9rvjk 27 18 of of IN cord-003318-abs9rvjk 27 19 protection/ protection/ CD cord-003318-abs9rvjk 27 20 deprotection deprotection NN cord-003318-abs9rvjk 27 21 steps step NNS cord-003318-abs9rvjk 27 22 due due IN cord-003318-abs9rvjk 27 23 to to IN cord-003318-abs9rvjk 27 24 the the DT cord-003318-abs9rvjk 27 25 high high JJ cord-003318-abs9rvjk 27 26 selectivity selectivity NN cord-003318-abs9rvjk 27 27 of of IN cord-003318-abs9rvjk 27 28 enzymes enzyme NNS cord-003318-abs9rvjk 27 29 . . . cord-003318-abs9rvjk 28 1 Theoretically theoretically RB cord-003318-abs9rvjk 28 2 , , , cord-003318-abs9rvjk 28 3 the the DT cord-003318-abs9rvjk 28 4 biosynthesis biosynthesis NN cord-003318-abs9rvjk 28 5 of of IN cord-003318-abs9rvjk 28 6 ASGs ASGs NNPS cord-003318-abs9rvjk 28 7 includes include VBZ cord-003318-abs9rvjk 28 8 two two CD cord-003318-abs9rvjk 28 9 steps step NNS cord-003318-abs9rvjk 28 10 . . . cord-003318-abs9rvjk 29 1 In in IN cord-003318-abs9rvjk 29 2 the the DT cord-003318-abs9rvjk 29 3 first first JJ cord-003318-abs9rvjk 29 4 reaction reaction NN cord-003318-abs9rvjk 29 5 , , , cord-003318-abs9rvjk 29 6 the the DT cord-003318-abs9rvjk 29 7 sugar sugar NN cord-003318-abs9rvjk 29 8 moiety moiety NN cord-003318-abs9rvjk 29 9 from from IN cord-003318-abs9rvjk 29 10 nucleotide nucleotide RB cord-003318-abs9rvjk 29 11 - - HYPH cord-003318-abs9rvjk 29 12 activated activate VBN cord-003318-abs9rvjk 29 13 glycosyl glycosyl JJ cord-003318-abs9rvjk 29 14 donors donor NNS cord-003318-abs9rvjk 29 15 was be VBD cord-003318-abs9rvjk 29 16 attached attach VBN cord-003318-abs9rvjk 29 17 to to IN cord-003318-abs9rvjk 29 18 steroids steroid NNS cord-003318-abs9rvjk 29 19 at at IN cord-003318-abs9rvjk 29 20 different different JJ cord-003318-abs9rvjk 29 21 positions position NNS cord-003318-abs9rvjk 29 22 , , , cord-003318-abs9rvjk 29 23 most most RBS cord-003318-abs9rvjk 29 24 commonly commonly RB cord-003318-abs9rvjk 29 25 at at IN cord-003318-abs9rvjk 29 26 the the DT cord-003318-abs9rvjk 29 27 C-3 C-3 NNP cord-003318-abs9rvjk 29 28 hydroxyl hydroxyl NN cord-003318-abs9rvjk 29 29 group group NN cord-003318-abs9rvjk 29 30 ( ( -LRB- cord-003318-abs9rvjk 29 31 OH oh UH cord-003318-abs9rvjk 29 32 ) ) -RRB- cord-003318-abs9rvjk 29 33 , , , cord-003318-abs9rvjk 29 34 under under IN cord-003318-abs9rvjk 29 35 the the DT cord-003318-abs9rvjk 29 36 action action NN cord-003318-abs9rvjk 29 37 of of IN cord-003318-abs9rvjk 29 38 nucleotide nucleotide JJ cord-003318-abs9rvjk 29 39 dependent dependent JJ cord-003318-abs9rvjk 29 40 SGTs sgt NNS cord-003318-abs9rvjk 29 41 15 15 CD cord-003318-abs9rvjk 29 42 , , , cord-003318-abs9rvjk 29 43 16 16 CD cord-003318-abs9rvjk 29 44 . . . cord-003318-abs9rvjk 30 1 The the DT cord-003318-abs9rvjk 30 2 glycosylation glycosylation NN cord-003318-abs9rvjk 30 3 of of IN cord-003318-abs9rvjk 30 4 a a DT cord-003318-abs9rvjk 30 5 hydroxyl hydroxyl NN cord-003318-abs9rvjk 30 6 group group NN cord-003318-abs9rvjk 30 7 at at IN cord-003318-abs9rvjk 30 8 the the DT cord-003318-abs9rvjk 30 9 C-3 C-3 NNP cord-003318-abs9rvjk 30 10 position position NN cord-003318-abs9rvjk 30 11 of of IN cord-003318-abs9rvjk 30 12 steroids steroid NNS cord-003318-abs9rvjk 30 13 was be VBD cord-003318-abs9rvjk 30 14 well well RB cord-003318-abs9rvjk 30 15 characterized characterize VBN cord-003318-abs9rvjk 30 16 and and CC cord-003318-abs9rvjk 30 17 a a DT cord-003318-abs9rvjk 30 18 few few JJ cord-003318-abs9rvjk 30 19 of of IN cord-003318-abs9rvjk 30 20 steroidal steroidal JJ cord-003318-abs9rvjk 30 21 3β 3β NNS cord-003318-abs9rvjk 30 22 - - HYPH cord-003318-abs9rvjk 30 23 glucosyltransferases glucosyltransferases NNPS cord-003318-abs9rvjk 30 24 were be VBD cord-003318-abs9rvjk 30 25 isolated isolate VBN cord-003318-abs9rvjk 30 26 from from IN cord-003318-abs9rvjk 30 27 diverse diverse JJ cord-003318-abs9rvjk 30 28 species specie NNS cord-003318-abs9rvjk 30 29 17 17 CD cord-003318-abs9rvjk 30 30 , , , cord-003318-abs9rvjk 30 31 18 18 CD cord-003318-abs9rvjk 30 32 . . . cord-003318-abs9rvjk 31 1 However however RB cord-003318-abs9rvjk 31 2 , , , cord-003318-abs9rvjk 31 3 the the DT cord-003318-abs9rvjk 31 4 reports report NNS cord-003318-abs9rvjk 31 5 of of IN cord-003318-abs9rvjk 31 6 SGTs sgt NNS cord-003318-abs9rvjk 31 7 specific specific JJ cord-003318-abs9rvjk 31 8 for for IN cord-003318-abs9rvjk 31 9 positions position NNS cord-003318-abs9rvjk 31 10 other other JJ cord-003318-abs9rvjk 31 11 than than IN cord-003318-abs9rvjk 31 12 C-3 C-3 NNP cord-003318-abs9rvjk 31 13 of of IN cord-003318-abs9rvjk 31 14 steroids steroid NNS cord-003318-abs9rvjk 31 15 are be VBP cord-003318-abs9rvjk 31 16 limited limited JJ cord-003318-abs9rvjk 31 17 . . . cord-003318-abs9rvjk 32 1 The the DT cord-003318-abs9rvjk 32 2 sugar sugar NN cord-003318-abs9rvjk 32 3 moieties moiety NNS cord-003318-abs9rvjk 32 4 of of IN cord-003318-abs9rvjk 32 5 the the DT cord-003318-abs9rvjk 32 6 resultant resultant JJ cord-003318-abs9rvjk 32 7 SGs SGs NNP cord-003318-abs9rvjk 32 8 can can MD cord-003318-abs9rvjk 32 9 further further RB cord-003318-abs9rvjk 32 10 be be VB cord-003318-abs9rvjk 32 11 acylated acylate VBN cord-003318-abs9rvjk 32 12 by by IN cord-003318-abs9rvjk 32 13 SGAs sga NNS cord-003318-abs9rvjk 32 14 to to TO cord-003318-abs9rvjk 32 15 form form VB cord-003318-abs9rvjk 32 16 ASGs asg NNS cord-003318-abs9rvjk 32 17 in in IN cord-003318-abs9rvjk 32 18 the the DT cord-003318-abs9rvjk 32 19 next next JJ cord-003318-abs9rvjk 32 20 step step NN cord-003318-abs9rvjk 32 21 1 1 CD cord-003318-abs9rvjk 32 22 , , , cord-003318-abs9rvjk 32 23 16 16 CD cord-003318-abs9rvjk 32 24 . . . cord-003318-abs9rvjk 33 1 Compared compare VBN cord-003318-abs9rvjk 33 2 to to IN cord-003318-abs9rvjk 33 3 SGTs sgt NNS cord-003318-abs9rvjk 33 4 , , , cord-003318-abs9rvjk 33 5 surprisingly surprisingly RB cord-003318-abs9rvjk 33 6 little little JJ cord-003318-abs9rvjk 33 7 is be VBZ cord-003318-abs9rvjk 33 8 known know VBN cord-003318-abs9rvjk 33 9 about about IN cord-003318-abs9rvjk 33 10 SGAs sga NNS cord-003318-abs9rvjk 33 11 . . . cord-003318-abs9rvjk 34 1 Up up IN cord-003318-abs9rvjk 34 2 to to IN cord-003318-abs9rvjk 34 3 date date NN cord-003318-abs9rvjk 34 4 , , , cord-003318-abs9rvjk 34 5 no no DT cord-003318-abs9rvjk 34 6 SGA SGA NNP cord-003318-abs9rvjk 34 7 genes gene NNS cord-003318-abs9rvjk 34 8 has have VBZ cord-003318-abs9rvjk 34 9 yet yet RB cord-003318-abs9rvjk 34 10 been be VBN cord-003318-abs9rvjk 34 11 cloned clone VBN cord-003318-abs9rvjk 34 12 , , , cord-003318-abs9rvjk 34 13 which which WDT cord-003318-abs9rvjk 34 14 in in IN cord-003318-abs9rvjk 34 15 turn turn NN cord-003318-abs9rvjk 34 16 limit limit VBP cord-003318-abs9rvjk 34 17 the the DT cord-003318-abs9rvjk 34 18 enzyme enzyme NN cord-003318-abs9rvjk 34 19 - - HYPH cord-003318-abs9rvjk 34 20 mediated mediate VBN cord-003318-abs9rvjk 34 21 biosynthesis biosynthesis NN cord-003318-abs9rvjk 34 22 of of IN cord-003318-abs9rvjk 34 23 ASGs asg NNS cord-003318-abs9rvjk 34 24 . . . cord-003318-abs9rvjk 35 1 Hence hence RB cord-003318-abs9rvjk 35 2 , , , cord-003318-abs9rvjk 35 3 the the DT cord-003318-abs9rvjk 35 4 successful successful JJ cord-003318-abs9rvjk 35 5 gene gene NN cord-003318-abs9rvjk 35 6 isolation isolation NN cord-003318-abs9rvjk 35 7 and and CC cord-003318-abs9rvjk 35 8 functional functional JJ cord-003318-abs9rvjk 35 9 characterization characterization NN cord-003318-abs9rvjk 35 10 of of IN cord-003318-abs9rvjk 35 11 SGAs sga NNS cord-003318-abs9rvjk 35 12 have have VBP cord-003318-abs9rvjk 35 13 become become VBN cord-003318-abs9rvjk 35 14 a a DT cord-003318-abs9rvjk 35 15 prominent prominent JJ cord-003318-abs9rvjk 35 16 challenge challenge NN cord-003318-abs9rvjk 35 17 for for IN cord-003318-abs9rvjk 35 18 bioproduction bioproduction NN cord-003318-abs9rvjk 35 19 of of IN cord-003318-abs9rvjk 35 20 ASGs asg NNS cord-003318-abs9rvjk 35 21 . . . cord-003318-abs9rvjk 36 1 Herein herein RB cord-003318-abs9rvjk 36 2 , , , cord-003318-abs9rvjk 36 3 the the DT cord-003318-abs9rvjk 36 4 functional functional JJ cord-003318-abs9rvjk 36 5 characterizations characterization NNS cord-003318-abs9rvjk 36 6 of of IN cord-003318-abs9rvjk 36 7 a a DT cord-003318-abs9rvjk 36 8 plant plant NN cord-003318-abs9rvjk 36 9 - - HYPH cord-003318-abs9rvjk 36 10 derived derive VBN cord-003318-abs9rvjk 36 11 SGT SGT NNP cord-003318-abs9rvjk 36 12 with with IN cord-003318-abs9rvjk 36 13 activity activity NN cord-003318-abs9rvjk 36 14 against against IN cord-003318-abs9rvjk 36 15 both both DT cord-003318-abs9rvjk 36 16 3β 3β CD cord-003318-abs9rvjk 36 17 - - HYPH cord-003318-abs9rvjk 36 18 and and CC cord-003318-abs9rvjk 36 19 17β 17β NNS cord-003318-abs9rvjk 36 20 - - : cord-003318-abs9rvjk 36 21 hydroxyl hydroxyl NN cord-003318-abs9rvjk 36 22 steroids steroid NNS cord-003318-abs9rvjk 36 23 , , , cord-003318-abs9rvjk 36 24 and and CC cord-003318-abs9rvjk 36 25 a a DT cord-003318-abs9rvjk 36 26 bacterial bacterial JJ cord-003318-abs9rvjk 36 27 SGA SGA NNP cord-003318-abs9rvjk 36 28 , , , cord-003318-abs9rvjk 36 29 as as RB cord-003318-abs9rvjk 36 30 well well RB cord-003318-abs9rvjk 36 31 as as IN cord-003318-abs9rvjk 36 32 their -PRON- PRP$ cord-003318-abs9rvjk 36 33 application application NN cord-003318-abs9rvjk 36 34 in in IN cord-003318-abs9rvjk 36 35 the the DT cord-003318-abs9rvjk 36 36 biosynthesis biosynthesis NN cord-003318-abs9rvjk 36 37 of of IN cord-003318-abs9rvjk 36 38 ASGs asg NNS cord-003318-abs9rvjk 36 39 are be VBP cord-003318-abs9rvjk 36 40 reported report VBN cord-003318-abs9rvjk 36 41 . . . cord-003318-abs9rvjk 37 1 Initially initially RB cord-003318-abs9rvjk 37 2 , , , cord-003318-abs9rvjk 37 3 a a DT cord-003318-abs9rvjk 37 4 steroidal steroidal JJ cord-003318-abs9rvjk 37 5 glycosyltransferase glycosyltransferase NN cord-003318-abs9rvjk 37 6 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 37 7 was be VBD cord-003318-abs9rvjk 37 8 isolated isolate VBN cord-003318-abs9rvjk 37 9 from from IN cord-003318-abs9rvjk 37 10 medicinal medicinal JJ cord-003318-abs9rvjk 37 11 plant plant NN cord-003318-abs9rvjk 37 12 O. O. NNP cord-003318-abs9rvjk 37 13 saundersiae saundersiae NN cord-003318-abs9rvjk 37 14 and and CC cord-003318-abs9rvjk 37 15 showed show VBD cord-003318-abs9rvjk 37 16 activities activity NNS cord-003318-abs9rvjk 37 17 for for IN cord-003318-abs9rvjk 37 18 3β 3β CD cord-003318-abs9rvjk 37 19 - - : cord-003318-abs9rvjk 37 20 and and CC cord-003318-abs9rvjk 37 21 17βhydroxyl 17βhydroxyl CD cord-003318-abs9rvjk 37 22 steroids steroid NNS cord-003318-abs9rvjk 37 23 . . . cord-003318-abs9rvjk 38 1 Unexpectedly unexpectedly RB cord-003318-abs9rvjk 38 2 , , , cord-003318-abs9rvjk 38 3 in in IN cord-003318-abs9rvjk 38 4 an an DT cord-003318-abs9rvjk 38 5 effort effort NN cord-003318-abs9rvjk 38 6 to to TO cord-003318-abs9rvjk 38 7 identify identify VB cord-003318-abs9rvjk 38 8 the the DT cord-003318-abs9rvjk 38 9 function function NN cord-003318-abs9rvjk 38 10 of of IN cord-003318-abs9rvjk 38 11 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 38 12 , , , cord-003318-abs9rvjk 38 13 we -PRON- PRP cord-003318-abs9rvjk 38 14 characterized characterize VBD cord-003318-abs9rvjk 38 15 LacA LacA NNP cord-003318-abs9rvjk 38 16 protein protein NN cord-003318-abs9rvjk 38 17 ( ( -LRB- cord-003318-abs9rvjk 38 18 designated designate VBN cord-003318-abs9rvjk 38 19 as as IN cord-003318-abs9rvjk 38 20 EsSGA1 EsSGA1 NNP cord-003318-abs9rvjk 38 21 ) ) -RRB- cord-003318-abs9rvjk 38 22 from from IN cord-003318-abs9rvjk 38 23 E. E. NNP cord-003318-abs9rvjk 38 24 coli coli NNS cord-003318-abs9rvjk 38 25 as as IN cord-003318-abs9rvjk 38 26 a a DT cord-003318-abs9rvjk 38 27 SGA SGA NNP cord-003318-abs9rvjk 38 28 , , , cord-003318-abs9rvjk 38 29 catalyzing catalyze VBG cord-003318-abs9rvjk 38 30 testosterone-17-Oβ testosterone-17-oβ CD cord-003318-abs9rvjk 38 31 - - HYPH cord-003318-abs9rvjk 38 32 glucoside glucoside NN cord-003318-abs9rvjk 38 33 ( ( -LRB- cord-003318-abs9rvjk 38 34 T-17β T-17β NNP cord-003318-abs9rvjk 38 35 - - HYPH cord-003318-abs9rvjk 38 36 G G NNP cord-003318-abs9rvjk 38 37 ) ) -RRB- cord-003318-abs9rvjk 38 38 and and CC cord-003318-abs9rvjk 38 39 estradiol-17-O estradiol-17-O NNS cord-003318-abs9rvjk 38 40 - - HYPH cord-003318-abs9rvjk 38 41 β β NN cord-003318-abs9rvjk 38 42 - - HYPH cord-003318-abs9rvjk 38 43 glucoside glucoside NN cord-003318-abs9rvjk 38 44 ( ( -LRB- cord-003318-abs9rvjk 38 45 E-17β E-17β NNP cord-003318-abs9rvjk 38 46 - - HYPH cord-003318-abs9rvjk 38 47 G G NNP cord-003318-abs9rvjk 38 48 ) ) -RRB- cord-003318-abs9rvjk 38 49 to to TO cord-003318-abs9rvjk 38 50 form form VB cord-003318-abs9rvjk 38 51 corresponding corresponding JJ cord-003318-abs9rvjk 38 52 acylates acylate NNS cord-003318-abs9rvjk 38 53 . . . cord-003318-abs9rvjk 39 1 Further further RB cord-003318-abs9rvjk 39 2 , , , cord-003318-abs9rvjk 39 3 under under IN cord-003318-abs9rvjk 39 4 the the DT cord-003318-abs9rvjk 39 5 synergistic synergistic JJ cord-003318-abs9rvjk 39 6 actions action NNS cord-003318-abs9rvjk 39 7 of of IN cord-003318-abs9rvjk 39 8 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 39 9 and and CC cord-003318-abs9rvjk 39 10 EsSGA1 EsSGA1 NNP cord-003318-abs9rvjk 39 11 , , , cord-003318-abs9rvjk 39 12 the the DT cord-003318-abs9rvjk 39 13 biosynthetic biosynthetic JJ cord-003318-abs9rvjk 39 14 preparation preparation NN cord-003318-abs9rvjk 39 15 of of IN cord-003318-abs9rvjk 39 16 two two CD cord-003318-abs9rvjk 39 17 acylated acylated JJ cord-003318-abs9rvjk 39 18 steroidal steroidal JJ cord-003318-abs9rvjk 39 19 glycosides glycoside NNS cord-003318-abs9rvjk 39 20 ( ( -LRB- cord-003318-abs9rvjk 39 21 ASGs ASGs NNP cord-003318-abs9rvjk 39 22 ) ) -RRB- cord-003318-abs9rvjk 39 23 , , , cord-003318-abs9rvjk 39 24 namely namely RB cord-003318-abs9rvjk 39 25 acetylated acetylated JJ cord-003318-abs9rvjk 39 26 T-17β T-17β NNP cord-003318-abs9rvjk 39 27 - - HYPH cord-003318-abs9rvjk 39 28 Gs Gs NNP cord-003318-abs9rvjk 39 29 ( ( -LRB- cord-003318-abs9rvjk 39 30 AT-17β AT-17β NNP cord-003318-abs9rvjk 39 31 - - HYPH cord-003318-abs9rvjk 39 32 Gs Gs NNP cord-003318-abs9rvjk 39 33 ) ) -RRB- cord-003318-abs9rvjk 39 34 and and CC cord-003318-abs9rvjk 39 35 E-17β E-17β NNP cord-003318-abs9rvjk 39 36 - - HYPH cord-003318-abs9rvjk 39 37 Gs Gs NNP cord-003318-abs9rvjk 39 38 ( ( -LRB- cord-003318-abs9rvjk 39 39 AE-17β AE-17β NNP cord-003318-abs9rvjk 39 40 - - HYPH cord-003318-abs9rvjk 39 41 Gs Gs NNP cord-003318-abs9rvjk 39 42 ) ) -RRB- cord-003318-abs9rvjk 39 43 , , , cord-003318-abs9rvjk 39 44 was be VBD cord-003318-abs9rvjk 39 45 first first RB cord-003318-abs9rvjk 39 46 achieved achieve VBN cord-003318-abs9rvjk 39 47 , , , cord-003318-abs9rvjk 39 48 thereby thereby RB cord-003318-abs9rvjk 39 49 yielding yield VBG cord-003318-abs9rvjk 39 50 four four CD cord-003318-abs9rvjk 39 51 monoacetylated monoacetylated JJ cord-003318-abs9rvjk 39 52 steroidal steroidal JJ cord-003318-abs9rvjk 39 53 glucosides glucoside NNS cord-003318-abs9rvjk 39 54 , , , cord-003318-abs9rvjk 39 55 namely namely RB cord-003318-abs9rvjk 39 56 2 2 CD cord-003318-abs9rvjk 39 57 0 0 CD cord-003318-abs9rvjk 39 58 -O -o CD cord-003318-abs9rvjk 39 59 , , , cord-003318-abs9rvjk 39 60 3 3 CD cord-003318-abs9rvjk 39 61 0 0 CD cord-003318-abs9rvjk 39 62 -O -o CD cord-003318-abs9rvjk 39 63 , , , cord-003318-abs9rvjk 39 64 4 4 CD cord-003318-abs9rvjk 39 65 0 0 CD cord-003318-abs9rvjk 39 66 -O -o CD cord-003318-abs9rvjk 39 67 and and CC cord-003318-abs9rvjk 39 68 6 6 CD cord-003318-abs9rvjk 39 69 0 0 CD cord-003318-abs9rvjk 39 70 -O -O : cord-003318-abs9rvjk 39 71 - - HYPH cord-003318-abs9rvjk 39 72 acylates acylates FW cord-003318-abs9rvjk 39 73 ( ( -LRB- cord-003318-abs9rvjk 39 74 Scheme scheme NN cord-003318-abs9rvjk 39 75 1 1 CD cord-003318-abs9rvjk 39 76 ) ) -RRB- cord-003318-abs9rvjk 39 77 . . . cord-003318-abs9rvjk 40 1 The the DT cord-003318-abs9rvjk 40 2 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 40 3 activities activity NNS cord-003318-abs9rvjk 40 4 of of IN cord-003318-abs9rvjk 40 5 these these DT cord-003318-abs9rvjk 40 6 monoacylates monoacylate NNS cord-003318-abs9rvjk 40 7 were be VBD cord-003318-abs9rvjk 40 8 evaluated evaluate VBN cord-003318-abs9rvjk 40 9 against against IN cord-003318-abs9rvjk 40 10 seven seven CD cord-003318-abs9rvjk 40 11 human human JJ cord-003318-abs9rvjk 40 12 tumor tumor NN cord-003318-abs9rvjk 40 13 cell cell NN cord-003318-abs9rvjk 40 14 lines line NNS cord-003318-abs9rvjk 40 15 ( ( -LRB- cord-003318-abs9rvjk 40 16 HCT116 HCT116 NNP cord-003318-abs9rvjk 40 17 , , , cord-003318-abs9rvjk 40 18 Bel7402 Bel7402 NNP cord-003318-abs9rvjk 40 19 , , , cord-003318-abs9rvjk 40 20 MGC803 MGC803 NNP cord-003318-abs9rvjk 40 21 , , , cord-003318-abs9rvjk 40 22 Capan2 Capan2 NNP cord-003318-abs9rvjk 40 23 , , , cord-003318-abs9rvjk 40 24 NCI NCI NNP cord-003318-abs9rvjk 40 25 - - HYPH cord-003318-abs9rvjk 40 26 H460 H460 NNP cord-003318-abs9rvjk 40 27 , , , cord-003318-abs9rvjk 40 28 NCI NCI NNP cord-003318-abs9rvjk 40 29 - - HYPH cord-003318-abs9rvjk 40 30 H1650 H1650 NNP cord-003318-abs9rvjk 40 31 and and CC cord-003318-abs9rvjk 40 32 A549 A549 NNP cord-003318-abs9rvjk 40 33 ) ) -RRB- cord-003318-abs9rvjk 40 34 and and CC cord-003318-abs9rvjk 40 35 3 3 CD cord-003318-abs9rvjk 40 36 0 0 CD cord-003318-abs9rvjk 40 37 -acetylated -acetylated CD cord-003318-abs9rvjk 40 38 testosterone17-O testosterone17-O NNP cord-003318-abs9rvjk 40 39 - - HYPH cord-003318-abs9rvjk 40 40 β β NN cord-003318-abs9rvjk 40 41 - - HYPH cord-003318-abs9rvjk 40 42 glucoside glucoside NN cord-003318-abs9rvjk 40 43 was be VBD cord-003318-abs9rvjk 40 44 observed observe VBN cord-003318-abs9rvjk 40 45 to to TO cord-003318-abs9rvjk 40 46 display display VB cord-003318-abs9rvjk 40 47 improved improve VBN cord-003318-abs9rvjk 40 48 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 40 49 activity activity NN cord-003318-abs9rvjk 40 50 against against IN cord-003318-abs9rvjk 40 51 these these DT cord-003318-abs9rvjk 40 52 seven seven CD cord-003318-abs9rvjk 40 53 cell cell NN cord-003318-abs9rvjk 40 54 lines line NNS cord-003318-abs9rvjk 40 55 ( ( -LRB- cord-003318-abs9rvjk 40 56 Scheme scheme NN cord-003318-abs9rvjk 40 57 1 1 CD cord-003318-abs9rvjk 40 58 ) ) -RRB- cord-003318-abs9rvjk 40 59 . . . cord-003318-abs9rvjk 41 1 The the DT cord-003318-abs9rvjk 41 2 species species NN cord-003318-abs9rvjk 41 3 O. O. NNP cord-003318-abs9rvjk 41 4 saundersiae saundersiae NN cord-003318-abs9rvjk 41 5 is be VBZ cord-003318-abs9rvjk 41 6 a a DT cord-003318-abs9rvjk 41 7 monocotyledonous monocotyledonous JJ cord-003318-abs9rvjk 41 8 plant plant NN cord-003318-abs9rvjk 41 9 rich rich JJ cord-003318-abs9rvjk 41 10 in in IN cord-003318-abs9rvjk 41 11 steroidal steroidal JJ cord-003318-abs9rvjk 41 12 glycosides glycoside NNS cord-003318-abs9rvjk 41 13 , , , cord-003318-abs9rvjk 41 14 suggesting suggest VBG cord-003318-abs9rvjk 41 15 that that IN cord-003318-abs9rvjk 41 16 it -PRON- PRP cord-003318-abs9rvjk 41 17 may may MD cord-003318-abs9rvjk 41 18 contain contain VB cord-003318-abs9rvjk 41 19 SGTs sgt NNS cord-003318-abs9rvjk 41 20 responsible responsible JJ cord-003318-abs9rvjk 41 21 for for IN cord-003318-abs9rvjk 41 22 the the DT cord-003318-abs9rvjk 41 23 glycosylation glycosylation NN cord-003318-abs9rvjk 41 24 of of IN cord-003318-abs9rvjk 41 25 steroidal steroidal JJ cord-003318-abs9rvjk 41 26 aglycons aglycon NNS cord-003318-abs9rvjk 41 27 [ [ -LRB- cord-003318-abs9rvjk 41 28 7 7 CD cord-003318-abs9rvjk 41 29 ] ] -RRB- cord-003318-abs9rvjk 42 1 [ [ -LRB- cord-003318-abs9rvjk 42 2 8 8 CD cord-003318-abs9rvjk 42 3 ] ] -RRB- cord-003318-abs9rvjk 42 4 [ [ -LRB- cord-003318-abs9rvjk 42 5 9 9 CD cord-003318-abs9rvjk 42 6 ] ] -RRB- cord-003318-abs9rvjk 42 7 . . . cord-003318-abs9rvjk 43 1 O. O. NNP cord-003318-abs9rvjk 43 2 saundersiae saundersiae NNP cord-003318-abs9rvjk 43 3 is be VBZ cord-003318-abs9rvjk 43 4 thus thus RB cord-003318-abs9rvjk 43 5 selected select VBN cord-003318-abs9rvjk 43 6 as as IN cord-003318-abs9rvjk 43 7 the the DT cord-003318-abs9rvjk 43 8 candidate candidate NN cord-003318-abs9rvjk 43 9 plant plant NN cord-003318-abs9rvjk 43 10 for for IN cord-003318-abs9rvjk 43 11 SGTs sgt NNS cord-003318-abs9rvjk 43 12 isolation isolation NN cord-003318-abs9rvjk 43 13 . . . cord-003318-abs9rvjk 44 1 The the DT cord-003318-abs9rvjk 44 2 transcriptome transcriptome NN cord-003318-abs9rvjk 44 3 of of IN cord-003318-abs9rvjk 44 4 O. O. NNP cord-003318-abs9rvjk 44 5 saundersiae saundersiae NNP cord-003318-abs9rvjk 44 6 was be VBD cord-003318-abs9rvjk 44 7 thus thus RB cord-003318-abs9rvjk 44 8 sequenced sequence VBN cord-003318-abs9rvjk 44 9 with with IN cord-003318-abs9rvjk 44 10 the the DT cord-003318-abs9rvjk 44 11 aim aim NN cord-003318-abs9rvjk 44 12 of of IN cord-003318-abs9rvjk 44 13 isolating isolate VBG cord-003318-abs9rvjk 44 14 genes gene NNS cord-003318-abs9rvjk 44 15 encoding encode VBG cord-003318-abs9rvjk 44 16 SGTs sgt NNS cord-003318-abs9rvjk 44 17 . . . cord-003318-abs9rvjk 45 1 A a DT cord-003318-abs9rvjk 45 2 total total NN cord-003318-abs9rvjk 45 3 of of IN cord-003318-abs9rvjk 45 4 92,995,146 92,995,146 CD cord-003318-abs9rvjk 45 5 raw raw JJ cord-003318-abs9rvjk 45 6 reads read NNS cord-003318-abs9rvjk 45 7 were be VBD cord-003318-abs9rvjk 45 8 generated generate VBN cord-003318-abs9rvjk 45 9 after after IN cord-003318-abs9rvjk 45 10 the the DT cord-003318-abs9rvjk 45 11 transcriptome transcriptome NN cord-003318-abs9rvjk 45 12 sequencing sequencing NN cord-003318-abs9rvjk 45 13 of of IN cord-003318-abs9rvjk 45 14 O. O. NNP cord-003318-abs9rvjk 45 15 saundersiae saundersiae NN cord-003318-abs9rvjk 45 16 . . . cord-003318-abs9rvjk 46 1 After after IN cord-003318-abs9rvjk 46 2 removal removal NN cord-003318-abs9rvjk 46 3 of of IN cord-003318-abs9rvjk 46 4 dirty dirty JJ cord-003318-abs9rvjk 46 5 reads read NNS cord-003318-abs9rvjk 46 6 with with IN cord-003318-abs9rvjk 46 7 adapters adapter NNS cord-003318-abs9rvjk 46 8 , , , cord-003318-abs9rvjk 46 9 unknown unknown JJ cord-003318-abs9rvjk 46 10 or or CC cord-003318-abs9rvjk 46 11 low low JJ cord-003318-abs9rvjk 46 12 quality quality NN cord-003318-abs9rvjk 46 13 bases basis NNS cord-003318-abs9rvjk 46 14 , , , cord-003318-abs9rvjk 46 15 a a DT cord-003318-abs9rvjk 46 16 total total NN cord-003318-abs9rvjk 46 17 of of IN cord-003318-abs9rvjk 46 18 82,518,740 82,518,740 CD cord-003318-abs9rvjk 46 19 clean clean JJ cord-003318-abs9rvjk 46 20 reads read NNS cord-003318-abs9rvjk 46 21 were be VBD cord-003318-abs9rvjk 46 22 retained retain VBN cord-003318-abs9rvjk 46 23 . . . cord-003318-abs9rvjk 47 1 These these DT cord-003318-abs9rvjk 47 2 clean clean JJ cord-003318-abs9rvjk 47 3 reads read NNS cord-003318-abs9rvjk 47 4 were be VBD cord-003318-abs9rvjk 47 5 combined combine VBN cord-003318-abs9rvjk 47 6 by by IN cord-003318-abs9rvjk 47 7 assembling assemble VBG cord-003318-abs9rvjk 47 8 soft soft JJ cord-003318-abs9rvjk 47 9 trinity trinity NN cord-003318-abs9rvjk 47 10 to to TO cord-003318-abs9rvjk 47 11 form form VB cord-003318-abs9rvjk 47 12 longer long JJR cord-003318-abs9rvjk 47 13 unigenes unigene NNS cord-003318-abs9rvjk 47 14 . . . cord-003318-abs9rvjk 48 1 Finally finally RB cord-003318-abs9rvjk 48 2 , , , cord-003318-abs9rvjk 48 3 an an DT cord-003318-abs9rvjk 48 4 RNA RNA NNP cord-003318-abs9rvjk 48 5 - - HYPH cord-003318-abs9rvjk 48 6 seq seq NN cord-003318-abs9rvjk 48 7 database database NN cord-003318-abs9rvjk 48 8 containing contain VBG cord-003318-abs9rvjk 48 9 107,084 107,084 CD cord-003318-abs9rvjk 48 10 unigenes unigene NNS cord-003318-abs9rvjk 48 11 with with IN cord-003318-abs9rvjk 48 12 mean mean JJ cord-003318-abs9rvjk 48 13 length length NN cord-003318-abs9rvjk 48 14 of of IN cord-003318-abs9rvjk 48 15 766 766 CD cord-003318-abs9rvjk 48 16 bp bp NNP cord-003318-abs9rvjk 48 17 was be VBD cord-003318-abs9rvjk 48 18 obtained obtain VBN cord-003318-abs9rvjk 48 19 . . . cord-003318-abs9rvjk 49 1 Next next RB cord-003318-abs9rvjk 49 2 , , , cord-003318-abs9rvjk 49 3 these these DT cord-003318-abs9rvjk 49 4 unigenes unigene NNS cord-003318-abs9rvjk 49 5 were be VBD cord-003318-abs9rvjk 49 6 aligned align VBN cord-003318-abs9rvjk 49 7 to to IN cord-003318-abs9rvjk 49 8 publicly publicly RB cord-003318-abs9rvjk 49 9 available available JJ cord-003318-abs9rvjk 49 10 protein protein NN cord-003318-abs9rvjk 49 11 databases database NNS cord-003318-abs9rvjk 49 12 for for IN cord-003318-abs9rvjk 49 13 functional functional JJ cord-003318-abs9rvjk 49 14 annotations annotation NNS cord-003318-abs9rvjk 49 15 , , , cord-003318-abs9rvjk 49 16 retrieving retrieve VBG cord-003318-abs9rvjk 49 17 unigenes unigene NNS cord-003318-abs9rvjk 49 18 displaying display VBG cord-003318-abs9rvjk 49 19 the the DT cord-003318-abs9rvjk 49 20 highest high JJS cord-003318-abs9rvjk 49 21 sequence sequence NN cord-003318-abs9rvjk 49 22 similarity similarity NN cord-003318-abs9rvjk 49 23 with with IN cord-003318-abs9rvjk 49 24 SGTs sgt NNS cord-003318-abs9rvjk 49 25 . . . cord-003318-abs9rvjk 50 1 Unigene unigene JJ cord-003318-abs9rvjk 50 2 32070 32070 CD cord-003318-abs9rvjk 50 3 with with IN cord-003318-abs9rvjk 50 4 2182 2182 CD cord-003318-abs9rvjk 50 5 bp bp NNP cord-003318-abs9rvjk 50 6 in in IN cord-003318-abs9rvjk 50 7 length length NN cord-003318-abs9rvjk 50 8 was be VBD cord-003318-abs9rvjk 50 9 thus thus RB cord-003318-abs9rvjk 50 10 retrieved retrieve VBN cord-003318-abs9rvjk 50 11 from from IN cord-003318-abs9rvjk 50 12 the the DT cord-003318-abs9rvjk 50 13 unigene unigene NN cord-003318-abs9rvjk 50 14 database database NN cord-003318-abs9rvjk 50 15 for for IN cord-003318-abs9rvjk 50 16 its -PRON- PRP$ cord-003318-abs9rvjk 50 17 high high JJ cord-003318-abs9rvjk 50 18 similarity similarity NN cord-003318-abs9rvjk 50 19 with with IN cord-003318-abs9rvjk 50 20 SGTs sgt NNS cord-003318-abs9rvjk 50 21 ( ( -LRB- cord-003318-abs9rvjk 50 22 Supplementary Supplementary NNP cord-003318-abs9rvjk 50 23 Information Information NNP cord-003318-abs9rvjk 50 24 Fig Fig NNP cord-003318-abs9rvjk 50 25 . . . cord-003318-abs9rvjk 50 26 _SP cord-003318-abs9rvjk 51 1 S1 S1 NNP cord-003318-abs9rvjk 51 2 ) ) -RRB- cord-003318-abs9rvjk 51 3 . . . cord-003318-abs9rvjk 52 1 Moreover moreover RB cord-003318-abs9rvjk 52 2 , , , cord-003318-abs9rvjk 52 3 ORF ORF NNP cord-003318-abs9rvjk 52 4 Finder Finder NNP cord-003318-abs9rvjk 52 5 result result NN cord-003318-abs9rvjk 52 6 showed show VBD cord-003318-abs9rvjk 52 7 that that IN cord-003318-abs9rvjk 52 8 this this DT cord-003318-abs9rvjk 52 9 unigene unigene NN cord-003318-abs9rvjk 52 10 contained contain VBD cord-003318-abs9rvjk 52 11 a a DT cord-003318-abs9rvjk 52 12 complete complete JJ cord-003318-abs9rvjk 52 13 open open JJ cord-003318-abs9rvjk 52 14 reading reading NN cord-003318-abs9rvjk 52 15 frame frame NN cord-003318-abs9rvjk 52 16 ( ( -LRB- cord-003318-abs9rvjk 52 17 ORF ORF NNP cord-003318-abs9rvjk 52 18 ) ) -RRB- cord-003318-abs9rvjk 52 19 of of IN cord-003318-abs9rvjk 52 20 1773 1773 CD cord-003318-abs9rvjk 52 21 bp bp NNP cord-003318-abs9rvjk 52 22 , , , cord-003318-abs9rvjk 52 23 starting start VBG cord-003318-abs9rvjk 52 24 at at IN cord-003318-abs9rvjk 52 25 nucleotide nucleotide JJ cord-003318-abs9rvjk 52 26 99 99 CD cord-003318-abs9rvjk 52 27 with with IN cord-003318-abs9rvjk 52 28 an an DT cord-003318-abs9rvjk 52 29 ATG ATG NNP cord-003318-abs9rvjk 52 30 start start NN cord-003318-abs9rvjk 52 31 codon codon NN cord-003318-abs9rvjk 52 32 and and CC cord-003318-abs9rvjk 52 33 ending end VBG cord-003318-abs9rvjk 52 34 at at IN cord-003318-abs9rvjk 52 35 position position NN cord-003318-abs9rvjk 52 36 1871 1871 CD cord-003318-abs9rvjk 52 37 with with IN cord-003318-abs9rvjk 52 38 a a DT cord-003318-abs9rvjk 52 39 TGA TGA NNP cord-003318-abs9rvjk 52 40 stop stop NN cord-003318-abs9rvjk 52 41 codon codon NN cord-003318-abs9rvjk 52 42 . . . cord-003318-abs9rvjk 53 1 The the DT cord-003318-abs9rvjk 53 2 unigene unigene NN cord-003318-abs9rvjk 53 3 contained contain VBD cord-003318-abs9rvjk 53 4 98 98 CD cord-003318-abs9rvjk 53 5 bp bp NNP cord-003318-abs9rvjk 53 6 of of IN cord-003318-abs9rvjk 53 7 5 5 CD cord-003318-abs9rvjk 53 8 0 0 CD cord-003318-abs9rvjk 53 9 -UTR -UTR : cord-003318-abs9rvjk 53 10 ( ( -LRB- cord-003318-abs9rvjk 53 11 untranslated untranslated JJ cord-003318-abs9rvjk 53 12 region region NN cord-003318-abs9rvjk 53 13 ) ) -RRB- cord-003318-abs9rvjk 53 14 and and CC cord-003318-abs9rvjk 53 15 311 311 CD cord-003318-abs9rvjk 53 16 bp bp NNS cord-003318-abs9rvjk 53 17 of of IN cord-003318-abs9rvjk 53 18 3 3 CD cord-003318-abs9rvjk 53 19 0 0 CD cord-003318-abs9rvjk 53 20 -UTR -utr NN cord-003318-abs9rvjk 53 21 . . . cord-003318-abs9rvjk 54 1 Therefore therefore RB cord-003318-abs9rvjk 54 2 , , , cord-003318-abs9rvjk 54 3 unigene unigene NN cord-003318-abs9rvjk 54 4 32070 32070 CD cord-003318-abs9rvjk 54 5 was be VBD cord-003318-abs9rvjk 54 6 selected select VBN cord-003318-abs9rvjk 54 7 for for IN cord-003318-abs9rvjk 54 8 further further JJ cord-003318-abs9rvjk 54 9 investigation investigation NN cord-003318-abs9rvjk 54 10 . . . cord-003318-abs9rvjk 55 1 To to TO cord-003318-abs9rvjk 55 2 verify verify VB cord-003318-abs9rvjk 55 3 the the DT cord-003318-abs9rvjk 55 4 identity identity NN cord-003318-abs9rvjk 55 5 of of IN cord-003318-abs9rvjk 55 6 unigene unigene NNP cord-003318-abs9rvjk 55 7 32070 32070 CD cord-003318-abs9rvjk 55 8 , , , cord-003318-abs9rvjk 55 9 a a DT cord-003318-abs9rvjk 55 10 nested nest VBN cord-003318-abs9rvjk 55 11 PCR PCR NNP cord-003318-abs9rvjk 55 12 assay assay NN cord-003318-abs9rvjk 55 13 was be VBD cord-003318-abs9rvjk 55 14 therefore therefore RB cord-003318-abs9rvjk 55 15 carried carry VBN cord-003318-abs9rvjk 55 16 out out RP cord-003318-abs9rvjk 55 17 to to TO cord-003318-abs9rvjk 55 18 amplify amplify VB cord-003318-abs9rvjk 55 19 the the DT cord-003318-abs9rvjk 55 20 cDNA cdna NN cord-003318-abs9rvjk 55 21 corresponding correspond VBG cord-003318-abs9rvjk 55 22 to to IN cord-003318-abs9rvjk 55 23 the the DT cord-003318-abs9rvjk 55 24 ORF ORF NNP cord-003318-abs9rvjk 55 25 of of IN cord-003318-abs9rvjk 55 26 unigene unigene NNP cord-003318-abs9rvjk 55 27 32070 32070 CD cord-003318-abs9rvjk 55 28 using use VBG cord-003318-abs9rvjk 55 29 gene gene NN cord-003318-abs9rvjk 55 30 - - HYPH cord-003318-abs9rvjk 55 31 specific specific JJ cord-003318-abs9rvjk 55 32 primers primer NNS cord-003318-abs9rvjk 55 33 ( ( -LRB- cord-003318-abs9rvjk 55 34 Supplementary Supplementary NNP cord-003318-abs9rvjk 55 35 Information Information NNP cord-003318-abs9rvjk 55 36 Table Table NNP cord-003318-abs9rvjk 55 37 S1 S1 NNP cord-003318-abs9rvjk 55 38 ) ) -RRB- cord-003318-abs9rvjk 55 39 . . . cord-003318-abs9rvjk 56 1 An an DT cord-003318-abs9rvjk 56 2 expected expected JJ cord-003318-abs9rvjk 56 3 band band NN cord-003318-abs9rvjk 56 4 with with IN cord-003318-abs9rvjk 56 5 approximately approximately RB cord-003318-abs9rvjk 56 6 1.7 1.7 CD cord-003318-abs9rvjk 56 7 kb kb NNP cord-003318-abs9rvjk 56 8 was be VBD cord-003318-abs9rvjk 56 9 obtained obtain VBN cord-003318-abs9rvjk 56 10 , , , cord-003318-abs9rvjk 56 11 as as IN cord-003318-abs9rvjk 56 12 observed observe VBN cord-003318-abs9rvjk 56 13 in in IN cord-003318-abs9rvjk 56 14 agarose agarose JJ cord-003318-abs9rvjk 56 15 gel gel NN cord-003318-abs9rvjk 56 16 electrophoresis electrophoresis NN cord-003318-abs9rvjk 56 17 ( ( -LRB- cord-003318-abs9rvjk 56 18 Supplementary Supplementary NNP cord-003318-abs9rvjk 56 19 Information Information NNP cord-003318-abs9rvjk 56 20 Fig Fig NNP cord-003318-abs9rvjk 56 21 . . . cord-003318-abs9rvjk 57 1 S2A S2A NNP cord-003318-abs9rvjk 57 2 ) ) -RRB- cord-003318-abs9rvjk 57 3 . . . cord-003318-abs9rvjk 58 1 The the DT cord-003318-abs9rvjk 58 2 amplicon amplicon NN cord-003318-abs9rvjk 58 3 was be VBD cord-003318-abs9rvjk 58 4 then then RB cord-003318-abs9rvjk 58 5 inserted insert VBN cord-003318-abs9rvjk 58 6 into into IN cord-003318-abs9rvjk 58 7 pEASY peasy JJ cord-003318-abs9rvjk 58 8 TM TM NNP cord-003318-abs9rvjk 58 9 -Blunt -blunt NN cord-003318-abs9rvjk 58 10 plasmid plasmid NNP cord-003318-abs9rvjk 58 11 ( ( -LRB- cord-003318-abs9rvjk 58 12 Supplementary Supplementary NNP cord-003318-abs9rvjk 58 13 Information Information NNP cord-003318-abs9rvjk 58 14 Table Table NNP cord-003318-abs9rvjk 58 15 S2 s2 NN cord-003318-abs9rvjk 58 16 ) ) -RRB- cord-003318-abs9rvjk 58 17 to to TO cord-003318-abs9rvjk 58 18 form form VB cord-003318-abs9rvjk 58 19 a a DT cord-003318-abs9rvjk 58 20 recombinant recombinant JJ cord-003318-abs9rvjk 58 21 vector vector NN cord-003318-abs9rvjk 58 22 for for IN cord-003318-abs9rvjk 58 23 sequencing sequencing NN cord-003318-abs9rvjk 58 24 . . . cord-003318-abs9rvjk 59 1 Results result NNS cord-003318-abs9rvjk 59 2 indicated indicate VBD cord-003318-abs9rvjk 59 3 that that IN cord-003318-abs9rvjk 59 4 the the DT cord-003318-abs9rvjk 59 5 amplified amplify VBN cord-003318-abs9rvjk 59 6 product product NN cord-003318-abs9rvjk 59 7 was be VBD cord-003318-abs9rvjk 59 8 100 100 CD cord-003318-abs9rvjk 59 9 % % NN cord-003318-abs9rvjk 59 10 identity identity NN cord-003318-abs9rvjk 59 11 with with IN cord-003318-abs9rvjk 59 12 that that DT cord-003318-abs9rvjk 59 13 of of IN cord-003318-abs9rvjk 59 14 unigene unigene NN cord-003318-abs9rvjk 59 15 32070 32070 CD cord-003318-abs9rvjk 59 16 , , , cord-003318-abs9rvjk 59 17 confirming confirm VBG cord-003318-abs9rvjk 59 18 unigene unigene NN cord-003318-abs9rvjk 59 19 32070 32070 CD cord-003318-abs9rvjk 59 20 was be VBD cord-003318-abs9rvjk 59 21 a a DT cord-003318-abs9rvjk 59 22 bona bona JJ cord-003318-abs9rvjk 59 23 fide fide JJ cord-003318-abs9rvjk 59 24 gene gene NN cord-003318-abs9rvjk 59 25 in in IN cord-003318-abs9rvjk 59 26 O. O. NNP cord-003318-abs9rvjk 59 27 saundersiae saundersiae NNP cord-003318-abs9rvjk 59 28 genome genome NN cord-003318-abs9rvjk 59 29 . . . cord-003318-abs9rvjk 60 1 The the DT cord-003318-abs9rvjk 60 2 1773bp 1773bp JJ cord-003318-abs9rvjk 60 3 ORF ORF NNP cord-003318-abs9rvjk 60 4 encoded encode VBD cord-003318-abs9rvjk 60 5 a a DT cord-003318-abs9rvjk 60 6 polypeptide polypeptide NN cord-003318-abs9rvjk 60 7 of of IN cord-003318-abs9rvjk 60 8 590 590 CD cord-003318-abs9rvjk 60 9 amino amino JJ cord-003318-abs9rvjk 60 10 acids acid NNS cord-003318-abs9rvjk 60 11 ( ( -LRB- cord-003318-abs9rvjk 60 12 aa aa NNP cord-003318-abs9rvjk 60 13 ) ) -RRB- cord-003318-abs9rvjk 60 14 with with IN cord-003318-abs9rvjk 60 15 a a DT cord-003318-abs9rvjk 60 16 predicted predict VBN cord-003318-abs9rvjk 60 17 molecular molecular JJ cord-003318-abs9rvjk 60 18 mass mass NN cord-003318-abs9rvjk 60 19 of of IN cord-003318-abs9rvjk 60 20 64.61 64.61 CD cord-003318-abs9rvjk 60 21 kDa kDa NNS cord-003318-abs9rvjk 60 22 and and CC cord-003318-abs9rvjk 60 23 pI pI NNP cord-003318-abs9rvjk 60 24 of of IN cord-003318-abs9rvjk 60 25 6.16 6.16 CD cord-003318-abs9rvjk 60 26 . . . cord-003318-abs9rvjk 61 1 Blast blast NN cord-003318-abs9rvjk 61 2 analysis analysis NN cord-003318-abs9rvjk 61 3 of of IN cord-003318-abs9rvjk 61 4 the the DT cord-003318-abs9rvjk 61 5 deduced deduce VBN cord-003318-abs9rvjk 61 6 protein protein NN cord-003318-abs9rvjk 61 7 revealed reveal VBD cord-003318-abs9rvjk 61 8 its -PRON- PRP$ cord-003318-abs9rvjk 61 9 predominant predominant JJ cord-003318-abs9rvjk 61 10 homology homology NN cord-003318-abs9rvjk 61 11 with with IN cord-003318-abs9rvjk 61 12 sterol sterol NN cord-003318-abs9rvjk 61 13 3β 3β CD cord-003318-abs9rvjk 61 14 - - HYPH cord-003318-abs9rvjk 61 15 glucosyltransferase glucosyltransferase NNP cord-003318-abs9rvjk 61 16 from from IN cord-003318-abs9rvjk 61 17 Elaeis Elaeis NNP cord-003318-abs9rvjk 61 18 guineensis guineensis NNP cord-003318-abs9rvjk 61 19 ( ( -LRB- cord-003318-abs9rvjk 61 20 XP_010933168.1 XP_010933168.1 NNP cord-003318-abs9rvjk 61 21 , , , cord-003318-abs9rvjk 61 22 85 85 CD cord-003318-abs9rvjk 61 23 % % NN cord-003318-abs9rvjk 61 24 ) ) -RRB- cord-003318-abs9rvjk 61 25 , , , cord-003318-abs9rvjk 61 26 Musa Musa NNP cord-003318-abs9rvjk 61 27 acuminata acuminata NN cord-003318-abs9rvjk 61 28 subsp subsp NN cord-003318-abs9rvjk 61 29 . . . cord-003318-abs9rvjk 62 1 Malaccensis Malaccensis NNP cord-003318-abs9rvjk 62 2 ( ( -LRB- cord-003318-abs9rvjk 62 3 XP_009397543.1 XP_009397543.1 NNP cord-003318-abs9rvjk 62 4 , , , cord-003318-abs9rvjk 62 5 83 83 CD cord-003318-abs9rvjk 62 6 % % NN cord-003318-abs9rvjk 62 7 ) ) -RRB- cord-003318-abs9rvjk 62 8 and and CC cord-003318-abs9rvjk 62 9 Anthurium Anthurium NNP cord-003318-abs9rvjk 62 10 amnicola amnicola NNP cord-003318-abs9rvjk 62 11 ( ( -LRB- cord-003318-abs9rvjk 62 12 JAT62313.1 JAT62313.1 NNP cord-003318-abs9rvjk 62 13 , , , cord-003318-abs9rvjk 62 14 81 81 CD cord-003318-abs9rvjk 62 15 % % NN cord-003318-abs9rvjk 62 16 ) ) -RRB- cord-003318-abs9rvjk 62 17 . . . cord-003318-abs9rvjk 63 1 The the DT cord-003318-abs9rvjk 63 2 cDNA cdna NN cord-003318-abs9rvjk 63 3 was be VBD cord-003318-abs9rvjk 63 4 therefore therefore RB cord-003318-abs9rvjk 63 5 designated designate VBN cord-003318-abs9rvjk 63 6 as as IN cord-003318-abs9rvjk 63 7 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 63 8 and and CC cord-003318-abs9rvjk 63 9 submitted submit VBN cord-003318-abs9rvjk 63 10 to to IN cord-003318-abs9rvjk 63 11 GenBank GenBank NNP cord-003318-abs9rvjk 63 12 library library NN cord-003318-abs9rvjk 63 13 with with IN cord-003318-abs9rvjk 63 14 an an DT cord-003318-abs9rvjk 63 15 accession accession NN cord-003318-abs9rvjk 63 16 number number NN cord-003318-abs9rvjk 63 17 of of IN cord-003318-abs9rvjk 63 18 MF688776 MF688776 NNP cord-003318-abs9rvjk 63 19 . . . cord-003318-abs9rvjk 64 1 The the DT cord-003318-abs9rvjk 64 2 sequence sequence NN cord-003318-abs9rvjk 64 3 analyses analysis NNS cord-003318-abs9rvjk 64 4 of of IN cord-003318-abs9rvjk 64 5 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 64 6 were be VBD cord-003318-abs9rvjk 64 7 first first RB cord-003318-abs9rvjk 64 8 assessed assess VBN cord-003318-abs9rvjk 64 9 with with IN cord-003318-abs9rvjk 64 10 the the DT cord-003318-abs9rvjk 64 11 aim aim NN cord-003318-abs9rvjk 64 12 to to TO cord-003318-abs9rvjk 64 13 direct direct VB cord-003318-abs9rvjk 64 14 its -PRON- PRP$ cord-003318-abs9rvjk 64 15 expression expression NN cord-003318-abs9rvjk 64 16 and and CC cord-003318-abs9rvjk 64 17 functional functional JJ cord-003318-abs9rvjk 64 18 verification verification NN cord-003318-abs9rvjk 64 19 . . . cord-003318-abs9rvjk 65 1 No no DT cord-003318-abs9rvjk 65 2 putative putative JJ cord-003318-abs9rvjk 65 3 trans trans NN cord-003318-abs9rvjk 65 4 - - NN cord-003318-abs9rvjk 65 5 membrane membrane NN cord-003318-abs9rvjk 65 6 domain domain NN cord-003318-abs9rvjk 65 7 was be VBD cord-003318-abs9rvjk 65 8 observed observe VBN cord-003318-abs9rvjk 65 9 in in IN cord-003318-abs9rvjk 65 10 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 65 11 based base VBN cord-003318-abs9rvjk 65 12 on on IN cord-003318-abs9rvjk 65 13 the the DT cord-003318-abs9rvjk 65 14 prediction prediction NN cord-003318-abs9rvjk 65 15 results result NNS cord-003318-abs9rvjk 65 16 by by IN cord-003318-abs9rvjk 65 17 TMHMM TMHMM NNP cord-003318-abs9rvjk 65 18 ( ( -LRB- cord-003318-abs9rvjk 65 19 http://www.cbs.dtu.dk/services/ http://www.cbs.dtu.dk/services/ NNP cord-003318-abs9rvjk 65 20 TMHMM/ TMHMM/ NNP cord-003318-abs9rvjk 65 21 ) ) -RRB- cord-003318-abs9rvjk 65 22 , , , cord-003318-abs9rvjk 65 23 suggesting suggest VBG cord-003318-abs9rvjk 65 24 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 65 25 is be VBZ cord-003318-abs9rvjk 65 26 a a DT cord-003318-abs9rvjk 65 27 cytoplasmic cytoplasmic JJ cord-003318-abs9rvjk 65 28 SGT SGT NNP cord-003318-abs9rvjk 65 29 and and CC cord-003318-abs9rvjk 65 30 may may MD cord-003318-abs9rvjk 65 31 be be VB cord-003318-abs9rvjk 65 32 expressed express VBN cord-003318-abs9rvjk 65 33 heterologously heterologously NNP cord-003318-abs9rvjk 65 34 in in IN cord-003318-abs9rvjk 65 35 E. E. NNP cord-003318-abs9rvjk 65 36 coli coli NNS cord-003318-abs9rvjk 65 37 in in IN cord-003318-abs9rvjk 65 38 a a DT cord-003318-abs9rvjk 65 39 soluble soluble JJ cord-003318-abs9rvjk 65 40 form form NN cord-003318-abs9rvjk 65 41 . . . cord-003318-abs9rvjk 66 1 Multiple multiple JJ cord-003318-abs9rvjk 66 2 alignment alignment NN cord-003318-abs9rvjk 66 3 of of IN cord-003318-abs9rvjk 66 4 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 66 5 and and CC cord-003318-abs9rvjk 66 6 other other JJ cord-003318-abs9rvjk 66 7 plant plant NN cord-003318-abs9rvjk 66 8 SGTs sgt NNS cord-003318-abs9rvjk 66 9 indicated indicate VBD cord-003318-abs9rvjk 66 10 that that IN cord-003318-abs9rvjk 66 11 the the DT cord-003318-abs9rvjk 66 12 middle middle NN cord-003318-abs9rvjk 66 13 and and CC cord-003318-abs9rvjk 66 14 C c NN cord-003318-abs9rvjk 66 15 - - HYPH cord-003318-abs9rvjk 66 16 terminal terminal NN cord-003318-abs9rvjk 66 17 parts part NNS cord-003318-abs9rvjk 66 18 of of IN cord-003318-abs9rvjk 66 19 these these DT cord-003318-abs9rvjk 66 20 SGTs sgt NNS cord-003318-abs9rvjk 66 21 were be VBD cord-003318-abs9rvjk 66 22 more more RBR cord-003318-abs9rvjk 66 23 conservative conservative JJ cord-003318-abs9rvjk 66 24 than than IN cord-003318-abs9rvjk 66 25 the the DT cord-003318-abs9rvjk 66 26 N n CD cord-003318-abs9rvjk 66 27 - - HYPH cord-003318-abs9rvjk 66 28 terminal terminal NN cord-003318-abs9rvjk 66 29 region region NN cord-003318-abs9rvjk 66 30 ( ( -LRB- cord-003318-abs9rvjk 66 31 Supplementary supplementary JJ cord-003318-abs9rvjk 66 32 _SP cord-003318-abs9rvjk 66 33 Information Information NNP cord-003318-abs9rvjk 66 34 Fig Fig NNP cord-003318-abs9rvjk 66 35 . . . cord-003318-abs9rvjk 66 36 S1 S1 NNP cord-003318-abs9rvjk 66 37 ) ) -RRB- cord-003318-abs9rvjk 66 38 , , , cord-003318-abs9rvjk 66 39 consistent consistent JJ cord-003318-abs9rvjk 66 40 with with IN cord-003318-abs9rvjk 66 41 previous previous JJ cord-003318-abs9rvjk 66 42 notion notion NN cord-003318-abs9rvjk 66 43 19 19 CD cord-003318-abs9rvjk 66 44 . . . cord-003318-abs9rvjk 67 1 Moreover moreover RB cord-003318-abs9rvjk 67 2 , , , cord-003318-abs9rvjk 67 3 two two CD cord-003318-abs9rvjk 67 4 conservative conservative JJ cord-003318-abs9rvjk 67 5 motifs motif NNS cord-003318-abs9rvjk 67 6 , , , cord-003318-abs9rvjk 67 7 namely namely RB cord-003318-abs9rvjk 67 8 a a DT cord-003318-abs9rvjk 67 9 putative putative JJ cord-003318-abs9rvjk 67 10 steroid steroid NN cord-003318-abs9rvjk 67 11 - - HYPH cord-003318-abs9rvjk 67 12 binding bind VBG cord-003318-abs9rvjk 67 13 domain domain NN cord-003318-abs9rvjk 67 14 ( ( -LRB- cord-003318-abs9rvjk 67 15 PSBD PSBD NNP cord-003318-abs9rvjk 67 16 ) ) -RRB- cord-003318-abs9rvjk 67 17 and and CC cord-003318-abs9rvjk 67 18 a a DT cord-003318-abs9rvjk 67 19 plant plant NN cord-003318-abs9rvjk 67 20 secondary secondary JJ cord-003318-abs9rvjk 67 21 product product NN cord-003318-abs9rvjk 67 22 glycosyltranferase glycosyltranferase NN cord-003318-abs9rvjk 67 23 box box NN cord-003318-abs9rvjk 67 24 ( ( -LRB- cord-003318-abs9rvjk 67 25 PSPG PSPG NNP cord-003318-abs9rvjk 67 26 ) ) -RRB- cord-003318-abs9rvjk 67 27 , , , cord-003318-abs9rvjk 67 28 were be VBD cord-003318-abs9rvjk 67 29 observed observe VBN cord-003318-abs9rvjk 67 30 in in IN cord-003318-abs9rvjk 67 31 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 67 32 ( ( -LRB- cord-003318-abs9rvjk 67 33 Supplementary Supplementary NNP cord-003318-abs9rvjk 67 34 Information Information NNP cord-003318-abs9rvjk 67 35 _SP cord-003318-abs9rvjk 67 36 Fig Fig NNP cord-003318-abs9rvjk 67 37 . . . cord-003318-abs9rvjk 67 38 S1 S1 NNP cord-003318-abs9rvjk 67 39 ) ) -RRB- cord-003318-abs9rvjk 67 40 . . . cord-003318-abs9rvjk 68 1 The the DT cord-003318-abs9rvjk 68 2 region region NN cord-003318-abs9rvjk 68 3 named name VBN cord-003318-abs9rvjk 68 4 PSBD PSBD NNP cord-003318-abs9rvjk 68 5 located locate VBN cord-003318-abs9rvjk 68 6 in in IN cord-003318-abs9rvjk 68 7 the the DT cord-003318-abs9rvjk 68 8 middle middle JJ cord-003318-abs9rvjk 68 9 part part NN cord-003318-abs9rvjk 68 10 of of IN cord-003318-abs9rvjk 68 11 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 68 12 and and CC cord-003318-abs9rvjk 68 13 was be VBD cord-003318-abs9rvjk 68 14 thought think VBN cord-003318-abs9rvjk 68 15 to to TO cord-003318-abs9rvjk 68 16 be be VB cord-003318-abs9rvjk 68 17 involved involve VBN cord-003318-abs9rvjk 68 18 in in IN cord-003318-abs9rvjk 68 19 the the DT cord-003318-abs9rvjk 68 20 binding binding NN cord-003318-abs9rvjk 68 21 of of IN cord-003318-abs9rvjk 68 22 steroidal steroidal JJ cord-003318-abs9rvjk 68 23 substrates substrate NNS cord-003318-abs9rvjk 68 24 19 19 CD cord-003318-abs9rvjk 68 25 . . . cord-003318-abs9rvjk 69 1 PSPG PSPG NNP cord-003318-abs9rvjk 69 2 box box NN cord-003318-abs9rvjk 69 3 is be VBZ cord-003318-abs9rvjk 69 4 about about RB cord-003318-abs9rvjk 69 5 40 40 CD cord-003318-abs9rvjk 69 6 aa aa NN cord-003318-abs9rvjk 69 7 in in IN cord-003318-abs9rvjk 69 8 length length NN cord-003318-abs9rvjk 69 9 and and CC cord-003318-abs9rvjk 69 10 close close RB cord-003318-abs9rvjk 69 11 to to IN cord-003318-abs9rvjk 69 12 the the DT cord-003318-abs9rvjk 69 13 carboxy carboxy JJ cord-003318-abs9rvjk 69 14 - - HYPH cord-003318-abs9rvjk 69 15 terminus terminus NN cord-003318-abs9rvjk 69 16 . . . cord-003318-abs9rvjk 70 1 This this DT cord-003318-abs9rvjk 70 2 box box NN cord-003318-abs9rvjk 70 3 is be VBZ cord-003318-abs9rvjk 70 4 a a DT cord-003318-abs9rvjk 70 5 characteristic characteristic JJ cord-003318-abs9rvjk 70 6 " " `` cord-003318-abs9rvjk 70 7 signature signature NN cord-003318-abs9rvjk 70 8 sequence sequence NN cord-003318-abs9rvjk 70 9 " " '' cord-003318-abs9rvjk 70 10 of of IN cord-003318-abs9rvjk 70 11 UDP udp NN cord-003318-abs9rvjk 70 12 glycosyltransferase glycosyltransferase NN cord-003318-abs9rvjk 70 13 and and CC cord-003318-abs9rvjk 70 14 deduced deduce VBN cord-003318-abs9rvjk 70 15 to to TO cord-003318-abs9rvjk 70 16 be be VB cord-003318-abs9rvjk 70 17 responsible responsible JJ cord-003318-abs9rvjk 70 18 for for IN cord-003318-abs9rvjk 70 19 the the DT cord-003318-abs9rvjk 70 20 binding binding NN cord-003318-abs9rvjk 70 21 of of IN cord-003318-abs9rvjk 70 22 the the DT cord-003318-abs9rvjk 70 23 UDP udp NN cord-003318-abs9rvjk 70 24 moiety moiety NN cord-003318-abs9rvjk 70 25 of of IN cord-003318-abs9rvjk 70 26 the the DT cord-003318-abs9rvjk 70 27 nucleotide nucleotide JJ cord-003318-abs9rvjk 70 28 sugar sugar NN cord-003318-abs9rvjk 70 29 20 20 CD cord-003318-abs9rvjk 70 30 . . . cord-003318-abs9rvjk 71 1 The the DT cord-003318-abs9rvjk 71 2 presence presence NN cord-003318-abs9rvjk 71 3 of of IN cord-003318-abs9rvjk 71 4 PSBD PSBD NNP cord-003318-abs9rvjk 71 5 and and CC cord-003318-abs9rvjk 71 6 PSPG PSPG NNP cord-003318-abs9rvjk 71 7 boxes box NNS cord-003318-abs9rvjk 71 8 suggests suggest VBZ cord-003318-abs9rvjk 71 9 that that IN cord-003318-abs9rvjk 71 10 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 71 11 may may MD cord-003318-abs9rvjk 71 12 be be VB cord-003318-abs9rvjk 71 13 involved involve VBN cord-003318-abs9rvjk 71 14 in in IN cord-003318-abs9rvjk 71 15 secondary secondary JJ cord-003318-abs9rvjk 71 16 metabolism metabolism NN cord-003318-abs9rvjk 71 17 , , , cord-003318-abs9rvjk 71 18 catalyzing catalyze VBG cord-003318-abs9rvjk 71 19 the the DT cord-003318-abs9rvjk 71 20 transfer transfer NN cord-003318-abs9rvjk 71 21 of of IN cord-003318-abs9rvjk 71 22 UDP udp NN cord-003318-abs9rvjk 71 23 - - HYPH cord-003318-abs9rvjk 71 24 sugars sugar NNS cord-003318-abs9rvjk 71 25 to to IN cord-003318-abs9rvjk 71 26 steroidal steroidal JJ cord-003318-abs9rvjk 71 27 substrates substrate NNS cord-003318-abs9rvjk 71 28 thereby thereby RB cord-003318-abs9rvjk 71 29 forming form VBG cord-003318-abs9rvjk 71 30 steroidal steroidal JJ cord-003318-abs9rvjk 71 31 glycosides glycoside NNS cord-003318-abs9rvjk 71 32 . . . cord-003318-abs9rvjk 72 1 The the DT cord-003318-abs9rvjk 72 2 phylogenetic phylogenetic JJ cord-003318-abs9rvjk 72 3 tree tree NN cord-003318-abs9rvjk 72 4 based base VBN cord-003318-abs9rvjk 72 5 on on IN cord-003318-abs9rvjk 72 6 deduced deduce VBN cord-003318-abs9rvjk 72 7 amino amino NN cord-003318-abs9rvjk 72 8 acid acid NN cord-003318-abs9rvjk 72 9 sequences sequence NNS cord-003318-abs9rvjk 72 10 of of IN cord-003318-abs9rvjk 72 11 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 72 12 and and CC cord-003318-abs9rvjk 72 13 other other JJ cord-003318-abs9rvjk 72 14 SGT1 SGT1 NNP cord-003318-abs9rvjk 72 15 was be VBD cord-003318-abs9rvjk 72 16 generated generate VBN cord-003318-abs9rvjk 72 17 by by IN cord-003318-abs9rvjk 72 18 MEGA MEGA NNP cord-003318-abs9rvjk 72 19 7.0 7.0 CD cord-003318-abs9rvjk 72 20 . . . cord-003318-abs9rvjk 73 1 As as IN cord-003318-abs9rvjk 73 2 Scheme scheme NN cord-003318-abs9rvjk 73 3 1 1 CD cord-003318-abs9rvjk 73 4 An an DT cord-003318-abs9rvjk 73 5 enzymatic enzymatic JJ cord-003318-abs9rvjk 73 6 two two CD cord-003318-abs9rvjk 73 7 - - HYPH cord-003318-abs9rvjk 73 8 step step NN cord-003318-abs9rvjk 73 9 synthesis synthesis NN cord-003318-abs9rvjk 73 10 of of IN cord-003318-abs9rvjk 73 11 AT-17β AT-17β NNP cord-003318-abs9rvjk 73 12 - - HYPH cord-003318-abs9rvjk 73 13 G g NN cord-003318-abs9rvjk 73 14 ( ( -LRB- cord-003318-abs9rvjk 73 15 8b-8e 8b-8e CD cord-003318-abs9rvjk 73 16 ) ) -RRB- cord-003318-abs9rvjk 73 17 and and CC cord-003318-abs9rvjk 73 18 AE-17β ae-17β NN cord-003318-abs9rvjk 73 19 - - HYPH cord-003318-abs9rvjk 73 20 G g NN cord-003318-abs9rvjk 73 21 ( ( -LRB- cord-003318-abs9rvjk 73 22 9b-9e 9b-9e CD cord-003318-abs9rvjk 73 23 ) ) -RRB- cord-003318-abs9rvjk 73 24 from from IN cord-003318-abs9rvjk 73 25 the the DT cord-003318-abs9rvjk 73 26 free free JJ cord-003318-abs9rvjk 73 27 steroids steroid NNS cord-003318-abs9rvjk 73 28 testosterone testosterone NN cord-003318-abs9rvjk 73 29 ( ( -LRB- cord-003318-abs9rvjk 73 30 8) 8) NNP cord-003318-abs9rvjk 73 31 and and CC cord-003318-abs9rvjk 73 32 estradiol estradiol NN cord-003318-abs9rvjk 73 33 ( ( -LRB- cord-003318-abs9rvjk 73 34 9 9 CD cord-003318-abs9rvjk 73 35 ) ) -RRB- cord-003318-abs9rvjk 73 36 . . . cord-003318-abs9rvjk 74 1 Firstly firstly RB cord-003318-abs9rvjk 74 2 , , , cord-003318-abs9rvjk 74 3 two two CD cord-003318-abs9rvjk 74 4 SGs sg NNS cord-003318-abs9rvjk 74 5 , , , cord-003318-abs9rvjk 74 6 T-17β T-17β NNP cord-003318-abs9rvjk 74 7 - - HYPH cord-003318-abs9rvjk 74 8 G g NN cord-003318-abs9rvjk 74 9 ( ( -LRB- cord-003318-abs9rvjk 74 10 8a 8a NN cord-003318-abs9rvjk 74 11 ) ) -RRB- cord-003318-abs9rvjk 74 12 and and CC cord-003318-abs9rvjk 74 13 E-17β E-17β NNP cord-003318-abs9rvjk 74 14 - - HYPH cord-003318-abs9rvjk 74 15 G g NN cord-003318-abs9rvjk 74 16 ( ( -LRB- cord-003318-abs9rvjk 74 17 9a 9a NN cord-003318-abs9rvjk 74 18 ) ) -RRB- cord-003318-abs9rvjk 74 19 , , , cord-003318-abs9rvjk 74 20 were be VBD cord-003318-abs9rvjk 74 21 prepared prepare VBN cord-003318-abs9rvjk 74 22 from from IN cord-003318-abs9rvjk 74 23 their -PRON- PRP$ cord-003318-abs9rvjk 74 24 corresponding correspond VBG cord-003318-abs9rvjk 74 25 steroidal steroidal JJ cord-003318-abs9rvjk 74 26 substrates substrate NNS cord-003318-abs9rvjk 74 27 testosterone testosterone NN cord-003318-abs9rvjk 74 28 ( ( -LRB- cord-003318-abs9rvjk 74 29 8) 8) NNP cord-003318-abs9rvjk 74 30 and and CC cord-003318-abs9rvjk 74 31 estradiol estradiol NN cord-003318-abs9rvjk 74 32 ( ( -LRB- cord-003318-abs9rvjk 74 33 9 9 CD cord-003318-abs9rvjk 74 34 ) ) -RRB- cord-003318-abs9rvjk 74 35 in in IN cord-003318-abs9rvjk 74 36 the the DT cord-003318-abs9rvjk 74 37 presence presence NN cord-003318-abs9rvjk 74 38 of of IN cord-003318-abs9rvjk 74 39 a a DT cord-003318-abs9rvjk 74 40 steroidal steroidal JJ cord-003318-abs9rvjk 74 41 glycosyltransferase glycosyltransferase NN cord-003318-abs9rvjk 74 42 OsSGT1 ossgt1 NN cord-003318-abs9rvjk 74 43 from from IN cord-003318-abs9rvjk 74 44 O. O. NNP cord-003318-abs9rvjk 74 45 saundersiae saundersiae NN cord-003318-abs9rvjk 74 46 . . . cord-003318-abs9rvjk 75 1 The the DT cord-003318-abs9rvjk 75 2 resulting result VBG cord-003318-abs9rvjk 75 3 T-17β T-17β NNP cord-003318-abs9rvjk 75 4 - - HYPH cord-003318-abs9rvjk 75 5 G g NN cord-003318-abs9rvjk 75 6 ( ( -LRB- cord-003318-abs9rvjk 75 7 8a 8a NN cord-003318-abs9rvjk 75 8 ) ) -RRB- cord-003318-abs9rvjk 75 9 was be VBD cord-003318-abs9rvjk 75 10 further further RB cord-003318-abs9rvjk 75 11 regioselectively regioselectively RB cord-003318-abs9rvjk 75 12 acetylated acetylated JJ cord-003318-abs9rvjk 75 13 under under IN cord-003318-abs9rvjk 75 14 the the DT cord-003318-abs9rvjk 75 15 action action NN cord-003318-abs9rvjk 75 16 of of IN cord-003318-abs9rvjk 75 17 an an DT cord-003318-abs9rvjk 75 18 acyltransferase acyltransferase JJ cord-003318-abs9rvjk 75 19 EcSGA1 ecsga1 NN cord-003318-abs9rvjk 75 20 from from IN cord-003318-abs9rvjk 75 21 E. E. NNP cord-003318-abs9rvjk 75 22 coli coli NNS cord-003318-abs9rvjk 75 23 , , , cord-003318-abs9rvjk 75 24 thereby thereby RB cord-003318-abs9rvjk 75 25 yielding yield VBG cord-003318-abs9rvjk 75 26 four four CD cord-003318-abs9rvjk 75 27 monoacetylated monoacetylated JJ cord-003318-abs9rvjk 75 28 steroidal steroidal JJ cord-003318-abs9rvjk 75 29 glucosides glucoside NNS cord-003318-abs9rvjk 75 30 ( ( -LRB- cord-003318-abs9rvjk 75 31 8b-8e 8b-8e CD cord-003318-abs9rvjk 75 32 ) ) -RRB- cord-003318-abs9rvjk 75 33 with with IN cord-003318-abs9rvjk 75 34 the the DT cord-003318-abs9rvjk 75 35 yield yield NN cord-003318-abs9rvjk 75 36 ratio ratio NN cord-003318-abs9rvjk 75 37 of of IN cord-003318-abs9rvjk 75 38 82:8:6:4 82:8:6:4 CD cord-003318-abs9rvjk 75 39 . . . cord-003318-abs9rvjk 76 1 Likewise likewise RB cord-003318-abs9rvjk 76 2 , , , cord-003318-abs9rvjk 76 3 E-17β E-17β NNP cord-003318-abs9rvjk 76 4 - - HYPH cord-003318-abs9rvjk 76 5 G G NNP cord-003318-abs9rvjk 76 6 ( ( -LRB- cord-003318-abs9rvjk 76 7 9a 9a NN cord-003318-abs9rvjk 76 8 ) ) -RRB- cord-003318-abs9rvjk 76 9 was be VBD cord-003318-abs9rvjk 76 10 acetylated acetylate VBN cord-003318-abs9rvjk 76 11 by by IN cord-003318-abs9rvjk 76 12 EcSGA1 ecsga1 NN cord-003318-abs9rvjk 76 13 to to TO cord-003318-abs9rvjk 76 14 form form VB cord-003318-abs9rvjk 76 15 monoacetylated monoacetylate VBN cord-003318-abs9rvjk 76 16 products product NNS cord-003318-abs9rvjk 76 17 9b-9e 9b-9e CD cord-003318-abs9rvjk 76 18 in in IN cord-003318-abs9rvjk 76 19 a a DT cord-003318-abs9rvjk 76 20 ratio ratio NN cord-003318-abs9rvjk 76 21 of of IN cord-003318-abs9rvjk 76 22 80:10:6:4 80:10:6:4 CD cord-003318-abs9rvjk 76 23 . . . cord-003318-abs9rvjk 77 1 shown show VBN cord-003318-abs9rvjk 77 2 in in IN cord-003318-abs9rvjk 77 3 Supplementary Supplementary NNP cord-003318-abs9rvjk 77 4 Information Information NNP cord-003318-abs9rvjk 77 5 Fig Fig NNP cord-003318-abs9rvjk 77 6 . . . cord-003318-abs9rvjk 78 1 S3 S3 NNP cord-003318-abs9rvjk 78 2 , , , cord-003318-abs9rvjk 78 3 all all DT cord-003318-abs9rvjk 78 4 selected select VBN cord-003318-abs9rvjk 78 5 SGTs sgt NNS cord-003318-abs9rvjk 78 6 were be VBD cord-003318-abs9rvjk 78 7 clusted cluste VBN cord-003318-abs9rvjk 78 8 into into IN cord-003318-abs9rvjk 78 9 four four CD cord-003318-abs9rvjk 78 10 clades clade NNS cord-003318-abs9rvjk 78 11 , , , cord-003318-abs9rvjk 78 12 Mon Mon NNP cord-003318-abs9rvjk 78 13 , , , cord-003318-abs9rvjk 78 14 Di Di NNP cord-003318-abs9rvjk 78 15 , , , cord-003318-abs9rvjk 78 16 Ba Ba NNP cord-003318-abs9rvjk 78 17 and and CC cord-003318-abs9rvjk 78 18 Fun Fun NNP cord-003318-abs9rvjk 78 19 clades clade NNS cord-003318-abs9rvjk 78 20 . . . cord-003318-abs9rvjk 79 1 The the DT cord-003318-abs9rvjk 79 2 four four CD cord-003318-abs9rvjk 79 3 clades clade NNS cord-003318-abs9rvjk 79 4 included include VBD cord-003318-abs9rvjk 79 5 SGTs sgt NNS cord-003318-abs9rvjk 79 6 from from IN cord-003318-abs9rvjk 79 7 monocots monocot NNS cord-003318-abs9rvjk 79 8 , , , cord-003318-abs9rvjk 79 9 dicots dicot NNS cord-003318-abs9rvjk 79 10 , , , cord-003318-abs9rvjk 79 11 bacteria bacteria NNS cord-003318-abs9rvjk 79 12 and and CC cord-003318-abs9rvjk 79 13 fungi fungus NNS cord-003318-abs9rvjk 79 14 , , , cord-003318-abs9rvjk 79 15 respectively respectively RB cord-003318-abs9rvjk 79 16 . . . cord-003318-abs9rvjk 80 1 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 80 2 belonged belong VBD cord-003318-abs9rvjk 80 3 to to IN cord-003318-abs9rvjk 80 4 Mon Mon NNP cord-003318-abs9rvjk 80 5 clade clade NN cord-003318-abs9rvjk 80 6 , , , cord-003318-abs9rvjk 80 7 suggesting suggest VBG cord-003318-abs9rvjk 80 8 that that IN cord-003318-abs9rvjk 80 9 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 80 10 was be VBD cord-003318-abs9rvjk 80 11 most most RBS cord-003318-abs9rvjk 80 12 similar similar JJ cord-003318-abs9rvjk 80 13 to to IN cord-003318-abs9rvjk 80 14 SGTs sgt NNS cord-003318-abs9rvjk 80 15 from from IN cord-003318-abs9rvjk 80 16 monocots monocot NNS cord-003318-abs9rvjk 80 17 . . . cord-003318-abs9rvjk 81 1 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 81 2 was be VBD cord-003318-abs9rvjk 81 3 then then RB cord-003318-abs9rvjk 81 4 inserted insert VBN cord-003318-abs9rvjk 81 5 into into IN cord-003318-abs9rvjk 81 6 pET-28a(þ pet-28a(þ NN cord-003318-abs9rvjk 81 7 ) ) -RRB- cord-003318-abs9rvjk 81 8 to to TO cord-003318-abs9rvjk 81 9 yield yield VB cord-003318-abs9rvjk 81 10 a a DT cord-003318-abs9rvjk 81 11 recombinant recombinant JJ cord-003318-abs9rvjk 81 12 pET28a pet28a JJ cord-003318-abs9rvjk 81 13 - - HYPH cord-003318-abs9rvjk 81 14 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 81 15 ( ( -LRB- cord-003318-abs9rvjk 81 16 Supplementary Supplementary NNP cord-003318-abs9rvjk 81 17 Information Information NNP cord-003318-abs9rvjk 81 18 Table Table NNP cord-003318-abs9rvjk 81 19 S2 S2 NNP cord-003318-abs9rvjk 81 20 ) ) -RRB- cord-003318-abs9rvjk 81 21 , , , cord-003318-abs9rvjk 81 22 which which WDT cord-003318-abs9rvjk 81 23 was be VBD cord-003318-abs9rvjk 81 24 transformed transform VBN cord-003318-abs9rvjk 81 25 into into IN cord-003318-abs9rvjk 81 26 Transetta(DE3 Transetta(DE3 NNP cord-003318-abs9rvjk 81 27 ) ) -RRB- cord-003318-abs9rvjk 82 1 ( ( -LRB- cord-003318-abs9rvjk 82 2 TransGen TransGen NNP cord-003318-abs9rvjk 82 3 , , , cord-003318-abs9rvjk 82 4 Beijing Beijing NNP cord-003318-abs9rvjk 82 5 , , , cord-003318-abs9rvjk 82 6 China China NNP cord-003318-abs9rvjk 82 7 ) ) -RRB- cord-003318-abs9rvjk 82 8 for for IN cord-003318-abs9rvjk 82 9 heterologous heterologous JJ cord-003318-abs9rvjk 82 10 expression expression NN cord-003318-abs9rvjk 82 11 . . . cord-003318-abs9rvjk 83 1 Sodium sodium NN cord-003318-abs9rvjk 83 2 dodecyl dodecyl NNP cord-003318-abs9rvjk 83 3 sulfate sulfate NN cord-003318-abs9rvjk 83 4 polyacrylamide polyacrylamide NN cord-003318-abs9rvjk 83 5 gel gel NN cord-003318-abs9rvjk 83 6 electrophoresis electrophoresis NN cord-003318-abs9rvjk 83 7 ( ( -LRB- cord-003318-abs9rvjk 83 8 SDS SDS NNP cord-003318-abs9rvjk 83 9 - - HYPH cord-003318-abs9rvjk 83 10 PAGE PAGE NNP cord-003318-abs9rvjk 83 11 ) ) -RRB- cord-003318-abs9rvjk 83 12 indicated indicate VBD cord-003318-abs9rvjk 83 13 that that IN cord-003318-abs9rvjk 83 14 most most JJS cord-003318-abs9rvjk 83 15 of of IN cord-003318-abs9rvjk 83 16 the the DT cord-003318-abs9rvjk 83 17 expressed express VBN cord-003318-abs9rvjk 83 18 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 83 19 protein protein NN cord-003318-abs9rvjk 83 20 was be VBD cord-003318-abs9rvjk 83 21 present present JJ cord-003318-abs9rvjk 83 22 in in IN cord-003318-abs9rvjk 83 23 the the DT cord-003318-abs9rvjk 83 24 form form NN cord-003318-abs9rvjk 83 25 of of IN cord-003318-abs9rvjk 83 26 insoluble insoluble JJ cord-003318-abs9rvjk 83 27 inclusion inclusion NN cord-003318-abs9rvjk 83 28 body body NN cord-003318-abs9rvjk 83 29 , , , cord-003318-abs9rvjk 83 30 which which WDT cord-003318-abs9rvjk 83 31 was be VBD cord-003318-abs9rvjk 83 32 regarded regard VBN cord-003318-abs9rvjk 83 33 to to TO cord-003318-abs9rvjk 83 34 be be VB cord-003318-abs9rvjk 83 35 devoid devoid JJ cord-003318-abs9rvjk 83 36 of of IN cord-003318-abs9rvjk 83 37 bioactivity bioactivity NN cord-003318-abs9rvjk 83 38 . . . cord-003318-abs9rvjk 84 1 It -PRON- PRP cord-003318-abs9rvjk 84 2 was be VBD cord-003318-abs9rvjk 84 3 well well RB cord-003318-abs9rvjk 84 4 known know VBN cord-003318-abs9rvjk 84 5 that that IN cord-003318-abs9rvjk 84 6 chaperone chaperone NN cord-003318-abs9rvjk 84 7 proteins protein NNS cord-003318-abs9rvjk 84 8 were be VBD cord-003318-abs9rvjk 84 9 able able JJ cord-003318-abs9rvjk 84 10 to to TO cord-003318-abs9rvjk 84 11 assist assist VB cord-003318-abs9rvjk 84 12 protein protein NN cord-003318-abs9rvjk 84 13 folding folding NN cord-003318-abs9rvjk 84 14 and and CC cord-003318-abs9rvjk 84 15 thus thus RB cord-003318-abs9rvjk 84 16 increase increase VB cord-003318-abs9rvjk 84 17 production production NN cord-003318-abs9rvjk 84 18 of of IN cord-003318-abs9rvjk 84 19 active active JJ cord-003318-abs9rvjk 84 20 protein protein NN cord-003318-abs9rvjk 84 21 21 21 CD cord-003318-abs9rvjk 84 22 . . . cord-003318-abs9rvjk 85 1 Therefore therefore RB cord-003318-abs9rvjk 85 2 , , , cord-003318-abs9rvjk 85 3 a a DT cord-003318-abs9rvjk 85 4 chaperone chaperone NN cord-003318-abs9rvjk 85 5 plasmid plasmid NN cord-003318-abs9rvjk 85 6 pGro7 pgro7 NN cord-003318-abs9rvjk 85 7 ( ( -LRB- cord-003318-abs9rvjk 85 8 Takara Takara NNP cord-003318-abs9rvjk 85 9 Biotechnology Biotechnology NNP cord-003318-abs9rvjk 85 10 Co. Co. NNP cord-003318-abs9rvjk 85 11 , , , cord-003318-abs9rvjk 85 12 Ltd. Ltd. NNP cord-003318-abs9rvjk 85 13 , , , cord-003318-abs9rvjk 85 14 Dalian Dalian NNP cord-003318-abs9rvjk 85 15 , , , cord-003318-abs9rvjk 85 16 China China NNP cord-003318-abs9rvjk 85 17 ) ) -RRB- cord-003318-abs9rvjk 85 18 was be VBD cord-003318-abs9rvjk 85 19 applied apply VBN cord-003318-abs9rvjk 85 20 to to TO cord-003318-abs9rvjk 85 21 be be VB cord-003318-abs9rvjk 85 22 co co VBN cord-003318-abs9rvjk 85 23 - - VBN cord-003318-abs9rvjk 85 24 expressed express VBN cord-003318-abs9rvjk 85 25 with with IN cord-003318-abs9rvjk 85 26 pET28aOsSGT1 pET28aOsSGT1 NNP cord-003318-abs9rvjk 85 27 in in IN cord-003318-abs9rvjk 85 28 BL21(DE3 BL21(DE3 NNP cord-003318-abs9rvjk 85 29 ) ) -RRB- cord-003318-abs9rvjk 86 1 ( ( -LRB- cord-003318-abs9rvjk 86 2 TransGen TransGen NNP cord-003318-abs9rvjk 86 3 , , , cord-003318-abs9rvjk 86 4 Beijing Beijing NNP cord-003318-abs9rvjk 86 5 , , , cord-003318-abs9rvjk 86 6 China China NNP cord-003318-abs9rvjk 86 7 ) ) -RRB- cord-003318-abs9rvjk 86 8 , , , cord-003318-abs9rvjk 86 9 facilitating facilitate VBG cord-003318-abs9rvjk 86 10 the the DT cord-003318-abs9rvjk 86 11 soluble soluble JJ cord-003318-abs9rvjk 86 12 expression expression NN cord-003318-abs9rvjk 86 13 of of IN cord-003318-abs9rvjk 86 14 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 86 15 . . . cord-003318-abs9rvjk 87 1 As as IN cord-003318-abs9rvjk 87 2 shown show VBN cord-003318-abs9rvjk 87 3 in in IN cord-003318-abs9rvjk 87 4 Supplementary Supplementary NNP cord-003318-abs9rvjk 87 5 Information Information NNP cord-003318-abs9rvjk 87 6 Table Table NNP cord-003318-abs9rvjk 87 7 S2 s2 NN cord-003318-abs9rvjk 87 8 , , , cord-003318-abs9rvjk 87 9 the the DT cord-003318-abs9rvjk 87 10 plasmid plasmid NN cord-003318-abs9rvjk 87 11 pGro7 pgro7 NN cord-003318-abs9rvjk 87 12 contains contain VBZ cord-003318-abs9rvjk 87 13 two two CD cord-003318-abs9rvjk 87 14 genes gene NNS cord-003318-abs9rvjk 87 15 encoding encode VBG cord-003318-abs9rvjk 87 16 chaperone chaperone NN cord-003318-abs9rvjk 87 17 proteins protein NNS cord-003318-abs9rvjk 87 18 GroES GroES NNP cord-003318-abs9rvjk 87 19 and and CC cord-003318-abs9rvjk 87 20 GroEL groel NN cord-003318-abs9rvjk 87 21 . . . cord-003318-abs9rvjk 88 1 Under under IN cord-003318-abs9rvjk 88 2 the the DT cord-003318-abs9rvjk 88 3 synergistic synergistic JJ cord-003318-abs9rvjk 88 4 action action NN cord-003318-abs9rvjk 88 5 of of IN cord-003318-abs9rvjk 88 6 chaperones chaperone NNS cord-003318-abs9rvjk 88 7 GroES GroES NNP cord-003318-abs9rvjk 88 8 and and CC cord-003318-abs9rvjk 88 9 GroEL GroEL NNP cord-003318-abs9rvjk 88 10 , , , cord-003318-abs9rvjk 88 11 an an DT cord-003318-abs9rvjk 88 12 intense intense JJ cord-003318-abs9rvjk 88 13 band band NN cord-003318-abs9rvjk 88 14 with with IN cord-003318-abs9rvjk 88 15 an an DT cord-003318-abs9rvjk 88 16 apparent apparent JJ cord-003318-abs9rvjk 88 17 molecular molecular JJ cord-003318-abs9rvjk 88 18 mass mass NN cord-003318-abs9rvjk 88 19 of of IN cord-003318-abs9rvjk 88 20 64 64 CD cord-003318-abs9rvjk 88 21 kDa kDa NNS cord-003318-abs9rvjk 88 22 was be VBD cord-003318-abs9rvjk 88 23 present present JJ cord-003318-abs9rvjk 88 24 in in IN cord-003318-abs9rvjk 88 25 the the DT cord-003318-abs9rvjk 88 26 crude crude JJ cord-003318-abs9rvjk 88 27 extract extract NN cord-003318-abs9rvjk 88 28 of of IN cord-003318-abs9rvjk 88 29 BL21(DE3)[pET28aOsSGT1þpGro7 bl21(de3)[pet28aossgt1þpgro7 NN cord-003318-abs9rvjk 88 30 ] ] -RRB- cord-003318-abs9rvjk 88 31 , , , cord-003318-abs9rvjk 88 32 but but CC cord-003318-abs9rvjk 88 33 not not RB cord-003318-abs9rvjk 88 34 in in IN cord-003318-abs9rvjk 88 35 the the DT cord-003318-abs9rvjk 88 36 crude crude JJ cord-003318-abs9rvjk 88 37 proteins protein NNS cord-003318-abs9rvjk 88 38 of of IN cord-003318-abs9rvjk 88 39 the the DT cord-003318-abs9rvjk 88 40 control control NN cord-003318-abs9rvjk 88 41 strain strain NN cord-003318-abs9rvjk 89 1 BL21(DE3)[pET-28a bl21(de3)[pet-28a NN cord-003318-abs9rvjk 90 1 ( ( -LRB- cord-003318-abs9rvjk 90 2 þ)þpGro7 þ)þpgro7 NN cord-003318-abs9rvjk 90 3 ] ] -RRB- cord-003318-abs9rvjk 91 1 ( ( -LRB- cord-003318-abs9rvjk 91 2 Supplementary Supplementary NNP cord-003318-abs9rvjk 91 3 Information Information NNP cord-003318-abs9rvjk 91 4 Fig Fig NNP cord-003318-abs9rvjk 91 5 . . . cord-003318-abs9rvjk 92 1 S2B S2B NNP cord-003318-abs9rvjk 92 2 ) ) -RRB- cord-003318-abs9rvjk 92 3 . . . cord-003318-abs9rvjk 93 1 The the DT cord-003318-abs9rvjk 93 2 immunoblot immunoblot NNP cord-003318-abs9rvjk 93 3 analysis analysis NN cord-003318-abs9rvjk 93 4 with with IN cord-003318-abs9rvjk 93 5 an an DT cord-003318-abs9rvjk 93 6 anti anti JJ cord-003318-abs9rvjk 93 7 - - JJ cord-003318-abs9rvjk 93 8 polyhistidine polyhistidine JJ cord-003318-abs9rvjk 93 9 tag tag NN cord-003318-abs9rvjk 93 10 antibody antibody NN cord-003318-abs9rvjk 93 11 showed show VBD cord-003318-abs9rvjk 93 12 a a DT cord-003318-abs9rvjk 93 13 bound bound JJ cord-003318-abs9rvjk 93 14 band band NN cord-003318-abs9rvjk 93 15 , , , cord-003318-abs9rvjk 93 16 but but CC cord-003318-abs9rvjk 93 17 the the DT cord-003318-abs9rvjk 93 18 control control NN cord-003318-abs9rvjk 93 19 extract extract NN cord-003318-abs9rvjk 93 20 did do VBD cord-003318-abs9rvjk 93 21 not not RB cord-003318-abs9rvjk 93 22 cross cross VB cord-003318-abs9rvjk 93 23 - - JJ cord-003318-abs9rvjk 93 24 react react VB cord-003318-abs9rvjk 93 25 with with IN cord-003318-abs9rvjk 93 26 the the DT cord-003318-abs9rvjk 93 27 antibody antibody NN cord-003318-abs9rvjk 93 28 ( ( -LRB- cord-003318-abs9rvjk 93 29 Supplementary Supplementary NNP cord-003318-abs9rvjk 93 30 Information Information NNP cord-003318-abs9rvjk 93 31 Fig Fig NNP cord-003318-abs9rvjk 93 32 . . . cord-003318-abs9rvjk 94 1 S2C S2C NNP cord-003318-abs9rvjk 94 2 ) ) -RRB- cord-003318-abs9rvjk 94 3 . . . cord-003318-abs9rvjk 95 1 These these DT cord-003318-abs9rvjk 95 2 data datum NNS cord-003318-abs9rvjk 95 3 collectively collectively RB cord-003318-abs9rvjk 95 4 indicated indicate VBD cord-003318-abs9rvjk 95 5 that that IN cord-003318-abs9rvjk 95 6 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 95 7 was be VBD cord-003318-abs9rvjk 95 8 successfully successfully RB cord-003318-abs9rvjk 95 9 expressed express VBN cord-003318-abs9rvjk 95 10 in in IN cord-003318-abs9rvjk 95 11 E. E. NNP cord-003318-abs9rvjk 95 12 coli coli NNS cord-003318-abs9rvjk 95 13 in in IN cord-003318-abs9rvjk 95 14 a a DT cord-003318-abs9rvjk 95 15 soluble soluble JJ cord-003318-abs9rvjk 95 16 form form NN cord-003318-abs9rvjk 95 17 ( ( -LRB- cord-003318-abs9rvjk 95 18 Supplementary supplementary JJ cord-003318-abs9rvjk 95 19 Information information NN cord-003318-abs9rvjk 95 20 Figs Figs NNPS cord-003318-abs9rvjk 95 21 . . . cord-003318-abs9rvjk 96 1 S2B S2B NNP cord-003318-abs9rvjk 96 2 and and CC cord-003318-abs9rvjk 96 3 2C 2C NNP cord-003318-abs9rvjk 96 4 ) ) -RRB- cord-003318-abs9rvjk 97 1 in in IN cord-003318-abs9rvjk 97 2 accord accord NN cord-003318-abs9rvjk 97 3 with with IN cord-003318-abs9rvjk 97 4 the the DT cord-003318-abs9rvjk 97 5 predicted predict VBN cord-003318-abs9rvjk 97 6 result result NN cord-003318-abs9rvjk 97 7 of of IN cord-003318-abs9rvjk 97 8 soluble soluble JJ cord-003318-abs9rvjk 97 9 expression expression NN cord-003318-abs9rvjk 97 10 of of IN cord-003318-abs9rvjk 97 11 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 97 12 . . . cord-003318-abs9rvjk 98 1 To to TO cord-003318-abs9rvjk 98 2 identify identify VB cord-003318-abs9rvjk 98 3 the the DT cord-003318-abs9rvjk 98 4 activity activity NN cord-003318-abs9rvjk 98 5 of of IN cord-003318-abs9rvjk 98 6 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 98 7 , , , cord-003318-abs9rvjk 98 8 the the DT cord-003318-abs9rvjk 98 9 OsSGT1-containing ossgt1-containe VBG cord-003318-abs9rvjk 98 10 crude crude JJ cord-003318-abs9rvjk 98 11 protein protein NN cord-003318-abs9rvjk 98 12 was be VBD cord-003318-abs9rvjk 98 13 used use VBN cord-003318-abs9rvjk 98 14 as as IN cord-003318-abs9rvjk 98 15 the the DT cord-003318-abs9rvjk 98 16 biocatalyst biocatalyst NN cord-003318-abs9rvjk 98 17 for for IN cord-003318-abs9rvjk 98 18 glycosylation glycosylation NN cord-003318-abs9rvjk 98 19 reactions reaction NNS cord-003318-abs9rvjk 98 20 . . . cord-003318-abs9rvjk 99 1 Each each DT cord-003318-abs9rvjk 99 2 member member NN cord-003318-abs9rvjk 99 3 of of IN cord-003318-abs9rvjk 99 4 the the DT cord-003318-abs9rvjk 99 5 acceptor acceptor NN cord-003318-abs9rvjk 99 6 library library NN cord-003318-abs9rvjk 99 7 ( ( -LRB- cord-003318-abs9rvjk 99 8 1 1 CD cord-003318-abs9rvjk 99 9 - - SYM cord-003318-abs9rvjk 99 10 49 49 CD cord-003318-abs9rvjk 99 11 , , , cord-003318-abs9rvjk 99 12 Fig Fig NNP cord-003318-abs9rvjk 99 13 . . . cord-003318-abs9rvjk 99 14 1B 1B NNP cord-003318-abs9rvjk 99 15 and and CC cord-003318-abs9rvjk 99 16 Supplementary Supplementary NNP cord-003318-abs9rvjk 99 17 Information Information NNP cord-003318-abs9rvjk 99 18 Fig Fig NNP cord-003318-abs9rvjk 99 19 . . . cord-003318-abs9rvjk 99 20 S4 S4 NNP cord-003318-abs9rvjk 99 21 ) ) -RRB- cord-003318-abs9rvjk 99 22 was be VBD cord-003318-abs9rvjk 99 23 first first RB cord-003318-abs9rvjk 99 24 assessed assess VBN cord-003318-abs9rvjk 99 25 as as IN cord-003318-abs9rvjk 99 26 sugar sugar NN cord-003318-abs9rvjk 99 27 Table Table NNP cord-003318-abs9rvjk 99 28 S3 S3 NNP cord-003318-abs9rvjk 99 29 ) ) -RRB- cord-003318-abs9rvjk 99 30 . . . cord-003318-abs9rvjk 100 1 Of of IN cord-003318-abs9rvjk 100 2 the the DT cord-003318-abs9rvjk 100 3 49 49 CD cord-003318-abs9rvjk 100 4 substrates substrate NNS cord-003318-abs9rvjk 100 5 , , , cord-003318-abs9rvjk 100 6 only only RB cord-003318-abs9rvjk 100 7 10 10 CD cord-003318-abs9rvjk 100 8 steroids steroid NNS cord-003318-abs9rvjk 100 9 were be VBD cord-003318-abs9rvjk 100 10 observed observe VBN cord-003318-abs9rvjk 100 11 to to TO cord-003318-abs9rvjk 100 12 be be VB cord-003318-abs9rvjk 100 13 glucosylated glucosylate VBN cord-003318-abs9rvjk 100 14 by by IN cord-003318-abs9rvjk 100 15 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 100 16 , , , cord-003318-abs9rvjk 100 17 forming form VBG cord-003318-abs9rvjk 100 18 corresponding correspond VBG cord-003318-abs9rvjk 100 19 monoglucosides monoglucoside NNS cord-003318-abs9rvjk 100 20 ( ( -LRB- cord-003318-abs9rvjk 100 21 Figs fig NNS cord-003318-abs9rvjk 100 22 . . . cord-003318-abs9rvjk 101 1 1 1 LS cord-003318-abs9rvjk 101 2 - - SYM cord-003318-abs9rvjk 101 3 3 3 CD cord-003318-abs9rvjk 101 4 and and CC cord-003318-abs9rvjk 101 5 Supplementary Supplementary NNP cord-003318-abs9rvjk 101 6 Information Information NNP cord-003318-abs9rvjk 101 7 Figs Figs NNPS cord-003318-abs9rvjk 101 8 . . . cord-003318-abs9rvjk 102 1 S5 S5 NNP cord-003318-abs9rvjk 102 2 - - HYPH cord-003318-abs9rvjk 102 3 14 14 CD cord-003318-abs9rvjk 102 4 ) ) -RRB- cord-003318-abs9rvjk 102 5 . . . cord-003318-abs9rvjk 103 1 The the DT cord-003318-abs9rvjk 103 2 ten ten CD cord-003318-abs9rvjk 103 3 steroids steroid NNS cord-003318-abs9rvjk 103 4 included include VBD cord-003318-abs9rvjk 103 5 seven seven CD cord-003318-abs9rvjk 103 6 3β 3β NNS cord-003318-abs9rvjk 103 7 - - HYPH cord-003318-abs9rvjk 103 8 hydroxysteroids hydroxysteroids NNP cord-003318-abs9rvjk 103 9 ( ( -LRB- cord-003318-abs9rvjk 103 10 1 1 CD cord-003318-abs9rvjk 103 11 - - SYM cord-003318-abs9rvjk 103 12 7 7 CD cord-003318-abs9rvjk 103 13 , , , cord-003318-abs9rvjk 103 14 Supplementary Supplementary NNP cord-003318-abs9rvjk 103 15 Information Information NNP cord-003318-abs9rvjk 103 16 Figs Figs NNPS cord-003318-abs9rvjk 103 17 . . . cord-003318-abs9rvjk 104 1 S5 S5 NNP cord-003318-abs9rvjk 104 2 - - HYPH cord-003318-abs9rvjk 104 3 11 11 CD cord-003318-abs9rvjk 104 4 ) ) -RRB- cord-003318-abs9rvjk 104 5 , , , cord-003318-abs9rvjk 104 6 two two CD cord-003318-abs9rvjk 104 7 17β 17β NNS cord-003318-abs9rvjk 104 8 - - HYPH cord-003318-abs9rvjk 104 9 hydroxylsteroids hydroxylsteroid NNS cord-003318-abs9rvjk 104 10 ( ( -LRB- cord-003318-abs9rvjk 104 11 8 8 CD cord-003318-abs9rvjk 104 12 - - SYM cord-003318-abs9rvjk 104 13 9 9 CD cord-003318-abs9rvjk 104 14 , , , cord-003318-abs9rvjk 104 15 Figs Figs NNPS cord-003318-abs9rvjk 104 16 . . . cord-003318-abs9rvjk 104 17 2 2 CD cord-003318-abs9rvjk 104 18 and and CC cord-003318-abs9rvjk 104 19 3 3 CD cord-003318-abs9rvjk 104 20 ) ) -RRB- cord-003318-abs9rvjk 104 21 and and CC cord-003318-abs9rvjk 104 22 one one CD cord-003318-abs9rvjk 104 23 3β,17β 3β,17β CD cord-003318-abs9rvjk 104 24 - - : cord-003318-abs9rvjk 104 25 dihydroxysteroid dihydroxysteroid NNP cord-003318-abs9rvjk 104 26 ( ( -LRB- cord-003318-abs9rvjk 104 27 10 10 CD cord-003318-abs9rvjk 104 28 , , , cord-003318-abs9rvjk 104 29 Supplementary Supplementary NNP cord-003318-abs9rvjk 104 30 Information Information NNP cord-003318-abs9rvjk 104 31 Fig Fig NNP cord-003318-abs9rvjk 104 32 . . . cord-003318-abs9rvjk 104 33 S14 S14 NNP cord-003318-abs9rvjk 104 34 ) ) -RRB- cord-003318-abs9rvjk 104 35 . . . cord-003318-abs9rvjk 105 1 The the DT cord-003318-abs9rvjk 105 2 reaction reaction NN cord-003318-abs9rvjk 105 3 activities activity NNS cord-003318-abs9rvjk 105 4 of of IN cord-003318-abs9rvjk 105 5 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 105 6 towards towards IN cord-003318-abs9rvjk 105 7 the the DT cord-003318-abs9rvjk 105 8 ten ten CD cord-003318-abs9rvjk 105 9 substrates substrate NNS cord-003318-abs9rvjk 105 10 indicated indicate VBD cord-003318-abs9rvjk 105 11 that that IN cord-003318-abs9rvjk 105 12 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 105 13 was be VBD cord-003318-abs9rvjk 105 14 an an DT cord-003318-abs9rvjk 105 15 SGT SGT NNP cord-003318-abs9rvjk 105 16 showing show VBG cord-003318-abs9rvjk 105 17 activities activity NNS cord-003318-abs9rvjk 105 18 towards towards IN cord-003318-abs9rvjk 105 19 both both DT cord-003318-abs9rvjk 105 20 3β 3β CD cord-003318-abs9rvjk 105 21 - - HYPH cord-003318-abs9rvjk 105 22 and and CC cord-003318-abs9rvjk 105 23 17β 17β NNS cord-003318-abs9rvjk 105 24 - - HYPH cord-003318-abs9rvjk 105 25 hydroxysteroids hydroxysteroid NNS cord-003318-abs9rvjk 105 26 , , , cord-003318-abs9rvjk 105 27 consistent consistent JJ cord-003318-abs9rvjk 105 28 with with IN cord-003318-abs9rvjk 105 29 the the DT cord-003318-abs9rvjk 105 30 predicted predict VBN cord-003318-abs9rvjk 105 31 result result NN cord-003318-abs9rvjk 105 32 by by IN cord-003318-abs9rvjk 105 33 bioinformatics bioinformatics NN cord-003318-abs9rvjk 105 34 analyses analysis NNS cord-003318-abs9rvjk 105 35 ( ( -LRB- cord-003318-abs9rvjk 105 36 Supplementary Supplementary NNP cord-003318-abs9rvjk 105 37 Information Information NNP cord-003318-abs9rvjk 105 38 Figs Figs NNPS cord-003318-abs9rvjk 105 39 . . . cord-003318-abs9rvjk 106 1 S1 S1 NNP cord-003318-abs9rvjk 106 2 and and CC cord-003318-abs9rvjk 106 3 S3 S3 NNP cord-003318-abs9rvjk 106 4 ) ) -RRB- cord-003318-abs9rvjk 106 5 . . . cord-003318-abs9rvjk 107 1 In in IN cord-003318-abs9rvjk 107 2 fact fact NN cord-003318-abs9rvjk 107 3 , , , cord-003318-abs9rvjk 107 4 the the DT cord-003318-abs9rvjk 107 5 reports report NNS cord-003318-abs9rvjk 107 6 of of IN cord-003318-abs9rvjk 107 7 SGTs sgt NNS cord-003318-abs9rvjk 107 8 with with IN cord-003318-abs9rvjk 107 9 glycosylation glycosylation NN cord-003318-abs9rvjk 107 10 activity activity NN cord-003318-abs9rvjk 107 11 against against IN cord-003318-abs9rvjk 107 12 steroids steroid NNS cord-003318-abs9rvjk 107 13 at at IN cord-003318-abs9rvjk 107 14 positions position NNS cord-003318-abs9rvjk 107 15 other other JJ cord-003318-abs9rvjk 107 16 than than IN cord-003318-abs9rvjk 107 17 C-3 C-3 NNP cord-003318-abs9rvjk 107 18 were be VBD cord-003318-abs9rvjk 107 19 limited limited JJ cord-003318-abs9rvjk 107 20 and and CC cord-003318-abs9rvjk 107 21 only only RB cord-003318-abs9rvjk 107 22 three three CD cord-003318-abs9rvjk 107 23 SGTs sgt NNS cord-003318-abs9rvjk 107 24 from from IN cord-003318-abs9rvjk 107 25 yeast yeast NN cord-003318-abs9rvjk 107 26 were be VBD cord-003318-abs9rvjk 107 27 verified verify VBN cord-003318-abs9rvjk 107 28 to to TO cord-003318-abs9rvjk 107 29 exhibit exhibit VB cord-003318-abs9rvjk 107 30 selectivity selectivity NN cord-003318-abs9rvjk 107 31 towards towards IN cord-003318-abs9rvjk 107 32 both both DT cord-003318-abs9rvjk 107 33 3β 3β CD cord-003318-abs9rvjk 107 34 - - HYPH cord-003318-abs9rvjk 107 35 and and CC cord-003318-abs9rvjk 107 36 17β 17β NNS cord-003318-abs9rvjk 107 37 - - : cord-003318-abs9rvjk 107 38 hydroxylsteroids hydroxylsteroids NNP cord-003318-abs9rvjk 107 39 17 17 CD cord-003318-abs9rvjk 107 40 . . . cord-003318-abs9rvjk 108 1 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 108 2 was be VBD cord-003318-abs9rvjk 108 3 therefore therefore RB cord-003318-abs9rvjk 108 4 viewed view VBN cord-003318-abs9rvjk 108 5 as as IN cord-003318-abs9rvjk 108 6 the the DT cord-003318-abs9rvjk 108 7 first first JJ cord-003318-abs9rvjk 108 8 plant plant NN cord-003318-abs9rvjk 108 9 SGT SGT NNP cord-003318-abs9rvjk 108 10 with with IN cord-003318-abs9rvjk 108 11 selectivity selectivity NN cord-003318-abs9rvjk 108 12 towards towards IN cord-003318-abs9rvjk 108 13 both both DT cord-003318-abs9rvjk 108 14 3β 3β CD cord-003318-abs9rvjk 108 15 - - HYPH cord-003318-abs9rvjk 108 16 and and CC cord-003318-abs9rvjk 108 17 17β 17β NNS cord-003318-abs9rvjk 108 18 - - HYPH cord-003318-abs9rvjk 108 19 hydroxylsteroids hydroxylsteroid NNS cord-003318-abs9rvjk 108 20 ( ( -LRB- cord-003318-abs9rvjk 108 21 Figs fig NNS cord-003318-abs9rvjk 108 22 . . . cord-003318-abs9rvjk 108 23 2 2 CD cord-003318-abs9rvjk 108 24 and and CC cord-003318-abs9rvjk 108 25 3 3 CD cord-003318-abs9rvjk 108 26 and and CC cord-003318-abs9rvjk 108 27 Supplementary Supplementary NNP cord-003318-abs9rvjk 108 28 Information Information NNP cord-003318-abs9rvjk 108 29 Figs Figs NNPS cord-003318-abs9rvjk 108 30 . . . cord-003318-abs9rvjk 109 1 S5 S5 NNP cord-003318-abs9rvjk 109 2 - - HYPH cord-003318-abs9rvjk 109 3 14 14 CD cord-003318-abs9rvjk 109 4 ) ) -RRB- cord-003318-abs9rvjk 109 5 . . . cord-003318-abs9rvjk 110 1 However however RB cord-003318-abs9rvjk 110 2 , , , cord-003318-abs9rvjk 110 3 the the DT cord-003318-abs9rvjk 110 4 glycosylation glycosylation NN cord-003318-abs9rvjk 110 5 activity activity NN cord-003318-abs9rvjk 110 6 of of IN cord-003318-abs9rvjk 110 7 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 110 8 towards towards IN cord-003318-abs9rvjk 110 9 17βhydroxyl 17βhydroxyl CD cord-003318-abs9rvjk 110 10 group group NN cord-003318-abs9rvjk 110 11 would would MD cord-003318-abs9rvjk 110 12 be be VB cord-003318-abs9rvjk 110 13 lost lose VBN cord-003318-abs9rvjk 110 14 if if IN cord-003318-abs9rvjk 110 15 additional additional JJ cord-003318-abs9rvjk 110 16 hydroxyl hydroxyl NN cord-003318-abs9rvjk 110 17 group group NN cord-003318-abs9rvjk 110 18 at at IN cord-003318-abs9rvjk 110 19 2β-(2β 2β-(2β CD cord-003318-abs9rvjk 110 20 - - HYPH cord-003318-abs9rvjk 110 21 OH oh NN cord-003318-abs9rvjk 110 22 - - HYPH cord-003318-abs9rvjk 110 23 testosterone testosterone NN cord-003318-abs9rvjk 110 24 , , , cord-003318-abs9rvjk 110 25 13 13 CD cord-003318-abs9rvjk 110 26 ) ) -RRB- cord-003318-abs9rvjk 110 27 , , , cord-003318-abs9rvjk 110 28 15β-(15β 15β-(15β CD cord-003318-abs9rvjk 110 29 - - HYPH cord-003318-abs9rvjk 110 30 OH oh NN cord-003318-abs9rvjk 110 31 - - HYPH cord-003318-abs9rvjk 110 32 testosterone testosterone NN cord-003318-abs9rvjk 110 33 , , , cord-003318-abs9rvjk 110 34 14 14 CD cord-003318-abs9rvjk 110 35 ) ) -RRB- cord-003318-abs9rvjk 110 36 , , , cord-003318-abs9rvjk 110 37 16β-(16β 16β-(16β CD cord-003318-abs9rvjk 110 38 - - HYPH cord-003318-abs9rvjk 110 39 OH oh NN cord-003318-abs9rvjk 110 40 - - HYPH cord-003318-abs9rvjk 110 41 testosterone testosterone NN cord-003318-abs9rvjk 110 42 , , , cord-003318-abs9rvjk 110 43 15 15 CD cord-003318-abs9rvjk 110 44 ) ) -RRB- cord-003318-abs9rvjk 110 45 , , , cord-003318-abs9rvjk 110 46 or or CC cord-003318-abs9rvjk 110 47 16α 16α NNS cord-003318-abs9rvjk 110 48 - - HYPH cord-003318-abs9rvjk 110 49 position position NN cord-003318-abs9rvjk 110 50 ( ( -LRB- cord-003318-abs9rvjk 110 51 16α 16α NNS cord-003318-abs9rvjk 110 52 - - HYPH cord-003318-abs9rvjk 110 53 OH oh NN cord-003318-abs9rvjk 110 54 - - HYPH cord-003318-abs9rvjk 110 55 testosterone testosterone NN cord-003318-abs9rvjk 110 56 , , , cord-003318-abs9rvjk 110 57 16 16 CD cord-003318-abs9rvjk 110 58 ) ) -RRB- cord-003318-abs9rvjk 110 59 , , , cord-003318-abs9rvjk 110 60 even even RB cord-003318-abs9rvjk 110 61 a a DT cord-003318-abs9rvjk 110 62 methyl methyl NN cord-003318-abs9rvjk 110 63 group group NN cord-003318-abs9rvjk 110 64 at at IN cord-003318-abs9rvjk 110 65 C17-position C17-position NNP cord-003318-abs9rvjk 110 66 ( ( -LRB- cord-003318-abs9rvjk 110 67 methyltestosterone methyltestosterone NNP cord-003318-abs9rvjk 110 68 and and CC cord-003318-abs9rvjk 110 69 its -PRON- PRP$ cord-003318-abs9rvjk 110 70 derivatives derivative NNS cord-003318-abs9rvjk 110 71 , , , cord-003318-abs9rvjk 110 72 17 17 CD cord-003318-abs9rvjk 110 73 - - SYM cord-003318-abs9rvjk 110 74 20 20 CD cord-003318-abs9rvjk 110 75 ) ) -RRB- cord-003318-abs9rvjk 110 76 was be VBD cord-003318-abs9rvjk 110 77 attached attach VBN cord-003318-abs9rvjk 110 78 to to IN cord-003318-abs9rvjk 110 79 testosterone testosterone NN cord-003318-abs9rvjk 110 80 ( ( -LRB- cord-003318-abs9rvjk 110 81 8) 8) NN cord-003318-abs9rvjk 110 82 , , , cord-003318-abs9rvjk 110 83 generating generate VBG cord-003318-abs9rvjk 110 84 not not RB cord-003318-abs9rvjk 110 85 any any DT cord-003318-abs9rvjk 110 86 glycosylated glycosylated JJ cord-003318-abs9rvjk 110 87 products product NNS cord-003318-abs9rvjk 110 88 . . . cord-003318-abs9rvjk 111 1 Moreover moreover RB cord-003318-abs9rvjk 111 2 , , , cord-003318-abs9rvjk 111 3 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 111 4 has have VBZ cord-003318-abs9rvjk 111 5 no no DT cord-003318-abs9rvjk 111 6 activity activity NN cord-003318-abs9rvjk 111 7 towards towards IN cord-003318-abs9rvjk 111 8 other other JJ cord-003318-abs9rvjk 111 9 compounds compound NNS cord-003318-abs9rvjk 111 10 , , , cord-003318-abs9rvjk 111 11 including include VBG cord-003318-abs9rvjk 111 12 steroids steroid NNS cord-003318-abs9rvjk 111 13 without without IN cord-003318-abs9rvjk 111 14 3β 3β CD cord-003318-abs9rvjk 111 15 - - HYPH cord-003318-abs9rvjk 111 16 and and CC cord-003318-abs9rvjk 111 17 17β 17β NNS cord-003318-abs9rvjk 111 18 - - : cord-003318-abs9rvjk 111 19 hydroxyl hydroxyl NN cord-003318-abs9rvjk 111 20 groups group NNS cord-003318-abs9rvjk 111 21 ( ( -LRB- cord-003318-abs9rvjk 111 22 11 11 CD cord-003318-abs9rvjk 111 23 - - SYM cord-003318-abs9rvjk 111 24 12 12 CD cord-003318-abs9rvjk 111 25 and and CC cord-003318-abs9rvjk 111 26 21 21 CD cord-003318-abs9rvjk 111 27 - - SYM cord-003318-abs9rvjk 111 28 24 24 CD cord-003318-abs9rvjk 111 29 ) ) -RRB- cord-003318-abs9rvjk 111 30 , , , cord-003318-abs9rvjk 111 31 flavonoids flavonoid NNS cord-003318-abs9rvjk 111 32 ( ( -LRB- cord-003318-abs9rvjk 111 33 25 25 CD cord-003318-abs9rvjk 111 34 - - SYM cord-003318-abs9rvjk 111 35 31 31 CD cord-003318-abs9rvjk 111 36 ) ) -RRB- cord-003318-abs9rvjk 111 37 , , , cord-003318-abs9rvjk 111 38 alkaloids alkaloid NNS cord-003318-abs9rvjk 111 39 ( ( -LRB- cord-003318-abs9rvjk 111 40 32 32 CD cord-003318-abs9rvjk 111 41 ) ) -RRB- cord-003318-abs9rvjk 111 42 ( ( -LRB- cord-003318-abs9rvjk 111 43 33 33 CD cord-003318-abs9rvjk 111 44 ) ) -RRB- cord-003318-abs9rvjk 111 45 ( ( -LRB- cord-003318-abs9rvjk 111 46 34 34 CD cord-003318-abs9rvjk 111 47 ) ) -RRB- cord-003318-abs9rvjk 111 48 ( ( -LRB- cord-003318-abs9rvjk 111 49 35 35 CD cord-003318-abs9rvjk 111 50 ) ) -RRB- cord-003318-abs9rvjk 111 51 ( ( -LRB- cord-003318-abs9rvjk 111 52 36 36 CD cord-003318-abs9rvjk 111 53 ) ) -RRB- cord-003318-abs9rvjk 111 54 ( ( -LRB- cord-003318-abs9rvjk 111 55 37 37 CD cord-003318-abs9rvjk 111 56 ) ) -RRB- cord-003318-abs9rvjk 111 57 ( ( -LRB- cord-003318-abs9rvjk 111 58 38 38 CD cord-003318-abs9rvjk 111 59 ) ) -RRB- cord-003318-abs9rvjk 111 60 , , , cord-003318-abs9rvjk 111 61 triterpenoids triterpenoid NNS cord-003318-abs9rvjk 111 62 ( ( -LRB- cord-003318-abs9rvjk 111 63 39 39 CD cord-003318-abs9rvjk 111 64 - - SYM cord-003318-abs9rvjk 111 65 42 42 CD cord-003318-abs9rvjk 111 66 ) ) -RRB- cord-003318-abs9rvjk 111 67 , , , cord-003318-abs9rvjk 111 68 phenolic phenolic JJ cord-003318-abs9rvjk 111 69 acids acid NNS cord-003318-abs9rvjk 111 70 ( ( -LRB- cord-003318-abs9rvjk 111 71 43 43 CD cord-003318-abs9rvjk 111 72 - - SYM cord-003318-abs9rvjk 111 73 47 47 CD cord-003318-abs9rvjk 111 74 ) ) -RRB- cord-003318-abs9rvjk 111 75 and and CC cord-003318-abs9rvjk 111 76 coumarins coumarin NNS cord-003318-abs9rvjk 111 77 ( ( -LRB- cord-003318-abs9rvjk 111 78 48 48 CD cord-003318-abs9rvjk 111 79 - - SYM cord-003318-abs9rvjk 111 80 49 49 CD cord-003318-abs9rvjk 111 81 ) ) -RRB- cord-003318-abs9rvjk 111 82 as as IN cord-003318-abs9rvjk 111 83 shown show VBN cord-003318-abs9rvjk 111 84 in in IN cord-003318-abs9rvjk 111 85 Supplementary Supplementary NNP cord-003318-abs9rvjk 111 86 Information Information NNP cord-003318-abs9rvjk 111 87 Fig Fig NNP cord-003318-abs9rvjk 111 88 . . . cord-003318-abs9rvjk 111 89 S4 S4 NNP cord-003318-abs9rvjk 111 90 . . . cord-003318-abs9rvjk 112 1 Among among IN cord-003318-abs9rvjk 112 2 10 10 CD cord-003318-abs9rvjk 112 3 reactive reactive JJ cord-003318-abs9rvjk 112 4 3β 3β NN cord-003318-abs9rvjk 112 5 - - HYPH cord-003318-abs9rvjk 112 6 and and CC cord-003318-abs9rvjk 112 7 17β 17β NNS cord-003318-abs9rvjk 112 8 - - : cord-003318-abs9rvjk 112 9 hydroxylsteroids hydroxylsteroid NNS cord-003318-abs9rvjk 112 10 , , , cord-003318-abs9rvjk 112 11 dehydroepiandrosterone dehydroepiandrosterone NNP cord-003318-abs9rvjk 112 12 ( ( -LRB- cord-003318-abs9rvjk 112 13 4 4 CD cord-003318-abs9rvjk 112 14 ) ) -RRB- cord-003318-abs9rvjk 112 15 had have VBD cord-003318-abs9rvjk 112 16 a a DT cord-003318-abs9rvjk 112 17 maximum maximum JJ cord-003318-abs9rvjk 112 18 conversion conversion NN cord-003318-abs9rvjk 112 19 approaching approach VBG cord-003318-abs9rvjk 112 20 100 100 CD cord-003318-abs9rvjk 112 21 % % NN cord-003318-abs9rvjk 112 22 , , , cord-003318-abs9rvjk 112 23 followed follow VBN cord-003318-abs9rvjk 112 24 by by IN cord-003318-abs9rvjk 112 25 diosgenin diosgenin NNP cord-003318-abs9rvjk 112 26 ( ( -LRB- cord-003318-abs9rvjk 112 27 5 5 CD cord-003318-abs9rvjk 112 28 ) ) -RRB- cord-003318-abs9rvjk 112 29 with with IN cord-003318-abs9rvjk 112 30 82 82 CD cord-003318-abs9rvjk 112 31 % % NN cord-003318-abs9rvjk 112 32 conversion conversion NN cord-003318-abs9rvjk 112 33 and and CC cord-003318-abs9rvjk 112 34 the the DT cord-003318-abs9rvjk 112 35 other other JJ cord-003318-abs9rvjk 112 36 compounds compound NNS cord-003318-abs9rvjk 112 37 having have VBG cord-003318-abs9rvjk 112 38 conversion conversion NN cord-003318-abs9rvjk 112 39 below below IN cord-003318-abs9rvjk 112 40 80 80 CD cord-003318-abs9rvjk 112 41 % % NN cord-003318-abs9rvjk 113 1 ( ( -LRB- cord-003318-abs9rvjk 113 2 Fig Fig NNP cord-003318-abs9rvjk 113 3 . . . cord-003318-abs9rvjk 113 4 1A 1a NN cord-003318-abs9rvjk 113 5 ) ) -RRB- cord-003318-abs9rvjk 113 6 . . . cord-003318-abs9rvjk 114 1 To to TO cord-003318-abs9rvjk 114 2 produce produce VB cord-003318-abs9rvjk 114 3 sufficient sufficient JJ cord-003318-abs9rvjk 114 4 glucosylated glucosylated JJ cord-003318-abs9rvjk 114 5 products product NNS cord-003318-abs9rvjk 114 6 for for IN cord-003318-abs9rvjk 114 7 structural structural JJ cord-003318-abs9rvjk 114 8 characterization characterization NN cord-003318-abs9rvjk 114 9 , , , cord-003318-abs9rvjk 114 10 scale scale NN cord-003318-abs9rvjk 114 11 - - HYPH cord-003318-abs9rvjk 114 12 up up NN cord-003318-abs9rvjk 114 13 of of IN cord-003318-abs9rvjk 114 14 OsSGT1-mediated ossgt1-mediated JJ cord-003318-abs9rvjk 114 15 reactions reaction NNS cord-003318-abs9rvjk 114 16 to to IN cord-003318-abs9rvjk 114 17 preparative preparative JJ cord-003318-abs9rvjk 114 18 scale scale NN cord-003318-abs9rvjk 114 19 ( ( -LRB- cord-003318-abs9rvjk 114 20 6 6 CD cord-003318-abs9rvjk 114 21 mL ml NN cord-003318-abs9rvjk 114 22 ) ) -RRB- cord-003318-abs9rvjk 114 23 was be VBD cord-003318-abs9rvjk 114 24 conducted conduct VBN cord-003318-abs9rvjk 114 25 . . . cord-003318-abs9rvjk 115 1 The the DT cord-003318-abs9rvjk 115 2 resultant resultant JJ cord-003318-abs9rvjk 115 3 glucosides glucoside NNS cord-003318-abs9rvjk 115 4 ( ( -LRB- cord-003318-abs9rvjk 115 5 9 9 CD cord-003318-abs9rvjk 115 6 ) ) -RRB- cord-003318-abs9rvjk 115 7 glycosylation glycosylation NN cord-003318-abs9rvjk 115 8 . . . cord-003318-abs9rvjk 116 1 HPLC HPLC NNP cord-003318-abs9rvjk 116 2 chromatogram chromatogram NNP cord-003318-abs9rvjk 116 3 of of IN cord-003318-abs9rvjk 116 4 reaction reaction NN cord-003318-abs9rvjk 116 5 product product NN cord-003318-abs9rvjk 116 6 of of IN cord-003318-abs9rvjk 116 7 estradiol estradiol NN cord-003318-abs9rvjk 116 8 ( ( -LRB- cord-003318-abs9rvjk 116 9 9 9 CD cord-003318-abs9rvjk 116 10 ) ) -RRB- cord-003318-abs9rvjk 116 11 incubated incubate VBN cord-003318-abs9rvjk 116 12 with with IN cord-003318-abs9rvjk 116 13 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 116 14 protein protein NN cord-003318-abs9rvjk 116 15 ( ( -LRB- cord-003318-abs9rvjk 116 16 a a LS cord-003318-abs9rvjk 116 17 ) ) -RRB- cord-003318-abs9rvjk 116 18 or or CC cord-003318-abs9rvjk 117 1 without without IN cord-003318-abs9rvjk 117 2 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 117 3 ( ( -LRB- cord-003318-abs9rvjk 117 4 b b NN cord-003318-abs9rvjk 117 5 ) ) -RRB- cord-003318-abs9rvjk 117 6 . . . cord-003318-abs9rvjk 118 1 UV UV NNP cord-003318-abs9rvjk 118 2 spectra spectrum NNS cord-003318-abs9rvjk 118 3 of of IN cord-003318-abs9rvjk 118 4 9 9 CD cord-003318-abs9rvjk 118 5 and and CC cord-003318-abs9rvjk 118 6 enzymatic enzymatic JJ cord-003318-abs9rvjk 118 7 product product NN cord-003318-abs9rvjk 118 8 9a 9a NN cord-003318-abs9rvjk 118 9 are be VBP cord-003318-abs9rvjk 118 10 shown show VBN cord-003318-abs9rvjk 118 11 in in IN cord-003318-abs9rvjk 118 12 upper upper JJ cord-003318-abs9rvjk 118 13 panels panel NNS cord-003318-abs9rvjk 118 14 . . . cord-003318-abs9rvjk 119 1 The the DT cord-003318-abs9rvjk 119 2 HPLC HPLC NNP cord-003318-abs9rvjk 119 3 conditions condition NNS cord-003318-abs9rvjk 119 4 are be VBP cord-003318-abs9rvjk 119 5 available available JJ cord-003318-abs9rvjk 119 6 in in IN cord-003318-abs9rvjk 119 7 Supplementary Supplementary NNP cord-003318-abs9rvjk 119 8 Information Information NNP cord-003318-abs9rvjk 119 9 Table Table NNP cord-003318-abs9rvjk 119 10 _SP cord-003318-abs9rvjk 119 11 S3 S3 NNP cord-003318-abs9rvjk 119 12 . . . cord-003318-abs9rvjk 119 13 were be VBD cord-003318-abs9rvjk 119 14 prepared prepare VBN cord-003318-abs9rvjk 119 15 by by IN cord-003318-abs9rvjk 119 16 HPLC HPLC NNP cord-003318-abs9rvjk 119 17 and and CC cord-003318-abs9rvjk 119 18 subjected subject VBN cord-003318-abs9rvjk 119 19 to to IN cord-003318-abs9rvjk 119 20 NMR NMR NNP cord-003318-abs9rvjk 119 21 analysis analysis NN cord-003318-abs9rvjk 119 22 for for IN cord-003318-abs9rvjk 119 23 structural structural JJ cord-003318-abs9rvjk 119 24 elucidation elucidation NN cord-003318-abs9rvjk 119 25 . . . cord-003318-abs9rvjk 120 1 To to TO cord-003318-abs9rvjk 120 2 determine determine VB cord-003318-abs9rvjk 120 3 the the DT cord-003318-abs9rvjk 120 4 glycosylation glycosylation NN cord-003318-abs9rvjk 120 5 sites site NNS cord-003318-abs9rvjk 120 6 of of IN cord-003318-abs9rvjk 120 7 1a-6a 1a-6a CD cord-003318-abs9rvjk 120 8 , , , cord-003318-abs9rvjk 120 9 8a 8a NN cord-003318-abs9rvjk 120 10 and and CC cord-003318-abs9rvjk 120 11 9a 9a NN cord-003318-abs9rvjk 120 12 , , , cord-003318-abs9rvjk 120 13 the the DT cord-003318-abs9rvjk 120 14 13 13 CD cord-003318-abs9rvjk 120 15 C c NN cord-003318-abs9rvjk 120 16 NMR nmr NN cord-003318-abs9rvjk 120 17 analyses analysis NNS cord-003318-abs9rvjk 120 18 of of IN cord-003318-abs9rvjk 120 19 the the DT cord-003318-abs9rvjk 120 20 corresponding correspond VBG cord-003318-abs9rvjk 120 21 aglycons aglycon NNS cord-003318-abs9rvjk 120 22 1 1 CD cord-003318-abs9rvjk 120 23 - - SYM cord-003318-abs9rvjk 120 24 6 6 CD cord-003318-abs9rvjk 120 25 , , , cord-003318-abs9rvjk 120 26 8 8 CD cord-003318-abs9rvjk 120 27 and and CC cord-003318-abs9rvjk 120 28 9 9 CD cord-003318-abs9rvjk 120 29 were be VBD cord-003318-abs9rvjk 120 30 also also RB cord-003318-abs9rvjk 120 31 performed perform VBN cord-003318-abs9rvjk 120 32 ( ( -LRB- cord-003318-abs9rvjk 120 33 Supplementary Supplementary NNP cord-003318-abs9rvjk 120 34 Information Information NNP cord-003318-abs9rvjk 120 35 Figs Figs NNPS cord-003318-abs9rvjk 120 36 . . . cord-003318-abs9rvjk 121 1 S15 S15 NNP cord-003318-abs9rvjk 121 2 - - HYPH cord-003318-abs9rvjk 121 3 22 22 NNP cord-003318-abs9rvjk 121 4 and and CC cord-003318-abs9rvjk 121 5 Table Table NNP cord-003318-abs9rvjk 121 6 S4 S4 NNP cord-003318-abs9rvjk 121 7 ) ) -RRB- cord-003318-abs9rvjk 121 8 . . . cord-003318-abs9rvjk 122 1 The the DT cord-003318-abs9rvjk 122 2 13 13 CD cord-003318-abs9rvjk 122 3 C c NN cord-003318-abs9rvjk 122 4 NMR nmr NN cord-003318-abs9rvjk 122 5 glycosylation glycosylation NN cord-003318-abs9rvjk 122 6 shifts shift NNS cord-003318-abs9rvjk 122 7 ( ( -LRB- cord-003318-abs9rvjk 122 8 Δδ Δδ NNP cord-003318-abs9rvjk 122 9 , , , cord-003318-abs9rvjk 122 10 δ δ NN cord-003318-abs9rvjk 122 11 glucoside glucoside NN cord-003318-abs9rvjk 122 12 -δ -δ : cord-003318-abs9rvjk 122 13 aglycon aglycon NNP cord-003318-abs9rvjk 122 14 ) ) -RRB- cord-003318-abs9rvjk 122 15 of of IN cord-003318-abs9rvjk 122 16 these these DT cord-003318-abs9rvjk 122 17 glycosides glycoside NNS cord-003318-abs9rvjk 122 18 were be VBD cord-003318-abs9rvjk 122 19 thus thus RB cord-003318-abs9rvjk 122 20 examined examine VBN cord-003318-abs9rvjk 122 21 to to TO cord-003318-abs9rvjk 122 22 ascertain ascertain VB cord-003318-abs9rvjk 122 23 the the DT cord-003318-abs9rvjk 122 24 glycosylation glycosylation NN cord-003318-abs9rvjk 122 25 position position NN cord-003318-abs9rvjk 122 26 ( ( -LRB- cord-003318-abs9rvjk 122 27 Table table NN cord-003318-abs9rvjk 122 28 1 1 CD cord-003318-abs9rvjk 122 29 , , , cord-003318-abs9rvjk 122 30 and and CC cord-003318-abs9rvjk 122 31 _SP cord-003318-abs9rvjk 122 32 Supplementary Supplementary NNP cord-003318-abs9rvjk 122 33 Information information NN cord-003318-abs9rvjk 122 34 Tables Tables NNPS cord-003318-abs9rvjk 122 35 S4 S4 NNP cord-003318-abs9rvjk 122 36 - - HYPH cord-003318-abs9rvjk 122 37 11 11 CD cord-003318-abs9rvjk 122 38 ) ) -RRB- cord-003318-abs9rvjk 122 39 . . . cord-003318-abs9rvjk 123 1 The the DT cord-003318-abs9rvjk 123 2 steroidal steroidal JJ cord-003318-abs9rvjk 123 3 glycosides glycoside NNS cord-003318-abs9rvjk 123 4 were be VBD cord-003318-abs9rvjk 123 5 observed observe VBN cord-003318-abs9rvjk 123 6 to to TO cord-003318-abs9rvjk 123 7 have have VB cord-003318-abs9rvjk 123 8 significant significant JJ cord-003318-abs9rvjk 123 9 glycosylation glycosylation NN cord-003318-abs9rvjk 123 10 shift shift NN cord-003318-abs9rvjk 123 11 Δδs Δδs NNP cord-003318-abs9rvjk 123 12 for for IN cord-003318-abs9rvjk 123 13 C-3 C-3 NNP cord-003318-abs9rvjk 123 14 ( ( -LRB- cord-003318-abs9rvjk 123 15 glycosides glycoside NNS cord-003318-abs9rvjk 123 16 1 1 CD cord-003318-abs9rvjk 123 17 - - SYM cord-003318-abs9rvjk 123 18 6 6 CD cord-003318-abs9rvjk 123 19 ) ) -RRB- cord-003318-abs9rvjk 123 20 or or CC cord-003318-abs9rvjk 123 21 C-17 C-17 NNP cord-003318-abs9rvjk 123 22 position position NN cord-003318-abs9rvjk 123 23 ( ( -LRB- cord-003318-abs9rvjk 123 24 compounds compound NNS cord-003318-abs9rvjk 123 25 8 8 CD cord-003318-abs9rvjk 123 26 - - SYM cord-003318-abs9rvjk 123 27 9 9 CD cord-003318-abs9rvjk 123 28 ) ) -RRB- cord-003318-abs9rvjk 123 29 , , , cord-003318-abs9rvjk 123 30 showing show VBG cord-003318-abs9rvjk 123 31 their -PRON- PRP$ cord-003318-abs9rvjk 123 32 3-or 3-or CD cord-003318-abs9rvjk 123 33 17-glycosides 17-glycosides CD cord-003318-abs9rvjk 123 34 . . . cord-003318-abs9rvjk 124 1 For for IN cord-003318-abs9rvjk 124 2 7a 7a NN cord-003318-abs9rvjk 124 3 and and CC cord-003318-abs9rvjk 124 4 10a 10a NNS cord-003318-abs9rvjk 124 5 , , , cord-003318-abs9rvjk 124 6 the the DT cord-003318-abs9rvjk 124 7 location location NN cord-003318-abs9rvjk 124 8 of of IN cord-003318-abs9rvjk 124 9 glucose glucose NN cord-003318-abs9rvjk 124 10 group group NN cord-003318-abs9rvjk 124 11 was be VBD cord-003318-abs9rvjk 124 12 determined determine VBN cord-003318-abs9rvjk 124 13 to to TO cord-003318-abs9rvjk 124 14 be be VB cord-003318-abs9rvjk 124 15 at at IN cord-003318-abs9rvjk 124 16 C-3 C-3 NNP cord-003318-abs9rvjk 124 17 based base VBN cord-003318-abs9rvjk 124 18 on on IN cord-003318-abs9rvjk 124 19 their -PRON- PRP$ cord-003318-abs9rvjk 124 20 HMBC HMBC NNP cord-003318-abs9rvjk 124 21 correlations correlation NNS cord-003318-abs9rvjk 124 22 between between IN cord-003318-abs9rvjk 124 23 H-1 H-1 NNP cord-003318-abs9rvjk 124 24 0 0 CD cord-003318-abs9rvjk 124 25 and and CC cord-003318-abs9rvjk 124 26 C-3 C-3 NNP cord-003318-abs9rvjk 124 27 ( ( -LRB- cord-003318-abs9rvjk 124 28 Supplementary Supplementary NNP cord-003318-abs9rvjk 124 29 Information Information NNP cord-003318-abs9rvjk 124 30 Figs Figs NNPS cord-003318-abs9rvjk 124 31 . . . cord-003318-abs9rvjk 125 1 S23 S23 NNP cord-003318-abs9rvjk 125 2 and and CC cord-003318-abs9rvjk 125 3 24 24 CD cord-003318-abs9rvjk 125 4 ) ) -RRB- cord-003318-abs9rvjk 125 5 . . . cord-003318-abs9rvjk 126 1 The the DT cord-003318-abs9rvjk 126 2 β β NN cord-003318-abs9rvjk 126 3 - - HYPH cord-003318-abs9rvjk 126 4 anomeric anomeric JJ cord-003318-abs9rvjk 126 5 configuration configuration NN cord-003318-abs9rvjk 126 6 of of IN cord-003318-abs9rvjk 126 7 the the DT cord-003318-abs9rvjk 126 8 D d NN cord-003318-abs9rvjk 126 9 - - HYPH cord-003318-abs9rvjk 126 10 glucose glucose NN cord-003318-abs9rvjk 126 11 unit unit NN cord-003318-abs9rvjk 126 12 in in IN cord-003318-abs9rvjk 126 13 these these DT cord-003318-abs9rvjk 126 14 ten ten CD cord-003318-abs9rvjk 126 15 glucosides glucoside NNS cord-003318-abs9rvjk 126 16 ( ( -LRB- cord-003318-abs9rvjk 126 17 1a-10a 1a-10a CD cord-003318-abs9rvjk 126 18 ) ) -RRB- cord-003318-abs9rvjk 126 19 was be VBD cord-003318-abs9rvjk 126 20 determined determine VBN cord-003318-abs9rvjk 126 21 from from IN cord-003318-abs9rvjk 126 22 the the DT cord-003318-abs9rvjk 126 23 large large JJ cord-003318-abs9rvjk 126 24 anomeric anomeric JJ cord-003318-abs9rvjk 126 25 proton proton NN cord-003318-abs9rvjk 126 26 - - HYPH cord-003318-abs9rvjk 126 27 coupling coupling NN cord-003318-abs9rvjk 126 28 constants constant NNS cord-003318-abs9rvjk 126 29 of of IN cord-003318-abs9rvjk 126 30 H-1 H-1 NNP cord-003318-abs9rvjk 126 31 0 0 NFP cord-003318-abs9rvjk 126 32 ( ( -LRB- cord-003318-abs9rvjk 126 33 J J NNP cord-003318-abs9rvjk 126 34 ¼ ¼ CD cord-003318-abs9rvjk 126 35 7.8 7.8 CD cord-003318-abs9rvjk 126 36 Hz Hz NNP cord-003318-abs9rvjk 126 37 ) ) -RRB- cord-003318-abs9rvjk 126 38 ( ( -LRB- cord-003318-abs9rvjk 126 39 Table table NN cord-003318-abs9rvjk 126 40 1 1 CD cord-003318-abs9rvjk 126 41 and and CC cord-003318-abs9rvjk 126 42 Supplementary Supplementary NNP cord-003318-abs9rvjk 126 43 Information Information NNP cord-003318-abs9rvjk 126 44 Tables Tables NNP cord-003318-abs9rvjk 126 45 S5 S5 NNP cord-003318-abs9rvjk 126 46 - - HYPH cord-003318-abs9rvjk 126 47 13 13 CD cord-003318-abs9rvjk 126 48 ) ) -RRB- cord-003318-abs9rvjk 126 49 . . . cord-003318-abs9rvjk 127 1 The the DT cord-003318-abs9rvjk 127 2 structures structure NNS cord-003318-abs9rvjk 127 3 of of IN cord-003318-abs9rvjk 127 4 these these DT cord-003318-abs9rvjk 127 5 glucosides glucoside NNS cord-003318-abs9rvjk 127 6 were be VBD cord-003318-abs9rvjk 127 7 thus thus RB cord-003318-abs9rvjk 127 8 assigned assign VBN cord-003318-abs9rvjk 127 9 to to IN cord-003318-abs9rvjk 127 10 3βglucosides 3βglucosides LS cord-003318-abs9rvjk 127 11 ( ( -LRB- cord-003318-abs9rvjk 127 12 1a-7a 1a-7a NN cord-003318-abs9rvjk 127 13 and and CC cord-003318-abs9rvjk 127 14 10a 10a NNS cord-003318-abs9rvjk 127 15 ) ) -RRB- cord-003318-abs9rvjk 127 16 or or CC cord-003318-abs9rvjk 127 17 17β 17β NNS cord-003318-abs9rvjk 127 18 - - HYPH cord-003318-abs9rvjk 127 19 glucosides glucoside NNS cord-003318-abs9rvjk 127 20 ( ( -LRB- cord-003318-abs9rvjk 127 21 8a 8a NN cord-003318-abs9rvjk 127 22 and and CC cord-003318-abs9rvjk 127 23 9a 9a CD cord-003318-abs9rvjk 127 24 ) ) -RRB- cord-003318-abs9rvjk 127 25 of of IN cord-003318-abs9rvjk 127 26 steroids steroid NNS cord-003318-abs9rvjk 127 27 based base VBN cord-003318-abs9rvjk 127 28 on on IN cord-003318-abs9rvjk 127 29 1 1 CD cord-003318-abs9rvjk 127 30 H h NN cord-003318-abs9rvjk 127 31 NMR nmr NN cord-003318-abs9rvjk 127 32 ( ( -LRB- cord-003318-abs9rvjk 127 33 1a-10a 1a-10a CD cord-003318-abs9rvjk 127 34 ) ) -RRB- cord-003318-abs9rvjk 127 35 and and CC cord-003318-abs9rvjk 127 36 13 13 CD cord-003318-abs9rvjk 127 37 C c NN cord-003318-abs9rvjk 127 38 NMR nmr NN cord-003318-abs9rvjk 127 39 ( ( -LRB- cord-003318-abs9rvjk 127 40 1a-10a 1a-10a CD cord-003318-abs9rvjk 127 41 ) ) -RRB- cord-003318-abs9rvjk 127 42 signals signal NNS cord-003318-abs9rvjk 127 43 , , , cord-003318-abs9rvjk 127 44 HSQC HSQC NNP cord-003318-abs9rvjk 127 45 ( ( -LRB- cord-003318-abs9rvjk 127 46 1a-2a 1a-2a CD cord-003318-abs9rvjk 127 47 , , , cord-003318-abs9rvjk 127 48 4a-7a 4a-7a CD cord-003318-abs9rvjk 127 49 , , , cord-003318-abs9rvjk 127 50 9a-10a 9a-10a CD cord-003318-abs9rvjk 127 51 ) ) -RRB- cord-003318-abs9rvjk 127 52 , , , cord-003318-abs9rvjk 127 53 HMBC HMBC NNP cord-003318-abs9rvjk 127 54 ( ( -LRB- cord-003318-abs9rvjk 127 55 7a-8a 7a-8a NNP cord-003318-abs9rvjk 127 56 , , , cord-003318-abs9rvjk 127 57 10a 10a CD cord-003318-abs9rvjk 127 58 ) ) -RRB- cord-003318-abs9rvjk 127 59 and and CC cord-003318-abs9rvjk 127 60 DEPT DEPT NNP cord-003318-abs9rvjk 127 61 ( ( -LRB- cord-003318-abs9rvjk 127 62 7a 7a NN cord-003318-abs9rvjk 127 63 , , , cord-003318-abs9rvjk 127 64 10a 10a CD cord-003318-abs9rvjk 127 65 ) ) -RRB- cord-003318-abs9rvjk 127 66 spectra spectra JJ cord-003318-abs9rvjk 127 67 ( ( -LRB- cord-003318-abs9rvjk 127 68 Table Table NNP cord-003318-abs9rvjk 127 69 1 1 CD cord-003318-abs9rvjk 127 70 , , , cord-003318-abs9rvjk 127 71 Supplementary Supplementary NNP cord-003318-abs9rvjk 127 72 Information Information NNP cord-003318-abs9rvjk 127 73 _SP cord-003318-abs9rvjk 127 74 Figs Figs NNP cord-003318-abs9rvjk 127 75 . . . cord-003318-abs9rvjk 128 1 S23 S23 NNP cord-003318-abs9rvjk 128 2 - - SYM cord-003318-abs9rvjk 128 3 45 45 CD cord-003318-abs9rvjk 128 4 and and CC cord-003318-abs9rvjk 128 5 Tables Tables NNP cord-003318-abs9rvjk 128 6 S5 S5 NNP cord-003318-abs9rvjk 128 7 - - HYPH cord-003318-abs9rvjk 128 8 13 13 CD cord-003318-abs9rvjk 128 9 ) ) -RRB- cord-003318-abs9rvjk 128 10 . . . cord-003318-abs9rvjk 129 1 These these DT cord-003318-abs9rvjk 129 2 data datum NNS cord-003318-abs9rvjk 129 3 collectively collectively RB cord-003318-abs9rvjk 129 4 showed show VBD cord-003318-abs9rvjk 129 5 that that IN cord-003318-abs9rvjk 129 6 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 129 7 was be VBD cord-003318-abs9rvjk 129 8 an an DT cord-003318-abs9rvjk 129 9 inverting invert VBG cord-003318-abs9rvjk 129 10 - - HYPH cord-003318-abs9rvjk 129 11 type type NN cord-003318-abs9rvjk 129 12 glycosyltransferase glycosyltransferase NN cord-003318-abs9rvjk 129 13 . . . cord-003318-abs9rvjk 130 1 In in IN cord-003318-abs9rvjk 130 2 the the DT cord-003318-abs9rvjk 130 3 preparation preparation NN cord-003318-abs9rvjk 130 4 of of IN cord-003318-abs9rvjk 130 5 T-17β T-17β NNP cord-003318-abs9rvjk 130 6 - - HYPH cord-003318-abs9rvjk 130 7 G g NN cord-003318-abs9rvjk 130 8 ( ( -LRB- cord-003318-abs9rvjk 130 9 8a 8a NN cord-003318-abs9rvjk 130 10 ) ) -RRB- cord-003318-abs9rvjk 130 11 , , , cord-003318-abs9rvjk 130 12 when when WRB cord-003318-abs9rvjk 130 13 the the DT cord-003318-abs9rvjk 130 14 concentrated concentrated JJ cord-003318-abs9rvjk 130 15 reaction reaction NN cord-003318-abs9rvjk 130 16 mixture mixture NN cord-003318-abs9rvjk 130 17 was be VBD cord-003318-abs9rvjk 130 18 separated separate VBN cord-003318-abs9rvjk 130 19 by by IN cord-003318-abs9rvjk 130 20 reversed reversed JJ cord-003318-abs9rvjk 130 21 phase phase NN cord-003318-abs9rvjk 130 22 highperformance highperformance JJ cord-003318-abs9rvjk 130 23 liquid liquid NN cord-003318-abs9rvjk 130 24 chromatography chromatography NN cord-003318-abs9rvjk 130 25 ( ( -LRB- cord-003318-abs9rvjk 130 26 RP rp NN cord-003318-abs9rvjk 130 27 - - HYPH cord-003318-abs9rvjk 130 28 HPLC HPLC NNP cord-003318-abs9rvjk 130 29 ) ) -RRB- cord-003318-abs9rvjk 130 30 , , , cord-003318-abs9rvjk 130 31 we -PRON- PRP cord-003318-abs9rvjk 130 32 accidentally accidentally RB cord-003318-abs9rvjk 130 33 discovered discover VBD cord-003318-abs9rvjk 130 34 that that IN cord-003318-abs9rvjk 130 35 in in IN cord-003318-abs9rvjk 130 36 addition addition NN cord-003318-abs9rvjk 130 37 to to IN cord-003318-abs9rvjk 130 38 the the DT cord-003318-abs9rvjk 130 39 major major JJ cord-003318-abs9rvjk 130 40 peak peak NN cord-003318-abs9rvjk 130 41 representing represent VBG cord-003318-abs9rvjk 130 42 T-17β T-17β NNP cord-003318-abs9rvjk 130 43 - - HYPH cord-003318-abs9rvjk 130 44 G g NN cord-003318-abs9rvjk 130 45 ( ( -LRB- cord-003318-abs9rvjk 130 46 8a 8a NN cord-003318-abs9rvjk 130 47 ) ) -RRB- cord-003318-abs9rvjk 130 48 , , , cord-003318-abs9rvjk 130 49 a a DT cord-003318-abs9rvjk 130 50 minor minor JJ cord-003318-abs9rvjk 130 51 peak peak NN cord-003318-abs9rvjk 130 52 ( ( -LRB- cord-003318-abs9rvjk 130 53 8b 8b NN cord-003318-abs9rvjk 130 54 ) ) -RRB- cord-003318-abs9rvjk 130 55 was be VBD cord-003318-abs9rvjk 130 56 also also RB cord-003318-abs9rvjk 130 57 present present JJ cord-003318-abs9rvjk 130 58 in in IN cord-003318-abs9rvjk 130 59 the the DT cord-003318-abs9rvjk 130 60 HPLC HPLC NNP cord-003318-abs9rvjk 130 61 profile profile NN cord-003318-abs9rvjk 130 62 ( ( -LRB- cord-003318-abs9rvjk 130 63 Supplementary Supplementary NNP cord-003318-abs9rvjk 130 64 Information Information NNP cord-003318-abs9rvjk 130 65 Fig Fig NNP cord-003318-abs9rvjk 130 66 . . . cord-003318-abs9rvjk 131 1 S46A S46A NNP cord-003318-abs9rvjk 131 2 ) ) -RRB- cord-003318-abs9rvjk 131 3 . . . cord-003318-abs9rvjk 132 1 The the DT cord-003318-abs9rvjk 132 2 minor minor JJ cord-003318-abs9rvjk 132 3 product product NN cord-003318-abs9rvjk 132 4 with with IN cord-003318-abs9rvjk 132 5 a a DT cord-003318-abs9rvjk 132 6 t t NN cord-003318-abs9rvjk 132 7 R r NN cord-003318-abs9rvjk 132 8 of of IN cord-003318-abs9rvjk 132 9 20.53 20.53 CD cord-003318-abs9rvjk 132 10 min min NN cord-003318-abs9rvjk 132 11 was be VBD cord-003318-abs9rvjk 132 12 also also RB cord-003318-abs9rvjk 132 13 subjected subject VBN cord-003318-abs9rvjk 132 14 to to IN cord-003318-abs9rvjk 132 15 LC LC NNP cord-003318-abs9rvjk 132 16 - - HYPH cord-003318-abs9rvjk 132 17 MS MS NNP cord-003318-abs9rvjk 132 18 analysis analysis NN cord-003318-abs9rvjk 132 19 . . . cord-003318-abs9rvjk 133 1 Surprisingly surprisingly RB cord-003318-abs9rvjk 133 2 , , , cord-003318-abs9rvjk 133 3 the the DT cord-003318-abs9rvjk 133 4 [ [ -LRB- cord-003318-abs9rvjk 133 5 M M NNP cord-003318-abs9rvjk 133 6 þ þ NNP cord-003318-abs9rvjk 133 7 H H NNP cord-003318-abs9rvjk 133 8 ] ] -RRB- cord-003318-abs9rvjk 134 1 þ þ LS cord-003318-abs9rvjk 134 2 value value NN cord-003318-abs9rvjk 134 3 of of IN cord-003318-abs9rvjk 134 4 the the DT cord-003318-abs9rvjk 134 5 minor minor JJ cord-003318-abs9rvjk 134 6 product product NN cord-003318-abs9rvjk 134 7 was be VBD cord-003318-abs9rvjk 134 8 assigned assign VBN cord-003318-abs9rvjk 134 9 to to IN cord-003318-abs9rvjk 134 10 493.3 493.3 CD cord-003318-abs9rvjk 134 11 , , , cord-003318-abs9rvjk 134 12 42 42 CD cord-003318-abs9rvjk 134 13 more more JJR cord-003318-abs9rvjk 134 14 than than IN cord-003318-abs9rvjk 134 15 that that DT cord-003318-abs9rvjk 134 16 of of IN cord-003318-abs9rvjk 134 17 monoglycosylated monoglycosylate VBN cord-003318-abs9rvjk 134 18 testosterone testosterone NN cord-003318-abs9rvjk 134 19 ( ( -LRB- cord-003318-abs9rvjk 134 20 Supplementary Supplementary NNP cord-003318-abs9rvjk 134 21 Information Information NNP cord-003318-abs9rvjk 134 22 Fig Fig NNP cord-003318-abs9rvjk 134 23 . . . cord-003318-abs9rvjk 135 1 S46B S46B NNP cord-003318-abs9rvjk 135 2 ) ) -RRB- cord-003318-abs9rvjk 135 3 . . . cord-003318-abs9rvjk 136 1 This this DT cord-003318-abs9rvjk 136 2 finding finding NN cord-003318-abs9rvjk 136 3 hints hint VBZ cord-003318-abs9rvjk 136 4 that that IN cord-003318-abs9rvjk 136 5 the the DT cord-003318-abs9rvjk 136 6 minor minor JJ cord-003318-abs9rvjk 136 7 product product NN cord-003318-abs9rvjk 136 8 may may MD cord-003318-abs9rvjk 136 9 be be VB cord-003318-abs9rvjk 136 10 an an DT cord-003318-abs9rvjk 136 11 acetylated acetylated JJ cord-003318-abs9rvjk 136 12 testosterone testosterone NN cord-003318-abs9rvjk 136 13 glucoside glucoside NN cord-003318-abs9rvjk 136 14 . . . cord-003318-abs9rvjk 137 1 To to TO cord-003318-abs9rvjk 137 2 characterize characterize VB cord-003318-abs9rvjk 137 3 the the DT cord-003318-abs9rvjk 137 4 exact exact JJ cord-003318-abs9rvjk 137 5 structure structure NN cord-003318-abs9rvjk 137 6 of of IN cord-003318-abs9rvjk 137 7 8b 8b NNP cord-003318-abs9rvjk 137 8 , , , cord-003318-abs9rvjk 137 9 the the DT cord-003318-abs9rvjk 137 10 minor minor JJ cord-003318-abs9rvjk 137 11 product product NN cord-003318-abs9rvjk 137 12 was be VBD cord-003318-abs9rvjk 137 13 prepared prepare VBN cord-003318-abs9rvjk 137 14 in in IN cord-003318-abs9rvjk 137 15 bulk bulk NN cord-003318-abs9rvjk 137 16 for for IN cord-003318-abs9rvjk 137 17 NMR NMR NNP cord-003318-abs9rvjk 137 18 experiment experiment NN cord-003318-abs9rvjk 137 19 ( ( -LRB- cord-003318-abs9rvjk 137 20 Supplementary Supplementary NNP cord-003318-abs9rvjk 137 21 Information Information NNP cord-003318-abs9rvjk 137 22 Figs Figs NNPS cord-003318-abs9rvjk 137 23 . . . cord-003318-abs9rvjk 138 1 S47 S47 NNP cord-003318-abs9rvjk 138 2 - - HYPH cord-003318-abs9rvjk 138 3 51 51 CD cord-003318-abs9rvjk 138 4 ) ) -RRB- cord-003318-abs9rvjk 138 5 . . . cord-003318-abs9rvjk 139 1 Details detail NNS cord-003318-abs9rvjk 139 2 of of IN cord-003318-abs9rvjk 139 3 1 1 CD cord-003318-abs9rvjk 139 4 H h NN cord-003318-abs9rvjk 139 5 and and CC cord-003318-abs9rvjk 139 6 13 13 CD cord-003318-abs9rvjk 139 7 C c NN cord-003318-abs9rvjk 139 8 NMR NMR NNP cord-003318-abs9rvjk 139 9 spectra spectrum NNS cord-003318-abs9rvjk 139 10 were be VBD cord-003318-abs9rvjk 139 11 tabulated tabulate VBN cord-003318-abs9rvjk 139 12 in in IN cord-003318-abs9rvjk 139 13 Table Table NNP cord-003318-abs9rvjk 139 14 2 2 CD cord-003318-abs9rvjk 139 15 . . . cord-003318-abs9rvjk 140 1 The the DT cord-003318-abs9rvjk 140 2 minor minor JJ cord-003318-abs9rvjk 140 3 product product NN cord-003318-abs9rvjk 140 4 was be VBD cord-003318-abs9rvjk 140 5 thus thus RB cord-003318-abs9rvjk 140 6 identified identify VBN cord-003318-abs9rvjk 140 7 as as IN cord-003318-abs9rvjk 140 8 6 6 CD cord-003318-abs9rvjk 140 9 0 0 CD cord-003318-abs9rvjk 141 1 -acetylated -acetylated JJ cord-003318-abs9rvjk 141 2 testosterone testosterone NN cord-003318-abs9rvjk 141 3 17-O 17-O NNS cord-003318-abs9rvjk 141 4 - - HYPH cord-003318-abs9rvjk 141 5 β β NN cord-003318-abs9rvjk 141 6 - - HYPH cord-003318-abs9rvjk 141 7 glucoside glucoside NN cord-003318-abs9rvjk 141 8 ( ( -LRB- cord-003318-abs9rvjk 141 9 6 6 CD cord-003318-abs9rvjk 141 10 0 0 CD cord-003318-abs9rvjk 141 11 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 141 12 - - HYPH cord-003318-abs9rvjk 141 13 G g NN cord-003318-abs9rvjk 141 14 , , , cord-003318-abs9rvjk 141 15 8b 8b NN cord-003318-abs9rvjk 141 16 ) ) -RRB- cord-003318-abs9rvjk 141 17 . . . cord-003318-abs9rvjk 142 1 To to TO cord-003318-abs9rvjk 142 2 test test VB cord-003318-abs9rvjk 142 3 if if IN cord-003318-abs9rvjk 142 4 the the DT cord-003318-abs9rvjk 142 5 acetylated acetylated JJ cord-003318-abs9rvjk 142 6 product product NN cord-003318-abs9rvjk 142 7 8b 8b NN cord-003318-abs9rvjk 142 8 was be VBD cord-003318-abs9rvjk 142 9 from from IN cord-003318-abs9rvjk 142 10 glucoside glucoside NN cord-003318-abs9rvjk 142 11 8a 8a NN cord-003318-abs9rvjk 142 12 , , , cord-003318-abs9rvjk 143 1 the the DT cord-003318-abs9rvjk 143 2 purified purify VBN cord-003318-abs9rvjk 143 3 glucoside glucoside NN cord-003318-abs9rvjk 143 4 8a 8a NN cord-003318-abs9rvjk 143 5 was be VBD cord-003318-abs9rvjk 143 6 used use VBN cord-003318-abs9rvjk 143 7 as as IN cord-003318-abs9rvjk 143 8 the the DT cord-003318-abs9rvjk 143 9 substrate substrate NN cord-003318-abs9rvjk 143 10 to to TO cord-003318-abs9rvjk 143 11 incubate incubate VB cord-003318-abs9rvjk 143 12 with with IN cord-003318-abs9rvjk 143 13 crude crude JJ cord-003318-abs9rvjk 143 14 extract extract NN cord-003318-abs9rvjk 143 15 of of IN cord-003318-abs9rvjk 143 16 E. E. NNP cord-003318-abs9rvjk 143 17 coli coli NNS cord-003318-abs9rvjk 143 18 expressing express VBG cord-003318-abs9rvjk 143 19 pET-28a(þ pet-28a(þ NN cord-003318-abs9rvjk 143 20 ) ) -RRB- cord-003318-abs9rvjk 143 21 or or CC cord-003318-abs9rvjk 143 22 pET28OsSGT1 pet28ossgt1 NN cord-003318-abs9rvjk 143 23 , , , cord-003318-abs9rvjk 143 24 respectively respectively RB cord-003318-abs9rvjk 143 25 . . . cord-003318-abs9rvjk 144 1 In in IN cord-003318-abs9rvjk 144 2 both both DT cord-003318-abs9rvjk 144 3 conditions condition NNS cord-003318-abs9rvjk 144 4 , , , cord-003318-abs9rvjk 144 5 we -PRON- PRP cord-003318-abs9rvjk 144 6 observed observe VBD cord-003318-abs9rvjk 144 7 the the DT cord-003318-abs9rvjk 144 8 presence presence NN cord-003318-abs9rvjk 144 9 of of IN cord-003318-abs9rvjk 144 10 8b 8b NNP cord-003318-abs9rvjk 144 11 ( ( -LRB- cord-003318-abs9rvjk 144 12 Supplementary Supplementary NNP cord-003318-abs9rvjk 144 13 Information Information NNP cord-003318-abs9rvjk 144 14 Fig Fig NNP cord-003318-abs9rvjk 144 15 . . . cord-003318-abs9rvjk 145 1 S52 S52 NNP cord-003318-abs9rvjk 145 2 ) ) -RRB- cord-003318-abs9rvjk 145 3 . . . cord-003318-abs9rvjk 146 1 On on IN cord-003318-abs9rvjk 146 2 the the DT cord-003318-abs9rvjk 146 3 contrary contrary NN cord-003318-abs9rvjk 146 4 , , , cord-003318-abs9rvjk 146 5 no no DT cord-003318-abs9rvjk 146 6 acetylated acetylated JJ cord-003318-abs9rvjk 146 7 product product NN cord-003318-abs9rvjk 146 8 8b 8b NN cord-003318-abs9rvjk 146 9 was be VBD cord-003318-abs9rvjk 146 10 detected detect VBN cord-003318-abs9rvjk 146 11 in in IN cord-003318-abs9rvjk 146 12 the the DT cord-003318-abs9rvjk 146 13 E. E. NNP cord-003318-abs9rvjk 146 14 coli coli NN cord-003318-abs9rvjk 146 15 lysate lysate NN cord-003318-abs9rvjk 146 16 without without IN cord-003318-abs9rvjk 146 17 the the DT cord-003318-abs9rvjk 146 18 addition addition NN cord-003318-abs9rvjk 146 19 of of IN cord-003318-abs9rvjk 146 20 substrate substrate NN cord-003318-abs9rvjk 146 21 8a 8a NN cord-003318-abs9rvjk 146 22 ( ( -LRB- cord-003318-abs9rvjk 146 23 Supplementary Supplementary NNP cord-003318-abs9rvjk 146 24 Information Information NNP cord-003318-abs9rvjk 146 25 Fig Fig NNP cord-003318-abs9rvjk 146 26 . . . cord-003318-abs9rvjk 146 27 S52 S52 NNP cord-003318-abs9rvjk 146 28 ) ) -RRB- cord-003318-abs9rvjk 146 29 . . . cord-003318-abs9rvjk 147 1 We -PRON- PRP cord-003318-abs9rvjk 147 2 therefore therefore RB cord-003318-abs9rvjk 147 3 inferred infer VBD cord-003318-abs9rvjk 147 4 that that IN cord-003318-abs9rvjk 147 5 testosterone testosterone NN cord-003318-abs9rvjk 147 6 ( ( -LRB- cord-003318-abs9rvjk 147 7 8) 8) NNP cord-003318-abs9rvjk 147 8 was be VBD cord-003318-abs9rvjk 147 9 first first RB cord-003318-abs9rvjk 147 10 glycosylated glycosylate VBN cord-003318-abs9rvjk 147 11 at at IN cord-003318-abs9rvjk 147 12 the the DT cord-003318-abs9rvjk 147 13 17β 17β NNS cord-003318-abs9rvjk 147 14 - - SYM cord-003318-abs9rvjk 147 15 hydroxyl hydroxyl NN cord-003318-abs9rvjk 147 16 group group NN cord-003318-abs9rvjk 147 17 by by IN cord-003318-abs9rvjk 147 18 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 147 19 to to TO cord-003318-abs9rvjk 147 20 form form VB cord-003318-abs9rvjk 147 21 T-17β T-17β NNP cord-003318-abs9rvjk 147 22 - - HYPH cord-003318-abs9rvjk 147 23 G g NN cord-003318-abs9rvjk 147 24 ( ( -LRB- cord-003318-abs9rvjk 147 25 8a 8a NN cord-003318-abs9rvjk 147 26 ) ) -RRB- cord-003318-abs9rvjk 147 27 , , , cord-003318-abs9rvjk 147 28 which which WDT cord-003318-abs9rvjk 147 29 was be VBD cord-003318-abs9rvjk 147 30 then then RB cord-003318-abs9rvjk 147 31 selectively selectively RB cord-003318-abs9rvjk 147 32 acetylated acetylate VBN cord-003318-abs9rvjk 147 33 at at IN cord-003318-abs9rvjk 147 34 C-6 C-6 NNP cord-003318-abs9rvjk 147 35 0 0 CD cord-003318-abs9rvjk 147 36 of of IN cord-003318-abs9rvjk 147 37 sugar sugar NN cord-003318-abs9rvjk 147 38 moiety moiety NN cord-003318-abs9rvjk 147 39 to to TO cord-003318-abs9rvjk 147 40 yield yield VB cord-003318-abs9rvjk 147 41 the the DT cord-003318-abs9rvjk 147 42 6 6 CD cord-003318-abs9rvjk 147 43 0 0 CD cord-003318-abs9rvjk 147 44 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 147 45 - - HYPH cord-003318-abs9rvjk 147 46 G g NN cord-003318-abs9rvjk 147 47 ( ( -LRB- cord-003318-abs9rvjk 147 48 8b 8b NN cord-003318-abs9rvjk 147 49 ) ) -RRB- cord-003318-abs9rvjk 147 50 by by IN cord-003318-abs9rvjk 147 51 a a DT cord-003318-abs9rvjk 147 52 soluble soluble JJ cord-003318-abs9rvjk 147 53 bacterial bacterial JJ cord-003318-abs9rvjk 147 54 acetyltransferase acetyltransferase NN cord-003318-abs9rvjk 147 55 ( ( -LRB- cord-003318-abs9rvjk 147 56 Supplementary Supplementary NNP cord-003318-abs9rvjk 147 57 Information Information NNP cord-003318-abs9rvjk 147 58 Fig Fig NNP cord-003318-abs9rvjk 147 59 . . . cord-003318-abs9rvjk 147 60 S52 S52 NNP cord-003318-abs9rvjk 147 61 ) ) -RRB- cord-003318-abs9rvjk 147 62 . . . cord-003318-abs9rvjk 148 1 Likewise likewise RB cord-003318-abs9rvjk 148 2 , , , cord-003318-abs9rvjk 148 3 two two CD cord-003318-abs9rvjk 148 4 metabolites metabolite NNS cord-003318-abs9rvjk 148 5 , , , cord-003318-abs9rvjk 148 6 E-17β E-17β NNP cord-003318-abs9rvjk 148 7 - - HYPH cord-003318-abs9rvjk 148 8 G G NNP cord-003318-abs9rvjk 148 9 ( ( -LRB- cord-003318-abs9rvjk 148 10 9a 9a NN cord-003318-abs9rvjk 148 11 ) ) -RRB- cord-003318-abs9rvjk 148 12 and and CC cord-003318-abs9rvjk 148 13 6 6 CD cord-003318-abs9rvjk 148 14 0 0 CD cord-003318-abs9rvjk 148 15 -acetylated -acetylated JJ cord-003318-abs9rvjk 148 16 estradiol estradiol NN cord-003318-abs9rvjk 148 17 17-O 17-o NN cord-003318-abs9rvjk 148 18 - - HYPH cord-003318-abs9rvjk 148 19 β β NN cord-003318-abs9rvjk 148 20 - - HYPH cord-003318-abs9rvjk 148 21 glucoside glucoside NN cord-003318-abs9rvjk 148 22 ( ( -LRB- cord-003318-abs9rvjk 148 23 6 6 CD cord-003318-abs9rvjk 148 24 0 0 CD cord-003318-abs9rvjk 148 25 -AE-17β -AE-17β NNS cord-003318-abs9rvjk 148 26 - - HYPH cord-003318-abs9rvjk 148 27 G g NN cord-003318-abs9rvjk 148 28 , , , cord-003318-abs9rvjk 148 29 9b 9b CD cord-003318-abs9rvjk 148 30 ) ) -RRB- cord-003318-abs9rvjk 148 31 , , , cord-003318-abs9rvjk 148 32 were be VBD cord-003318-abs9rvjk 148 33 detected detect VBN cord-003318-abs9rvjk 148 34 in in IN cord-003318-abs9rvjk 148 35 the the DT cord-003318-abs9rvjk 148 36 concentrated concentrated JJ cord-003318-abs9rvjk 148 37 OsSGT1-catalyzed ossgt1-catalyzed JJ cord-003318-abs9rvjk 148 38 reaction reaction NN cord-003318-abs9rvjk 148 39 mixture mixture NN cord-003318-abs9rvjk 148 40 of of IN cord-003318-abs9rvjk 148 41 estradiol estradiol NN cord-003318-abs9rvjk 148 42 ( ( -LRB- cord-003318-abs9rvjk 148 43 9 9 CD cord-003318-abs9rvjk 148 44 ) ) -RRB- cord-003318-abs9rvjk 148 45 as as IN cord-003318-abs9rvjk 148 46 shown show VBN cord-003318-abs9rvjk 148 47 in in IN cord-003318-abs9rvjk 148 48 Supplementary Supplementary NNP cord-003318-abs9rvjk 148 49 Information Information NNP cord-003318-abs9rvjk 148 50 Figs Figs NNPS cord-003318-abs9rvjk 148 51 . . . cord-003318-abs9rvjk 149 1 S53 S53 NNP cord-003318-abs9rvjk 149 2 - - HYPH cord-003318-abs9rvjk 149 3 55 55 CD cord-003318-abs9rvjk 149 4 , , , cord-003318-abs9rvjk 149 5 Tables Tables NNPS cord-003318-abs9rvjk 149 6 S11 S11 NNP cord-003318-abs9rvjk 149 7 and and CC cord-003318-abs9rvjk 149 8 S14 S14 NNP cord-003318-abs9rvjk 149 9 . . . cord-003318-abs9rvjk 150 1 These these DT cord-003318-abs9rvjk 150 2 data datum NNS cord-003318-abs9rvjk 150 3 collectively collectively RB cord-003318-abs9rvjk 150 4 revealed reveal VBD cord-003318-abs9rvjk 150 5 that that IN cord-003318-abs9rvjk 150 6 E. E. NNP cord-003318-abs9rvjk 150 7 coli coli VBZ cord-003318-abs9rvjk 150 8 cell cell NN cord-003318-abs9rvjk 150 9 contained contain VBN cord-003318-abs9rvjk 150 10 at at IN cord-003318-abs9rvjk 150 11 least least JJS cord-003318-abs9rvjk 150 12 one one CD cord-003318-abs9rvjk 150 13 SGAs sga NNS cord-003318-abs9rvjk 150 14 specific specific JJ cord-003318-abs9rvjk 150 15 for for IN cord-003318-abs9rvjk 150 16 the the DT cord-003318-abs9rvjk 150 17 acetylation acetylation NN cord-003318-abs9rvjk 150 18 of of IN cord-003318-abs9rvjk 150 19 steroidal steroidal JJ cord-003318-abs9rvjk 150 20 17β 17β NNS cord-003318-abs9rvjk 150 21 - - HYPH cord-003318-abs9rvjk 150 22 glycosides glycoside NNS cord-003318-abs9rvjk 150 23 . . . cord-003318-abs9rvjk 151 1 Moreover moreover RB cord-003318-abs9rvjk 151 2 , , , cord-003318-abs9rvjk 151 3 the the DT cord-003318-abs9rvjk 151 4 sugar sugar NN cord-003318-abs9rvjk 151 5 donor donor NN cord-003318-abs9rvjk 151 6 promiscuity promiscuity NN cord-003318-abs9rvjk 151 7 of of IN cord-003318-abs9rvjk 151 8 OsSGT1-catalyzed ossgt1-catalyzed JJ cord-003318-abs9rvjk 151 9 glycosylation glycosylation NN cord-003318-abs9rvjk 151 10 reactions reaction NNS cord-003318-abs9rvjk 151 11 was be VBD cord-003318-abs9rvjk 151 12 also also RB cord-003318-abs9rvjk 151 13 investigated investigate VBN cord-003318-abs9rvjk 151 14 . . . cord-003318-abs9rvjk 152 1 β β LS cord-003318-abs9rvjk 152 2 - - : cord-003318-abs9rvjk 152 3 Sitosterol Sitosterol NNP cord-003318-abs9rvjk 152 4 ( ( -LRB- cord-003318-abs9rvjk 152 5 2 2 CD cord-003318-abs9rvjk 152 6 ) ) -RRB- cord-003318-abs9rvjk 152 7 and and CC cord-003318-abs9rvjk 152 8 testosterone testosterone NN cord-003318-abs9rvjk 152 9 ( ( -LRB- cord-003318-abs9rvjk 152 10 8) 8) NNP cord-003318-abs9rvjk 152 11 were be VBD cord-003318-abs9rvjk 152 12 chosen choose VBN cord-003318-abs9rvjk 152 13 as as IN cord-003318-abs9rvjk 152 14 the the DT cord-003318-abs9rvjk 152 15 sugar sugar NN cord-003318-abs9rvjk 152 16 acceptors acceptor NNS cord-003318-abs9rvjk 152 17 to to TO cord-003318-abs9rvjk 152 18 react react VB cord-003318-abs9rvjk 152 19 with with IN cord-003318-abs9rvjk 152 20 varied varied JJ cord-003318-abs9rvjk 152 21 sugar sugar NN cord-003318-abs9rvjk 152 22 donors donor NNS cord-003318-abs9rvjk 152 23 listed list VBN cord-003318-abs9rvjk 152 24 in in IN cord-003318-abs9rvjk 152 25 the the DT cord-003318-abs9rvjk 152 26 Supplementary Supplementary NNP cord-003318-abs9rvjk 152 27 Experimental Experimental NNP cord-003318-abs9rvjk 152 28 Section Section NNP cord-003318-abs9rvjk 152 29 , , , cord-003318-abs9rvjk 152 30 respectively respectively RB cord-003318-abs9rvjk 152 31 . . . cord-003318-abs9rvjk 153 1 Results result NNS cord-003318-abs9rvjk 153 2 demonstrated demonstrate VBD cord-003318-abs9rvjk 153 3 that that IN cord-003318-abs9rvjk 153 4 both both CC cord-003318-abs9rvjk 153 5 β β NN cord-003318-abs9rvjk 153 6 - - HYPH cord-003318-abs9rvjk 153 7 sitosterol sitosterol NNP cord-003318-abs9rvjk 153 8 ( ( -LRB- cord-003318-abs9rvjk 153 9 2 2 CD cord-003318-abs9rvjk 153 10 ) ) -RRB- cord-003318-abs9rvjk 153 11 and and CC cord-003318-abs9rvjk 153 12 testosterone testosterone NN cord-003318-abs9rvjk 153 13 ( ( -LRB- cord-003318-abs9rvjk 153 14 8) 8) NNP cord-003318-abs9rvjk 153 15 had have VBD cord-003318-abs9rvjk 153 16 no no DT cord-003318-abs9rvjk 153 17 reactive reactive JJ cord-003318-abs9rvjk 153 18 activity activity NN cord-003318-abs9rvjk 153 19 towards towards IN cord-003318-abs9rvjk 153 20 other other JJ cord-003318-abs9rvjk 153 21 UDP udp NN cord-003318-abs9rvjk 153 22 - - HYPH cord-003318-abs9rvjk 153 23 activated activate VBN cord-003318-abs9rvjk 153 24 nucleotides nucleotide NNS cord-003318-abs9rvjk 153 25 except except IN cord-003318-abs9rvjk 153 26 UDP udp NN cord-003318-abs9rvjk 153 27 - - HYPH cord-003318-abs9rvjk 153 28 Glc Glc NNP cord-003318-abs9rvjk 153 29 under under IN cord-003318-abs9rvjk 153 30 the the DT cord-003318-abs9rvjk 153 31 action action NN cord-003318-abs9rvjk 153 32 of of IN cord-003318-abs9rvjk 153 33 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 153 34 , , , cord-003318-abs9rvjk 153 35 indicating indicate VBG cord-003318-abs9rvjk 153 36 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 153 37 was be VBD cord-003318-abs9rvjk 153 38 specific specific JJ cord-003318-abs9rvjk 153 39 for for IN cord-003318-abs9rvjk 153 40 UDP udp NN cord-003318-abs9rvjk 153 41 - - HYPH cord-003318-abs9rvjk 153 42 Glc Glc NNP cord-003318-abs9rvjk 153 43 . . . cord-003318-abs9rvjk 154 1 To to TO cord-003318-abs9rvjk 154 2 characterize characterize VB cord-003318-abs9rvjk 154 3 the the DT cord-003318-abs9rvjk 154 4 genes gene NNS cord-003318-abs9rvjk 154 5 encoding encode VBG cord-003318-abs9rvjk 154 6 SGAs sga NNS cord-003318-abs9rvjk 154 7 , , , cord-003318-abs9rvjk 154 8 the the DT cord-003318-abs9rvjk 154 9 first first JJ cord-003318-abs9rvjk 154 10 task task NN cord-003318-abs9rvjk 154 11 was be VBD cord-003318-abs9rvjk 154 12 to to TO cord-003318-abs9rvjk 154 13 analyze analyze VB cord-003318-abs9rvjk 154 14 the the DT cord-003318-abs9rvjk 154 15 genome genome NN cord-003318-abs9rvjk 154 16 sequence sequence NN cord-003318-abs9rvjk 154 17 of of IN cord-003318-abs9rvjk 154 18 BL21(DE3 BL21(DE3 NNP cord-003318-abs9rvjk 154 19 ) ) -RRB- cord-003318-abs9rvjk 154 20 , , , cord-003318-abs9rvjk 154 21 which which WDT cord-003318-abs9rvjk 154 22 was be VBD cord-003318-abs9rvjk 154 23 public public JJ cord-003318-abs9rvjk 154 24 in in IN cord-003318-abs9rvjk 154 25 NCBI NCBI NNP cord-003318-abs9rvjk 154 26 database database NN cord-003318-abs9rvjk 154 27 ( ( -LRB- cord-003318-abs9rvjk 155 1 Accession Accession NNP cord-003318-abs9rvjk 155 2 No no NN cord-003318-abs9rvjk 155 3 . . . cord-003318-abs9rvjk 155 4 CP001509.3 CP001509.3 NNP cord-003318-abs9rvjk 155 5 ) ) -RRB- cord-003318-abs9rvjk 155 6 . . . cord-003318-abs9rvjk 156 1 This this DT cord-003318-abs9rvjk 156 2 bacterial bacterial JJ cord-003318-abs9rvjk 156 3 strain strain NN cord-003318-abs9rvjk 156 4 contains contain VBZ cord-003318-abs9rvjk 156 5 at at IN cord-003318-abs9rvjk 156 6 least least JJS cord-003318-abs9rvjk 156 7 35 35 CD cord-003318-abs9rvjk 156 8 putative putative JJ cord-003318-abs9rvjk 156 9 acetyltransferase acetyltransferase NN cord-003318-abs9rvjk 156 10 genes gene NNS cord-003318-abs9rvjk 156 11 , , , cord-003318-abs9rvjk 156 12 in in IN cord-003318-abs9rvjk 156 13 which which WDT cord-003318-abs9rvjk 156 14 lacA lacA NNP cord-003318-abs9rvjk 156 15 , , , cord-003318-abs9rvjk 156 16 maa maa NNP cord-003318-abs9rvjk 156 17 and and CC cord-003318-abs9rvjk 156 18 wecH wecH NNP cord-003318-abs9rvjk 156 19 , , , cord-003318-abs9rvjk 156 20 were be VBD cord-003318-abs9rvjk 156 21 predicted predict VBN cord-003318-abs9rvjk 156 22 to to TO cord-003318-abs9rvjk 156 23 encode encode VB cord-003318-abs9rvjk 156 24 O o NN cord-003318-abs9rvjk 156 25 - - HYPH cord-003318-abs9rvjk 156 26 acetyltransferase acetyltransferase NN cord-003318-abs9rvjk 156 27 ( ( -LRB- cord-003318-abs9rvjk 156 28 Supplementary Supplementary NNP cord-003318-abs9rvjk 156 29 Information Information NNP cord-003318-abs9rvjk 156 30 Table Table NNP cord-003318-abs9rvjk 156 31 S15 S15 NNP cord-003318-abs9rvjk 156 32 ) ) -RRB- cord-003318-abs9rvjk 156 33 . . . cord-003318-abs9rvjk 157 1 As as IN cord-003318-abs9rvjk 157 2 shown show VBN cord-003318-abs9rvjk 157 3 in in IN cord-003318-abs9rvjk 157 4 Supplementary Supplementary NNP cord-003318-abs9rvjk 157 5 Information Information NNP cord-003318-abs9rvjk 157 6 Fig Fig NNP cord-003318-abs9rvjk 157 7 . . . cord-003318-abs9rvjk 158 1 S56 s56 JJ cord-003318-abs9rvjk 158 2 , , , cord-003318-abs9rvjk 158 3 further further JJ cord-003318-abs9rvjk 158 4 sequence sequence NN cord-003318-abs9rvjk 158 5 analyses analysis NNS cord-003318-abs9rvjk 158 6 revealed reveal VBD cord-003318-abs9rvjk 158 7 WecH WecH NNP cord-003318-abs9rvjk 158 8 protein protein NN cord-003318-abs9rvjk 158 9 was be VBD cord-003318-abs9rvjk 158 10 a a DT cord-003318-abs9rvjk 158 11 membrane membrane NN cord-003318-abs9rvjk 158 12 - - HYPH cord-003318-abs9rvjk 158 13 bound bind VBN cord-003318-abs9rvjk 158 14 protein protein NN cord-003318-abs9rvjk 158 15 with with IN cord-003318-abs9rvjk 158 16 a a DT cord-003318-abs9rvjk 158 17 total total NN cord-003318-abs9rvjk 158 18 of of IN cord-003318-abs9rvjk 158 19 10 10 CD cord-003318-abs9rvjk 158 20 membrane membrane NN cord-003318-abs9rvjk 158 21 - - HYPH cord-003318-abs9rvjk 158 22 spanning span VBG cord-003318-abs9rvjk 158 23 helixes helix NNS cord-003318-abs9rvjk 158 24 , , , cord-003318-abs9rvjk 158 25 inconsistent inconsistent JJ cord-003318-abs9rvjk 158 26 with with IN cord-003318-abs9rvjk 158 27 the the DT cord-003318-abs9rvjk 158 28 above above JJ cord-003318-abs9rvjk 158 29 results result NNS cord-003318-abs9rvjk 158 30 , , , cord-003318-abs9rvjk 158 31 in in IN cord-003318-abs9rvjk 158 32 which which WDT cord-003318-abs9rvjk 158 33 the the DT cord-003318-abs9rvjk 158 34 candidate candidate NN cord-003318-abs9rvjk 158 35 acetyltransferase acetyltransferase NNP cord-003318-abs9rvjk 158 36 was be VBD cord-003318-abs9rvjk 158 37 determined determine VBN cord-003318-abs9rvjk 158 38 to to TO cord-003318-abs9rvjk 158 39 be be VB cord-003318-abs9rvjk 158 40 a a DT cord-003318-abs9rvjk 158 41 soluble soluble JJ cord-003318-abs9rvjk 158 42 protein protein NN cord-003318-abs9rvjk 158 43 in in IN cord-003318-abs9rvjk 158 44 bacterial bacterial JJ cord-003318-abs9rvjk 158 45 lysate lysate NN cord-003318-abs9rvjk 158 46 . . . cord-003318-abs9rvjk 159 1 LacA LacA NNP cord-003318-abs9rvjk 159 2 and and CC cord-003318-abs9rvjk 159 3 Maa Maa NNP cord-003318-abs9rvjk 159 4 proteins protein NNS cord-003318-abs9rvjk 159 5 were be VBD cord-003318-abs9rvjk 159 6 predicted predict VBN cord-003318-abs9rvjk 159 7 to to TO cord-003318-abs9rvjk 159 8 have have VB cord-003318-abs9rvjk 159 9 no no DT cord-003318-abs9rvjk 159 10 transmembrane transmembrane NNP cord-003318-abs9rvjk 159 11 helixes helix NNS cord-003318-abs9rvjk 159 12 , , , cord-003318-abs9rvjk 159 13 suggesting suggest VBG cord-003318-abs9rvjk 159 14 their -PRON- PRP$ cord-003318-abs9rvjk 159 15 soluble soluble JJ cord-003318-abs9rvjk 159 16 form form NN cord-003318-abs9rvjk 159 17 in in IN cord-003318-abs9rvjk 159 18 bacterial bacterial NN cord-003318-abs9rvjk 159 19 . . . cord-003318-abs9rvjk 160 1 Thus thus RB cord-003318-abs9rvjk 160 2 , , , cord-003318-abs9rvjk 160 3 the the DT cord-003318-abs9rvjk 160 4 remaining remain VBG cord-003318-abs9rvjk 160 5 two two CD cord-003318-abs9rvjk 160 6 genes gene NNS cord-003318-abs9rvjk 160 7 , , , cord-003318-abs9rvjk 160 8 lacA laca ADD cord-003318-abs9rvjk 160 9 and and CC cord-003318-abs9rvjk 160 10 maa maa NNP cord-003318-abs9rvjk 160 11 , , , cord-003318-abs9rvjk 160 12 were be VBD cord-003318-abs9rvjk 160 13 further further RB cord-003318-abs9rvjk 160 14 investigated investigate VBN cord-003318-abs9rvjk 160 15 . . . cord-003318-abs9rvjk 161 1 First first RB cord-003318-abs9rvjk 161 2 , , , cord-003318-abs9rvjk 161 3 the the DT cord-003318-abs9rvjk 161 4 entire entire JJ cord-003318-abs9rvjk 161 5 ORFs orfs NN cord-003318-abs9rvjk 161 6 of of IN cord-003318-abs9rvjk 161 7 the the DT cord-003318-abs9rvjk 161 8 two two CD cord-003318-abs9rvjk 161 9 genes gene NNS cord-003318-abs9rvjk 161 10 were be VBD cord-003318-abs9rvjk 161 11 isolated isolate VBN cord-003318-abs9rvjk 161 12 from from IN cord-003318-abs9rvjk 161 13 bacterial bacterial JJ cord-003318-abs9rvjk 161 14 genome genome NN cord-003318-abs9rvjk 161 15 using use VBG cord-003318-abs9rvjk 161 16 gene gene NN cord-003318-abs9rvjk 161 17 - - HYPH cord-003318-abs9rvjk 161 18 specific specific JJ cord-003318-abs9rvjk 161 19 primers primer NNS cord-003318-abs9rvjk 161 20 ( ( -LRB- cord-003318-abs9rvjk 161 21 Supplementary Supplementary NNP cord-003318-abs9rvjk 161 22 Information Information NNP cord-003318-abs9rvjk 161 23 Fig Fig NNP cord-003318-abs9rvjk 161 24 . . . cord-003318-abs9rvjk 162 1 S57A S57A NNP cord-003318-abs9rvjk 162 2 and and CC cord-003318-abs9rvjk 162 3 Table Table NNP cord-003318-abs9rvjk 162 4 S1 S1 NNP cord-003318-abs9rvjk 162 5 ) ) -RRB- cord-003318-abs9rvjk 162 6 . . . cord-003318-abs9rvjk 163 1 The the DT cord-003318-abs9rvjk 163 2 ORFs orfs NN cord-003318-abs9rvjk 163 3 of of IN cord-003318-abs9rvjk 163 4 lacA lacA NNP cord-003318-abs9rvjk 163 5 and and CC cord-003318-abs9rvjk 163 6 maa maa NNP cord-003318-abs9rvjk 163 7 genes gene NNS cord-003318-abs9rvjk 163 8 were be VBD cord-003318-abs9rvjk 163 9 612 612 CD cord-003318-abs9rvjk 163 10 and and CC cord-003318-abs9rvjk 163 11 552 552 CD cord-003318-abs9rvjk 163 12 bp bp NN cord-003318-abs9rvjk 163 13 encoding encoding NN cord-003318-abs9rvjk 163 14 polypeptides polypeptide NNS cord-003318-abs9rvjk 163 15 of of IN cord-003318-abs9rvjk 163 16 203 203 CD cord-003318-abs9rvjk 163 17 and and CC cord-003318-abs9rvjk 163 18 183 183 CD cord-003318-abs9rvjk 163 19 aa aa NNP cord-003318-abs9rvjk 163 20 , , , cord-003318-abs9rvjk 163 21 respectively respectively RB cord-003318-abs9rvjk 163 22 . . . cord-003318-abs9rvjk 164 1 The the DT cord-003318-abs9rvjk 164 2 predicted predict VBN cord-003318-abs9rvjk 164 3 molecular molecular JJ cord-003318-abs9rvjk 164 4 weights weight NNS cord-003318-abs9rvjk 164 5 of of IN cord-003318-abs9rvjk 164 6 the the DT cord-003318-abs9rvjk 164 7 two two CD cord-003318-abs9rvjk 164 8 proteins protein NNS cord-003318-abs9rvjk 164 9 were be VBD cord-003318-abs9rvjk 164 10 22.77 22.77 CD cord-003318-abs9rvjk 164 11 and and CC cord-003318-abs9rvjk 164 12 20.1 20.1 CD cord-003318-abs9rvjk 164 13 kDa kDa NNS cord-003318-abs9rvjk 164 14 . . . cord-003318-abs9rvjk 165 1 The the DT cord-003318-abs9rvjk 165 2 two two CD cord-003318-abs9rvjk 165 3 genes gene NNS cord-003318-abs9rvjk 165 4 were be VBD cord-003318-abs9rvjk 165 5 then then RB cord-003318-abs9rvjk 165 6 inserted insert VBN cord-003318-abs9rvjk 165 7 into into IN cord-003318-abs9rvjk 165 8 pET-28a(þ pet-28a(þ NN cord-003318-abs9rvjk 165 9 ) ) -RRB- cord-003318-abs9rvjk 165 10 to to TO cord-003318-abs9rvjk 165 11 generate generate VB cord-003318-abs9rvjk 165 12 two two CD cord-003318-abs9rvjk 165 13 recombinant recombinant JJ cord-003318-abs9rvjk 165 14 vectors vector NNS cord-003318-abs9rvjk 165 15 , , , cord-003318-abs9rvjk 165 16 which which WDT cord-003318-abs9rvjk 165 17 were be VBD cord-003318-abs9rvjk 165 18 introduced introduce VBN cord-003318-abs9rvjk 165 19 into into IN cord-003318-abs9rvjk 165 20 BL21(DE3 BL21(DE3 NNP cord-003318-abs9rvjk 165 21 ) ) -RRB- cord-003318-abs9rvjk 165 22 for for IN cord-003318-abs9rvjk 165 23 heterologous heterologous JJ cord-003318-abs9rvjk 165 24 expression expression NN cord-003318-abs9rvjk 165 25 . . . cord-003318-abs9rvjk 166 1 After after IN cord-003318-abs9rvjk 166 2 isopropyl isopropyl NN cord-003318-abs9rvjk 166 3 - - HYPH cord-003318-abs9rvjk 166 4 β β NN cord-003318-abs9rvjk 166 5 - - HYPH cord-003318-abs9rvjk 166 6 D D NNP cord-003318-abs9rvjk 166 7 - - HYPH cord-003318-abs9rvjk 166 8 thiogalactoside thiogalactoside NN cord-003318-abs9rvjk 166 9 ( ( -LRB- cord-003318-abs9rvjk 166 10 IPTG IPTG NNP cord-003318-abs9rvjk 166 11 ) ) -RRB- cord-003318-abs9rvjk 166 12 induction induction NN cord-003318-abs9rvjk 166 13 , , , cord-003318-abs9rvjk 166 14 the the DT cord-003318-abs9rvjk 166 15 accumulation accumulation NN cord-003318-abs9rvjk 166 16 of of IN cord-003318-abs9rvjk 166 17 approximately approximately RB cord-003318-abs9rvjk 166 18 23 23 CD cord-003318-abs9rvjk 166 19 or or CC cord-003318-abs9rvjk 166 20 20 20 CD cord-003318-abs9rvjk 166 21 kDa kDa NNS cord-003318-abs9rvjk 166 22 was be VBD cord-003318-abs9rvjk 166 23 observed observe VBN cord-003318-abs9rvjk 166 24 in in IN cord-003318-abs9rvjk 166 25 the the DT cord-003318-abs9rvjk 166 26 lysate lysate NN cord-003318-abs9rvjk 166 27 of of IN cord-003318-abs9rvjk 166 28 bacterial bacterial JJ cord-003318-abs9rvjk 166 29 strain strain NN cord-003318-abs9rvjk 166 30 harboring harbor VBG cord-003318-abs9rvjk 166 31 pET28a pet28a NN cord-003318-abs9rvjk 166 32 - - HYPH cord-003318-abs9rvjk 166 33 lacA lacA VBN cord-003318-abs9rvjk 166 34 or or CC cord-003318-abs9rvjk 166 35 pET28a pET28a NNP cord-003318-abs9rvjk 166 36 - - HYPH cord-003318-abs9rvjk 166 37 maa maa NNP cord-003318-abs9rvjk 166 38 ( ( -LRB- cord-003318-abs9rvjk 167 1 Supplementary supplementary JJ cord-003318-abs9rvjk 167 2 Information Information NNP cord-003318-abs9rvjk 167 3 Fig Fig NNP cord-003318-abs9rvjk 167 4 . . . cord-003318-abs9rvjk 167 5 S57B s57b NN cord-003318-abs9rvjk 167 6 ) ) -RRB- cord-003318-abs9rvjk 167 7 . . . cord-003318-abs9rvjk 168 1 Moreover moreover RB cord-003318-abs9rvjk 168 2 , , , cord-003318-abs9rvjk 168 3 the the DT cord-003318-abs9rvjk 168 4 presence presence NN cord-003318-abs9rvjk 168 5 of of IN cord-003318-abs9rvjk 168 6 bacterially bacterially RB cord-003318-abs9rvjk 168 7 - - HYPH cord-003318-abs9rvjk 168 8 expressed express VBN cord-003318-abs9rvjk 168 9 His -PRON- PRP$ cord-003318-abs9rvjk 168 10 - - HYPH cord-003318-abs9rvjk 168 11 LacA LacA NNP cord-003318-abs9rvjk 168 12 or or CC cord-003318-abs9rvjk 168 13 His -PRON- PRP$ cord-003318-abs9rvjk 168 14 - - HYPH cord-003318-abs9rvjk 168 15 Maa Maa NNP cord-003318-abs9rvjk 168 16 fusion fusion NN cord-003318-abs9rvjk 168 17 protein protein NN cord-003318-abs9rvjk 168 18 in in IN cord-003318-abs9rvjk 168 19 the the DT cord-003318-abs9rvjk 168 20 bacterial bacterial JJ cord-003318-abs9rvjk 168 21 lysate lysate NN cord-003318-abs9rvjk 168 22 was be VBD cord-003318-abs9rvjk 168 23 verified verify VBN cord-003318-abs9rvjk 168 24 by by IN cord-003318-abs9rvjk 168 25 Western western JJ cord-003318-abs9rvjk 168 26 - - HYPH cord-003318-abs9rvjk 168 27 blot blot NN cord-003318-abs9rvjk 168 28 with with IN cord-003318-abs9rvjk 168 29 anti anti JJ cord-003318-abs9rvjk 168 30 - - JJ cord-003318-abs9rvjk 168 31 His -PRON- PRP$ cord-003318-abs9rvjk 168 32 antibody antibody NN cord-003318-abs9rvjk 168 33 ( ( -LRB- cord-003318-abs9rvjk 168 34 Supplementary supplementary JJ cord-003318-abs9rvjk 168 35 _SP cord-003318-abs9rvjk 168 36 Information Information NNP cord-003318-abs9rvjk 168 37 Fig Fig NNP cord-003318-abs9rvjk 168 38 . . . cord-003318-abs9rvjk 169 1 S57C S57C NNP cord-003318-abs9rvjk 169 2 ) ) -RRB- cord-003318-abs9rvjk 169 3 . . . cord-003318-abs9rvjk 170 1 The the DT cord-003318-abs9rvjk 170 2 expressed express VBN cord-003318-abs9rvjk 170 3 LacA LacA NNP cord-003318-abs9rvjk 170 4 or or CC cord-003318-abs9rvjk 170 5 Maa Maa NNP cord-003318-abs9rvjk 170 6 protein protein NN cord-003318-abs9rvjk 170 7 was be VBD cord-003318-abs9rvjk 170 8 then then RB cord-003318-abs9rvjk 170 9 purified purify VBN cord-003318-abs9rvjk 170 10 to to IN cord-003318-abs9rvjk 170 11 near near IN cord-003318-abs9rvjk 170 12 homogeneity homogeneity NN cord-003318-abs9rvjk 170 13 by by IN cord-003318-abs9rvjk 170 14 affinity affinity NN cord-003318-abs9rvjk 170 15 chromatography chromatography NN cord-003318-abs9rvjk 170 16 ( ( -LRB- cord-003318-abs9rvjk 170 17 Supplementary Supplementary NNP cord-003318-abs9rvjk 170 18 Information Information NNP cord-003318-abs9rvjk 170 19 Fig Fig NNP cord-003318-abs9rvjk 170 20 . . . cord-003318-abs9rvjk 170 21 S57B s57b NN cord-003318-abs9rvjk 170 22 ) ) -RRB- cord-003318-abs9rvjk 170 23 . . . cord-003318-abs9rvjk 171 1 The the DT cord-003318-abs9rvjk 171 2 purified purify VBN cord-003318-abs9rvjk 171 3 His -PRON- PRP$ cord-003318-abs9rvjk 171 4 - - HYPH cord-003318-abs9rvjk 171 5 LacA LacA NNP cord-003318-abs9rvjk 171 6 or or CC cord-003318-abs9rvjk 171 7 His -PRON- PRP$ cord-003318-abs9rvjk 171 8 - - HYPH cord-003318-abs9rvjk 171 9 Maa Maa NNP cord-003318-abs9rvjk 171 10 fusion fusion NN cord-003318-abs9rvjk 171 11 protein protein NN cord-003318-abs9rvjk 171 12 was be VBD cord-003318-abs9rvjk 171 13 used use VBN cord-003318-abs9rvjk 171 14 as as IN cord-003318-abs9rvjk 171 15 the the DT cord-003318-abs9rvjk 171 16 biocatalyst biocatalyst NN cord-003318-abs9rvjk 171 17 to to TO cord-003318-abs9rvjk 171 18 react react VB cord-003318-abs9rvjk 171 19 with with IN cord-003318-abs9rvjk 171 20 T-17β T-17β NNS cord-003318-abs9rvjk 171 21 - - HYPH cord-003318-abs9rvjk 171 22 G g NN cord-003318-abs9rvjk 171 23 ( ( -LRB- cord-003318-abs9rvjk 171 24 8a 8a NN cord-003318-abs9rvjk 171 25 ) ) -RRB- cord-003318-abs9rvjk 171 26 and and CC cord-003318-abs9rvjk 171 27 acetyl acetyl NN cord-003318-abs9rvjk 171 28 - - HYPH cord-003318-abs9rvjk 171 29 CoA. coa. NN cord-003318-abs9rvjk 172 1 The the DT cord-003318-abs9rvjk 172 2 reactions reaction NNS cord-003318-abs9rvjk 172 3 were be VBD cord-003318-abs9rvjk 172 4 monitored monitor VBN cord-003318-abs9rvjk 172 5 by by IN cord-003318-abs9rvjk 172 6 HPLC HPLC NNP cord-003318-abs9rvjk 172 7 - - HYPH cord-003318-abs9rvjk 172 8 UV UV NNP cord-003318-abs9rvjk 172 9 / / SYM cord-003318-abs9rvjk 172 10 MS MS NNP cord-003318-abs9rvjk 172 11 analysis analysis NN cord-003318-abs9rvjk 172 12 using use VBG cord-003318-abs9rvjk 172 13 the the DT cord-003318-abs9rvjk 172 14 method method NN cord-003318-abs9rvjk 172 15 E e NN cord-003318-abs9rvjk 172 16 ( ( -LRB- cord-003318-abs9rvjk 172 17 Supplementary Supplementary NNP cord-003318-abs9rvjk 172 18 Information information NN cord-003318-abs9rvjk 172 19 Table Table NNP cord-003318-abs9rvjk 172 20 S3 S3 NNP cord-003318-abs9rvjk 172 21 ) ) -RRB- cord-003318-abs9rvjk 172 22 . . . cord-003318-abs9rvjk 173 1 As as IN cord-003318-abs9rvjk 173 2 shown show VBN cord-003318-abs9rvjk 173 3 in in IN cord-003318-abs9rvjk 173 4 Fig Fig NNP cord-003318-abs9rvjk 173 5 . . . cord-003318-abs9rvjk 174 1 4 4 LS cord-003318-abs9rvjk 174 2 , , , cord-003318-abs9rvjk 174 3 6 6 CD cord-003318-abs9rvjk 174 4 0 0 CD cord-003318-abs9rvjk 174 5 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 174 6 - - HYPH cord-003318-abs9rvjk 174 7 G g NN cord-003318-abs9rvjk 174 8 ( ( -LRB- cord-003318-abs9rvjk 174 9 8b 8b NN cord-003318-abs9rvjk 174 10 ) ) -RRB- cord-003318-abs9rvjk 174 11 was be VBD cord-003318-abs9rvjk 174 12 detected detect VBN cord-003318-abs9rvjk 174 13 in in IN cord-003318-abs9rvjk 174 14 LacA LacA NNP cord-003318-abs9rvjk 174 15 - - HYPH cord-003318-abs9rvjk 174 16 catalyzed catalyze VBN cord-003318-abs9rvjk 174 17 bioconversion bioconversion NN cord-003318-abs9rvjk 174 18 of of IN cord-003318-abs9rvjk 174 19 T-17β T-17β NNP cord-003318-abs9rvjk 174 20 - - HYPH cord-003318-abs9rvjk 174 21 G g NN cord-003318-abs9rvjk 174 22 ( ( -LRB- cord-003318-abs9rvjk 174 23 8a 8a NN cord-003318-abs9rvjk 174 24 ) ) -RRB- cord-003318-abs9rvjk 174 25 , , , cord-003318-abs9rvjk 174 26 attesting attest VBG cord-003318-abs9rvjk 174 27 lacA laca ADD cord-003318-abs9rvjk 174 28 encoded encode VBD cord-003318-abs9rvjk 174 29 a a DT cord-003318-abs9rvjk 174 30 SGA SGA NNP cord-003318-abs9rvjk 174 31 ( ( -LRB- cord-003318-abs9rvjk 174 32 Fig Fig NNP cord-003318-abs9rvjk 174 33 . . NNP cord-003318-abs9rvjk 174 34 4 4 CD cord-003318-abs9rvjk 174 35 , , , cord-003318-abs9rvjk 174 36 upper upper JJ cord-003318-abs9rvjk 174 37 panel panel NN cord-003318-abs9rvjk 174 38 ) ) -RRB- cord-003318-abs9rvjk 174 39 . . . cord-003318-abs9rvjk 175 1 On on IN cord-003318-abs9rvjk 175 2 the the DT cord-003318-abs9rvjk 175 3 contrary contrary NN cord-003318-abs9rvjk 175 4 , , , cord-003318-abs9rvjk 175 5 there there EX cord-003318-abs9rvjk 175 6 were be VBD cord-003318-abs9rvjk 175 7 not not RB cord-003318-abs9rvjk 175 8 any any DT cord-003318-abs9rvjk 175 9 new new JJ cord-003318-abs9rvjk 175 10 products product NNS cord-003318-abs9rvjk 175 11 in in IN cord-003318-abs9rvjk 175 12 Maa Maa NNP cord-003318-abs9rvjk 175 13 - - HYPH cord-003318-abs9rvjk 175 14 mediated mediate VBN cord-003318-abs9rvjk 175 15 reaction reaction NN cord-003318-abs9rvjk 175 16 . . . cord-003318-abs9rvjk 176 1 LacA LacA NNP cord-003318-abs9rvjk 176 2 was be VBD cord-003318-abs9rvjk 176 3 thus thus RB cord-003318-abs9rvjk 176 4 designated designate VBN cord-003318-abs9rvjk 176 5 as as IN cord-003318-abs9rvjk 176 6 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 176 7 ( ( -LRB- cord-003318-abs9rvjk 176 8 E. E. NNP cord-003318-abs9rvjk 176 9 coli coli VBZ cord-003318-abs9rvjk 176 10 steroidal steroidal JJ cord-003318-abs9rvjk 176 11 glucoside glucoside NN cord-003318-abs9rvjk 176 12 acetyltransferase acetyltransferase NNP cord-003318-abs9rvjk 176 13 ) ) -RRB- cord-003318-abs9rvjk 176 14 for for IN cord-003318-abs9rvjk 176 15 convenience convenience NN cord-003318-abs9rvjk 176 16 hereinafter hereinafter NNS cord-003318-abs9rvjk 176 17 and and CC cord-003318-abs9rvjk 176 18 submitted submit VBN cord-003318-abs9rvjk 176 19 to to IN cord-003318-abs9rvjk 176 20 GenBank GenBank NNP cord-003318-abs9rvjk 176 21 with with IN cord-003318-abs9rvjk 176 22 an an DT cord-003318-abs9rvjk 176 23 accession accession NN cord-003318-abs9rvjk 176 24 number number NN cord-003318-abs9rvjk 176 25 of of IN cord-003318-abs9rvjk 176 26 MF688777 MF688777 NNP cord-003318-abs9rvjk 176 27 . . . cord-003318-abs9rvjk 177 1 It -PRON- PRP cord-003318-abs9rvjk 177 2 is be VBZ cord-003318-abs9rvjk 177 3 generally generally RB cord-003318-abs9rvjk 177 4 accepted accept VBN cord-003318-abs9rvjk 177 5 that that IN cord-003318-abs9rvjk 177 6 hydrolases hydrolase NNS cord-003318-abs9rvjk 177 7 and and CC cord-003318-abs9rvjk 177 8 acyltransferases acyltransferase NNS cord-003318-abs9rvjk 177 9 are be VBP cord-003318-abs9rvjk 177 10 two two CD cord-003318-abs9rvjk 177 11 classes class NNS cord-003318-abs9rvjk 177 12 of of IN cord-003318-abs9rvjk 177 13 enzymes enzyme NNS cord-003318-abs9rvjk 177 14 responsible responsible JJ cord-003318-abs9rvjk 177 15 for for IN cord-003318-abs9rvjk 177 16 acylation acylation NN cord-003318-abs9rvjk 177 17 reactions reaction NNS cord-003318-abs9rvjk 177 18 of of IN cord-003318-abs9rvjk 177 19 SGs SGs NNP cord-003318-abs9rvjk 177 20 22 22 CD cord-003318-abs9rvjk 177 21 . . . cord-003318-abs9rvjk 178 1 The the DT cord-003318-abs9rvjk 178 2 enzymatic enzymatic JJ cord-003318-abs9rvjk 178 3 acylations acylation NNS cord-003318-abs9rvjk 178 4 reported report VBN cord-003318-abs9rvjk 178 5 now now RB cord-003318-abs9rvjk 178 6 are be VBP cord-003318-abs9rvjk 178 7 largely largely RB cord-003318-abs9rvjk 178 8 performed perform VBN cord-003318-abs9rvjk 178 9 by by IN cord-003318-abs9rvjk 178 10 hydrolases hydrolase NNS cord-003318-abs9rvjk 178 11 like like IN cord-003318-abs9rvjk 178 12 lipases lipase NNS cord-003318-abs9rvjk 178 13 22 22 CD cord-003318-abs9rvjk 178 14 . . . cord-003318-abs9rvjk 179 1 On on IN cord-003318-abs9rvjk 179 2 the the DT cord-003318-abs9rvjk 179 3 other other JJ cord-003318-abs9rvjk 179 4 hand hand NN cord-003318-abs9rvjk 179 5 , , , cord-003318-abs9rvjk 179 6 not not RB cord-003318-abs9rvjk 179 7 any any DT cord-003318-abs9rvjk 179 8 genes gene NNS cord-003318-abs9rvjk 179 9 encoding encode VBG cord-003318-abs9rvjk 179 10 SGAs sga NNS cord-003318-abs9rvjk 179 11 are be VBP cord-003318-abs9rvjk 179 12 isolated isolate VBN cord-003318-abs9rvjk 179 13 up up IN cord-003318-abs9rvjk 179 14 to to IN cord-003318-abs9rvjk 179 15 date date NN cord-003318-abs9rvjk 179 16 16 16 CD cord-003318-abs9rvjk 179 17 , , , cord-003318-abs9rvjk 179 18 22 22 CD cord-003318-abs9rvjk 179 19 . . . cord-003318-abs9rvjk 180 1 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 180 2 is be VBZ cord-003318-abs9rvjk 180 3 therefore therefore RB cord-003318-abs9rvjk 180 4 regarded regard VBN cord-003318-abs9rvjk 180 5 as as IN cord-003318-abs9rvjk 180 6 the the DT cord-003318-abs9rvjk 180 7 first first JJ cord-003318-abs9rvjk 180 8 steroidal steroidal JJ cord-003318-abs9rvjk 180 9 glycoside glycoside NN cord-003318-abs9rvjk 180 10 acyltransferase acyltransferase NN cord-003318-abs9rvjk 180 11 catalyzing catalyze VBG cord-003318-abs9rvjk 180 12 the the DT cord-003318-abs9rvjk 180 13 attachment attachment NN cord-003318-abs9rvjk 180 14 of of IN cord-003318-abs9rvjk 180 15 acyl acyl NNP cord-003318-abs9rvjk 180 16 groups group NNS cord-003318-abs9rvjk 180 17 into into IN cord-003318-abs9rvjk 180 18 the the DT cord-003318-abs9rvjk 180 19 hydroxyl hydroxyl NN cord-003318-abs9rvjk 180 20 groups group NNS cord-003318-abs9rvjk 180 21 of of IN cord-003318-abs9rvjk 180 22 steroidal steroidal JJ cord-003318-abs9rvjk 180 23 17β 17β NNS cord-003318-abs9rvjk 180 24 - - : cord-003318-abs9rvjk 180 25 glycosides glycoside NNS cord-003318-abs9rvjk 180 26 , , , cord-003318-abs9rvjk 180 27 to to IN cord-003318-abs9rvjk 180 28 our -PRON- PRP$ cord-003318-abs9rvjk 180 29 knowledge knowledge NN cord-003318-abs9rvjk 180 30 . . . cord-003318-abs9rvjk 181 1 Also also RB cord-003318-abs9rvjk 181 2 , , , cord-003318-abs9rvjk 181 3 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 181 4 was be VBD cord-003318-abs9rvjk 181 5 observed observe VBN cord-003318-abs9rvjk 181 6 to to TO cord-003318-abs9rvjk 181 7 catalyze catalyze VB cord-003318-abs9rvjk 181 8 another another DT cord-003318-abs9rvjk 181 9 steroidal steroidal JJ cord-003318-abs9rvjk 181 10 17βglycoside 17βglycoside NN cord-003318-abs9rvjk 181 11 , , , cord-003318-abs9rvjk 181 12 E-17β E-17β NNP cord-003318-abs9rvjk 181 13 - - HYPH cord-003318-abs9rvjk 181 14 G G NNP cord-003318-abs9rvjk 181 15 ( ( -LRB- cord-003318-abs9rvjk 181 16 9a 9a NN cord-003318-abs9rvjk 181 17 ) ) -RRB- cord-003318-abs9rvjk 181 18 , , , cord-003318-abs9rvjk 181 19 to to TO cord-003318-abs9rvjk 181 20 form form VB cord-003318-abs9rvjk 181 21 corresponding correspond VBG cord-003318-abs9rvjk 181 22 acylate acylate NNP cord-003318-abs9rvjk 181 23 ( ( -LRB- cord-003318-abs9rvjk 181 24 9b 9b NNS cord-003318-abs9rvjk 181 25 , , , cord-003318-abs9rvjk 181 26 Fig Fig NNP cord-003318-abs9rvjk 181 27 . . NNP cord-003318-abs9rvjk 181 28 5 5 CD cord-003318-abs9rvjk 181 29 , , , cord-003318-abs9rvjk 181 30 upper upper JJ cord-003318-abs9rvjk 181 31 panel panel NN cord-003318-abs9rvjk 181 32 ) ) -RRB- cord-003318-abs9rvjk 181 33 . . . cord-003318-abs9rvjk 182 1 On on IN cord-003318-abs9rvjk 182 2 the the DT cord-003318-abs9rvjk 182 3 other other JJ cord-003318-abs9rvjk 182 4 hand hand NN cord-003318-abs9rvjk 182 5 , , , cord-003318-abs9rvjk 182 6 the the DT cord-003318-abs9rvjk 182 7 other other JJ cord-003318-abs9rvjk 182 8 glucosides glucoside NNS cord-003318-abs9rvjk 182 9 listed list VBN cord-003318-abs9rvjk 182 10 in in IN cord-003318-abs9rvjk 182 11 Supplementary Supplementary NNP cord-003318-abs9rvjk 182 12 Information Information NNP cord-003318-abs9rvjk 182 13 Fig Fig NNP cord-003318-abs9rvjk 182 14 . . . cord-003318-abs9rvjk 183 1 S58 S58 NNP cord-003318-abs9rvjk 183 2 could could MD cord-003318-abs9rvjk 183 3 not not RB cord-003318-abs9rvjk 183 4 be be VB cord-003318-abs9rvjk 183 5 acetylated acetylate VBN cord-003318-abs9rvjk 183 6 by by IN cord-003318-abs9rvjk 183 7 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 183 8 , , , cord-003318-abs9rvjk 183 9 testifying testify VBG cord-003318-abs9rvjk 183 10 EcSGA1 ecsga1 NN cord-003318-abs9rvjk 183 11 was be VBD cord-003318-abs9rvjk 183 12 specific specific JJ cord-003318-abs9rvjk 183 13 to to IN cord-003318-abs9rvjk 183 14 steroidal steroidal JJ cord-003318-abs9rvjk 183 15 17β 17β NNS cord-003318-abs9rvjk 183 16 - - HYPH cord-003318-abs9rvjk 183 17 glycosides glycoside NNS cord-003318-abs9rvjk 183 18 . . . cord-003318-abs9rvjk 184 1 Moreover moreover RB cord-003318-abs9rvjk 184 2 , , , cord-003318-abs9rvjk 184 3 the the DT cord-003318-abs9rvjk 184 4 acyl acyl NN cord-003318-abs9rvjk 184 5 donor donor NN cord-003318-abs9rvjk 184 6 promiscuity promiscuity NN cord-003318-abs9rvjk 184 7 of of IN cord-003318-abs9rvjk 184 8 EcSGA1 ecsga1 NN cord-003318-abs9rvjk 184 9 was be VBD cord-003318-abs9rvjk 184 10 investigated investigate VBN cord-003318-abs9rvjk 184 11 . . . cord-003318-abs9rvjk 185 1 T-17β T-17β NNP cord-003318-abs9rvjk 185 2 - - HYPH cord-003318-abs9rvjk 185 3 G g NN cord-003318-abs9rvjk 185 4 ( ( -LRB- cord-003318-abs9rvjk 185 5 8a 8a NN cord-003318-abs9rvjk 185 6 ) ) -RRB- cord-003318-abs9rvjk 185 7 or or CC cord-003318-abs9rvjk 185 8 E-17β E-17β NNP cord-003318-abs9rvjk 185 9 - - HYPH cord-003318-abs9rvjk 185 10 G g NN cord-003318-abs9rvjk 185 11 ( ( -LRB- cord-003318-abs9rvjk 185 12 9a 9a NN cord-003318-abs9rvjk 185 13 ) ) -RRB- cord-003318-abs9rvjk 185 14 was be VBD cord-003318-abs9rvjk 185 15 used use VBN cord-003318-abs9rvjk 185 16 as as IN cord-003318-abs9rvjk 185 17 the the DT cord-003318-abs9rvjk 185 18 acyl acyl NN cord-003318-abs9rvjk 185 19 acceptor acceptor NN cord-003318-abs9rvjk 185 20 to to TO cord-003318-abs9rvjk 185 21 react react VB cord-003318-abs9rvjk 185 22 with with IN cord-003318-abs9rvjk 185 23 different different JJ cord-003318-abs9rvjk 185 24 acyl acyl NN cord-003318-abs9rvjk 185 25 donors donor NNS cord-003318-abs9rvjk 185 26 ( ( -LRB- cord-003318-abs9rvjk 185 27 acetyl acetyl NNP cord-003318-abs9rvjk 185 28 - - HYPH cord-003318-abs9rvjk 185 29 CoA CoA NNP cord-003318-abs9rvjk 185 30 , , , cord-003318-abs9rvjk 185 31 succinyl succinyl NNP cord-003318-abs9rvjk 185 32 - - HYPH cord-003318-abs9rvjk 185 33 CoA CoA NNP cord-003318-abs9rvjk 185 34 , , , cord-003318-abs9rvjk 185 35 arachidonoyl arachidonoyl NNP cord-003318-abs9rvjk 185 36 - - HYPH cord-003318-abs9rvjk 185 37 CoA CoA NNP cord-003318-abs9rvjk 185 38 , , , cord-003318-abs9rvjk 185 39 palmitoyl palmitoyl NNP cord-003318-abs9rvjk 185 40 - - HYPH cord-003318-abs9rvjk 185 41 CoA CoA NNP cord-003318-abs9rvjk 185 42 and and CC cord-003318-abs9rvjk 185 43 acetoacetyl acetoacetyl NNP cord-003318-abs9rvjk 185 44 - - HYPH cord-003318-abs9rvjk 185 45 CoA CoA NNP cord-003318-abs9rvjk 185 46 ) ) -RRB- cord-003318-abs9rvjk 185 47 under under IN cord-003318-abs9rvjk 185 48 the the DT cord-003318-abs9rvjk 185 49 action action NN cord-003318-abs9rvjk 185 50 of of IN cord-003318-abs9rvjk 185 51 the the DT cord-003318-abs9rvjk 185 52 purified purify VBN cord-003318-abs9rvjk 185 53 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 185 54 . . . cord-003318-abs9rvjk 186 1 Results result NNS cord-003318-abs9rvjk 186 2 manifested manifest VBD cord-003318-abs9rvjk 186 3 that that IN cord-003318-abs9rvjk 186 4 neither neither CC cord-003318-abs9rvjk 186 5 T-17β T-17β NNP cord-003318-abs9rvjk 186 6 - - HYPH cord-003318-abs9rvjk 186 7 G g NN cord-003318-abs9rvjk 186 8 ( ( -LRB- cord-003318-abs9rvjk 186 9 8a 8a NN cord-003318-abs9rvjk 186 10 ) ) -RRB- cord-003318-abs9rvjk 186 11 nor nor CC cord-003318-abs9rvjk 186 12 E-17β E-17β NNP cord-003318-abs9rvjk 186 13 - - HYPH cord-003318-abs9rvjk 186 14 G g NN cord-003318-abs9rvjk 186 15 ( ( -LRB- cord-003318-abs9rvjk 186 16 9a 9a NN cord-003318-abs9rvjk 186 17 ) ) -RRB- cord-003318-abs9rvjk 186 18 could could MD cord-003318-abs9rvjk 186 19 react react VB cord-003318-abs9rvjk 186 20 with with IN cord-003318-abs9rvjk 186 21 these these DT cord-003318-abs9rvjk 186 22 acyl acyl NN cord-003318-abs9rvjk 186 23 donors donor NNS cord-003318-abs9rvjk 186 24 except except IN cord-003318-abs9rvjk 186 25 acetyl acetyl NN cord-003318-abs9rvjk 186 26 - - HYPH cord-003318-abs9rvjk 186 27 CoA CoA NNP cord-003318-abs9rvjk 186 28 , , , cord-003318-abs9rvjk 186 29 indicating indicate VBG cord-003318-abs9rvjk 186 30 that that IN cord-003318-abs9rvjk 186 31 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 186 32 had have VBD cord-003318-abs9rvjk 186 33 strict strict JJ cord-003318-abs9rvjk 186 34 donor donor NN cord-003318-abs9rvjk 186 35 selectivity selectivity NN cord-003318-abs9rvjk 186 36 . . . cord-003318-abs9rvjk 187 1 After after IN cord-003318-abs9rvjk 187 2 careful careful JJ cord-003318-abs9rvjk 187 3 check check NN cord-003318-abs9rvjk 187 4 of of IN cord-003318-abs9rvjk 187 5 EcSGA1-catalyzed ecsga1-catalyzed JJ cord-003318-abs9rvjk 187 6 reaction reaction NN cord-003318-abs9rvjk 187 7 mixture mixture NN cord-003318-abs9rvjk 187 8 in in IN cord-003318-abs9rvjk 187 9 HPLC HPLC NNP cord-003318-abs9rvjk 187 10 profile profile NN cord-003318-abs9rvjk 187 11 , , , cord-003318-abs9rvjk 187 12 we -PRON- PRP cord-003318-abs9rvjk 187 13 have have VBP cord-003318-abs9rvjk 187 14 found find VBN cord-003318-abs9rvjk 187 15 several several JJ cord-003318-abs9rvjk 187 16 other other JJ cord-003318-abs9rvjk 187 17 minor minor JJ cord-003318-abs9rvjk 187 18 peaks peak NNS cord-003318-abs9rvjk 187 19 adjacent adjacent JJ cord-003318-abs9rvjk 187 20 to to IN cord-003318-abs9rvjk 187 21 the the DT cord-003318-abs9rvjk 187 22 major major JJ cord-003318-abs9rvjk 187 23 product product NN cord-003318-abs9rvjk 187 24 8b 8b NN cord-003318-abs9rvjk 187 25 ( ( -LRB- cord-003318-abs9rvjk 187 26 Fig Fig NNP cord-003318-abs9rvjk 187 27 . . NNP cord-003318-abs9rvjk 187 28 4 4 CD cord-003318-abs9rvjk 187 29 , , , cord-003318-abs9rvjk 187 30 upper upper JJ cord-003318-abs9rvjk 187 31 panel panel NN cord-003318-abs9rvjk 187 32 ) ) -RRB- cord-003318-abs9rvjk 187 33 . . . cord-003318-abs9rvjk 188 1 These these DT cord-003318-abs9rvjk 188 2 minor minor JJ cord-003318-abs9rvjk 188 3 peaks peak NNS cord-003318-abs9rvjk 188 4 are be VBP cord-003318-abs9rvjk 188 5 so so RB cord-003318-abs9rvjk 188 6 close close JJ cord-003318-abs9rvjk 188 7 that that IN cord-003318-abs9rvjk 188 8 we -PRON- PRP cord-003318-abs9rvjk 188 9 could could MD cord-003318-abs9rvjk 188 10 not not RB cord-003318-abs9rvjk 188 11 distinguish distinguish VB cord-003318-abs9rvjk 188 12 . . . cord-003318-abs9rvjk 189 1 Therefore therefore RB cord-003318-abs9rvjk 189 2 , , , cord-003318-abs9rvjk 189 3 an an DT cord-003318-abs9rvjk 189 4 efficient efficient JJ cord-003318-abs9rvjk 189 5 HPLC HPLC NNP cord-003318-abs9rvjk 189 6 method method NN cord-003318-abs9rvjk 189 7 , , , cord-003318-abs9rvjk 189 8 namely namely RB cord-003318-abs9rvjk 189 9 method method NN cord-003318-abs9rvjk 189 10 I -PRON- PRP cord-003318-abs9rvjk 189 11 ( ( -LRB- cord-003318-abs9rvjk 189 12 Supplementary supplementary JJ cord-003318-abs9rvjk 189 13 Information information NN cord-003318-abs9rvjk 189 14 _SP cord-003318-abs9rvjk 189 15 Table Table NNP cord-003318-abs9rvjk 189 16 S3 S3 NNP cord-003318-abs9rvjk 189 17 ) ) -RRB- cord-003318-abs9rvjk 189 18 , , , cord-003318-abs9rvjk 189 19 was be VBD cord-003318-abs9rvjk 189 20 developed develop VBN cord-003318-abs9rvjk 189 21 to to TO cord-003318-abs9rvjk 189 22 separate separate VB cord-003318-abs9rvjk 189 23 these these DT cord-003318-abs9rvjk 189 24 peaks peak NNS cord-003318-abs9rvjk 189 25 . . . cord-003318-abs9rvjk 190 1 As as IN cord-003318-abs9rvjk 190 2 shown show VBN cord-003318-abs9rvjk 190 3 in in IN cord-003318-abs9rvjk 190 4 Fig Fig NNP cord-003318-abs9rvjk 190 5 . . . cord-003318-abs9rvjk 190 6 4 4 LS cord-003318-abs9rvjk 190 7 ( ( -LRB- cord-003318-abs9rvjk 190 8 lower low JJR cord-003318-abs9rvjk 190 9 panel panel NN cord-003318-abs9rvjk 190 10 ) ) -RRB- cord-003318-abs9rvjk 190 11 , , , cord-003318-abs9rvjk 190 12 besides besides IN cord-003318-abs9rvjk 190 13 the the DT cord-003318-abs9rvjk 190 14 major major JJ cord-003318-abs9rvjk 190 15 product product NN cord-003318-abs9rvjk 190 16 8b 8b NN cord-003318-abs9rvjk 190 17 ( ( -LRB- cord-003318-abs9rvjk 190 18 t t NN cord-003318-abs9rvjk 190 19 R R NNP cord-003318-abs9rvjk 190 20 ¼ ¼ CD cord-003318-abs9rvjk 190 21 25.860 25.860 CD cord-003318-abs9rvjk 190 22 min min NNP cord-003318-abs9rvjk 190 23 ) ) -RRB- cord-003318-abs9rvjk 190 24 , , , cord-003318-abs9rvjk 190 25 we -PRON- PRP cord-003318-abs9rvjk 190 26 observed observe VBD cord-003318-abs9rvjk 190 27 three three CD cord-003318-abs9rvjk 190 28 other other JJ cord-003318-abs9rvjk 190 29 minor minor JJ cord-003318-abs9rvjk 190 30 peaks peak NNS cord-003318-abs9rvjk 190 31 at at IN cord-003318-abs9rvjk 190 32 t t NNP cord-003318-abs9rvjk 190 33 R R NNP cord-003318-abs9rvjk 190 34 ¼ ¼ NNP cord-003318-abs9rvjk 190 35 18.243 18.243 CD cord-003318-abs9rvjk 190 36 , , , cord-003318-abs9rvjk 190 37 19.013 19.013 CD cord-003318-abs9rvjk 190 38 Table table NN cord-003318-abs9rvjk 190 39 S3 S3 NNP cord-003318-abs9rvjk 190 40 ) ) -RRB- cord-003318-abs9rvjk 190 41 . . . cord-003318-abs9rvjk 191 1 Lower low JJR cord-003318-abs9rvjk 191 2 panel panel NN cord-003318-abs9rvjk 191 3 , , , cord-003318-abs9rvjk 191 4 HPLC HPLC NNP cord-003318-abs9rvjk 191 5 profile profile NN cord-003318-abs9rvjk 191 6 of of IN cord-003318-abs9rvjk 191 7 acetylated acetylated JJ cord-003318-abs9rvjk 191 8 products product NNS cord-003318-abs9rvjk 191 9 of of IN cord-003318-abs9rvjk 191 10 8a 8a NN cord-003318-abs9rvjk 191 11 separated separate VBN cord-003318-abs9rvjk 191 12 by by IN cord-003318-abs9rvjk 191 13 chromatogramic chromatogramic JJ cord-003318-abs9rvjk 191 14 method method NN cord-003318-abs9rvjk 192 1 I -PRON- PRP cord-003318-abs9rvjk 192 2 ( ( -LRB- cord-003318-abs9rvjk 192 3 Supplementary Supplementary NNP cord-003318-abs9rvjk 192 4 Information Information NNP cord-003318-abs9rvjk 192 5 Table Table NNP cord-003318-abs9rvjk 192 6 S3 S3 NNP cord-003318-abs9rvjk 192 7 ) ) -RRB- cord-003318-abs9rvjk 192 8 . . . cord-003318-abs9rvjk 193 1 and and CC cord-003318-abs9rvjk 193 2 23.680 23.680 CD cord-003318-abs9rvjk 193 3 min min NNP cord-003318-abs9rvjk 193 4 , , , cord-003318-abs9rvjk 193 5 respectively respectively RB cord-003318-abs9rvjk 193 6 . . . cord-003318-abs9rvjk 194 1 The the DT cord-003318-abs9rvjk 194 2 LC LC NNP cord-003318-abs9rvjk 194 3 - - HYPH cord-003318-abs9rvjk 194 4 MS MS NNP cord-003318-abs9rvjk 194 5 measurement measurement NN cord-003318-abs9rvjk 194 6 of of IN cord-003318-abs9rvjk 194 7 these these DT cord-003318-abs9rvjk 194 8 minor minor JJ cord-003318-abs9rvjk 194 9 peaks peak NNS cord-003318-abs9rvjk 194 10 showed show VBD cord-003318-abs9rvjk 194 11 that that IN cord-003318-abs9rvjk 194 12 all all DT cord-003318-abs9rvjk 194 13 of of IN cord-003318-abs9rvjk 194 14 them -PRON- PRP cord-003318-abs9rvjk 194 15 have have VBP cord-003318-abs9rvjk 194 16 an an DT cord-003318-abs9rvjk 195 1 [ [ -LRB- cord-003318-abs9rvjk 195 2 M M NNP cord-003318-abs9rvjk 195 3 þ þ NNP cord-003318-abs9rvjk 195 4 Na Na NNP cord-003318-abs9rvjk 195 5 ] ] -RRB- cord-003318-abs9rvjk 196 1 þ þ LS cord-003318-abs9rvjk 196 2 value value NN cord-003318-abs9rvjk 196 3 of of IN cord-003318-abs9rvjk 196 4 515.3 515.3 CD cord-003318-abs9rvjk 196 5 , , , cord-003318-abs9rvjk 196 6 thus thus RB cord-003318-abs9rvjk 196 7 suggesting suggest VBG cord-003318-abs9rvjk 196 8 their -PRON- PRP$ cord-003318-abs9rvjk 196 9 monoacetylated monoacetylate VBN cord-003318-abs9rvjk 196 10 testosterone testosterone NN cord-003318-abs9rvjk 196 11 glucosides glucoside NNS cord-003318-abs9rvjk 196 12 ( ( -LRB- cord-003318-abs9rvjk 196 13 Supplementary Supplementary NNP cord-003318-abs9rvjk 196 14 Information Information NNP cord-003318-abs9rvjk 196 15 Fig Fig NNP cord-003318-abs9rvjk 196 16 . . . cord-003318-abs9rvjk 197 1 S59 S59 NNP cord-003318-abs9rvjk 197 2 ) ) -RRB- cord-003318-abs9rvjk 197 3 . . . cord-003318-abs9rvjk 198 1 Likewise likewise RB cord-003318-abs9rvjk 198 2 , , , cord-003318-abs9rvjk 198 3 E-17β E-17β NNP cord-003318-abs9rvjk 198 4 - - HYPH cord-003318-abs9rvjk 198 5 G G NNP cord-003318-abs9rvjk 198 6 ( ( -LRB- cord-003318-abs9rvjk 198 7 9a 9a NN cord-003318-abs9rvjk 198 8 , , , cord-003318-abs9rvjk 198 9 t t NN cord-003318-abs9rvjk 198 10 R R NNP cord-003318-abs9rvjk 198 11 ¼ ¼ NNP cord-003318-abs9rvjk 198 12 13.587 13.587 CD cord-003318-abs9rvjk 198 13 min min NNP cord-003318-abs9rvjk 198 14 ) ) -RRB- cord-003318-abs9rvjk 198 15 was be VBD cord-003318-abs9rvjk 198 16 observed observe VBN cord-003318-abs9rvjk 198 17 to to TO cord-003318-abs9rvjk 198 18 form form VB cord-003318-abs9rvjk 198 19 four four CD cord-003318-abs9rvjk 198 20 acetylated acetylated JJ cord-003318-abs9rvjk 198 21 glucosides glucoside NNS cord-003318-abs9rvjk 198 22 using use VBG cord-003318-abs9rvjk 198 23 purified purify VBN cord-003318-abs9rvjk 198 24 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 198 25 as as IN cord-003318-abs9rvjk 198 26 the the DT cord-003318-abs9rvjk 198 27 biocatalyst biocatalyst NN cord-003318-abs9rvjk 198 28 ( ( -LRB- cord-003318-abs9rvjk 198 29 Fig Fig NNP cord-003318-abs9rvjk 198 30 . . . cord-003318-abs9rvjk 198 31 5 5 CD cord-003318-abs9rvjk 198 32 ) ) -RRB- cord-003318-abs9rvjk 198 33 . . . cord-003318-abs9rvjk 199 1 Besides besides IN cord-003318-abs9rvjk 199 2 the the DT cord-003318-abs9rvjk 199 3 well well RB cord-003318-abs9rvjk 199 4 - - HYPH cord-003318-abs9rvjk 199 5 characterized characterize VBN cord-003318-abs9rvjk 199 6 6 6 CD cord-003318-abs9rvjk 199 7 0 0 CD cord-003318-abs9rvjk 199 8 -AE-17β -AE-17β NNS cord-003318-abs9rvjk 199 9 - - HYPH cord-003318-abs9rvjk 199 10 G g NN cord-003318-abs9rvjk 199 11 ( ( -LRB- cord-003318-abs9rvjk 199 12 9b 9b NNS cord-003318-abs9rvjk 199 13 , , , cord-003318-abs9rvjk 199 14 t t NNP cord-003318-abs9rvjk 199 15 R R NNP cord-003318-abs9rvjk 199 16 ¼ ¼ CD cord-003318-abs9rvjk 199 17 15.247 15.247 CD cord-003318-abs9rvjk 199 18 min min NNP cord-003318-abs9rvjk 199 19 ) ) -RRB- cord-003318-abs9rvjk 199 20 , , , cord-003318-abs9rvjk 199 21 the the DT cord-003318-abs9rvjk 199 22 other other JJ cord-003318-abs9rvjk 199 23 three three CD cord-003318-abs9rvjk 199 24 products product NNS cord-003318-abs9rvjk 199 25 were be VBD cord-003318-abs9rvjk 199 26 determined determine VBN cord-003318-abs9rvjk 199 27 to to TO cord-003318-abs9rvjk 199 28 be be VB cord-003318-abs9rvjk 199 29 monoacetylated monoacetylate VBN cord-003318-abs9rvjk 199 30 estradiol estradiol NNP cord-003318-abs9rvjk 199 31 glucosides glucoside NNS cord-003318-abs9rvjk 199 32 based base VBN cord-003318-abs9rvjk 199 33 on on IN cord-003318-abs9rvjk 199 34 their -PRON- PRP$ cord-003318-abs9rvjk 199 35 MS MS NNP cord-003318-abs9rvjk 199 36 data datum NNS cord-003318-abs9rvjk 199 37 ( ( -LRB- cord-003318-abs9rvjk 199 38 Supplementary Supplementary NNP cord-003318-abs9rvjk 199 39 Information Information NNP cord-003318-abs9rvjk 199 40 Fig Fig NNP cord-003318-abs9rvjk 199 41 . . . cord-003318-abs9rvjk 199 42 S60 S60 NNP cord-003318-abs9rvjk 199 43 ) ) -RRB- cord-003318-abs9rvjk 199 44 . . . cord-003318-abs9rvjk 200 1 It -PRON- PRP cord-003318-abs9rvjk 200 2 was be VBD cord-003318-abs9rvjk 200 3 assumed assume VBN cord-003318-abs9rvjk 200 4 that that IN cord-003318-abs9rvjk 200 5 EcSGA1 ecsga1 NN cord-003318-abs9rvjk 200 6 could could MD cord-003318-abs9rvjk 200 7 introduce introduce VB cord-003318-abs9rvjk 200 8 an an DT cord-003318-abs9rvjk 200 9 acyl acyl NN cord-003318-abs9rvjk 200 10 group group NN cord-003318-abs9rvjk 200 11 into into IN cord-003318-abs9rvjk 200 12 different different JJ cord-003318-abs9rvjk 200 13 hydroxyl hydroxyl NN cord-003318-abs9rvjk 200 14 groups group NNS cord-003318-abs9rvjk 200 15 of of IN cord-003318-abs9rvjk 200 16 steroidal steroidal JJ cord-003318-abs9rvjk 200 17 17β 17β NNS cord-003318-abs9rvjk 200 18 - - HYPH cord-003318-abs9rvjk 200 19 glycosides glycoside NNS cord-003318-abs9rvjk 200 20 , , , cord-003318-abs9rvjk 200 21 generating generate VBG cord-003318-abs9rvjk 200 22 varied varied JJ cord-003318-abs9rvjk 200 23 monoacetylated monoacetylated JJ cord-003318-abs9rvjk 200 24 products product NNS cord-003318-abs9rvjk 200 25 ( ( -LRB- cord-003318-abs9rvjk 200 26 Figs fig NNS cord-003318-abs9rvjk 200 27 . . . cord-003318-abs9rvjk 201 1 4 4 CD cord-003318-abs9rvjk 201 2 and and CC cord-003318-abs9rvjk 201 3 5 5 CD cord-003318-abs9rvjk 201 4 ) ) -RRB- cord-003318-abs9rvjk 201 5 . . . cord-003318-abs9rvjk 202 1 To to TO cord-003318-abs9rvjk 202 2 obtain obtain VB cord-003318-abs9rvjk 202 3 sufficient sufficient JJ cord-003318-abs9rvjk 202 4 amount amount NN cord-003318-abs9rvjk 202 5 of of IN cord-003318-abs9rvjk 202 6 monoacetylated monoacetylate VBN cord-003318-abs9rvjk 202 7 testosterone testosterone NN cord-003318-abs9rvjk 202 8 glucosides glucoside NNS cord-003318-abs9rvjk 202 9 for for IN cord-003318-abs9rvjk 202 10 structural structural JJ cord-003318-abs9rvjk 202 11 characterization characterization NN cord-003318-abs9rvjk 202 12 and and CC cord-003318-abs9rvjk 202 13 further further JJ cord-003318-abs9rvjk 202 14 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 202 15 assay assay NN cord-003318-abs9rvjk 202 16 , , , cord-003318-abs9rvjk 202 17 an an DT cord-003318-abs9rvjk 202 18 enzymatic enzymatic JJ cord-003318-abs9rvjk 202 19 two two CD cord-003318-abs9rvjk 202 20 - - HYPH cord-003318-abs9rvjk 202 21 step step NN cord-003318-abs9rvjk 202 22 process process NN cord-003318-abs9rvjk 202 23 for for IN cord-003318-abs9rvjk 202 24 AT-17β AT-17β NNP cord-003318-abs9rvjk 202 25 - - HYPH cord-003318-abs9rvjk 202 26 Gs Gs NNP cord-003318-abs9rvjk 202 27 ( ( -LRB- cord-003318-abs9rvjk 202 28 8b-8e 8b-8e NN cord-003318-abs9rvjk 202 29 ) ) -RRB- cord-003318-abs9rvjk 202 30 was be VBD cord-003318-abs9rvjk 202 31 developed develop VBN cord-003318-abs9rvjk 202 32 ( ( -LRB- cord-003318-abs9rvjk 202 33 Scheme scheme NN cord-003318-abs9rvjk 202 34 1 1 CD cord-003318-abs9rvjk 202 35 ) ) -RRB- cord-003318-abs9rvjk 202 36 . . . cord-003318-abs9rvjk 203 1 Firstly firstly RB cord-003318-abs9rvjk 203 2 , , , cord-003318-abs9rvjk 203 3 the the DT cord-003318-abs9rvjk 203 4 whole whole JJ cord-003318-abs9rvjk 203 5 cell cell NN cord-003318-abs9rvjk 203 6 biotransformation biotransformation NN cord-003318-abs9rvjk 203 7 for for IN cord-003318-abs9rvjk 203 8 the the DT cord-003318-abs9rvjk 203 9 formation formation NN cord-003318-abs9rvjk 203 10 of of IN cord-003318-abs9rvjk 203 11 AT-17β AT-17β NNP cord-003318-abs9rvjk 203 12 - - HYPH cord-003318-abs9rvjk 203 13 Gs Gs NNP cord-003318-abs9rvjk 203 14 ( ( -LRB- cord-003318-abs9rvjk 203 15 8b-8e 8b-8e NN cord-003318-abs9rvjk 203 16 ) ) -RRB- cord-003318-abs9rvjk 203 17 was be VBD cord-003318-abs9rvjk 203 18 exploited exploit VBN cord-003318-abs9rvjk 203 19 due due IN cord-003318-abs9rvjk 203 20 to to IN cord-003318-abs9rvjk 203 21 its -PRON- PRP$ cord-003318-abs9rvjk 203 22 simple simple JJ cord-003318-abs9rvjk 203 23 catalyst catalyst NN cord-003318-abs9rvjk 203 24 preparation preparation NN cord-003318-abs9rvjk 203 25 . . . cord-003318-abs9rvjk 204 1 When when WRB cord-003318-abs9rvjk 204 2 testosterone testosterone NN cord-003318-abs9rvjk 204 3 ( ( -LRB- cord-003318-abs9rvjk 204 4 8) 8) NNP cord-003318-abs9rvjk 204 5 was be VBD cord-003318-abs9rvjk 204 6 incubated incubate VBN cord-003318-abs9rvjk 204 7 with with IN cord-003318-abs9rvjk 204 8 the the DT cord-003318-abs9rvjk 204 9 engineered engineer VBN cord-003318-abs9rvjk 204 10 strain strain NN cord-003318-abs9rvjk 204 11 BL21(DE3)[pET28a BL21(DE3)[pET28a NNP cord-003318-abs9rvjk 204 12 - - HYPH cord-003318-abs9rvjk 204 13 OsSGT1þpGro7 OsSGT1þpGro7 NNP cord-003318-abs9rvjk 204 14 ] ] -RRB- cord-003318-abs9rvjk 204 15 , , , cord-003318-abs9rvjk 204 16 not not RB cord-003318-abs9rvjk 204 17 any any DT cord-003318-abs9rvjk 204 18 new new JJ cord-003318-abs9rvjk 204 19 products product NNS cord-003318-abs9rvjk 204 20 were be VBD cord-003318-abs9rvjk 204 21 detected detect VBN cord-003318-abs9rvjk 204 22 . . . cord-003318-abs9rvjk 205 1 On on IN cord-003318-abs9rvjk 205 2 the the DT cord-003318-abs9rvjk 205 3 other other JJ cord-003318-abs9rvjk 205 4 hand hand NN cord-003318-abs9rvjk 205 5 , , , cord-003318-abs9rvjk 205 6 when when WRB cord-003318-abs9rvjk 205 7 T-17β T-17β NNP cord-003318-abs9rvjk 205 8 - - HYPH cord-003318-abs9rvjk 205 9 G g NN cord-003318-abs9rvjk 205 10 ( ( -LRB- cord-003318-abs9rvjk 205 11 8a 8a NN cord-003318-abs9rvjk 205 12 ) ) -RRB- cord-003318-abs9rvjk 205 13 was be VBD cord-003318-abs9rvjk 205 14 added add VBN cord-003318-abs9rvjk 205 15 into into IN cord-003318-abs9rvjk 205 16 the the DT cord-003318-abs9rvjk 205 17 same same JJ cord-003318-abs9rvjk 205 18 whole whole JJ cord-003318-abs9rvjk 205 19 - - HYPH cord-003318-abs9rvjk 205 20 cell cell NN cord-003318-abs9rvjk 205 21 system system NN cord-003318-abs9rvjk 205 22 , , , cord-003318-abs9rvjk 205 23 6 6 CD cord-003318-abs9rvjk 205 24 0 0 CD cord-003318-abs9rvjk 205 25 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 205 26 - - HYPH cord-003318-abs9rvjk 205 27 G g NN cord-003318-abs9rvjk 205 28 ( ( -LRB- cord-003318-abs9rvjk 205 29 8b 8b NN cord-003318-abs9rvjk 205 30 ) ) -RRB- cord-003318-abs9rvjk 205 31 was be VBD cord-003318-abs9rvjk 205 32 present present JJ cord-003318-abs9rvjk 205 33 in in IN cord-003318-abs9rvjk 205 34 the the DT cord-003318-abs9rvjk 205 35 reaction reaction NN cord-003318-abs9rvjk 205 36 mixture mixture NN cord-003318-abs9rvjk 205 37 ( ( -LRB- cord-003318-abs9rvjk 205 38 Supplementary supplementary JJ cord-003318-abs9rvjk 205 39 _SP cord-003318-abs9rvjk 205 40 Information Information NNP cord-003318-abs9rvjk 205 41 Fig Fig NNP cord-003318-abs9rvjk 205 42 . . . cord-003318-abs9rvjk 206 1 S61 S61 NNP cord-003318-abs9rvjk 206 2 ) ) -RRB- cord-003318-abs9rvjk 206 3 . . . cord-003318-abs9rvjk 207 1 These these DT cord-003318-abs9rvjk 207 2 data datum NNS cord-003318-abs9rvjk 207 3 indicated indicate VBD cord-003318-abs9rvjk 207 4 that that IN cord-003318-abs9rvjk 207 5 testosterone testosterone NN cord-003318-abs9rvjk 207 6 ( ( -LRB- cord-003318-abs9rvjk 207 7 8) 8) NNP cord-003318-abs9rvjk 207 8 could could MD cord-003318-abs9rvjk 207 9 not not RB cord-003318-abs9rvjk 207 10 be be VB cord-003318-abs9rvjk 207 11 transported transport VBN cord-003318-abs9rvjk 207 12 into into IN cord-003318-abs9rvjk 207 13 the the DT cord-003318-abs9rvjk 207 14 cell cell NN cord-003318-abs9rvjk 207 15 while while IN cord-003318-abs9rvjk 207 16 the the DT cord-003318-abs9rvjk 207 17 glycosylation glycosylation NN cord-003318-abs9rvjk 207 18 of of IN cord-003318-abs9rvjk 207 19 testosterone testosterone NN cord-003318-abs9rvjk 207 20 ( ( -LRB- cord-003318-abs9rvjk 207 21 8) 8) NNP cord-003318-abs9rvjk 207 22 significantly significantly RB cord-003318-abs9rvjk 207 23 improved improve VBD cord-003318-abs9rvjk 207 24 the the DT cord-003318-abs9rvjk 207 25 intercellular intercellular JJ cord-003318-abs9rvjk 207 26 transport transport NN cord-003318-abs9rvjk 207 27 . . . cord-003318-abs9rvjk 208 1 Thus thus RB cord-003318-abs9rvjk 208 2 , , , cord-003318-abs9rvjk 208 3 the the DT cord-003318-abs9rvjk 208 4 formation formation NN cord-003318-abs9rvjk 208 5 of of IN cord-003318-abs9rvjk 208 6 AT-17β AT-17β NNP cord-003318-abs9rvjk 208 7 - - HYPH cord-003318-abs9rvjk 208 8 Gs Gs NNP cord-003318-abs9rvjk 208 9 ( ( -LRB- cord-003318-abs9rvjk 208 10 8b-8e 8b-8e CD cord-003318-abs9rvjk 208 11 ) ) -RRB- cord-003318-abs9rvjk 208 12 from from IN cord-003318-abs9rvjk 208 13 testosterone testosterone NN cord-003318-abs9rvjk 208 14 ( ( -LRB- cord-003318-abs9rvjk 208 15 8) 8) NN cord-003318-abs9rvjk 208 16 using use VBG cord-003318-abs9rvjk 208 17 the the DT cord-003318-abs9rvjk 208 18 single single JJ cord-003318-abs9rvjk 208 19 whole whole JJ cord-003318-abs9rvjk 208 20 - - HYPH cord-003318-abs9rvjk 208 21 cell cell NN cord-003318-abs9rvjk 208 22 biocatalyst biocatalyst NN cord-003318-abs9rvjk 208 23 is be VBZ cord-003318-abs9rvjk 208 24 infeasible infeasible JJ cord-003318-abs9rvjk 208 25 . . . cord-003318-abs9rvjk 209 1 A a DT cord-003318-abs9rvjk 209 2 two two CD cord-003318-abs9rvjk 209 3 - - HYPH cord-003318-abs9rvjk 209 4 step step NN cord-003318-abs9rvjk 209 5 process process NN cord-003318-abs9rvjk 209 6 is be VBZ cord-003318-abs9rvjk 209 7 therefore therefore RB cord-003318-abs9rvjk 209 8 established establish VBN cord-003318-abs9rvjk 209 9 to to TO cord-003318-abs9rvjk 209 10 address address VB cord-003318-abs9rvjk 209 11 this this DT cord-003318-abs9rvjk 209 12 limitation limitation NN cord-003318-abs9rvjk 209 13 . . . cord-003318-abs9rvjk 210 1 Specifically specifically RB cord-003318-abs9rvjk 210 2 , , , cord-003318-abs9rvjk 210 3 OsSGT1-catalyzed ossgt1-catalyzed JJ cord-003318-abs9rvjk 210 4 reaction reaction NN cord-003318-abs9rvjk 210 5 was be VBD cord-003318-abs9rvjk 210 6 performed perform VBN cord-003318-abs9rvjk 210 7 in in IN cord-003318-abs9rvjk 210 8 the the DT cord-003318-abs9rvjk 210 9 membrane membrane NN cord-003318-abs9rvjk 210 10 - - HYPH cord-003318-abs9rvjk 210 11 free free JJ cord-003318-abs9rvjk 210 12 crude crude JJ cord-003318-abs9rvjk 210 13 cell cell NN cord-003318-abs9rvjk 210 14 extract extract NN cord-003318-abs9rvjk 210 15 of of IN cord-003318-abs9rvjk 210 16 BL21 BL21 NNP cord-003318-abs9rvjk 210 17 ( ( -LRB- cord-003318-abs9rvjk 210 18 DE3)[pET28a DE3)[pET28a NNP cord-003318-abs9rvjk 210 19 - - HYPH cord-003318-abs9rvjk 210 20 OsSGT1þpGro7 OsSGT1þpGro7 NNP cord-003318-abs9rvjk 210 21 ] ] -RRB- cord-003318-abs9rvjk 210 22 , , , cord-003318-abs9rvjk 210 23 while while IN cord-003318-abs9rvjk 210 24 EcSGA1-mediated ecsga1-mediated CC cord-003318-abs9rvjk 210 25 acetylation acetylation NN cord-003318-abs9rvjk 210 26 was be VBD cord-003318-abs9rvjk 210 27 conducted conduct VBN cord-003318-abs9rvjk 210 28 in in IN cord-003318-abs9rvjk 210 29 the the DT cord-003318-abs9rvjk 210 30 whole whole JJ cord-003318-abs9rvjk 210 31 - - HYPH cord-003318-abs9rvjk 210 32 cell cell NN cord-003318-abs9rvjk 210 33 system system NN cord-003318-abs9rvjk 210 34 of of IN cord-003318-abs9rvjk 210 35 BL21(DE3)[pET28a BL21(DE3)[pET28a NNP cord-003318-abs9rvjk 210 36 - - HYPH cord-003318-abs9rvjk 210 37 EsSGA1 EsSGA1 NNP cord-003318-abs9rvjk 210 38 ] ] -RRB- cord-003318-abs9rvjk 210 39 . . . cord-003318-abs9rvjk 211 1 The the DT cord-003318-abs9rvjk 211 2 optimal optimal JJ cord-003318-abs9rvjk 211 3 pH ph NN cord-003318-abs9rvjk 211 4 and and CC cord-003318-abs9rvjk 211 5 temperature temperature NN cord-003318-abs9rvjk 211 6 of of IN cord-003318-abs9rvjk 211 7 OsSGT1-catalyzed ossgt1-catalyzed JJ cord-003318-abs9rvjk 211 8 reaction reaction NN cord-003318-abs9rvjk 211 9 using use VBG cord-003318-abs9rvjk 211 10 the the DT cord-003318-abs9rvjk 211 11 cell cell NN cord-003318-abs9rvjk 211 12 - - HYPH cord-003318-abs9rvjk 211 13 free free JJ cord-003318-abs9rvjk 211 14 extract extract NN cord-003318-abs9rvjk 211 15 of of IN cord-003318-abs9rvjk 211 16 BL21(DE3)[pET28a BL21(DE3)[pET28a NNP cord-003318-abs9rvjk 211 17 - - HYPH cord-003318-abs9rvjk 211 18 OsSGT1þp OsSGT1þp NNP cord-003318-abs9rvjk 211 19 - - HYPH cord-003318-abs9rvjk 211 20 Gro7 Gro7 NNP cord-003318-abs9rvjk 211 21 ] ] -RRB- cord-003318-abs9rvjk 211 22 as as IN cord-003318-abs9rvjk 211 23 the the DT cord-003318-abs9rvjk 211 24 biocatalyst biocatalyst NN cord-003318-abs9rvjk 211 25 were be VBD cord-003318-abs9rvjk 211 26 first first RB cord-003318-abs9rvjk 211 27 determined determined JJ cord-003318-abs9rvjk 211 28 to to TO cord-003318-abs9rvjk 211 29 be be VB cord-003318-abs9rvjk 211 30 alkaline alkaline JJ cord-003318-abs9rvjk 211 31 pH pH NNP cord-003318-abs9rvjk 211 32 value value NN cord-003318-abs9rvjk 211 33 of of IN cord-003318-abs9rvjk 211 34 11 11 CD cord-003318-abs9rvjk 211 35 and and CC cord-003318-abs9rvjk 211 36 50 50 CD cord-003318-abs9rvjk 211 37 1C 1c NN cord-003318-abs9rvjk 211 38 , , , cord-003318-abs9rvjk 211 39 respectively respectively RB cord-003318-abs9rvjk 211 40 ( ( -LRB- cord-003318-abs9rvjk 211 41 Supplementary Supplementary NNP cord-003318-abs9rvjk 211 42 Information Information NNP cord-003318-abs9rvjk 211 43 Fig Fig NNP cord-003318-abs9rvjk 211 44 . . . cord-003318-abs9rvjk 212 1 S62 S62 NNP cord-003318-abs9rvjk 212 2 ) ) -RRB- cord-003318-abs9rvjk 212 3 . . . cord-003318-abs9rvjk 213 1 Next next RB cord-003318-abs9rvjk 213 2 , , , cord-003318-abs9rvjk 213 3 the the DT cord-003318-abs9rvjk 213 4 100 100 CD cord-003318-abs9rvjk 213 5 μL μl NN cord-003318-abs9rvjk 213 6 screening screening NN cord-003318-abs9rvjk 213 7 scale scale NN cord-003318-abs9rvjk 213 8 of of IN cord-003318-abs9rvjk 213 9 OsSGT1-catalyzed ossgt1-catalyzed JJ cord-003318-abs9rvjk 213 10 glycosylation glycosylation NN cord-003318-abs9rvjk 213 11 reaction reaction NN cord-003318-abs9rvjk 213 12 was be VBD cord-003318-abs9rvjk 213 13 scaled scale VBN cord-003318-abs9rvjk 213 14 to to IN cord-003318-abs9rvjk 213 15 53 53 CD cord-003318-abs9rvjk 213 16 mL ml NN cord-003318-abs9rvjk 213 17 scale scale NN cord-003318-abs9rvjk 213 18 , , , cord-003318-abs9rvjk 213 19 in in IN cord-003318-abs9rvjk 213 20 which which WDT cord-003318-abs9rvjk 213 21 152 152 CD cord-003318-abs9rvjk 213 22 mg mg NNP cord-003318-abs9rvjk 213 23 testosterone testosterone NN cord-003318-abs9rvjk 213 24 ( ( -LRB- cord-003318-abs9rvjk 213 25 8) 8) NNP cord-003318-abs9rvjk 213 26 were be VBD cord-003318-abs9rvjk 213 27 glycosylated glycosylate VBN cord-003318-abs9rvjk 213 28 to to TO cord-003318-abs9rvjk 213 29 form form VB cord-003318-abs9rvjk 213 30 61 61 CD cord-003318-abs9rvjk 213 31 mg mg NNP cord-003318-abs9rvjk 213 32 T-17β T-17β NNP cord-003318-abs9rvjk 213 33 - - HYPH cord-003318-abs9rvjk 213 34 G G NNP cord-003318-abs9rvjk 213 35 ( ( -LRB- cord-003318-abs9rvjk 213 36 8a 8a NN cord-003318-abs9rvjk 213 37 ) ) -RRB- cord-003318-abs9rvjk 213 38 under under IN cord-003318-abs9rvjk 213 39 optimized optimize VBN cord-003318-abs9rvjk 213 40 conditions condition NNS cord-003318-abs9rvjk 213 41 ( ( -LRB- cord-003318-abs9rvjk 213 42 Scheme scheme NN cord-003318-abs9rvjk 213 43 1 1 CD cord-003318-abs9rvjk 213 44 ) ) -RRB- cord-003318-abs9rvjk 213 45 . . . cord-003318-abs9rvjk 214 1 The the DT cord-003318-abs9rvjk 214 2 resultant resultant JJ cord-003318-abs9rvjk 214 3 T-17β T-17β NNS cord-003318-abs9rvjk 214 4 - - HYPH cord-003318-abs9rvjk 214 5 G g NN cord-003318-abs9rvjk 214 6 ( ( -LRB- cord-003318-abs9rvjk 214 7 8a 8a NN cord-003318-abs9rvjk 214 8 ) ) -RRB- cord-003318-abs9rvjk 214 9 was be VBD cord-003318-abs9rvjk 214 10 subsequently subsequently RB cord-003318-abs9rvjk 214 11 used use VBN cord-003318-abs9rvjk 214 12 as as IN cord-003318-abs9rvjk 214 13 the the DT cord-003318-abs9rvjk 214 14 substrate substrate NN cord-003318-abs9rvjk 214 15 applied apply VBN cord-003318-abs9rvjk 214 16 in in IN cord-003318-abs9rvjk 214 17 the the DT cord-003318-abs9rvjk 214 18 scale scale NN cord-003318-abs9rvjk 214 19 - - HYPH cord-003318-abs9rvjk 214 20 up up NN cord-003318-abs9rvjk 214 21 of of IN cord-003318-abs9rvjk 214 22 the the DT cord-003318-abs9rvjk 214 23 whole whole JJ cord-003318-abs9rvjk 214 24 - - HYPH cord-003318-abs9rvjk 214 25 cell cell NN cord-003318-abs9rvjk 214 26 system system NN cord-003318-abs9rvjk 214 27 of of IN cord-003318-abs9rvjk 214 28 BL21(DE3)[pET28a BL21(DE3)[pET28a NNP cord-003318-abs9rvjk 214 29 - - HYPH cord-003318-abs9rvjk 214 30 EsSGA1 EsSGA1 NNP cord-003318-abs9rvjk 214 31 ] ] -RRB- cord-003318-abs9rvjk 214 32 ( ( -LRB- cord-003318-abs9rvjk 214 33 135 135 CD cord-003318-abs9rvjk 214 34 mL ml NN cord-003318-abs9rvjk 214 35 ) ) -RRB- cord-003318-abs9rvjk 214 36 under under IN cord-003318-abs9rvjk 214 37 optimized optimize VBN cord-003318-abs9rvjk 214 38 pH pH NNP cord-003318-abs9rvjk 214 39 5.0 5.0 CD cord-003318-abs9rvjk 214 40 and and CC cord-003318-abs9rvjk 214 41 40 40 CD cord-003318-abs9rvjk 214 42 1C. 1c. CD cord-003318-abs9rvjk 215 1 The the DT cord-003318-abs9rvjk 215 2 resulting result VBG cord-003318-abs9rvjk 215 3 reaction reaction NN cord-003318-abs9rvjk 215 4 mixture mixture NN cord-003318-abs9rvjk 215 5 was be VBD cord-003318-abs9rvjk 215 6 subjected subject VBN cord-003318-abs9rvjk 215 7 to to IN cord-003318-abs9rvjk 215 8 high high JJ cord-003318-abs9rvjk 215 9 - - HYPH cord-003318-abs9rvjk 215 10 performance performance NN cord-003318-abs9rvjk 215 11 liquid liquid NN cord-003318-abs9rvjk 215 12 chromatography chromatography NN cord-003318-abs9rvjk 215 13 - - HYPH cord-003318-abs9rvjk 215 14 solid solid JJ cord-003318-abs9rvjk 215 15 phase phase NN cord-003318-abs9rvjk 215 16 extraction extraction NN cord-003318-abs9rvjk 215 17 - - HYPH cord-003318-abs9rvjk 215 18 NMR nmr NN cord-003318-abs9rvjk 215 19 spectroscopy spectroscopy NN cord-003318-abs9rvjk 215 20 ( ( -LRB- cord-003318-abs9rvjk 215 21 HPLC HPLC NNP cord-003318-abs9rvjk 215 22 - - HYPH cord-003318-abs9rvjk 215 23 SPE SPE NNP cord-003318-abs9rvjk 215 24 - - HYPH cord-003318-abs9rvjk 215 25 NMR NMR NNP cord-003318-abs9rvjk 215 26 ) ) -RRB- cord-003318-abs9rvjk 215 27 measurement measurement NN cord-003318-abs9rvjk 215 28 . . . cord-003318-abs9rvjk 216 1 Comparison comparison NN cord-003318-abs9rvjk 216 2 of of IN cord-003318-abs9rvjk 216 3 the the DT cord-003318-abs9rvjk 216 4 1 1 CD cord-003318-abs9rvjk 216 5 H h NN cord-003318-abs9rvjk 216 6 and and CC cord-003318-abs9rvjk 216 7 13 13 CD cord-003318-abs9rvjk 216 8 C c NN cord-003318-abs9rvjk 216 9 NMR NMR NNP cord-003318-abs9rvjk 216 10 spectra spectrum NNS cord-003318-abs9rvjk 216 11 of of IN cord-003318-abs9rvjk 216 12 8c-8e 8c-8e CD cord-003318-abs9rvjk 216 13 with with IN cord-003318-abs9rvjk 216 14 those those DT cord-003318-abs9rvjk 216 15 of of IN cord-003318-abs9rvjk 216 16 8b 8b NN cord-003318-abs9rvjk 216 17 suggested suggest VBD cord-003318-abs9rvjk 216 18 that that IN cord-003318-abs9rvjk 216 19 compounds compound NNS cord-003318-abs9rvjk 216 20 8c-8e 8c-8e CD cord-003318-abs9rvjk 216 21 had have VBD cord-003318-abs9rvjk 216 22 the the DT cord-003318-abs9rvjk 216 23 same same JJ cord-003318-abs9rvjk 216 24 framework framework NN cord-003318-abs9rvjk 216 25 as as IN cord-003318-abs9rvjk 216 26 8b 8b NN cord-003318-abs9rvjk 216 27 and and CC cord-003318-abs9rvjk 216 28 the the DT cord-003318-abs9rvjk 216 29 structural structural JJ cord-003318-abs9rvjk 216 30 difference difference NN cord-003318-abs9rvjk 216 31 might may MD cord-003318-abs9rvjk 216 32 be be VB cord-003318-abs9rvjk 216 33 the the DT cord-003318-abs9rvjk 216 34 position position NN cord-003318-abs9rvjk 216 35 of of IN cord-003318-abs9rvjk 216 36 the the DT cord-003318-abs9rvjk 216 37 acetyl acetyl NNP cord-003318-abs9rvjk 216 38 group group NN cord-003318-abs9rvjk 216 39 . . . cord-003318-abs9rvjk 217 1 The the DT cord-003318-abs9rvjk 217 2 location location NN cord-003318-abs9rvjk 217 3 of of IN cord-003318-abs9rvjk 217 4 acetyl acetyl NN cord-003318-abs9rvjk 217 5 group group NN cord-003318-abs9rvjk 217 6 was be VBD cord-003318-abs9rvjk 217 7 determined determine VBN cord-003318-abs9rvjk 217 8 to to TO cord-003318-abs9rvjk 217 9 be be VB cord-003318-abs9rvjk 217 10 at at IN cord-003318-abs9rvjk 217 11 C-2 C-2 NNP cord-003318-abs9rvjk 217 12 0 0 CD cord-003318-abs9rvjk 217 13 based base VBN cord-003318-abs9rvjk 217 14 on on IN cord-003318-abs9rvjk 217 15 the the DT cord-003318-abs9rvjk 217 16 HMBC HMBC NNP cord-003318-abs9rvjk 217 17 correlations correlation NNS cord-003318-abs9rvjk 217 18 between between IN cord-003318-abs9rvjk 217 19 H-2 H-2 NNP cord-003318-abs9rvjk 217 20 0 0 CD cord-003318-abs9rvjk 217 21 ( ( -LRB- cord-003318-abs9rvjk 217 22 δ δ NN cord-003318-abs9rvjk 217 23 4.68 4.68 CD cord-003318-abs9rvjk 217 24 ) ) -RRB- cord-003318-abs9rvjk 217 25 and and CC cord-003318-abs9rvjk 217 26 C-1 C-1 NNP cord-003318-abs9rvjk 217 27 " " '' cord-003318-abs9rvjk 217 28 ( ( -LRB- cord-003318-abs9rvjk 217 29 δ δ NN cord-003318-abs9rvjk 217 30 170.3 170.3 CD cord-003318-abs9rvjk 217 31 ) ) -RRB- cord-003318-abs9rvjk 217 32 as as IN cord-003318-abs9rvjk 217 33 shown show VBN cord-003318-abs9rvjk 217 34 in in IN cord-003318-abs9rvjk 217 35 Supplementary Supplementary NNP cord-003318-abs9rvjk 217 36 _SP cord-003318-abs9rvjk 217 37 Information Information NNP cord-003318-abs9rvjk 217 38 Fig Fig NNP cord-003318-abs9rvjk 217 39 . . . cord-003318-abs9rvjk 218 1 S63 S63 NNP cord-003318-abs9rvjk 218 2 . . . cord-003318-abs9rvjk 219 1 Thus thus RB cord-003318-abs9rvjk 219 2 , , , cord-003318-abs9rvjk 219 3 compound compound NN cord-003318-abs9rvjk 219 4 8c 8c CD cord-003318-abs9rvjk 219 5 was be VBD cord-003318-abs9rvjk 219 6 assigned assign VBN cord-003318-abs9rvjk 219 7 as as IN cord-003318-abs9rvjk 219 8 2 2 CD cord-003318-abs9rvjk 219 9 0 0 CD cord-003318-abs9rvjk 219 10 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 219 11 - - HYPH cord-003318-abs9rvjk 219 12 G. g. NN cord-003318-abs9rvjk 220 1 The the DT cord-003318-abs9rvjk 220 2 isolated isolate VBN cord-003318-abs9rvjk 220 3 glucose glucose NN cord-003318-abs9rvjk 220 4 proton proton NN cord-003318-abs9rvjk 220 5 at at IN cord-003318-abs9rvjk 220 6 δ δ NN cord-003318-abs9rvjk 220 7 4.91 4.91 CD cord-003318-abs9rvjk 220 8 ( ( -LRB- cord-003318-abs9rvjk 220 9 H-3 H-3 NNP cord-003318-abs9rvjk 220 10 0 0 CD cord-003318-abs9rvjk 220 11 ) ) -RRB- cord-003318-abs9rvjk 220 12 of of IN cord-003318-abs9rvjk 220 13 compound compound NN cord-003318-abs9rvjk 220 14 8d 8d NNP cord-003318-abs9rvjk 220 15 exhibited exhibit VBD cord-003318-abs9rvjk 220 16 long long JJ cord-003318-abs9rvjk 220 17 - - HYPH cord-003318-abs9rvjk 220 18 range range NN cord-003318-abs9rvjk 220 19 correlations correlation NNS cord-003318-abs9rvjk 220 20 with with IN cord-003318-abs9rvjk 220 21 carbonyl carbonyl NN cord-003318-abs9rvjk 220 22 carbons carbon NNS cord-003318-abs9rvjk 220 23 at at IN cord-003318-abs9rvjk 220 24 δ δ NNP cord-003318-abs9rvjk 220 25 172.7 172.7 CD cord-003318-abs9rvjk 220 26 ( ( -LRB- cord-003318-abs9rvjk 220 27 Supplementary Supplementary NNP cord-003318-abs9rvjk 220 28 Information Information NNP cord-003318-abs9rvjk 220 29 Fig Fig NNP cord-003318-abs9rvjk 220 30 . . . cord-003318-abs9rvjk 221 1 S64 S64 NNP cord-003318-abs9rvjk 221 2 ) ) -RRB- cord-003318-abs9rvjk 221 3 . . . cord-003318-abs9rvjk 222 1 Moreover moreover RB cord-003318-abs9rvjk 222 2 , , , cord-003318-abs9rvjk 222 3 H-4 H-4 NNP cord-003318-abs9rvjk 222 4 0 0 CD cord-003318-abs9rvjk 223 1 ( ( -LRB- cord-003318-abs9rvjk 223 2 δ δ NN cord-003318-abs9rvjk 223 3 4.73 4.73 CD cord-003318-abs9rvjk 223 4 ) ) -RRB- cord-003318-abs9rvjk 223 5 of of IN cord-003318-abs9rvjk 223 6 compound compound NN cord-003318-abs9rvjk 223 7 8e 8e NN cord-003318-abs9rvjk 223 8 showed show VBD cord-003318-abs9rvjk 223 9 long long JJ cord-003318-abs9rvjk 223 10 - - HYPH cord-003318-abs9rvjk 223 11 range range NN cord-003318-abs9rvjk 223 12 Table Table NNP cord-003318-abs9rvjk 223 13 S3 S3 NNP cord-003318-abs9rvjk 223 14 ) ) -RRB- cord-003318-abs9rvjk 223 15 . . . cord-003318-abs9rvjk 224 1 Lower low JJR cord-003318-abs9rvjk 224 2 panel panel NN cord-003318-abs9rvjk 224 3 , , , cord-003318-abs9rvjk 224 4 HPLC HPLC NNP cord-003318-abs9rvjk 224 5 profile profile NN cord-003318-abs9rvjk 224 6 of of IN cord-003318-abs9rvjk 224 7 acetylated acetylated JJ cord-003318-abs9rvjk 224 8 products product NNS cord-003318-abs9rvjk 224 9 of of IN cord-003318-abs9rvjk 224 10 9a 9a NN cord-003318-abs9rvjk 224 11 separated separate VBN cord-003318-abs9rvjk 224 12 by by IN cord-003318-abs9rvjk 224 13 chromatogramic chromatogramic JJ cord-003318-abs9rvjk 224 14 method method NN cord-003318-abs9rvjk 224 15 ( ( -LRB- cord-003318-abs9rvjk 224 16 Supplementary Supplementary NNP cord-003318-abs9rvjk 224 17 Information Information NNP cord-003318-abs9rvjk 224 18 Table Table NNP cord-003318-abs9rvjk 224 19 S3 S3 NNP cord-003318-abs9rvjk 224 20 ) ) -RRB- cord-003318-abs9rvjk 224 21 . . . cord-003318-abs9rvjk 225 1 correlations correlation NNS cord-003318-abs9rvjk 225 2 with with IN cord-003318-abs9rvjk 225 3 C-1 C-1 NNP cord-003318-abs9rvjk 225 4 " " '' cord-003318-abs9rvjk 225 5 ( ( -LRB- cord-003318-abs9rvjk 225 6 δ δ NNP cord-003318-abs9rvjk 225 7 170.7 170.7 CD cord-003318-abs9rvjk 225 8 ) ) -RRB- cord-003318-abs9rvjk 225 9 , , , cord-003318-abs9rvjk 225 10 as as IN cord-003318-abs9rvjk 225 11 revealed reveal VBN cord-003318-abs9rvjk 225 12 by by IN cord-003318-abs9rvjk 225 13 the the DT cord-003318-abs9rvjk 225 14 HMBC HMBC NNP cord-003318-abs9rvjk 225 15 spectrum spectrum NN cord-003318-abs9rvjk 225 16 ( ( -LRB- cord-003318-abs9rvjk 225 17 Supplementary Supplementary NNP cord-003318-abs9rvjk 225 18 Information Information NNP cord-003318-abs9rvjk 225 19 Fig Fig NNP cord-003318-abs9rvjk 225 20 . . . cord-003318-abs9rvjk 225 21 S65 S65 NNP cord-003318-abs9rvjk 225 22 ) ) -RRB- cord-003318-abs9rvjk 225 23 . . . cord-003318-abs9rvjk 226 1 These these DT cord-003318-abs9rvjk 226 2 data datum NNS cord-003318-abs9rvjk 226 3 supported support VBD cord-003318-abs9rvjk 226 4 that that IN cord-003318-abs9rvjk 226 5 the the DT cord-003318-abs9rvjk 226 6 structure structure NN cord-003318-abs9rvjk 226 7 of of IN cord-003318-abs9rvjk 226 8 8d 8d NNP cord-003318-abs9rvjk 226 9 and and CC cord-003318-abs9rvjk 226 10 8e 8e NNP cord-003318-abs9rvjk 226 11 was be VBD cord-003318-abs9rvjk 226 12 elucidated elucidate VBN cord-003318-abs9rvjk 226 13 as as IN cord-003318-abs9rvjk 226 14 3 3 CD cord-003318-abs9rvjk 226 15 0 0 SYM cord-003318-abs9rvjk 226 16 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 226 17 - - HYPH cord-003318-abs9rvjk 226 18 G g NN cord-003318-abs9rvjk 226 19 and and CC cord-003318-abs9rvjk 226 20 4 4 CD cord-003318-abs9rvjk 226 21 0 0 CD cord-003318-abs9rvjk 226 22 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 226 23 - - HYPH cord-003318-abs9rvjk 226 24 G g NN cord-003318-abs9rvjk 226 25 , , , cord-003318-abs9rvjk 226 26 respectively respectively RB cord-003318-abs9rvjk 226 27 . . . cord-003318-abs9rvjk 227 1 Hence hence RB cord-003318-abs9rvjk 227 2 , , , cord-003318-abs9rvjk 227 3 the the DT cord-003318-abs9rvjk 227 4 three three CD cord-003318-abs9rvjk 227 5 trace trace NN cord-003318-abs9rvjk 227 6 products product NNS cord-003318-abs9rvjk 227 7 at at IN cord-003318-abs9rvjk 227 8 t t NNP cord-003318-abs9rvjk 227 9 R R NNP cord-003318-abs9rvjk 227 10 ¼ ¼ NNP cord-003318-abs9rvjk 227 11 18.243 18.243 CD cord-003318-abs9rvjk 227 12 , , , cord-003318-abs9rvjk 227 13 19.013 19.013 CD cord-003318-abs9rvjk 227 14 and and CC cord-003318-abs9rvjk 227 15 23.680 23.680 CD cord-003318-abs9rvjk 227 16 min min NNP cord-003318-abs9rvjk 227 17 were be VBD cord-003318-abs9rvjk 227 18 thus thus RB cord-003318-abs9rvjk 227 19 assigned assign VBN cord-003318-abs9rvjk 227 20 to to TO cord-003318-abs9rvjk 227 21 be be VB cord-003318-abs9rvjk 227 22 3 3 CD cord-003318-abs9rvjk 227 23 0 0 CD cord-003318-abs9rvjk 227 24 -(8d -(8d NNS cord-003318-abs9rvjk 227 25 ) ) -RRB- cord-003318-abs9rvjk 227 26 , , , cord-003318-abs9rvjk 227 27 4 4 CD cord-003318-abs9rvjk 227 28 0 0 CD cord-003318-abs9rvjk 227 29 -(8e -(8e CD cord-003318-abs9rvjk 227 30 ) ) -RRB- cord-003318-abs9rvjk 227 31 and and CC cord-003318-abs9rvjk 227 32 2 2 CD cord-003318-abs9rvjk 227 33 0 0 CD cord-003318-abs9rvjk 227 34 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 227 35 - - HYPH cord-003318-abs9rvjk 227 36 G g NN cord-003318-abs9rvjk 227 37 ( ( -LRB- cord-003318-abs9rvjk 227 38 8c 8c CD cord-003318-abs9rvjk 227 39 ) ) -RRB- cord-003318-abs9rvjk 227 40 based base VBN cord-003318-abs9rvjk 227 41 on on IN cord-003318-abs9rvjk 227 42 their -PRON- PRP$ cord-003318-abs9rvjk 227 43 respective respective JJ cord-003318-abs9rvjk 227 44 NMR NMR NNP cord-003318-abs9rvjk 227 45 data datum NNS cord-003318-abs9rvjk 227 46 ( ( -LRB- cord-003318-abs9rvjk 227 47 Tables Tables NNP cord-003318-abs9rvjk 227 48 3 3 CD cord-003318-abs9rvjk 227 49 - - SYM cord-003318-abs9rvjk 227 50 5 5 CD cord-003318-abs9rvjk 227 51 and and CC cord-003318-abs9rvjk 227 52 Supplementary supplementary JJ cord-003318-abs9rvjk 227 53 _SP cord-003318-abs9rvjk 227 54 Information Information NNP cord-003318-abs9rvjk 227 55 Figs Figs NNPS cord-003318-abs9rvjk 227 56 . . . cord-003318-abs9rvjk 228 1 S63 S63 NNP cord-003318-abs9rvjk 228 2 - - HYPH cord-003318-abs9rvjk 228 3 77 77 CD cord-003318-abs9rvjk 228 4 ) ) -RRB- cord-003318-abs9rvjk 228 5 . . . cord-003318-abs9rvjk 229 1 These these DT cord-003318-abs9rvjk 229 2 data datum NNS cord-003318-abs9rvjk 229 3 indicate indicate VBP cord-003318-abs9rvjk 229 4 that that IN cord-003318-abs9rvjk 229 5 EcSGA1 ecsga1 NN cord-003318-abs9rvjk 229 6 can can MD cord-003318-abs9rvjk 229 7 effectively effectively RB cord-003318-abs9rvjk 229 8 introduce introduce VB cord-003318-abs9rvjk 229 9 the the DT cord-003318-abs9rvjk 229 10 acetyl acetyl NN cord-003318-abs9rvjk 229 11 group group NN cord-003318-abs9rvjk 229 12 into into IN cord-003318-abs9rvjk 229 13 the the DT cord-003318-abs9rvjk 229 14 primary primary JJ cord-003318-abs9rvjk 229 15 hydroxyl hydroxyl NN cord-003318-abs9rvjk 229 16 group group NN cord-003318-abs9rvjk 229 17 and and CC cord-003318-abs9rvjk 229 18 each each DT cord-003318-abs9rvjk 229 19 secondary secondary JJ cord-003318-abs9rvjk 229 20 hydroxyl hydroxyl NN cord-003318-abs9rvjk 229 21 group group NN cord-003318-abs9rvjk 229 22 of of IN cord-003318-abs9rvjk 229 23 T-17β T-17β NNP cord-003318-abs9rvjk 229 24 - - HYPH cord-003318-abs9rvjk 229 25 G G NNP cord-003318-abs9rvjk 229 26 ( ( -LRB- cord-003318-abs9rvjk 229 27 8a 8a NN cord-003318-abs9rvjk 229 28 ) ) -RRB- cord-003318-abs9rvjk 229 29 , , , cord-003318-abs9rvjk 229 30 yielding yield VBG cord-003318-abs9rvjk 229 31 four four CD cord-003318-abs9rvjk 229 32 monoacylates monoacylate NNS cord-003318-abs9rvjk 229 33 without without IN cord-003318-abs9rvjk 229 34 the the DT cord-003318-abs9rvjk 229 35 formation formation NN cord-003318-abs9rvjk 229 36 of of IN cord-003318-abs9rvjk 229 37 diacylates diacylate NNS cord-003318-abs9rvjk 229 38 ( ( -LRB- cord-003318-abs9rvjk 229 39 Fig Fig NNP cord-003318-abs9rvjk 229 40 . . NNP cord-003318-abs9rvjk 229 41 4 4 CD cord-003318-abs9rvjk 229 42 and and CC cord-003318-abs9rvjk 229 43 Scheme scheme NN cord-003318-abs9rvjk 229 44 1 1 CD cord-003318-abs9rvjk 229 45 ) ) -RRB- cord-003318-abs9rvjk 229 46 . . . cord-003318-abs9rvjk 230 1 Because because IN cord-003318-abs9rvjk 230 2 the the DT cord-003318-abs9rvjk 230 3 primary primary JJ cord-003318-abs9rvjk 230 4 C(6 C(6 NNP cord-003318-abs9rvjk 230 5 0 0 NFP cord-003318-abs9rvjk 230 6 ) ) -RRB- cord-003318-abs9rvjk 230 7 -OH -OH , cord-003318-abs9rvjk 230 8 was be VBD cord-003318-abs9rvjk 230 9 the the DT cord-003318-abs9rvjk 230 10 most most RBS cord-003318-abs9rvjk 230 11 reactive reactive JJ cord-003318-abs9rvjk 230 12 of of IN cord-003318-abs9rvjk 230 13 the the DT cord-003318-abs9rvjk 230 14 four four CD cord-003318-abs9rvjk 230 15 hydroxyl hydroxyl NN cord-003318-abs9rvjk 230 16 groups group NNS cord-003318-abs9rvjk 230 17 in in IN cord-003318-abs9rvjk 230 18 T-17β T-17β NNP cord-003318-abs9rvjk 230 19 - - HYPH cord-003318-abs9rvjk 230 20 G g NN cord-003318-abs9rvjk 230 21 ( ( -LRB- cord-003318-abs9rvjk 230 22 8a 8a NN cord-003318-abs9rvjk 230 23 ) ) -RRB- cord-003318-abs9rvjk 230 24 , , , cord-003318-abs9rvjk 230 25 acetylation acetylation NN cord-003318-abs9rvjk 230 26 of of IN cord-003318-abs9rvjk 230 27 T-17β T-17β NNP cord-003318-abs9rvjk 230 28 - - HYPH cord-003318-abs9rvjk 230 29 G g NN cord-003318-abs9rvjk 230 30 ( ( -LRB- cord-003318-abs9rvjk 230 31 8a 8a NN cord-003318-abs9rvjk 230 32 ) ) -RRB- cord-003318-abs9rvjk 230 33 took take VBD cord-003318-abs9rvjk 230 34 place place NN cord-003318-abs9rvjk 230 35 preferentially preferentially RB cord-003318-abs9rvjk 230 36 at at IN cord-003318-abs9rvjk 230 37 the the DT cord-003318-abs9rvjk 230 38 C C NNP cord-003318-abs9rvjk 230 39 ( ( -LRB- cord-003318-abs9rvjk 230 40 6 6 CD cord-003318-abs9rvjk 230 41 0 0 CD cord-003318-abs9rvjk 230 42 ) ) -RRB- cord-003318-abs9rvjk 230 43 -OH -oh NN cord-003318-abs9rvjk 230 44 , , , cord-003318-abs9rvjk 230 45 giving give VBG cord-003318-abs9rvjk 230 46 6 6 CD cord-003318-abs9rvjk 230 47 0 0 CD cord-003318-abs9rvjk 230 48 -O -o CD cord-003318-abs9rvjk 230 49 - - HYPH cord-003318-abs9rvjk 230 50 acylate acylate JJ cord-003318-abs9rvjk 230 51 predominantly predominantly RB cord-003318-abs9rvjk 230 52 in in IN cord-003318-abs9rvjk 230 53 82 82 CD cord-003318-abs9rvjk 230 54 % % NN cord-003318-abs9rvjk 230 55 yield yield NN cord-003318-abs9rvjk 230 56 ( ( -LRB- cord-003318-abs9rvjk 230 57 Fig Fig NNP cord-003318-abs9rvjk 230 58 . . . cord-003318-abs9rvjk 230 59 4 4 CD cord-003318-abs9rvjk 230 60 and and CC cord-003318-abs9rvjk 230 61 Scheme scheme NN cord-003318-abs9rvjk 230 62 1 1 CD cord-003318-abs9rvjk 230 63 ) ) -RRB- cord-003318-abs9rvjk 230 64 . . . cord-003318-abs9rvjk 231 1 Also also RB cord-003318-abs9rvjk 231 2 , , , cord-003318-abs9rvjk 231 3 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 231 4 can can MD cord-003318-abs9rvjk 231 5 regioselectively regioselectively RB cord-003318-abs9rvjk 231 6 acetylate acetylate VB cord-003318-abs9rvjk 231 7 each each DT cord-003318-abs9rvjk 231 8 secondary secondary JJ cord-003318-abs9rvjk 231 9 hydroxyl hydroxyl NN cord-003318-abs9rvjk 231 10 of of IN cord-003318-abs9rvjk 231 11 T-17β T-17β NNP cord-003318-abs9rvjk 231 12 - - HYPH cord-003318-abs9rvjk 231 13 G g NN cord-003318-abs9rvjk 231 14 ( ( -LRB- cord-003318-abs9rvjk 231 15 8a 8a NN cord-003318-abs9rvjk 231 16 ) ) -RRB- cord-003318-abs9rvjk 231 17 in in IN cord-003318-abs9rvjk 231 18 the the DT cord-003318-abs9rvjk 231 19 presence presence NN cord-003318-abs9rvjk 231 20 of of IN cord-003318-abs9rvjk 231 21 the the DT cord-003318-abs9rvjk 231 22 primary primary JJ cord-003318-abs9rvjk 231 23 hydroxyl hydroxyl NN cord-003318-abs9rvjk 231 24 group group NN cord-003318-abs9rvjk 231 25 , , , cord-003318-abs9rvjk 231 26 giving give VBG cord-003318-abs9rvjk 231 27 2 2 CD cord-003318-abs9rvjk 231 28 0 0 CD cord-003318-abs9rvjk 231 29 -(8c -(8c CD cord-003318-abs9rvjk 231 30 ) ) -RRB- cord-003318-abs9rvjk 231 31 , , , cord-003318-abs9rvjk 231 32 3 3 CD cord-003318-abs9rvjk 231 33 0 0 CD cord-003318-abs9rvjk 231 34 -(8d -(8d NN cord-003318-abs9rvjk 231 35 ) ) -RRB- cord-003318-abs9rvjk 231 36 and and CC cord-003318-abs9rvjk 231 37 4 4 CD cord-003318-abs9rvjk 231 38 0 0 CD cord-003318-abs9rvjk 231 39 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 231 40 - - HYPH cord-003318-abs9rvjk 231 41 G g NN cord-003318-abs9rvjk 231 42 ( ( -LRB- cord-003318-abs9rvjk 231 43 8e 8e NN cord-003318-abs9rvjk 231 44 ) ) -RRB- cord-003318-abs9rvjk 231 45 in in IN cord-003318-abs9rvjk 231 46 8 8 CD cord-003318-abs9rvjk 231 47 % % NN cord-003318-abs9rvjk 231 48 , , , cord-003318-abs9rvjk 231 49 6 6 CD cord-003318-abs9rvjk 231 50 % % NN cord-003318-abs9rvjk 231 51 and and CC cord-003318-abs9rvjk 231 52 4 4 CD cord-003318-abs9rvjk 231 53 % % NN cord-003318-abs9rvjk 231 54 yield yield NN cord-003318-abs9rvjk 231 55 , , , cord-003318-abs9rvjk 231 56 respectively respectively RB cord-003318-abs9rvjk 231 57 . . . cord-003318-abs9rvjk 232 1 These these DT cord-003318-abs9rvjk 232 2 data datum NNS cord-003318-abs9rvjk 232 3 revealed reveal VBD cord-003318-abs9rvjk 232 4 the the DT cord-003318-abs9rvjk 232 5 reactivity reactivity NN cord-003318-abs9rvjk 232 6 trend trend NN cord-003318-abs9rvjk 232 7 of of IN cord-003318-abs9rvjk 232 8 hydroxyls hydroxyls NNP cord-003318-abs9rvjk 232 9 is be VBZ cord-003318-abs9rvjk 232 10 6 6 CD cord-003318-abs9rvjk 232 11 0 0 CD cord-003318-abs9rvjk 232 12 -OH4 -oh4 NN cord-003318-abs9rvjk 232 13 42 42 CD cord-003318-abs9rvjk 232 14 0 0 CD cord-003318-abs9rvjk 232 15 -OH43 -oh43 NN cord-003318-abs9rvjk 232 16 0 0 CD cord-003318-abs9rvjk 232 17 -OH44 -OH44 VBD cord-003318-abs9rvjk 232 18 0 0 CD cord-003318-abs9rvjk 232 19 -OH -oh NN cord-003318-abs9rvjk 232 20 . . . cord-003318-abs9rvjk 233 1 Likewise likewise RB cord-003318-abs9rvjk 233 2 , , , cord-003318-abs9rvjk 233 3 the the DT cord-003318-abs9rvjk 233 4 formation formation NN cord-003318-abs9rvjk 233 5 of of IN cord-003318-abs9rvjk 233 6 four four CD cord-003318-abs9rvjk 233 7 monoacylates monoacylate NNS cord-003318-abs9rvjk 233 8 was be VBD cord-003318-abs9rvjk 233 9 also also RB cord-003318-abs9rvjk 233 10 present present JJ cord-003318-abs9rvjk 233 11 in in IN cord-003318-abs9rvjk 233 12 EcSGA1-catalyzed ecsga1-catalyzed JJ cord-003318-abs9rvjk 233 13 acylation acylation NN cord-003318-abs9rvjk 233 14 of of IN cord-003318-abs9rvjk 233 15 E-17β E-17β NNP cord-003318-abs9rvjk 233 16 - - HYPH cord-003318-abs9rvjk 233 17 G G NNP cord-003318-abs9rvjk 233 18 ( ( -LRB- cord-003318-abs9rvjk 233 19 9a 9a NN cord-003318-abs9rvjk 233 20 , , , cord-003318-abs9rvjk 233 21 t t NN cord-003318-abs9rvjk 233 22 R R NNP cord-003318-abs9rvjk 233 23 ¼ ¼ NNP cord-003318-abs9rvjk 233 24 13.587 13.587 CD cord-003318-abs9rvjk 233 25 min min NNP cord-003318-abs9rvjk 233 26 , , , cord-003318-abs9rvjk 233 27 Fig Fig NNP cord-003318-abs9rvjk 233 28 . . NNP cord-003318-abs9rvjk 233 29 5 5 CD cord-003318-abs9rvjk 233 30 ) ) -RRB- cord-003318-abs9rvjk 233 31 . . . cord-003318-abs9rvjk 234 1 In in IN cord-003318-abs9rvjk 234 2 addition addition NN cord-003318-abs9rvjk 234 3 to to IN cord-003318-abs9rvjk 234 4 the the DT cord-003318-abs9rvjk 234 5 well well RB cord-003318-abs9rvjk 234 6 - - HYPH cord-003318-abs9rvjk 234 7 characterized characterize VBN cord-003318-abs9rvjk 234 8 major major JJ cord-003318-abs9rvjk 234 9 product product NN cord-003318-abs9rvjk 234 10 9b 9b NNS cord-003318-abs9rvjk 234 11 , , , cord-003318-abs9rvjk 234 12 there there EX cord-003318-abs9rvjk 234 13 are be VBP cord-003318-abs9rvjk 234 14 three three CD cord-003318-abs9rvjk 234 15 trace trace NN cord-003318-abs9rvjk 234 16 products product NNS cord-003318-abs9rvjk 234 17 9c-9e 9c-9e CD cord-003318-abs9rvjk 234 18 . . . cord-003318-abs9rvjk 235 1 Because because IN cord-003318-abs9rvjk 235 2 of of IN cord-003318-abs9rvjk 235 3 their -PRON- PRP$ cord-003318-abs9rvjk 235 4 trace trace NN cord-003318-abs9rvjk 235 5 amount amount NN cord-003318-abs9rvjk 235 6 , , , cord-003318-abs9rvjk 235 7 we -PRON- PRP cord-003318-abs9rvjk 235 8 did do VBD cord-003318-abs9rvjk 235 9 not not RB cord-003318-abs9rvjk 235 10 further further RB cord-003318-abs9rvjk 235 11 enrich enrich VB cord-003318-abs9rvjk 235 12 these these DT cord-003318-abs9rvjk 235 13 monoacetylated monoacetylate VBN cord-003318-abs9rvjk 235 14 estradiol estradiol NNP cord-003318-abs9rvjk 235 15 glucosides glucoside NNS cord-003318-abs9rvjk 235 16 for for IN cord-003318-abs9rvjk 235 17 NMR NMR NNP cord-003318-abs9rvjk 235 18 analysis analysis NN cord-003318-abs9rvjk 235 19 . . . cord-003318-abs9rvjk 236 1 However however RB cord-003318-abs9rvjk 236 2 , , , cord-003318-abs9rvjk 236 3 according accord VBG cord-003318-abs9rvjk 236 4 to to IN cord-003318-abs9rvjk 236 5 the the DT cord-003318-abs9rvjk 236 6 catalytic catalytic JJ cord-003318-abs9rvjk 236 7 behavior behavior NN cord-003318-abs9rvjk 236 8 of of IN cord-003318-abs9rvjk 236 9 EcSGA1 ecsga1 NN cord-003318-abs9rvjk 236 10 towards towards IN cord-003318-abs9rvjk 236 11 T-17β T-17β NNP cord-003318-abs9rvjk 236 12 - - HYPH cord-003318-abs9rvjk 236 13 G g NN cord-003318-abs9rvjk 236 14 ( ( -LRB- cord-003318-abs9rvjk 236 15 8a 8a NN cord-003318-abs9rvjk 236 16 ) ) -RRB- cord-003318-abs9rvjk 236 17 , , , cord-003318-abs9rvjk 236 18 it -PRON- PRP cord-003318-abs9rvjk 236 19 was be VBD cord-003318-abs9rvjk 236 20 easy easy JJ cord-003318-abs9rvjk 236 21 to to TO cord-003318-abs9rvjk 236 22 infer infer VB cord-003318-abs9rvjk 236 23 that that IN cord-003318-abs9rvjk 236 24 these these DT cord-003318-abs9rvjk 236 25 products product NNS cord-003318-abs9rvjk 236 26 were be VBD cord-003318-abs9rvjk 236 27 most most RBS cord-003318-abs9rvjk 236 28 likely likely JJ cord-003318-abs9rvjk 236 29 2 2 CD cord-003318-abs9rvjk 236 30 0 0 CD cord-003318-abs9rvjk 236 31 -(9c -(9c NNS cord-003318-abs9rvjk 236 32 , , , cord-003318-abs9rvjk 236 33 t t NN cord-003318-abs9rvjk 236 34 R R NNP cord-003318-abs9rvjk 236 35 ¼ ¼ NNP cord-003318-abs9rvjk 236 36 14.513 14.513 CD cord-003318-abs9rvjk 236 37 min min NNP cord-003318-abs9rvjk 236 38 ) ) -RRB- cord-003318-abs9rvjk 236 39 , , , cord-003318-abs9rvjk 236 40 3 3 CD cord-003318-abs9rvjk 236 41 0 0 CD cord-003318-abs9rvjk 236 42 -(9d -(9d CD cord-003318-abs9rvjk 236 43 , , , cord-003318-abs9rvjk 236 44 t t NN cord-003318-abs9rvjk 236 45 R R NNP cord-003318-abs9rvjk 236 46 ¼ ¼ CD cord-003318-abs9rvjk 236 47 13.873 13.873 CD cord-003318-abs9rvjk 236 48 min min NNP cord-003318-abs9rvjk 236 49 ) ) -RRB- cord-003318-abs9rvjk 236 50 and and CC cord-003318-abs9rvjk 236 51 4 4 CD cord-003318-abs9rvjk 236 52 0 0 CD cord-003318-abs9rvjk 237 1 -AE-17β -ae-17β LS cord-003318-abs9rvjk 237 2 - - : cord-003318-abs9rvjk 237 3 G G NNP cord-003318-abs9rvjk 237 4 ( ( -LRB- cord-003318-abs9rvjk 237 5 9e 9e NNP cord-003318-abs9rvjk 237 6 , , , cord-003318-abs9rvjk 237 7 t t NNP cord-003318-abs9rvjk 237 8 R R NNP cord-003318-abs9rvjk 237 9 ¼ ¼ NNP cord-003318-abs9rvjk 237 10 14.213 14.213 CD cord-003318-abs9rvjk 237 11 min min NNP cord-003318-abs9rvjk 237 12 , , , cord-003318-abs9rvjk 237 13 Fig Fig NNP cord-003318-abs9rvjk 237 14 . . NNP cord-003318-abs9rvjk 237 15 5 5 CD cord-003318-abs9rvjk 237 16 ) ) -RRB- cord-003318-abs9rvjk 237 17 . . . cord-003318-abs9rvjk 238 1 The the DT cord-003318-abs9rvjk 238 2 order order NN cord-003318-abs9rvjk 238 3 of of IN cord-003318-abs9rvjk 238 4 reactivity reactivity NN cord-003318-abs9rvjk 238 5 of of IN cord-003318-abs9rvjk 238 6 the the DT cord-003318-abs9rvjk 238 7 hydroxyls hydroxyls NN cord-003318-abs9rvjk 238 8 was be VBD cord-003318-abs9rvjk 238 9 determined determine VBN cord-003318-abs9rvjk 238 10 as as IN cord-003318-abs9rvjk 238 11 6 6 CD cord-003318-abs9rvjk 238 12 0 0 CD cord-003318-abs9rvjk 238 13 -OH442 -oh442 SYM cord-003318-abs9rvjk 238 14 0 0 CD cord-003318-abs9rvjk 238 15 -OH43 -oh43 NN cord-003318-abs9rvjk 238 16 0 0 CD cord-003318-abs9rvjk 238 17 -OH4 -oh4 NN cord-003318-abs9rvjk 238 18 4 4 CD cord-003318-abs9rvjk 238 19 0 0 CD cord-003318-abs9rvjk 238 20 -OH -oh NN cord-003318-abs9rvjk 238 21 with with IN cord-003318-abs9rvjk 238 22 a a DT cord-003318-abs9rvjk 238 23 yield yield NN cord-003318-abs9rvjk 238 24 ratio ratio NN cord-003318-abs9rvjk 238 25 of of IN cord-003318-abs9rvjk 238 26 80:10:6:4 80:10:6:4 CD cord-003318-abs9rvjk 239 1 ( ( -LRB- cord-003318-abs9rvjk 239 2 Fig Fig NNP cord-003318-abs9rvjk 239 3 . . NNP cord-003318-abs9rvjk 239 4 5 5 CD cord-003318-abs9rvjk 239 5 ) ) -RRB- cord-003318-abs9rvjk 239 6 . . . cord-003318-abs9rvjk 240 1 Regioselective Regioselective NNP cord-003318-abs9rvjk 240 2 acylation acylation NN cord-003318-abs9rvjk 240 3 of of IN cord-003318-abs9rvjk 240 4 one one CD cord-003318-abs9rvjk 240 5 of of IN cord-003318-abs9rvjk 240 6 the the DT cord-003318-abs9rvjk 240 7 multiple multiple JJ cord-003318-abs9rvjk 240 8 hydroxyl hydroxyl NN cord-003318-abs9rvjk 240 9 groups group NNS cord-003318-abs9rvjk 240 10 in in IN cord-003318-abs9rvjk 240 11 SGs SGs NNP cord-003318-abs9rvjk 240 12 is be VBZ cord-003318-abs9rvjk 240 13 the the DT cord-003318-abs9rvjk 240 14 major major JJ cord-003318-abs9rvjk 240 15 obstacle obstacle NN cord-003318-abs9rvjk 240 16 to to IN cord-003318-abs9rvjk 240 17 the the DT cord-003318-abs9rvjk 240 18 synthesis synthesis NN cord-003318-abs9rvjk 240 19 of of IN cord-003318-abs9rvjk 240 20 SGEs sge NNS cord-003318-abs9rvjk 240 21 and and CC cord-003318-abs9rvjk 240 22 direct direct JJ cord-003318-abs9rvjk 240 23 methods method NNS cord-003318-abs9rvjk 240 24 for for IN cord-003318-abs9rvjk 240 25 site site NN cord-003318-abs9rvjk 240 26 - - HYPH cord-003318-abs9rvjk 240 27 selective selective JJ cord-003318-abs9rvjk 240 28 acylation acylation NN cord-003318-abs9rvjk 240 29 of of IN cord-003318-abs9rvjk 240 30 unprotected unprotected JJ cord-003318-abs9rvjk 240 31 SGs SGs NNP cord-003318-abs9rvjk 240 32 have have VBP cord-003318-abs9rvjk 240 33 rarely rarely RB cord-003318-abs9rvjk 240 34 been be VBN cord-003318-abs9rvjk 240 35 documented document VBN cord-003318-abs9rvjk 240 36 . . . cord-003318-abs9rvjk 241 1 In in IN cord-003318-abs9rvjk 241 2 this this DT cord-003318-abs9rvjk 241 3 contribution contribution NN cord-003318-abs9rvjk 241 4 , , , cord-003318-abs9rvjk 241 5 we -PRON- PRP cord-003318-abs9rvjk 241 6 successfully successfully RB cord-003318-abs9rvjk 241 7 achieved achieve VBD cord-003318-abs9rvjk 241 8 the the DT cord-003318-abs9rvjk 241 9 regioselective regioselective JJ cord-003318-abs9rvjk 241 10 acylation acylation NN cord-003318-abs9rvjk 241 11 of of IN cord-003318-abs9rvjk 241 12 fully fully RB cord-003318-abs9rvjk 241 13 unprotected unprotected JJ cord-003318-abs9rvjk 241 14 SGs SGs NNP cord-003318-abs9rvjk 241 15 using use VBG cord-003318-abs9rvjk 241 16 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 241 17 as as IN cord-003318-abs9rvjk 241 18 the the DT cord-003318-abs9rvjk 241 19 biocatalyst biocatalyst NN cord-003318-abs9rvjk 241 20 , , , cord-003318-abs9rvjk 241 21 thereby thereby RB cord-003318-abs9rvjk 241 22 leading lead VBG cord-003318-abs9rvjk 241 23 to to IN cord-003318-abs9rvjk 241 24 an an DT cord-003318-abs9rvjk 241 25 extremely extremely RB cord-003318-abs9rvjk 241 26 short short JJ cord-003318-abs9rvjk 241 27 - - HYPH cord-003318-abs9rvjk 241 28 step step NN cord-003318-abs9rvjk 241 29 synthesis synthesis NN cord-003318-abs9rvjk 241 30 of of IN cord-003318-abs9rvjk 241 31 ASGs asg NNS cord-003318-abs9rvjk 241 32 . . . cord-003318-abs9rvjk 242 1 Acetylated Acetylated NNP cord-003318-abs9rvjk 242 2 steroidal steroidal JJ cord-003318-abs9rvjk 242 3 glucosides glucoside NNS cord-003318-abs9rvjk 242 4 , , , cord-003318-abs9rvjk 242 5 namely namely RB cord-003318-abs9rvjk 242 6 8b 8b NNP cord-003318-abs9rvjk 242 7 , , , cord-003318-abs9rvjk 242 8 8c 8c CD cord-003318-abs9rvjk 242 9 , , , cord-003318-abs9rvjk 242 10 8d 8d NNP cord-003318-abs9rvjk 242 11 and and CC cord-003318-abs9rvjk 242 12 8e 8e NNP cord-003318-abs9rvjk 242 13 , , , cord-003318-abs9rvjk 242 14 together together RB cord-003318-abs9rvjk 242 15 with with IN cord-003318-abs9rvjk 242 16 9b 9b NNS cord-003318-abs9rvjk 242 17 were be VBD cord-003318-abs9rvjk 242 18 tested test VBN cord-003318-abs9rvjk 242 19 for for IN cord-003318-abs9rvjk 242 20 their -PRON- PRP$ cord-003318-abs9rvjk 242 21 in in FW cord-003318-abs9rvjk 242 22 vitro vitro FW cord-003318-abs9rvjk 242 23 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 242 24 against against IN cord-003318-abs9rvjk 242 25 seven seven CD cord-003318-abs9rvjk 242 26 human human JJ cord-003318-abs9rvjk 242 27 cancer cancer NN cord-003318-abs9rvjk 242 28 cell cell NN cord-003318-abs9rvjk 242 29 lines line NNS cord-003318-abs9rvjk 242 30 including include VBG cord-003318-abs9rvjk 242 31 HCT116 HCT116 NNP cord-003318-abs9rvjk 242 32 , , , cord-003318-abs9rvjk 242 33 Bel7402 Bel7402 NNP cord-003318-abs9rvjk 242 34 , , , cord-003318-abs9rvjk 242 35 MGC803 MGC803 NNP cord-003318-abs9rvjk 242 36 , , , cord-003318-abs9rvjk 242 37 Capan2 Capan2 NNP cord-003318-abs9rvjk 242 38 , , , cord-003318-abs9rvjk 242 39 NCI NCI NNP cord-003318-abs9rvjk 242 40 - - HYPH cord-003318-abs9rvjk 242 41 H460 H460 NNP cord-003318-abs9rvjk 242 42 , , , cord-003318-abs9rvjk 242 43 NCI NCI NNP cord-003318-abs9rvjk 242 44 - - HYPH cord-003318-abs9rvjk 242 45 H1650 H1650 NNP cord-003318-abs9rvjk 242 46 and and CC cord-003318-abs9rvjk 242 47 A549 A549 NNP cord-003318-abs9rvjk 242 48 . . . cord-003318-abs9rvjk 243 1 The the DT cord-003318-abs9rvjk 243 2 results result NNS cord-003318-abs9rvjk 243 3 indicated indicate VBD cord-003318-abs9rvjk 243 4 that that IN cord-003318-abs9rvjk 243 5 3 3 CD cord-003318-abs9rvjk 243 6 0 0 CD cord-003318-abs9rvjk 243 7 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 243 8 - - HYPH cord-003318-abs9rvjk 243 9 G g NN cord-003318-abs9rvjk 243 10 ( ( -LRB- cord-003318-abs9rvjk 243 11 8d 8d NNP cord-003318-abs9rvjk 243 12 ) ) -RRB- cord-003318-abs9rvjk 243 13 exhibited exhibit VBD cord-003318-abs9rvjk 243 14 a a DT cord-003318-abs9rvjk 243 15 wide wide JJ cord-003318-abs9rvjk 243 16 spectrum spectrum NN cord-003318-abs9rvjk 243 17 of of IN cord-003318-abs9rvjk 243 18 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 243 19 activities activity NNS cord-003318-abs9rvjk 243 20 against against IN cord-003318-abs9rvjk 243 21 the the DT cord-003318-abs9rvjk 243 22 tested test VBN cord-003318-abs9rvjk 243 23 cell cell NN cord-003318-abs9rvjk 243 24 lines line NNS cord-003318-abs9rvjk 243 25 ( ( -LRB- cord-003318-abs9rvjk 243 26 Table Table NNP cord-003318-abs9rvjk 243 27 6 6 CD cord-003318-abs9rvjk 243 28 ) ) -RRB- cord-003318-abs9rvjk 243 29 . . . cord-003318-abs9rvjk 244 1 6 6 CD cord-003318-abs9rvjk 244 2 0 0 CD cord-003318-abs9rvjk 244 3 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 244 4 - - HYPH cord-003318-abs9rvjk 244 5 G g NN cord-003318-abs9rvjk 244 6 ( ( -LRB- cord-003318-abs9rvjk 244 7 8b 8b NN cord-003318-abs9rvjk 244 8 ) ) -RRB- cord-003318-abs9rvjk 244 9 displayed display VBD cord-003318-abs9rvjk 244 10 much much RB cord-003318-abs9rvjk 244 11 less less JJR cord-003318-abs9rvjk 244 12 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 244 13 than than IN cord-003318-abs9rvjk 244 14 3 3 CD cord-003318-abs9rvjk 244 15 0 0 CD cord-003318-abs9rvjk 244 16 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 244 17 - - HYPH cord-003318-abs9rvjk 244 18 G g NN cord-003318-abs9rvjk 244 19 ( ( -LRB- cord-003318-abs9rvjk 244 20 8d 8d NNP cord-003318-abs9rvjk 244 21 ) ) -RRB- cord-003318-abs9rvjk 244 22 but but CC cord-003318-abs9rvjk 244 23 showed show VBD cord-003318-abs9rvjk 244 24 a a DT cord-003318-abs9rvjk 244 25 mild mild JJ cord-003318-abs9rvjk 244 26 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 244 27 against against IN cord-003318-abs9rvjk 244 28 human human JJ cord-003318-abs9rvjk 244 29 non non JJ cord-003318-abs9rvjk 244 30 - - JJ cord-003318-abs9rvjk 244 31 small small JJ cord-003318-abs9rvjk 244 32 cell cell NN cord-003318-abs9rvjk 244 33 lung lung NN cord-003318-abs9rvjk 244 34 carcinoma carcinoma NN cord-003318-abs9rvjk 244 35 cell cell NN cord-003318-abs9rvjk 244 36 line line NN cord-003318-abs9rvjk 244 37 NCI NCI NNP cord-003318-abs9rvjk 244 38 - - HYPH cord-003318-abs9rvjk 244 39 H1650 H1650 NNP cord-003318-abs9rvjk 244 40 with with IN cord-003318-abs9rvjk 244 41 IC IC NNP cord-003318-abs9rvjk 244 42 50 50 CD cord-003318-abs9rvjk 244 43 values value NNS cord-003318-abs9rvjk 244 44 of of IN cord-003318-abs9rvjk 244 45 26.5 26.5 CD cord-003318-abs9rvjk 244 46 μmol μmol NNP cord-003318-abs9rvjk 244 47 / / SYM cord-003318-abs9rvjk 244 48 L L NNP cord-003318-abs9rvjk 244 49 ( ( -LRB- cord-003318-abs9rvjk 244 50 Table Table NNP cord-003318-abs9rvjk 244 51 6 6 CD cord-003318-abs9rvjk 244 52 ) ) -RRB- cord-003318-abs9rvjk 244 53 . . . cord-003318-abs9rvjk 245 1 On on IN cord-003318-abs9rvjk 245 2 the the DT cord-003318-abs9rvjk 245 3 contrary contrary NN cord-003318-abs9rvjk 245 4 , , , cord-003318-abs9rvjk 245 5 the the DT cord-003318-abs9rvjk 245 6 control control NN cord-003318-abs9rvjk 245 7 T-17β T-17β NNP cord-003318-abs9rvjk 245 8 - - HYPH cord-003318-abs9rvjk 245 9 G G NNP cord-003318-abs9rvjk 245 10 ( ( -LRB- cord-003318-abs9rvjk 245 11 8a 8a NN cord-003318-abs9rvjk 245 12 ) ) -RRB- cord-003318-abs9rvjk 245 13 did do VBD cord-003318-abs9rvjk 245 14 not not RB cord-003318-abs9rvjk 245 15 display display VB cord-003318-abs9rvjk 245 16 significant significant JJ cord-003318-abs9rvjk 245 17 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 245 18 towards towards IN cord-003318-abs9rvjk 245 19 these these DT cord-003318-abs9rvjk 245 20 tested test VBN cord-003318-abs9rvjk 245 21 cell cell NN cord-003318-abs9rvjk 245 22 lines line NNS cord-003318-abs9rvjk 245 23 ( ( -LRB- cord-003318-abs9rvjk 245 24 IC IC NNP cord-003318-abs9rvjk 245 25 50 50 CD cord-003318-abs9rvjk 245 26 450.0 450.0 CD cord-003318-abs9rvjk 245 27 μmol μmol NNP cord-003318-abs9rvjk 245 28 / / SYM cord-003318-abs9rvjk 245 29 L L NNP cord-003318-abs9rvjk 245 30 ) ) -RRB- cord-003318-abs9rvjk 245 31 . . . cord-003318-abs9rvjk 246 1 These these DT cord-003318-abs9rvjk 246 2 evidences evidence NNS cord-003318-abs9rvjk 246 3 revealed reveal VBD cord-003318-abs9rvjk 246 4 that that IN cord-003318-abs9rvjk 246 5 the the DT cord-003318-abs9rvjk 246 6 acyl acyl NN cord-003318-abs9rvjk 246 7 groups group NNS cord-003318-abs9rvjk 246 8 of of IN cord-003318-abs9rvjk 246 9 SGEs sge NNS cord-003318-abs9rvjk 246 10 are be VBP cord-003318-abs9rvjk 246 11 of of IN cord-003318-abs9rvjk 246 12 importance importance NN cord-003318-abs9rvjk 246 13 to to IN cord-003318-abs9rvjk 246 14 their -PRON- PRP$ cord-003318-abs9rvjk 246 15 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 246 16 and and CC cord-003318-abs9rvjk 246 17 direct direct JJ cord-003318-abs9rvjk 246 18 regioselective regioselective JJ cord-003318-abs9rvjk 246 19 acylation acylation NN cord-003318-abs9rvjk 246 20 of of IN cord-003318-abs9rvjk 246 21 SGs SGs NNP cord-003318-abs9rvjk 246 22 is be VBZ cord-003318-abs9rvjk 246 23 thus thus RB cord-003318-abs9rvjk 246 24 believed believe VBN cord-003318-abs9rvjk 246 25 as as IN cord-003318-abs9rvjk 246 26 a a DT cord-003318-abs9rvjk 246 27 powerful powerful JJ cord-003318-abs9rvjk 246 28 tool tool NN cord-003318-abs9rvjk 246 29 for for IN cord-003318-abs9rvjk 246 30 the the DT cord-003318-abs9rvjk 246 31 discovery discovery NN cord-003318-abs9rvjk 246 32 of of IN cord-003318-abs9rvjk 246 33 drug drug NN cord-003318-abs9rvjk 246 34 candidates candidate NNS cord-003318-abs9rvjk 246 35 . . . cord-003318-abs9rvjk 247 1 Acylated acylated JJ cord-003318-abs9rvjk 247 2 steroidal steroidal JJ cord-003318-abs9rvjk 247 3 glycosides glycoside NNS cord-003318-abs9rvjk 247 4 have have VBP cord-003318-abs9rvjk 247 5 attracted attract VBN cord-003318-abs9rvjk 247 6 our -PRON- PRP$ cord-003318-abs9rvjk 247 7 attentions attention NNS cord-003318-abs9rvjk 247 8 primarily primarily RB cord-003318-abs9rvjk 247 9 due due IN cord-003318-abs9rvjk 247 10 to to IN cord-003318-abs9rvjk 247 11 their -PRON- PRP$ cord-003318-abs9rvjk 247 12 biological biological JJ cord-003318-abs9rvjk 247 13 and and CC cord-003318-abs9rvjk 247 14 pharmacological pharmacological JJ cord-003318-abs9rvjk 247 15 significances significance NNS cord-003318-abs9rvjk 247 16 2,10,11,23 2,10,11,23 CD cord-003318-abs9rvjk 247 17 . . . cord-003318-abs9rvjk 248 1 There there EX cord-003318-abs9rvjk 248 2 are be VBP cord-003318-abs9rvjk 248 3 two two CD cord-003318-abs9rvjk 248 4 enzymes enzyme NNS cord-003318-abs9rvjk 248 5 , , , cord-003318-abs9rvjk 248 6 namely namely RB cord-003318-abs9rvjk 248 7 SGTs sgt NNS cord-003318-abs9rvjk 248 8 and and CC cord-003318-abs9rvjk 248 9 SGAs sga NNS cord-003318-abs9rvjk 248 10 , , , cord-003318-abs9rvjk 248 11 responsible responsible JJ cord-003318-abs9rvjk 248 12 for for IN cord-003318-abs9rvjk 248 13 the the DT cord-003318-abs9rvjk 248 14 biosynthesis biosynthesis NN cord-003318-abs9rvjk 248 15 of of IN cord-003318-abs9rvjk 248 16 ASGs asg NNS cord-003318-abs9rvjk 248 17 . . . cord-003318-abs9rvjk 249 1 To to TO cord-003318-abs9rvjk 249 2 synthesize synthesize VB cord-003318-abs9rvjk 249 3 ASGs asg NNS cord-003318-abs9rvjk 249 4 , , , cord-003318-abs9rvjk 249 5 the the DT cord-003318-abs9rvjk 249 6 primary primary JJ cord-003318-abs9rvjk 249 7 premise premise NN cord-003318-abs9rvjk 249 8 is be VBZ cord-003318-abs9rvjk 249 9 to to TO cord-003318-abs9rvjk 249 10 obtain obtain VB cord-003318-abs9rvjk 249 11 glycosyltransferases glycosyltransferase NNS cord-003318-abs9rvjk 249 12 capable capable JJ cord-003318-abs9rvjk 249 13 of of IN cord-003318-abs9rvjk 249 14 catalyzing catalyze VBG cord-003318-abs9rvjk 249 15 the the DT cord-003318-abs9rvjk 249 16 formation formation NN cord-003318-abs9rvjk 249 17 of of IN cord-003318-abs9rvjk 249 18 SGs SGs NNP cord-003318-abs9rvjk 249 19 from from IN cord-003318-abs9rvjk 249 20 the the DT cord-003318-abs9rvjk 249 21 abundantly abundantly RB cord-003318-abs9rvjk 249 22 available available JJ cord-003318-abs9rvjk 249 23 free free JJ cord-003318-abs9rvjk 249 24 steroids steroid NNS cord-003318-abs9rvjk 249 25 . . . cord-003318-abs9rvjk 250 1 O. O. NNP cord-003318-abs9rvjk 250 2 saundersiae saundersiae NNP cord-003318-abs9rvjk 250 3 is be VBZ cord-003318-abs9rvjk 250 4 thus thus RB cord-003318-abs9rvjk 250 5 selected select VBN cord-003318-abs9rvjk 250 6 as as IN cord-003318-abs9rvjk 250 7 the the DT cord-003318-abs9rvjk 250 8 candidate candidate NN cord-003318-abs9rvjk 250 9 plant plant NN cord-003318-abs9rvjk 250 10 for for IN cord-003318-abs9rvjk 250 11 SGTs sgt NNS cord-003318-abs9rvjk 250 12 isolation isolation NN cord-003318-abs9rvjk 250 13 . . . cord-003318-abs9rvjk 251 1 O. O. NNP cord-003318-abs9rvjk 251 2 saundersiae saundersiae NNP cord-003318-abs9rvjk 251 3 is be VBZ cord-003318-abs9rvjk 251 4 a a DT cord-003318-abs9rvjk 251 5 monocotyledonous monocotyledonous JJ cord-003318-abs9rvjk 251 6 plant plant NN cord-003318-abs9rvjk 251 7 rich rich JJ cord-003318-abs9rvjk 251 8 in in IN cord-003318-abs9rvjk 251 9 acylated acylated JJ cord-003318-abs9rvjk 251 10 steroidal steroidal JJ cord-003318-abs9rvjk 251 11 glycosides glycoside NNS cord-003318-abs9rvjk 251 12 , , , cord-003318-abs9rvjk 251 13 suggesting suggest VBG cord-003318-abs9rvjk 251 14 that that IN cord-003318-abs9rvjk 251 15 it -PRON- PRP cord-003318-abs9rvjk 251 16 may may MD cord-003318-abs9rvjk 251 17 contain contain VB cord-003318-abs9rvjk 251 18 SGTs sgt NNS cord-003318-abs9rvjk 251 19 and and CC cord-003318-abs9rvjk 251 20 SGAs sga NNS cord-003318-abs9rvjk 251 21 responsible responsible JJ cord-003318-abs9rvjk 251 22 for for IN cord-003318-abs9rvjk 251 23 the the DT cord-003318-abs9rvjk 251 24 biosynthesis biosynthesis NN cord-003318-abs9rvjk 251 25 of of IN cord-003318-abs9rvjk 251 26 ASGs ASGs NNPS cord-003318-abs9rvjk 251 27 23 23 CD cord-003318-abs9rvjk 251 28 . . . cord-003318-abs9rvjk 252 1 Thus thus RB cord-003318-abs9rvjk 252 2 , , , cord-003318-abs9rvjk 252 3 the the DT cord-003318-abs9rvjk 252 4 transcriptome transcriptome NN cord-003318-abs9rvjk 252 5 of of IN cord-003318-abs9rvjk 252 6 O. O. NNP cord-003318-abs9rvjk 252 7 saundersiae saundersiae NNP cord-003318-abs9rvjk 252 8 was be VBD cord-003318-abs9rvjk 252 9 sequenced sequence VBN cord-003318-abs9rvjk 252 10 with with IN cord-003318-abs9rvjk 252 11 the the DT cord-003318-abs9rvjk 252 12 aim aim NN cord-003318-abs9rvjk 252 13 to to TO cord-003318-abs9rvjk 252 14 facilitate facilitate VB cord-003318-abs9rvjk 252 15 the the DT cord-003318-abs9rvjk 252 16 genes gene NNS cord-003318-abs9rvjk 252 17 discovery discovery NN cord-003318-abs9rvjk 252 18 . . . cord-003318-abs9rvjk 253 1 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 253 2 was be VBD cord-003318-abs9rvjk 253 3 then then RB cord-003318-abs9rvjk 253 4 isolated isolate VBN cord-003318-abs9rvjk 253 5 from from IN cord-003318-abs9rvjk 253 6 O. O. NNP cord-003318-abs9rvjk 253 7 saundersiae saundersiae NN cord-003318-abs9rvjk 253 8 based base VBN cord-003318-abs9rvjk 253 9 on on IN cord-003318-abs9rvjk 253 10 the the DT cord-003318-abs9rvjk 253 11 RNA RNA NNP cord-003318-abs9rvjk 253 12 - - HYPH cord-003318-abs9rvjk 253 13 Seq Seq NNP cord-003318-abs9rvjk 253 14 data datum NNS cord-003318-abs9rvjk 253 15 . . . cord-003318-abs9rvjk 254 1 Subsequently subsequently RB cord-003318-abs9rvjk 254 2 , , , cord-003318-abs9rvjk 254 3 OsSGT1-containing ossgt1-containe VBG cord-003318-abs9rvjk 254 4 cell cell NN cord-003318-abs9rvjk 254 5 - - HYPH cord-003318-abs9rvjk 254 6 free free JJ cord-003318-abs9rvjk 254 7 extract extract NN cord-003318-abs9rvjk 254 8 was be VBD cord-003318-abs9rvjk 254 9 used use VBN cord-003318-abs9rvjk 254 10 as as IN cord-003318-abs9rvjk 254 11 the the DT cord-003318-abs9rvjk 254 12 biocatalyst biocatalyst NN cord-003318-abs9rvjk 254 13 for for IN cord-003318-abs9rvjk 254 14 glycosylations glycosylation NNS cord-003318-abs9rvjk 254 15 of of IN cord-003318-abs9rvjk 254 16 49 49 CD cord-003318-abs9rvjk 254 17 structurally structurally RB cord-003318-abs9rvjk 254 18 diverse diverse JJ cord-003318-abs9rvjk 254 19 drug drug NN cord-003318-abs9rvjk 254 20 - - HYPH cord-003318-abs9rvjk 254 21 like like JJ cord-003318-abs9rvjk 254 22 scaffolds scaffold NNS cord-003318-abs9rvjk 254 23 . . . cord-003318-abs9rvjk 255 1 The the DT cord-003318-abs9rvjk 255 2 use use NN cord-003318-abs9rvjk 255 3 of of IN cord-003318-abs9rvjk 255 4 cell cell NN cord-003318-abs9rvjk 255 5 - - HYPH cord-003318-abs9rvjk 255 6 free free JJ cord-003318-abs9rvjk 255 7 extract extract NN cord-003318-abs9rvjk 255 8 offers offer VBZ cord-003318-abs9rvjk 255 9 a a DT cord-003318-abs9rvjk 255 10 number number NN cord-003318-abs9rvjk 255 11 of of IN cord-003318-abs9rvjk 255 12 advantages advantage NNS cord-003318-abs9rvjk 255 13 . . . cord-003318-abs9rvjk 256 1 Unlike unlike IN cord-003318-abs9rvjk 256 2 the the DT cord-003318-abs9rvjk 256 3 ambitious ambitious JJ cord-003318-abs9rvjk 256 4 purification purification NN cord-003318-abs9rvjk 256 5 procedures procedure NNS cord-003318-abs9rvjk 256 6 , , , cord-003318-abs9rvjk 256 7 the the DT cord-003318-abs9rvjk 256 8 preparation preparation NN cord-003318-abs9rvjk 256 9 of of IN cord-003318-abs9rvjk 256 10 cell cell NN cord-003318-abs9rvjk 256 11 - - HYPH cord-003318-abs9rvjk 256 12 free free JJ cord-003318-abs9rvjk 256 13 extract extract NN cord-003318-abs9rvjk 256 14 was be VBD cord-003318-abs9rvjk 256 15 simple simple JJ cord-003318-abs9rvjk 256 16 and and CC cord-003318-abs9rvjk 256 17 timesaving timesaving JJ cord-003318-abs9rvjk 256 18 . . . cord-003318-abs9rvjk 257 1 Moreover moreover RB cord-003318-abs9rvjk 257 2 , , , cord-003318-abs9rvjk 257 3 compared compare VBD cord-003318-abs9rvjk 257 4 the the DT cord-003318-abs9rvjk 257 5 purified purify VBN cord-003318-abs9rvjk 257 6 enzymes enzyme NNS cord-003318-abs9rvjk 257 7 , , , cord-003318-abs9rvjk 257 8 the the DT cord-003318-abs9rvjk 257 9 recombinant recombinant JJ cord-003318-abs9rvjk 257 10 proteins protein NNS cord-003318-abs9rvjk 257 11 used use VBN cord-003318-abs9rvjk 257 12 in in IN cord-003318-abs9rvjk 257 13 crude crude JJ cord-003318-abs9rvjk 257 14 extract extract NN cord-003318-abs9rvjk 257 15 - - HYPH cord-003318-abs9rvjk 257 16 based base VBN cord-003318-abs9rvjk 257 17 system system NN cord-003318-abs9rvjk 257 18 were be VBD cord-003318-abs9rvjk 257 19 more more RBR cord-003318-abs9rvjk 257 20 stable stable JJ cord-003318-abs9rvjk 257 21 . . . cord-003318-abs9rvjk 258 1 Steroidal steroidal JJ cord-003318-abs9rvjk 258 2 glycosides glycoside NNS cord-003318-abs9rvjk 258 3 are be VBP cord-003318-abs9rvjk 258 4 one one CD cord-003318-abs9rvjk 258 5 of of IN cord-003318-abs9rvjk 258 6 the the DT cord-003318-abs9rvjk 258 7 main main JJ cord-003318-abs9rvjk 258 8 sources source NNS cord-003318-abs9rvjk 258 9 of of IN cord-003318-abs9rvjk 258 10 innovative innovative JJ cord-003318-abs9rvjk 258 11 drugs drug NNS cord-003318-abs9rvjk 258 12 17 17 CD cord-003318-abs9rvjk 258 13 . . . cord-003318-abs9rvjk 259 1 SGT SGT NNP cord-003318-abs9rvjk 259 2 - - HYPH cord-003318-abs9rvjk 259 3 catalyzed catalyze VBN cord-003318-abs9rvjk 259 4 glycodiversification glycodiversification NN cord-003318-abs9rvjk 259 5 of of IN cord-003318-abs9rvjk 259 6 steroids steroid NNS cord-003318-abs9rvjk 259 7 could could MD cord-003318-abs9rvjk 259 8 expand expand VB cord-003318-abs9rvjk 259 9 the the DT cord-003318-abs9rvjk 259 10 molecular molecular JJ cord-003318-abs9rvjk 259 11 diversification diversification NN cord-003318-abs9rvjk 259 12 , , , cord-003318-abs9rvjk 259 13 thereby thereby RB cord-003318-abs9rvjk 259 14 facilitating facilitate VBG cord-003318-abs9rvjk 259 15 the the DT cord-003318-abs9rvjk 259 16 discovery discovery NN cord-003318-abs9rvjk 259 17 of of IN cord-003318-abs9rvjk 259 18 pharmacological pharmacological JJ cord-003318-abs9rvjk 259 19 leads lead NNS cord-003318-abs9rvjk 259 20 . . . cord-003318-abs9rvjk 260 1 Thus thus RB cord-003318-abs9rvjk 260 2 , , , cord-003318-abs9rvjk 260 3 the the DT cord-003318-abs9rvjk 260 4 search search NN cord-003318-abs9rvjk 260 5 of of IN cord-003318-abs9rvjk 260 6 SGTs sgt NNS cord-003318-abs9rvjk 260 7 with with IN cord-003318-abs9rvjk 260 8 catalytic catalytic JJ cord-003318-abs9rvjk 260 9 promiscuity promiscuity NN cord-003318-abs9rvjk 260 10 may may MD cord-003318-abs9rvjk 260 11 provide provide VB cord-003318-abs9rvjk 260 12 potent potent JJ cord-003318-abs9rvjk 260 13 biocatalysts biocatalyst NNS cord-003318-abs9rvjk 260 14 for for IN cord-003318-abs9rvjk 260 15 glycodiversification glycodiversification NN cord-003318-abs9rvjk 260 16 . . . cord-003318-abs9rvjk 261 1 Therefore therefore RB cord-003318-abs9rvjk 261 2 , , , cord-003318-abs9rvjk 261 3 a a DT cord-003318-abs9rvjk 261 4 library library NN cord-003318-abs9rvjk 261 5 containing contain VBG cord-003318-abs9rvjk 261 6 49 49 CD cord-003318-abs9rvjk 261 7 structural structural JJ cord-003318-abs9rvjk 261 8 diverse diverse JJ cord-003318-abs9rvjk 261 9 drug drug NN cord-003318-abs9rvjk 261 10 - - HYPH cord-003318-abs9rvjk 261 11 like like JJ cord-003318-abs9rvjk 261 12 molecules molecule NNS cord-003318-abs9rvjk 261 13 was be VBD cord-003318-abs9rvjk 261 14 utilized utilize VBN cord-003318-abs9rvjk 261 15 to to TO cord-003318-abs9rvjk 261 16 react react VB cord-003318-abs9rvjk 261 17 with with IN cord-003318-abs9rvjk 261 18 the the DT cord-003318-abs9rvjk 261 19 recombinant recombinant JJ cord-003318-abs9rvjk 261 20 OsSGT1 ossgt1 NN cord-003318-abs9rvjk 261 21 with with IN cord-003318-abs9rvjk 261 22 the the DT cord-003318-abs9rvjk 261 23 aim aim NN cord-003318-abs9rvjk 261 24 to to TO cord-003318-abs9rvjk 261 25 explore explore VB cord-003318-abs9rvjk 261 26 the the DT cord-003318-abs9rvjk 261 27 substrate substrate JJ cord-003318-abs9rvjk 261 28 flexibility flexibility NN cord-003318-abs9rvjk 261 29 of of IN cord-003318-abs9rvjk 261 30 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 261 31 . . . cord-003318-abs9rvjk 262 1 In in IN cord-003318-abs9rvjk 262 2 vitro vitro FW cord-003318-abs9rvjk 262 3 enzymatic enzymatic JJ cord-003318-abs9rvjk 262 4 analyses analysis NNS cord-003318-abs9rvjk 262 5 revealed reveal VBD cord-003318-abs9rvjk 262 6 that that IN cord-003318-abs9rvjk 262 7 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 262 8 was be VBD cord-003318-abs9rvjk 262 9 active active JJ cord-003318-abs9rvjk 262 10 against against IN cord-003318-abs9rvjk 262 11 various various JJ cord-003318-abs9rvjk 262 12 steroids steroid NNS cord-003318-abs9rvjk 262 13 , , , cord-003318-abs9rvjk 262 14 including include VBG cord-003318-abs9rvjk 262 15 physterols physterol NNS cord-003318-abs9rvjk 262 16 ( ( -LRB- cord-003318-abs9rvjk 262 17 1 1 CD cord-003318-abs9rvjk 262 18 - - SYM cord-003318-abs9rvjk 262 19 3 3 CD cord-003318-abs9rvjk 262 20 , , , cord-003318-abs9rvjk 262 21 Supplementary Supplementary NNP cord-003318-abs9rvjk 262 22 Information Information NNP cord-003318-abs9rvjk 262 23 Figs Figs NNPS cord-003318-abs9rvjk 262 24 . . . cord-003318-abs9rvjk 263 1 S5 S5 NNP cord-003318-abs9rvjk 263 2 - - HYPH cord-003318-abs9rvjk 263 3 7 7 CD cord-003318-abs9rvjk 263 4 ) ) -RRB- cord-003318-abs9rvjk 264 1 , , , cord-003318-abs9rvjk 264 2 steroid steroid NN cord-003318-abs9rvjk 264 3 hormones hormone NNS cord-003318-abs9rvjk 264 4 ( ( -LRB- cord-003318-abs9rvjk 264 5 4 4 CD cord-003318-abs9rvjk 264 6 , , , cord-003318-abs9rvjk 264 7 7 7 CD cord-003318-abs9rvjk 264 8 - - SYM cord-003318-abs9rvjk 264 9 10 10 CD cord-003318-abs9rvjk 264 10 , , , cord-003318-abs9rvjk 264 11 Figs Figs NNPS cord-003318-abs9rvjk 264 12 . . . cord-003318-abs9rvjk 264 13 2 2 CD cord-003318-abs9rvjk 264 14 and and CC cord-003318-abs9rvjk 264 15 3 3 CD cord-003318-abs9rvjk 264 16 , , , cord-003318-abs9rvjk 264 17 and and CC cord-003318-abs9rvjk 264 18 Supplementary Supplementary NNP cord-003318-abs9rvjk 264 19 Information Information NNP cord-003318-abs9rvjk 264 20 Figs Figs NNPS cord-003318-abs9rvjk 264 21 . . . cord-003318-abs9rvjk 264 22 S8 S8 NNP cord-003318-abs9rvjk 264 23 , , , cord-003318-abs9rvjk 264 24 S11 S11 NNP cord-003318-abs9rvjk 264 25 and and CC cord-003318-abs9rvjk 264 26 S14 S14 NNP cord-003318-abs9rvjk 264 27 ) ) -RRB- cord-003318-abs9rvjk 264 28 , , , cord-003318-abs9rvjk 264 29 steroidal steroidal JJ cord-003318-abs9rvjk 264 30 sapogenin sapogenin NNS cord-003318-abs9rvjk 264 31 ( ( -LRB- cord-003318-abs9rvjk 264 32 5 5 CD cord-003318-abs9rvjk 264 33 , , , cord-003318-abs9rvjk 264 34 Supplementary Supplementary NNP cord-003318-abs9rvjk 264 35 Information Information NNP cord-003318-abs9rvjk 264 36 _SP cord-003318-abs9rvjk 265 1 Fig fig NN cord-003318-abs9rvjk 265 2 . . . cord-003318-abs9rvjk 265 3 S9 S9 NNP cord-003318-abs9rvjk 265 4 ) ) -RRB- cord-003318-abs9rvjk 265 5 and and CC cord-003318-abs9rvjk 265 6 cardiac cardiac JJ cord-003318-abs9rvjk 265 7 aglycon aglycon NN cord-003318-abs9rvjk 265 8 ( ( -LRB- cord-003318-abs9rvjk 265 9 6 6 CD cord-003318-abs9rvjk 265 10 , , , cord-003318-abs9rvjk 265 11 Supplementary Supplementary NNP cord-003318-abs9rvjk 265 12 Information Information NNP cord-003318-abs9rvjk 265 13 _SP cord-003318-abs9rvjk 266 1 Fig fig NN cord-003318-abs9rvjk 266 2 . . . cord-003318-abs9rvjk 266 3 S10 S10 NNP cord-003318-abs9rvjk 266 4 ) ) -RRB- cord-003318-abs9rvjk 266 5 , , , cord-003318-abs9rvjk 266 6 exhibiting exhibit VBG cord-003318-abs9rvjk 266 7 a a DT cord-003318-abs9rvjk 266 8 wider wide JJR cord-003318-abs9rvjk 266 9 substrate substrate NN cord-003318-abs9rvjk 266 10 range range NN cord-003318-abs9rvjk 266 11 than than IN cord-003318-abs9rvjk 266 12 that that DT cord-003318-abs9rvjk 266 13 of of IN cord-003318-abs9rvjk 266 14 previously previously RB cord-003318-abs9rvjk 266 15 identified identify VBN cord-003318-abs9rvjk 266 16 SGTs sgt NNS cord-003318-abs9rvjk 266 17 from from IN cord-003318-abs9rvjk 266 18 plant plant NN cord-003318-abs9rvjk 266 19 18 18 CD cord-003318-abs9rvjk 266 20 , , , cord-003318-abs9rvjk 266 21 24 24 CD cord-003318-abs9rvjk 266 22 . . . cord-003318-abs9rvjk 267 1 To to TO cord-003318-abs9rvjk 267 2 investigate investigate VB cord-003318-abs9rvjk 267 3 the the DT cord-003318-abs9rvjk 267 4 regioselectivity regioselectivity NN cord-003318-abs9rvjk 267 5 of of IN cord-003318-abs9rvjk 267 6 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 267 7 , , , cord-003318-abs9rvjk 267 8 diversified diversify VBN cord-003318-abs9rvjk 267 9 steroids steroid NNS cord-003318-abs9rvjk 267 10 were be VBD cord-003318-abs9rvjk 267 11 selected select VBN cord-003318-abs9rvjk 267 12 as as IN cord-003318-abs9rvjk 267 13 the the DT cord-003318-abs9rvjk 267 14 sugar sugar NN cord-003318-abs9rvjk 267 15 acceptors acceptor NNS cord-003318-abs9rvjk 267 16 for for IN cord-003318-abs9rvjk 267 17 OsSGT1-catalyzed OsSGT1-catalyzed NNP cord-003318-abs9rvjk 267 18 glycosylations glycosylation NNS cord-003318-abs9rvjk 267 19 . . . cord-003318-abs9rvjk 268 1 As as IN cord-003318-abs9rvjk 268 2 illustrated illustrate VBN cord-003318-abs9rvjk 268 3 in in IN cord-003318-abs9rvjk 268 4 Figs Figs NNP cord-003318-abs9rvjk 268 5 . . . cord-003318-abs9rvjk 269 1 1 1 LS cord-003318-abs9rvjk 269 2 - - SYM cord-003318-abs9rvjk 269 3 3 3 CD cord-003318-abs9rvjk 269 4 and and CC cord-003318-abs9rvjk 269 5 Supplementary Supplementary NNP cord-003318-abs9rvjk 269 6 Information Information NNP cord-003318-abs9rvjk 269 7 S5 S5 NNP cord-003318-abs9rvjk 269 8 - - HYPH cord-003318-abs9rvjk 269 9 14 14 CD cord-003318-abs9rvjk 269 10 , , , cord-003318-abs9rvjk 269 11 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 269 12 specifically specifically RB cord-003318-abs9rvjk 269 13 attacked attack VBD cord-003318-abs9rvjk 269 14 the the DT cord-003318-abs9rvjk 269 15 hydroxyl hydroxyl NN cord-003318-abs9rvjk 269 16 groups group NNS cord-003318-abs9rvjk 269 17 at at IN cord-003318-abs9rvjk 269 18 C-3 C-3 NNP cord-003318-abs9rvjk 269 19 and and CC cord-003318-abs9rvjk 269 20 C-17 C-17 NNP cord-003318-abs9rvjk 269 21 positions position NNS cord-003318-abs9rvjk 269 22 , , , cord-003318-abs9rvjk 269 23 but but CC cord-003318-abs9rvjk 269 24 no no DT cord-003318-abs9rvjk 269 25 activities activity NNS cord-003318-abs9rvjk 269 26 towards towards IN cord-003318-abs9rvjk 269 27 hydroxyl hydroxyl NN cord-003318-abs9rvjk 269 28 groups group NNS cord-003318-abs9rvjk 269 29 at at IN cord-003318-abs9rvjk 269 30 C-2 C-2 NNP cord-003318-abs9rvjk 269 31 ( ( -LRB- cord-003318-abs9rvjk 269 32 13 13 CD cord-003318-abs9rvjk 269 33 , , , cord-003318-abs9rvjk 269 34 18 18 CD cord-003318-abs9rvjk 269 35 ) ) -RRB- cord-003318-abs9rvjk 269 36 , , , cord-003318-abs9rvjk 269 37 C-7 C-7 NNP cord-003318-abs9rvjk 269 38 ( ( -LRB- cord-003318-abs9rvjk 269 39 22 22 CD cord-003318-abs9rvjk 269 40 ) ) -RRB- cord-003318-abs9rvjk 269 41 , , , cord-003318-abs9rvjk 269 42 C-11 C-11 NNP cord-003318-abs9rvjk 269 43 ( ( -LRB- cord-003318-abs9rvjk 269 44 23 23 CD cord-003318-abs9rvjk 269 45 ) ) -RRB- cord-003318-abs9rvjk 269 46 , , , cord-003318-abs9rvjk 269 47 C-12 C-12 NNP cord-003318-abs9rvjk 269 48 ( ( -LRB- cord-003318-abs9rvjk 269 49 22 22 CD cord-003318-abs9rvjk 269 50 ) ) -RRB- cord-003318-abs9rvjk 269 51 , , , cord-003318-abs9rvjk 269 52 C-14(6 C-14(6 NNS cord-003318-abs9rvjk 269 53 ) ) -RRB- cord-003318-abs9rvjk 269 54 , , , cord-003318-abs9rvjk 269 55 C-15 C-15 NNP cord-003318-abs9rvjk 269 56 ( ( -LRB- cord-003318-abs9rvjk 269 57 14 14 CD cord-003318-abs9rvjk 269 58 ) ) -RRB- cord-003318-abs9rvjk 269 59 , , , cord-003318-abs9rvjk 269 60 C-16 C-16 NNP cord-003318-abs9rvjk 269 61 ( ( -LRB- cord-003318-abs9rvjk 269 62 15 15 CD cord-003318-abs9rvjk 269 63 , , , cord-003318-abs9rvjk 269 64 16 16 CD cord-003318-abs9rvjk 269 65 and and CC cord-003318-abs9rvjk 269 66 19 19 CD cord-003318-abs9rvjk 269 67 ) ) -RRB- cord-003318-abs9rvjk 269 68 and and CC cord-003318-abs9rvjk 269 69 C-21 C-21 NNP cord-003318-abs9rvjk 269 70 ( ( -LRB- cord-003318-abs9rvjk 269 71 23 23 CD cord-003318-abs9rvjk 269 72 and and CC cord-003318-abs9rvjk 269 73 24 24 CD cord-003318-abs9rvjk 269 74 ) ) -RRB- cord-003318-abs9rvjk 269 75 . . . cord-003318-abs9rvjk 270 1 When when WRB cord-003318-abs9rvjk 270 2 steroids steroid NNS cord-003318-abs9rvjk 270 3 having have VBG cord-003318-abs9rvjk 270 4 two two CD cord-003318-abs9rvjk 270 5 potentially potentially RB cord-003318-abs9rvjk 270 6 reactive reactive JJ cord-003318-abs9rvjk 270 7 hydroxyl hydroxyl NN cord-003318-abs9rvjk 270 8 groups group NNS cord-003318-abs9rvjk 270 9 , , , cord-003318-abs9rvjk 270 10 like like IN cord-003318-abs9rvjk 270 11 17α 17α CD cord-003318-abs9rvjk 270 12 - - : cord-003318-abs9rvjk 270 13 hydroxypregnenolone hydroxypregnenolone NNP cord-003318-abs9rvjk 270 14 ( ( -LRB- cord-003318-abs9rvjk 270 15 7 7 CD cord-003318-abs9rvjk 270 16 ) ) -RRB- cord-003318-abs9rvjk 270 17 or or CC cord-003318-abs9rvjk 270 18 androstenediol androstenediol NNP cord-003318-abs9rvjk 270 19 ( ( -LRB- cord-003318-abs9rvjk 270 20 10 10 CD cord-003318-abs9rvjk 270 21 ) ) -RRB- cord-003318-abs9rvjk 270 22 , , , cord-003318-abs9rvjk 270 23 were be VBD cord-003318-abs9rvjk 270 24 used use VBN cord-003318-abs9rvjk 270 25 as as IN cord-003318-abs9rvjk 270 26 the the DT cord-003318-abs9rvjk 270 27 substrate substrate NN cord-003318-abs9rvjk 270 28 for for IN cord-003318-abs9rvjk 270 29 OsSGT1-assisted ossgt1-assiste VBN cord-003318-abs9rvjk 270 30 glycosylation glycosylation NN cord-003318-abs9rvjk 270 31 , , , cord-003318-abs9rvjk 270 32 only only RB cord-003318-abs9rvjk 270 33 glycosides glycoside NNS cord-003318-abs9rvjk 270 34 with with IN cord-003318-abs9rvjk 270 35 a a DT cord-003318-abs9rvjk 270 36 glycosyl glycosyl JJ cord-003318-abs9rvjk 270 37 substituent substituent NN cord-003318-abs9rvjk 270 38 in in IN cord-003318-abs9rvjk 270 39 C-3 C-3 NNP cord-003318-abs9rvjk 270 40 position position NN cord-003318-abs9rvjk 270 41 were be VBD cord-003318-abs9rvjk 270 42 detected detect VBN cord-003318-abs9rvjk 270 43 in in IN cord-003318-abs9rvjk 270 44 the the DT cord-003318-abs9rvjk 270 45 reaction reaction NN cord-003318-abs9rvjk 270 46 mixture mixture NN cord-003318-abs9rvjk 270 47 , , , cord-003318-abs9rvjk 270 48 suggesting suggest VBG cord-003318-abs9rvjk 270 49 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 270 50 exhibited exhibit VBD cord-003318-abs9rvjk 270 51 prominent prominent JJ cord-003318-abs9rvjk 270 52 regioselectivity regioselectivity NN cord-003318-abs9rvjk 270 53 towards towards IN cord-003318-abs9rvjk 270 54 the the DT cord-003318-abs9rvjk 270 55 3-OH 3-oh CD cord-003318-abs9rvjk 270 56 of of IN cord-003318-abs9rvjk 270 57 both both DT cord-003318-abs9rvjk 270 58 substrates substrate NNS cord-003318-abs9rvjk 270 59 ( ( -LRB- cord-003318-abs9rvjk 270 60 Supplementary supplementary JJ cord-003318-abs9rvjk 270 61 Information Information NNP cord-003318-abs9rvjk 270 62 Figs Figs NNPS cord-003318-abs9rvjk 270 63 . . . cord-003318-abs9rvjk 271 1 S11 S11 NNP cord-003318-abs9rvjk 271 2 and and CC cord-003318-abs9rvjk 271 3 S14 S14 NNP cord-003318-abs9rvjk 271 4 ) ) -RRB- cord-003318-abs9rvjk 271 5 . . . cord-003318-abs9rvjk 272 1 Also also RB cord-003318-abs9rvjk 272 2 , , , cord-003318-abs9rvjk 272 3 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 272 4 The the DT cord-003318-abs9rvjk 272 5 stereoselectivity stereoselectivity NN cord-003318-abs9rvjk 272 6 of of IN cord-003318-abs9rvjk 272 7 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 272 8 was be VBD cord-003318-abs9rvjk 272 9 also also RB cord-003318-abs9rvjk 272 10 assessed assess VBN cord-003318-abs9rvjk 272 11 in in IN cord-003318-abs9rvjk 272 12 this this DT cord-003318-abs9rvjk 272 13 study study NN cord-003318-abs9rvjk 272 14 . . . cord-003318-abs9rvjk 273 1 Estradiol Estradiol NNP cord-003318-abs9rvjk 273 2 ( ( -LRB- cord-003318-abs9rvjk 273 3 9 9 CD cord-003318-abs9rvjk 273 4 ) ) -RRB- cord-003318-abs9rvjk 273 5 and and CC cord-003318-abs9rvjk 273 6 α α NN cord-003318-abs9rvjk 273 7 - - HYPH cord-003318-abs9rvjk 273 8 estradiol estradiol NN cord-003318-abs9rvjk 273 9 ( ( -LRB- cord-003318-abs9rvjk 273 10 12 12 CD cord-003318-abs9rvjk 273 11 ) ) -RRB- cord-003318-abs9rvjk 273 12 differ differ VBP cord-003318-abs9rvjk 273 13 for for IN cord-003318-abs9rvjk 273 14 the the DT cord-003318-abs9rvjk 273 15 configuration configuration NN cord-003318-abs9rvjk 273 16 of of IN cord-003318-abs9rvjk 273 17 the the DT cord-003318-abs9rvjk 273 18 hydroxyl hydroxyl NN cord-003318-abs9rvjk 273 19 group group NN cord-003318-abs9rvjk 273 20 at at IN cord-003318-abs9rvjk 273 21 C-17 C-17 NNP cord-003318-abs9rvjk 273 22 position position NN cord-003318-abs9rvjk 273 23 . . . cord-003318-abs9rvjk 274 1 When when WRB cord-003318-abs9rvjk 274 2 each each DT cord-003318-abs9rvjk 274 3 of of IN cord-003318-abs9rvjk 274 4 the the DT cord-003318-abs9rvjk 274 5 two two CD cord-003318-abs9rvjk 274 6 compounds compound NNS cord-003318-abs9rvjk 274 7 was be VBD cord-003318-abs9rvjk 274 8 used use VBN cord-003318-abs9rvjk 274 9 to to TO cord-003318-abs9rvjk 274 10 react react VB cord-003318-abs9rvjk 274 11 with with IN cord-003318-abs9rvjk 274 12 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 274 13 , , , cord-003318-abs9rvjk 274 14 only only RB cord-003318-abs9rvjk 274 15 β β NN cord-003318-abs9rvjk 274 16 - - HYPH cord-003318-abs9rvjk 274 17 configurated configurate VBN cord-003318-abs9rvjk 274 18 glycosides glycoside NNS cord-003318-abs9rvjk 274 19 were be VBD cord-003318-abs9rvjk 274 20 generated generate VBN cord-003318-abs9rvjk 274 21 ( ( -LRB- cord-003318-abs9rvjk 274 22 Fig Fig NNP cord-003318-abs9rvjk 274 23 . . . cord-003318-abs9rvjk 274 24 3 3 CD cord-003318-abs9rvjk 274 25 ) ) -RRB- cord-003318-abs9rvjk 274 26 . . . cord-003318-abs9rvjk 275 1 Likewise likewise RB cord-003318-abs9rvjk 275 2 , , , cord-003318-abs9rvjk 275 3 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 275 4 showed show VBD cord-003318-abs9rvjk 275 5 βselective βselective JJ cord-003318-abs9rvjk 275 6 glycosylation glycosylation NN cord-003318-abs9rvjk 275 7 towards towards IN cord-003318-abs9rvjk 275 8 the the DT cord-003318-abs9rvjk 275 9 hydroxyl hydroxyl NN cord-003318-abs9rvjk 275 10 group group NN cord-003318-abs9rvjk 275 11 at at IN cord-003318-abs9rvjk 275 12 C-3 C-3 NNP cord-003318-abs9rvjk 275 13 position position NN cord-003318-abs9rvjk 275 14 . . . cord-003318-abs9rvjk 276 1 Cumulatively cumulatively RB cord-003318-abs9rvjk 276 2 , , , cord-003318-abs9rvjk 276 3 these these DT cord-003318-abs9rvjk 276 4 evidences evidence NNS cord-003318-abs9rvjk 276 5 revealed reveal VBD cord-003318-abs9rvjk 276 6 that that IN cord-003318-abs9rvjk 276 7 OsSGT1catalyzed OsSGT1catalyzed NNP cord-003318-abs9rvjk 276 8 glycosylations glycosylation NNS cord-003318-abs9rvjk 276 9 were be VBD cord-003318-abs9rvjk 276 10 conducted conduct VBN cord-003318-abs9rvjk 276 11 in in IN cord-003318-abs9rvjk 276 12 a a DT cord-003318-abs9rvjk 276 13 region region NN cord-003318-abs9rvjk 276 14 - - HYPH cord-003318-abs9rvjk 276 15 and and CC cord-003318-abs9rvjk 276 16 stereoselective stereoselective JJ cord-003318-abs9rvjk 276 17 fashion fashion NN cord-003318-abs9rvjk 276 18 . . . cord-003318-abs9rvjk 277 1 One one CD cord-003318-abs9rvjk 277 2 of of IN cord-003318-abs9rvjk 277 3 the the DT cord-003318-abs9rvjk 277 4 most most RBS cord-003318-abs9rvjk 277 5 striking striking JJ cord-003318-abs9rvjk 277 6 findings finding NNS cord-003318-abs9rvjk 277 7 of of IN cord-003318-abs9rvjk 277 8 this this DT cord-003318-abs9rvjk 277 9 study study NN cord-003318-abs9rvjk 277 10 is be VBZ cord-003318-abs9rvjk 277 11 the the DT cord-003318-abs9rvjk 277 12 characterization characterization NN cord-003318-abs9rvjk 277 13 of of IN cord-003318-abs9rvjk 277 14 bacterial bacterial JJ cord-003318-abs9rvjk 277 15 LacA LacA NNP cord-003318-abs9rvjk 277 16 protein protein NN cord-003318-abs9rvjk 277 17 as as IN cord-003318-abs9rvjk 277 18 a a DT cord-003318-abs9rvjk 277 19 steroidal steroidal JJ cord-003318-abs9rvjk 277 20 glycoside glycoside NN cord-003318-abs9rvjk 277 21 acyltransferase acyltransferase NN cord-003318-abs9rvjk 277 22 . . . cord-003318-abs9rvjk 278 1 It -PRON- PRP cord-003318-abs9rvjk 278 2 is be VBZ cord-003318-abs9rvjk 278 3 well well RB cord-003318-abs9rvjk 278 4 known know VBN cord-003318-abs9rvjk 278 5 that that IN cord-003318-abs9rvjk 278 6 lacA lacA NNP cord-003318-abs9rvjk 278 7 is be VBZ cord-003318-abs9rvjk 278 8 one one CD cord-003318-abs9rvjk 278 9 of of IN cord-003318-abs9rvjk 278 10 three three CD cord-003318-abs9rvjk 278 11 structural structural JJ cord-003318-abs9rvjk 278 12 genes gene NNS cord-003318-abs9rvjk 278 13 ( ( -LRB- cord-003318-abs9rvjk 278 14 lacZ lacz CD cord-003318-abs9rvjk 278 15 , , , cord-003318-abs9rvjk 278 16 lacY lacY NNP cord-003318-abs9rvjk 278 17 and and CC cord-003318-abs9rvjk 278 18 lacA lacA NNP cord-003318-abs9rvjk 278 19 ) ) -RRB- cord-003318-abs9rvjk 278 20 in in IN cord-003318-abs9rvjk 278 21 lac lac NNP cord-003318-abs9rvjk 278 22 operon operon NN cord-003318-abs9rvjk 278 23 25 25 CD cord-003318-abs9rvjk 278 24 , , , cord-003318-abs9rvjk 278 25 26 26 CD cord-003318-abs9rvjk 278 26 . . . cord-003318-abs9rvjk 279 1 The the DT cord-003318-abs9rvjk 279 2 function function NN cord-003318-abs9rvjk 279 3 of of IN cord-003318-abs9rvjk 279 4 LacZ LacZ NNP cord-003318-abs9rvjk 279 5 and and CC cord-003318-abs9rvjk 279 6 LacY LacY NNP cord-003318-abs9rvjk 279 7 is be VBZ cord-003318-abs9rvjk 279 8 well well RB cord-003318-abs9rvjk 279 9 - - HYPH cord-003318-abs9rvjk 279 10 characterized characterize VBN cord-003318-abs9rvjk 279 11 25 25 CD cord-003318-abs9rvjk 279 12 , , , cord-003318-abs9rvjk 279 13 26 26 CD cord-003318-abs9rvjk 279 14 . . . cord-003318-abs9rvjk 280 1 LacZ LacZ NNP cord-003318-abs9rvjk 280 2 encodes encode VBZ cord-003318-abs9rvjk 280 3 a a DT cord-003318-abs9rvjk 280 4 βgalactosidase βgalactosidase NN cord-003318-abs9rvjk 280 5 , , , cord-003318-abs9rvjk 280 6 catalyzing catalyze VBG cord-003318-abs9rvjk 280 7 the the DT cord-003318-abs9rvjk 280 8 cleavage cleavage NN cord-003318-abs9rvjk 280 9 of of IN cord-003318-abs9rvjk 280 10 lactose lactose NN cord-003318-abs9rvjk 280 11 into into IN cord-003318-abs9rvjk 280 12 glucose glucose NN cord-003318-abs9rvjk 280 13 and and CC cord-003318-abs9rvjk 280 14 galactose galactose NN cord-003318-abs9rvjk 280 15 . . . cord-003318-abs9rvjk 281 1 LacY LacY NNP cord-003318-abs9rvjk 281 2 encodes encode VBZ cord-003318-abs9rvjk 281 3 a a DT cord-003318-abs9rvjk 281 4 lactose lactose NN cord-003318-abs9rvjk 281 5 permease permease NN cord-003318-abs9rvjk 281 6 responsible responsible JJ cord-003318-abs9rvjk 281 7 for for IN cord-003318-abs9rvjk 281 8 lactose lactose NN cord-003318-abs9rvjk 281 9 uptake uptake NN cord-003318-abs9rvjk 281 10 25 25 CD cord-003318-abs9rvjk 281 11 , , , cord-003318-abs9rvjk 281 12 26 26 CD cord-003318-abs9rvjk 281 13 . . . cord-003318-abs9rvjk 282 1 The the DT cord-003318-abs9rvjk 282 2 third third JJ cord-003318-abs9rvjk 282 3 structural structural JJ cord-003318-abs9rvjk 282 4 protein protein NN cord-003318-abs9rvjk 282 5 encoded encode VBN cord-003318-abs9rvjk 282 6 by by IN cord-003318-abs9rvjk 282 7 lacA laca PRP$ cord-003318-abs9rvjk 282 8 gene gene NN cord-003318-abs9rvjk 282 9 in in IN cord-003318-abs9rvjk 282 10 lac lac NNP cord-003318-abs9rvjk 282 11 operon operon NN cord-003318-abs9rvjk 282 12 was be VBD cord-003318-abs9rvjk 282 13 initially initially RB cord-003318-abs9rvjk 282 14 inferred infer VBN cord-003318-abs9rvjk 282 15 to to TO cord-003318-abs9rvjk 282 16 be be VB cord-003318-abs9rvjk 282 17 an an DT cord-003318-abs9rvjk 282 18 acetyltransferase acetyltransferase NN cord-003318-abs9rvjk 282 19 . . . cord-003318-abs9rvjk 283 1 The the DT cord-003318-abs9rvjk 283 2 exact exact JJ cord-003318-abs9rvjk 283 3 action action NN cord-003318-abs9rvjk 283 4 of of IN cord-003318-abs9rvjk 283 5 this this DT cord-003318-abs9rvjk 283 6 protein protein NN cord-003318-abs9rvjk 283 7 , , , cord-003318-abs9rvjk 283 8 however however RB cord-003318-abs9rvjk 283 9 , , , cord-003318-abs9rvjk 283 10 remains remain VBZ cord-003318-abs9rvjk 283 11 in in IN cord-003318-abs9rvjk 283 12 doubt doubt NN cord-003318-abs9rvjk 283 13 until until IN cord-003318-abs9rvjk 283 14 now now RB cord-003318-abs9rvjk 283 15 . . . cord-003318-abs9rvjk 284 1 In in IN cord-003318-abs9rvjk 284 2 this this DT cord-003318-abs9rvjk 284 3 investigation investigation NN cord-003318-abs9rvjk 284 4 , , , cord-003318-abs9rvjk 284 5 in in IN cord-003318-abs9rvjk 284 6 an an DT cord-003318-abs9rvjk 284 7 effort effort NN cord-003318-abs9rvjk 284 8 to to TO cord-003318-abs9rvjk 284 9 identify identify VB cord-003318-abs9rvjk 284 10 the the DT cord-003318-abs9rvjk 284 11 function function NN cord-003318-abs9rvjk 284 12 of of IN cord-003318-abs9rvjk 284 13 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 284 14 , , , cord-003318-abs9rvjk 284 15 we -PRON- PRP cord-003318-abs9rvjk 284 16 unexpectedly unexpectedly RB cord-003318-abs9rvjk 284 17 characterized characterize VBD cord-003318-abs9rvjk 284 18 LacA LacA NNP cord-003318-abs9rvjk 284 19 protein protein NN cord-003318-abs9rvjk 284 20 from from IN cord-003318-abs9rvjk 284 21 E. E. NNP cord-003318-abs9rvjk 284 22 coli coli NNS cord-003318-abs9rvjk 284 23 as as IN cord-003318-abs9rvjk 284 24 a a DT cord-003318-abs9rvjk 284 25 SGA SGA NNP cord-003318-abs9rvjk 284 26 . . . cord-003318-abs9rvjk 285 1 In in IN cord-003318-abs9rvjk 285 2 vitro vitro FW cord-003318-abs9rvjk 285 3 enzymatic enzymatic JJ cord-003318-abs9rvjk 285 4 analyses analysis NNS cord-003318-abs9rvjk 285 5 revealed reveal VBD cord-003318-abs9rvjk 285 6 that that IN cord-003318-abs9rvjk 285 7 LacA LacA NNP cord-003318-abs9rvjk 285 8 protein protein NN cord-003318-abs9rvjk 285 9 could could MD cord-003318-abs9rvjk 285 10 specifically specifically RB cord-003318-abs9rvjk 285 11 catalyze catalyze VB cord-003318-abs9rvjk 285 12 the the DT cord-003318-abs9rvjk 285 13 attachment attachment NN cord-003318-abs9rvjk 285 14 of of IN cord-003318-abs9rvjk 285 15 acyl acyl NNP cord-003318-abs9rvjk 285 16 groups group NNS cord-003318-abs9rvjk 285 17 into into IN cord-003318-abs9rvjk 285 18 the the DT cord-003318-abs9rvjk 285 19 hydroxyl hydroxyl NN cord-003318-abs9rvjk 285 20 groups group NNS cord-003318-abs9rvjk 285 21 of of IN cord-003318-abs9rvjk 285 22 sugar sugar NN cord-003318-abs9rvjk 285 23 moieties moiety NNS cord-003318-abs9rvjk 285 24 of of IN cord-003318-abs9rvjk 285 25 steroidal steroidal JJ cord-003318-abs9rvjk 285 26 17β- 17β- JJ cord-003318-abs9rvjk 285 27 glycosides glycoside NNS cord-003318-abs9rvjk 285 28 ( ( -LRB- cord-003318-abs9rvjk 285 29 Figs Figs NNPS cord-003318-abs9rvjk 285 30 . . . cord-003318-abs9rvjk 286 1 4 4 CD cord-003318-abs9rvjk 286 2 and and CC cord-003318-abs9rvjk 286 3 5 5 CD cord-003318-abs9rvjk 286 4 ) ) -RRB- cord-003318-abs9rvjk 286 5 . . . cord-003318-abs9rvjk 287 1 Although although IN cord-003318-abs9rvjk 287 2 we -PRON- PRP cord-003318-abs9rvjk 287 3 have have VBP cord-003318-abs9rvjk 287 4 no no DT cord-003318-abs9rvjk 287 5 evidences evidence NNS cord-003318-abs9rvjk 287 6 for for IN cord-003318-abs9rvjk 287 7 the the DT cord-003318-abs9rvjk 287 8 role role NN cord-003318-abs9rvjk 287 9 of of IN cord-003318-abs9rvjk 287 10 LacA LacA NNP cord-003318-abs9rvjk 287 11 protein protein NN cord-003318-abs9rvjk 287 12 in in IN cord-003318-abs9rvjk 287 13 vivo vivo NN cord-003318-abs9rvjk 287 14 , , , cord-003318-abs9rvjk 287 15 these these DT cord-003318-abs9rvjk 287 16 findings finding NNS cord-003318-abs9rvjk 287 17 in in IN cord-003318-abs9rvjk 287 18 the the DT cord-003318-abs9rvjk 287 19 present present JJ cord-003318-abs9rvjk 287 20 work work NN cord-003318-abs9rvjk 287 21 may may MD cord-003318-abs9rvjk 287 22 provide provide VB cord-003318-abs9rvjk 287 23 a a DT cord-003318-abs9rvjk 287 24 starting starting NN cord-003318-abs9rvjk 287 25 point point NN cord-003318-abs9rvjk 287 26 for for IN cord-003318-abs9rvjk 287 27 identifying identify VBG cord-003318-abs9rvjk 287 28 the the DT cord-003318-abs9rvjk 287 29 exact exact JJ cord-003318-abs9rvjk 287 30 activity activity NN cord-003318-abs9rvjk 287 31 of of IN cord-003318-abs9rvjk 287 32 LacA LacA NNP cord-003318-abs9rvjk 287 33 protein protein NN cord-003318-abs9rvjk 287 34 in in IN cord-003318-abs9rvjk 287 35 lactose lactose JJ cord-003318-abs9rvjk 287 36 metabolism metabolism NN cord-003318-abs9rvjk 287 37 . . . cord-003318-abs9rvjk 288 1 The the DT cord-003318-abs9rvjk 288 2 bottleneck bottleneck NN cord-003318-abs9rvjk 288 3 in in IN cord-003318-abs9rvjk 288 4 enzymatic enzymatic JJ cord-003318-abs9rvjk 288 5 synthesis synthesis NN cord-003318-abs9rvjk 288 6 of of IN cord-003318-abs9rvjk 288 7 ASGs ASGs NNPS cord-003318-abs9rvjk 288 8 is be VBZ cord-003318-abs9rvjk 288 9 the the DT cord-003318-abs9rvjk 288 10 lack lack NN cord-003318-abs9rvjk 288 11 of of IN cord-003318-abs9rvjk 288 12 well well RB cord-003318-abs9rvjk 288 13 - - HYPH cord-003318-abs9rvjk 288 14 characterized characterize VBN cord-003318-abs9rvjk 288 15 SGAs sga NNS cord-003318-abs9rvjk 288 16 . . . cord-003318-abs9rvjk 289 1 The the DT cord-003318-abs9rvjk 289 2 successful successful JJ cord-003318-abs9rvjk 289 3 characterization characterization NN cord-003318-abs9rvjk 289 4 of of IN cord-003318-abs9rvjk 289 5 LacA LacA NNP cord-003318-abs9rvjk 289 6 made make VBD cord-003318-abs9rvjk 289 7 it -PRON- PRP cord-003318-abs9rvjk 289 8 to to TO cord-003318-abs9rvjk 289 9 be be VB cord-003318-abs9rvjk 289 10 the the DT cord-003318-abs9rvjk 289 11 first first JJ cord-003318-abs9rvjk 289 12 SGA SGA NNP cord-003318-abs9rvjk 289 13 and and CC cord-003318-abs9rvjk 289 14 LacA LacA NNP cord-003318-abs9rvjk 289 15 protein protein NN cord-003318-abs9rvjk 289 16 was be VBD cord-003318-abs9rvjk 289 17 thus thus RB cord-003318-abs9rvjk 289 18 designated designate VBN cord-003318-abs9rvjk 289 19 as as IN cord-003318-abs9rvjk 289 20 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 289 21 . . . cord-003318-abs9rvjk 290 1 A a DT cord-003318-abs9rvjk 290 2 novel novel NN cord-003318-abs9rvjk 290 3 enzymatic enzymatic JJ cord-003318-abs9rvjk 290 4 two two CD cord-003318-abs9rvjk 290 5 - - HYPH cord-003318-abs9rvjk 290 6 step step NN cord-003318-abs9rvjk 290 7 synthesis synthesis NN cord-003318-abs9rvjk 290 8 of of IN cord-003318-abs9rvjk 290 9 AT-17β AT-17β NNP cord-003318-abs9rvjk 290 10 - - HYPH cord-003318-abs9rvjk 290 11 Gs Gs NNP cord-003318-abs9rvjk 290 12 and and CC cord-003318-abs9rvjk 290 13 AE-17β AE-17β NNP cord-003318-abs9rvjk 290 14 - - HYPH cord-003318-abs9rvjk 290 15 Gs Gs NNP cord-003318-abs9rvjk 290 16 from from IN cord-003318-abs9rvjk 290 17 the the DT cord-003318-abs9rvjk 290 18 abundantly abundantly RB cord-003318-abs9rvjk 290 19 available available JJ cord-003318-abs9rvjk 290 20 free free JJ cord-003318-abs9rvjk 290 21 steroids steroid NNS cord-003318-abs9rvjk 290 22 under under IN cord-003318-abs9rvjk 290 23 the the DT cord-003318-abs9rvjk 290 24 sequential sequential JJ cord-003318-abs9rvjk 290 25 actions action NNS cord-003318-abs9rvjk 290 26 of of IN cord-003318-abs9rvjk 290 27 a a DT cord-003318-abs9rvjk 290 28 steroidal steroidal JJ cord-003318-abs9rvjk 290 29 glycosyltransferase glycosyltransferase NN cord-003318-abs9rvjk 291 1 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 291 2 from from IN cord-003318-abs9rvjk 291 3 O. O. NNP cord-003318-abs9rvjk 291 4 saundersiae saundersiae NN cord-003318-abs9rvjk 291 5 and and CC cord-003318-abs9rvjk 292 1 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 292 2 was be VBD cord-003318-abs9rvjk 292 3 achieved achieve VBN cord-003318-abs9rvjk 292 4 . . . cord-003318-abs9rvjk 293 1 The the DT cord-003318-abs9rvjk 293 2 two two CD cord-003318-abs9rvjk 293 3 - - HYPH cord-003318-abs9rvjk 293 4 step step NN cord-003318-abs9rvjk 293 5 process process NN cord-003318-abs9rvjk 293 6 is be VBZ cord-003318-abs9rvjk 293 7 characterized characterize VBN cord-003318-abs9rvjk 293 8 by by IN cord-003318-abs9rvjk 293 9 acyltransferase acyltransferase NN cord-003318-abs9rvjk 293 10 - - HYPH cord-003318-abs9rvjk 293 11 catalyzed catalyze VBN cord-003318-abs9rvjk 293 12 regioselective regioselective NNP cord-003318-abs9rvjk 293 13 acylations acylation NNS cord-003318-abs9rvjk 293 14 of of IN cord-003318-abs9rvjk 293 15 all all DT cord-003318-abs9rvjk 293 16 hydroxyl hydroxyl NN cord-003318-abs9rvjk 293 17 groups group NNS cord-003318-abs9rvjk 293 18 of of IN cord-003318-abs9rvjk 293 19 unprotected unprotected JJ cord-003318-abs9rvjk 293 20 SGs SGs NNP cord-003318-abs9rvjk 293 21 in in IN cord-003318-abs9rvjk 293 22 the the DT cord-003318-abs9rvjk 293 23 late late JJ cord-003318-abs9rvjk 293 24 stage stage NN cord-003318-abs9rvjk 293 25 , , , cord-003318-abs9rvjk 293 26 thereby thereby RB cord-003318-abs9rvjk 293 27 significantly significantly RB cord-003318-abs9rvjk 293 28 streamlining streamline VBG cord-003318-abs9rvjk 293 29 the the DT cord-003318-abs9rvjk 293 30 synthetic synthetic JJ cord-003318-abs9rvjk 293 31 route route NN cord-003318-abs9rvjk 293 32 towards towards IN cord-003318-abs9rvjk 293 33 ASGs asg NNS cord-003318-abs9rvjk 293 34 and and CC cord-003318-abs9rvjk 293 35 thus thus RB cord-003318-abs9rvjk 293 36 forming form VBG cord-003318-abs9rvjk 293 37 four four CD cord-003318-abs9rvjk 293 38 monoacylates monoacylate NNS cord-003318-abs9rvjk 293 39 . . . cord-003318-abs9rvjk 294 1 Regioselective Regioselective NNP cord-003318-abs9rvjk 294 2 acylation acylation NN cord-003318-abs9rvjk 294 3 could could MD cord-003318-abs9rvjk 294 4 expand expand VB cord-003318-abs9rvjk 294 5 molecular molecular JJ cord-003318-abs9rvjk 294 6 diversity diversity NN cord-003318-abs9rvjk 294 7 , , , cord-003318-abs9rvjk 294 8 thereby thereby RB cord-003318-abs9rvjk 294 9 facilitating facilitate VBG cord-003318-abs9rvjk 294 10 the the DT cord-003318-abs9rvjk 294 11 discovery discovery NN cord-003318-abs9rvjk 294 12 of of IN cord-003318-abs9rvjk 294 13 pharmaceutical pharmaceutical JJ cord-003318-abs9rvjk 294 14 leads lead NNS cord-003318-abs9rvjk 294 15 . . . cord-003318-abs9rvjk 295 1 In in IN cord-003318-abs9rvjk 295 2 this this DT cord-003318-abs9rvjk 295 3 investigation investigation NN cord-003318-abs9rvjk 295 4 , , , cord-003318-abs9rvjk 295 5 EcSGA1-catalyzed ecsga1-catalyzed JJ cord-003318-abs9rvjk 295 6 acetylation acetylation NN cord-003318-abs9rvjk 295 7 of of IN cord-003318-abs9rvjk 295 8 two two CD cord-003318-abs9rvjk 295 9 steroid steroid NN cord-003318-abs9rvjk 295 10 17βglucosides 17βglucosides CD cord-003318-abs9rvjk 295 11 ( ( -LRB- cord-003318-abs9rvjk 295 12 T-17β T-17β NNP cord-003318-abs9rvjk 295 13 - - HYPH cord-003318-abs9rvjk 295 14 G G NNP cord-003318-abs9rvjk 295 15 and and CC cord-003318-abs9rvjk 295 16 E-17β E-17β NNP cord-003318-abs9rvjk 295 17 - - HYPH cord-003318-abs9rvjk 295 18 G G NNP cord-003318-abs9rvjk 295 19 ) ) -RRB- cord-003318-abs9rvjk 295 20 leaded lead VBD cord-003318-abs9rvjk 295 21 to to IN cord-003318-abs9rvjk 295 22 the the DT cord-003318-abs9rvjk 295 23 production production NN cord-003318-abs9rvjk 295 24 of of IN cord-003318-abs9rvjk 295 25 eight eight CD cord-003318-abs9rvjk 295 26 new new JJ cord-003318-abs9rvjk 295 27 monoacylates monoacylate NNS cord-003318-abs9rvjk 295 28 . . . cord-003318-abs9rvjk 296 1 Furthermore furthermore RB cord-003318-abs9rvjk 296 2 , , , cord-003318-abs9rvjk 296 3 the the DT cord-003318-abs9rvjk 296 4 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 296 5 activities activity NNS cord-003318-abs9rvjk 296 6 of of IN cord-003318-abs9rvjk 296 7 these these DT cord-003318-abs9rvjk 296 8 monoacylates monoacylate NNS cord-003318-abs9rvjk 296 9 were be VBD cord-003318-abs9rvjk 296 10 tested test VBN cord-003318-abs9rvjk 296 11 and and CC cord-003318-abs9rvjk 296 12 3 3 CD cord-003318-abs9rvjk 296 13 0 0 CD cord-003318-abs9rvjk 296 14 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 296 15 - - HYPH cord-003318-abs9rvjk 296 16 G g NN cord-003318-abs9rvjk 296 17 was be VBD cord-003318-abs9rvjk 296 18 observed observe VBN cord-003318-abs9rvjk 296 19 to to TO cord-003318-abs9rvjk 296 20 display display VB cord-003318-abs9rvjk 296 21 improved improved JJ cord-003318-abs9rvjk 296 22 activities activity NNS cord-003318-abs9rvjk 296 23 towards towards IN cord-003318-abs9rvjk 296 24 seven seven CD cord-003318-abs9rvjk 296 25 human human JJ cord-003318-abs9rvjk 296 26 tumor tumor NN cord-003318-abs9rvjk 296 27 cell cell NN cord-003318-abs9rvjk 296 28 lines line NNS cord-003318-abs9rvjk 296 29 , , , cord-003318-abs9rvjk 296 30 suggesting suggest VBG cord-003318-abs9rvjk 296 31 this this DT cord-003318-abs9rvjk 296 32 compound compound NN cord-003318-abs9rvjk 296 33 had have VBD cord-003318-abs9rvjk 296 34 promisingly promisingly RB cord-003318-abs9rvjk 296 35 pharmacological pharmacological JJ cord-003318-abs9rvjk 296 36 potential potential NN cord-003318-abs9rvjk 296 37 . . . cord-003318-abs9rvjk 297 1 This this DT cord-003318-abs9rvjk 297 2 study study NN cord-003318-abs9rvjk 297 3 therefore therefore RB cord-003318-abs9rvjk 297 4 reports report VBZ cord-003318-abs9rvjk 297 5 for for IN cord-003318-abs9rvjk 297 6 the the DT cord-003318-abs9rvjk 297 7 first first JJ cord-003318-abs9rvjk 297 8 time time NN cord-003318-abs9rvjk 297 9 a a DT cord-003318-abs9rvjk 297 10 novel novel JJ cord-003318-abs9rvjk 297 11 synthetic synthetic JJ cord-003318-abs9rvjk 297 12 process process NN cord-003318-abs9rvjk 297 13 for for IN cord-003318-abs9rvjk 297 14 the the DT cord-003318-abs9rvjk 297 15 green green JJ cord-003318-abs9rvjk 297 16 preparation preparation NN cord-003318-abs9rvjk 297 17 of of IN cord-003318-abs9rvjk 297 18 acylated acylated JJ cord-003318-abs9rvjk 297 19 steroidal steroidal JJ cord-003318-abs9rvjk 297 20 glycosides glycoside NNS cord-003318-abs9rvjk 297 21 with with IN cord-003318-abs9rvjk 297 22 medicinal medicinal JJ cord-003318-abs9rvjk 297 23 interest interest NN cord-003318-abs9rvjk 297 24 . . . cord-003318-abs9rvjk 298 1 A a DT cord-003318-abs9rvjk 298 2 steroidal steroidal JJ cord-003318-abs9rvjk 298 3 glycosyltransferase glycosyltransferase NN cord-003318-abs9rvjk 298 4 OsSGT1 ossgt1 NN cord-003318-abs9rvjk 298 5 from from IN cord-003318-abs9rvjk 298 6 O. O. NNP cord-003318-abs9rvjk 298 7 saundersiae saundersiae NNP cord-003318-abs9rvjk 298 8 was be VBD cord-003318-abs9rvjk 298 9 identified identify VBN cord-003318-abs9rvjk 298 10 to to TO cord-003318-abs9rvjk 298 11 be be VB cord-003318-abs9rvjk 298 12 the the DT cord-003318-abs9rvjk 298 13 first first JJ cord-003318-abs9rvjk 298 14 plant plant NN cord-003318-abs9rvjk 298 15 SGT SGT NNP cord-003318-abs9rvjk 298 16 with with IN cord-003318-abs9rvjk 298 17 selectivity selectivity NN cord-003318-abs9rvjk 298 18 towards towards IN cord-003318-abs9rvjk 298 19 both both DT cord-003318-abs9rvjk 298 20 3β 3β CD cord-003318-abs9rvjk 298 21 - - HYPH cord-003318-abs9rvjk 298 22 and and CC cord-003318-abs9rvjk 298 23 17β 17β NNS cord-003318-abs9rvjk 298 24 - - HYPH cord-003318-abs9rvjk 298 25 hydroxylsteroids hydroxylsteroid NNS cord-003318-abs9rvjk 298 26 . . . cord-003318-abs9rvjk 299 1 One one CD cord-003318-abs9rvjk 299 2 of of IN cord-003318-abs9rvjk 299 3 the the DT cord-003318-abs9rvjk 299 4 most most RBS cord-003318-abs9rvjk 299 5 striking striking JJ cord-003318-abs9rvjk 299 6 findings finding NNS cord-003318-abs9rvjk 299 7 of of IN cord-003318-abs9rvjk 299 8 this this DT cord-003318-abs9rvjk 299 9 study study NN cord-003318-abs9rvjk 299 10 is be VBZ cord-003318-abs9rvjk 299 11 the the DT cord-003318-abs9rvjk 299 12 characterization characterization NN cord-003318-abs9rvjk 299 13 of of IN cord-003318-abs9rvjk 299 14 bacterial bacterial JJ cord-003318-abs9rvjk 299 15 LacA LacA NNP cord-003318-abs9rvjk 299 16 protein protein NN cord-003318-abs9rvjk 299 17 as as IN cord-003318-abs9rvjk 299 18 a a DT cord-003318-abs9rvjk 299 19 steroidal steroidal JJ cord-003318-abs9rvjk 299 20 glycoside glycoside NN cord-003318-abs9rvjk 299 21 acyltransferase acyltransferase NN cord-003318-abs9rvjk 299 22 , , , cord-003318-abs9rvjk 299 23 catalyzing catalyze VBG cord-003318-abs9rvjk 299 24 the the DT cord-003318-abs9rvjk 299 25 attachment attachment NN cord-003318-abs9rvjk 299 26 of of IN cord-003318-abs9rvjk 299 27 acyl acyl NNP cord-003318-abs9rvjk 299 28 groups group NNS cord-003318-abs9rvjk 299 29 into into IN cord-003318-abs9rvjk 299 30 the the DT cord-003318-abs9rvjk 299 31 hydroxyl hydroxyl NN cord-003318-abs9rvjk 299 32 groups group NNS cord-003318-abs9rvjk 299 33 of of IN cord-003318-abs9rvjk 299 34 steroidal steroidal JJ cord-003318-abs9rvjk 299 35 17β 17β NNS cord-003318-abs9rvjk 299 36 - - HYPH cord-003318-abs9rvjk 299 37 glycosides glycoside NNS cord-003318-abs9rvjk 299 38 . . . cord-003318-abs9rvjk 300 1 A a DT cord-003318-abs9rvjk 300 2 novel novel NN cord-003318-abs9rvjk 300 3 enzymatic enzymatic JJ cord-003318-abs9rvjk 300 4 two two CD cord-003318-abs9rvjk 300 5 - - HYPH cord-003318-abs9rvjk 300 6 step step NN cord-003318-abs9rvjk 300 7 synthesis synthesis NN cord-003318-abs9rvjk 300 8 of of IN cord-003318-abs9rvjk 300 9 AT-17β AT-17β NNP cord-003318-abs9rvjk 300 10 - - HYPH cord-003318-abs9rvjk 300 11 Gs Gs NNP cord-003318-abs9rvjk 300 12 and and CC cord-003318-abs9rvjk 300 13 AE-17β AE-17β NNP cord-003318-abs9rvjk 300 14 - - HYPH cord-003318-abs9rvjk 300 15 Gs Gs NNP cord-003318-abs9rvjk 300 16 from from IN cord-003318-abs9rvjk 300 17 the the DT cord-003318-abs9rvjk 300 18 abundantly abundantly RB cord-003318-abs9rvjk 300 19 available available JJ cord-003318-abs9rvjk 300 20 free free JJ cord-003318-abs9rvjk 300 21 steroids steroid NNS cord-003318-abs9rvjk 300 22 under under IN cord-003318-abs9rvjk 300 23 the the DT cord-003318-abs9rvjk 300 24 sequential sequential JJ cord-003318-abs9rvjk 300 25 actions action NNS cord-003318-abs9rvjk 300 26 of of IN cord-003318-abs9rvjk 300 27 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 300 28 and and CC cord-003318-abs9rvjk 300 29 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 300 30 was be VBD cord-003318-abs9rvjk 300 31 achieved achieve VBN cord-003318-abs9rvjk 300 32 . . . cord-003318-abs9rvjk 301 1 The the DT cord-003318-abs9rvjk 301 2 two two CD cord-003318-abs9rvjk 301 3 - - HYPH cord-003318-abs9rvjk 301 4 step step NN cord-003318-abs9rvjk 301 5 process process NN cord-003318-abs9rvjk 301 6 is be VBZ cord-003318-abs9rvjk 301 7 characterized characterize VBN cord-003318-abs9rvjk 301 8 by by IN cord-003318-abs9rvjk 301 9 acyltransferase acyltransferase NN cord-003318-abs9rvjk 301 10 - - HYPH cord-003318-abs9rvjk 301 11 catalyzed catalyze VBN cord-003318-abs9rvjk 301 12 regioselective regioselective NNP cord-003318-abs9rvjk 301 13 acylations acylation NNS cord-003318-abs9rvjk 301 14 of of IN cord-003318-abs9rvjk 301 15 all all DT cord-003318-abs9rvjk 301 16 hydroxyl hydroxyl NN cord-003318-abs9rvjk 301 17 groups group NNS cord-003318-abs9rvjk 301 18 of of IN cord-003318-abs9rvjk 301 19 unprotected unprotected JJ cord-003318-abs9rvjk 301 20 SGs SGs NNP cord-003318-abs9rvjk 301 21 in in IN cord-003318-abs9rvjk 301 22 the the DT cord-003318-abs9rvjk 301 23 late late JJ cord-003318-abs9rvjk 301 24 stage stage NN cord-003318-abs9rvjk 301 25 , , , cord-003318-abs9rvjk 301 26 thereby thereby RB cord-003318-abs9rvjk 301 27 significantly significantly RB cord-003318-abs9rvjk 301 28 streamlining streamline VBG cord-003318-abs9rvjk 301 29 the the DT cord-003318-abs9rvjk 301 30 synthetic synthetic JJ cord-003318-abs9rvjk 301 31 route route NN cord-003318-abs9rvjk 301 32 towards towards IN cord-003318-abs9rvjk 301 33 ASGs asg NNS cord-003318-abs9rvjk 301 34 and and CC cord-003318-abs9rvjk 301 35 thus thus RB cord-003318-abs9rvjk 301 36 forming form VBG cord-003318-abs9rvjk 301 37 four four CD cord-003318-abs9rvjk 301 38 monoacylates monoacylate NNS cord-003318-abs9rvjk 301 39 . . . cord-003318-abs9rvjk 302 1 Moreover moreover RB cord-003318-abs9rvjk 302 2 , , , cord-003318-abs9rvjk 302 3 the the DT cord-003318-abs9rvjk 302 4 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 302 5 activities activity NNS cord-003318-abs9rvjk 302 6 of of IN cord-003318-abs9rvjk 302 7 these these DT cord-003318-abs9rvjk 302 8 monoacylates monoacylate NNS cord-003318-abs9rvjk 302 9 were be VBD cord-003318-abs9rvjk 302 10 tested test VBN cord-003318-abs9rvjk 302 11 and and CC cord-003318-abs9rvjk 302 12 3 3 CD cord-003318-abs9rvjk 302 13 0 0 CD cord-003318-abs9rvjk 302 14 -AT-17β -AT-17β NNS cord-003318-abs9rvjk 302 15 - - HYPH cord-003318-abs9rvjk 302 16 G g NN cord-003318-abs9rvjk 302 17 was be VBD cord-003318-abs9rvjk 302 18 observed observe VBN cord-003318-abs9rvjk 302 19 to to TO cord-003318-abs9rvjk 302 20 display display VB cord-003318-abs9rvjk 302 21 improved improved JJ cord-003318-abs9rvjk 302 22 activities activity NNS cord-003318-abs9rvjk 302 23 towards towards IN cord-003318-abs9rvjk 302 24 seven seven CD cord-003318-abs9rvjk 302 25 human human JJ cord-003318-abs9rvjk 302 26 tumor tumor NN cord-003318-abs9rvjk 302 27 cell cell NN cord-003318-abs9rvjk 302 28 lines line NNS cord-003318-abs9rvjk 302 29 . . . cord-003318-abs9rvjk 303 1 This this DT cord-003318-abs9rvjk 303 2 study study NN cord-003318-abs9rvjk 303 3 therefore therefore RB cord-003318-abs9rvjk 303 4 reports report VBZ cord-003318-abs9rvjk 303 5 for for IN cord-003318-abs9rvjk 303 6 the the DT cord-003318-abs9rvjk 303 7 first first JJ cord-003318-abs9rvjk 303 8 time time NN cord-003318-abs9rvjk 303 9 a a DT cord-003318-abs9rvjk 303 10 novel novel JJ cord-003318-abs9rvjk 303 11 synthetic synthetic JJ cord-003318-abs9rvjk 303 12 process process NN cord-003318-abs9rvjk 303 13 for for IN cord-003318-abs9rvjk 303 14 the the DT cord-003318-abs9rvjk 303 15 green green JJ cord-003318-abs9rvjk 303 16 preparation preparation NN cord-003318-abs9rvjk 303 17 of of IN cord-003318-abs9rvjk 303 18 acylated acylated JJ cord-003318-abs9rvjk 303 19 steroidal steroidal JJ cord-003318-abs9rvjk 303 20 glycosides glycoside NNS cord-003318-abs9rvjk 303 21 with with IN cord-003318-abs9rvjk 303 22 medicinal medicinal JJ cord-003318-abs9rvjk 303 23 interest interest NN cord-003318-abs9rvjk 303 24 . . . cord-003318-abs9rvjk 304 1 In in IN cord-003318-abs9rvjk 304 2 this this DT cord-003318-abs9rvjk 304 3 contribution contribution NN cord-003318-abs9rvjk 304 4 , , , cord-003318-abs9rvjk 304 5 four four CD cord-003318-abs9rvjk 304 6 compound compound NN cord-003318-abs9rvjk 304 7 libraries library NNS cord-003318-abs9rvjk 304 8 , , , cord-003318-abs9rvjk 304 9 namely namely RB cord-003318-abs9rvjk 304 10 sugar sugar NN cord-003318-abs9rvjk 304 11 acceptor acceptor NN cord-003318-abs9rvjk 304 12 , , , cord-003318-abs9rvjk 304 13 sugar sugar NN cord-003318-abs9rvjk 304 14 donor donor NN cord-003318-abs9rvjk 304 15 , , , cord-003318-abs9rvjk 304 16 acyl acyl NN cord-003318-abs9rvjk 304 17 acceptor acceptor NN cord-003318-abs9rvjk 304 18 and and CC cord-003318-abs9rvjk 304 19 acyl acyl NNP cord-003318-abs9rvjk 304 20 donor donor NN cord-003318-abs9rvjk 304 21 libraries library NNS cord-003318-abs9rvjk 304 22 , , , cord-003318-abs9rvjk 304 23 were be VBD cord-003318-abs9rvjk 304 24 provided provide VBN cord-003318-abs9rvjk 304 25 for for IN cord-003318-abs9rvjk 304 26 enzyme enzyme NN cord-003318-abs9rvjk 304 27 - - HYPH cord-003318-abs9rvjk 304 28 mediated mediate VBN cord-003318-abs9rvjk 304 29 reactions reaction NNS cord-003318-abs9rvjk 304 30 . . . cord-003318-abs9rvjk 305 1 The the DT cord-003318-abs9rvjk 305 2 compounds compound NNS cord-003318-abs9rvjk 305 3 listed list VBN cord-003318-abs9rvjk 305 4 in in IN cord-003318-abs9rvjk 305 5 Fig Fig NNP cord-003318-abs9rvjk 305 6 . . NNP cord-003318-abs9rvjk 305 7 1 1 CD cord-003318-abs9rvjk 305 8 and and CC cord-003318-abs9rvjk 305 9 Supplementary Supplementary NNP cord-003318-abs9rvjk 305 10 Information Information NNP cord-003318-abs9rvjk 305 11 Fig Fig NNP cord-003318-abs9rvjk 305 12 . . . cord-003318-abs9rvjk 306 1 S4 S4 NNS cord-003318-abs9rvjk 306 2 include include VBP cord-003318-abs9rvjk 306 3 diverse diverse JJ cord-003318-abs9rvjk 306 4 structures structure NNS cord-003318-abs9rvjk 306 5 like like IN cord-003318-abs9rvjk 306 6 steroids steroid NNS cord-003318-abs9rvjk 306 7 , , , cord-003318-abs9rvjk 306 8 flavonoids flavonoid NNS cord-003318-abs9rvjk 306 9 ( ( -LRB- cord-003318-abs9rvjk 306 10 25 25 CD cord-003318-abs9rvjk 306 11 ) ) -RRB- cord-003318-abs9rvjk 306 12 ( ( -LRB- cord-003318-abs9rvjk 306 13 26 26 CD cord-003318-abs9rvjk 306 14 ) ) -RRB- cord-003318-abs9rvjk 306 15 ( ( -LRB- cord-003318-abs9rvjk 306 16 27 27 CD cord-003318-abs9rvjk 306 17 ) ) -RRB- cord-003318-abs9rvjk 306 18 ( ( -LRB- cord-003318-abs9rvjk 306 19 28 28 CD cord-003318-abs9rvjk 306 20 ) ) -RRB- cord-003318-abs9rvjk 306 21 ( ( -LRB- cord-003318-abs9rvjk 306 22 29 29 CD cord-003318-abs9rvjk 306 23 ) ) -RRB- cord-003318-abs9rvjk 306 24 ( ( -LRB- cord-003318-abs9rvjk 306 25 30 30 CD cord-003318-abs9rvjk 306 26 ) ) -RRB- cord-003318-abs9rvjk 306 27 ( ( -LRB- cord-003318-abs9rvjk 306 28 31 31 CD cord-003318-abs9rvjk 306 29 ) ) -RRB- cord-003318-abs9rvjk 306 30 , , , cord-003318-abs9rvjk 306 31 alkaloids alkaloid NNS cord-003318-abs9rvjk 306 32 ( ( -LRB- cord-003318-abs9rvjk 306 33 32 32 CD cord-003318-abs9rvjk 306 34 ) ) -RRB- cord-003318-abs9rvjk 306 35 ( ( -LRB- cord-003318-abs9rvjk 306 36 33 33 CD cord-003318-abs9rvjk 306 37 ) ) -RRB- cord-003318-abs9rvjk 306 38 ( ( -LRB- cord-003318-abs9rvjk 306 39 34 34 CD cord-003318-abs9rvjk 306 40 ) ) -RRB- cord-003318-abs9rvjk 306 41 ( ( -LRB- cord-003318-abs9rvjk 306 42 35 35 CD cord-003318-abs9rvjk 306 43 ) ) -RRB- cord-003318-abs9rvjk 306 44 ( ( -LRB- cord-003318-abs9rvjk 306 45 36 36 CD cord-003318-abs9rvjk 306 46 ) ) -RRB- cord-003318-abs9rvjk 306 47 ( ( -LRB- cord-003318-abs9rvjk 306 48 37 37 CD cord-003318-abs9rvjk 306 49 ) ) -RRB- cord-003318-abs9rvjk 306 50 ( ( -LRB- cord-003318-abs9rvjk 306 51 38 38 CD cord-003318-abs9rvjk 306 52 ) ) -RRB- cord-003318-abs9rvjk 306 53 , , , cord-003318-abs9rvjk 306 54 triterpenoids triterpenoid NNS cord-003318-abs9rvjk 306 55 ( ( -LRB- cord-003318-abs9rvjk 306 56 39 39 CD cord-003318-abs9rvjk 306 57 - - SYM cord-003318-abs9rvjk 306 58 42 42 CD cord-003318-abs9rvjk 306 59 ) ) -RRB- cord-003318-abs9rvjk 306 60 , , , cord-003318-abs9rvjk 306 61 phenolic phenolic JJ cord-003318-abs9rvjk 306 62 acids acid NNS cord-003318-abs9rvjk 306 63 ( ( -LRB- cord-003318-abs9rvjk 306 64 43 43 CD cord-003318-abs9rvjk 306 65 - - SYM cord-003318-abs9rvjk 306 66 47 47 CD cord-003318-abs9rvjk 306 67 ) ) -RRB- cord-003318-abs9rvjk 306 68 and and CC cord-003318-abs9rvjk 306 69 coumarins coumarin NNS cord-003318-abs9rvjk 306 70 ( ( -LRB- cord-003318-abs9rvjk 306 71 48 48 CD cord-003318-abs9rvjk 306 72 - - SYM cord-003318-abs9rvjk 306 73 49 49 CD cord-003318-abs9rvjk 306 74 ) ) -RRB- cord-003318-abs9rvjk 306 75 are be VBP cord-003318-abs9rvjk 306 76 used use VBN cord-003318-abs9rvjk 306 77 as as IN cord-003318-abs9rvjk 306 78 the the DT cord-003318-abs9rvjk 306 79 sugar sugar NN cord-003318-abs9rvjk 306 80 acceptors acceptor NNS cord-003318-abs9rvjk 306 81 for for IN cord-003318-abs9rvjk 306 82 OsSGT1-catalyzed ossgt1-catalyzed JJ cord-003318-abs9rvjk 306 83 glycosylation glycosylation NN cord-003318-abs9rvjk 306 84 reactions reaction NNS cord-003318-abs9rvjk 306 85 ( ( -LRB- cord-003318-abs9rvjk 306 86 Fig fig NN cord-003318-abs9rvjk 306 87 . . . cord-003318-abs9rvjk 306 88 1 1 CD cord-003318-abs9rvjk 306 89 and and CC cord-003318-abs9rvjk 306 90 Supplementary Supplementary NNP cord-003318-abs9rvjk 306 91 Information Information NNP cord-003318-abs9rvjk 306 92 Fig Fig NNP cord-003318-abs9rvjk 306 93 . . . cord-003318-abs9rvjk 306 94 S4 S4 NNP cord-003318-abs9rvjk 306 95 ) ) -RRB- cord-003318-abs9rvjk 306 96 . . . cord-003318-abs9rvjk 307 1 The the DT cord-003318-abs9rvjk 307 2 sugar sugar NN cord-003318-abs9rvjk 307 3 donors donor NNS cord-003318-abs9rvjk 307 4 consist consist VBP cord-003318-abs9rvjk 307 5 of of IN cord-003318-abs9rvjk 307 6 seven seven CD cord-003318-abs9rvjk 307 7 UDP udp NN cord-003318-abs9rvjk 307 8 - - HYPH cord-003318-abs9rvjk 307 9 activated activate VBN cord-003318-abs9rvjk 307 10 nucleotides nucleotide NNS cord-003318-abs9rvjk 307 11 , , , cord-003318-abs9rvjk 307 12 among among IN cord-003318-abs9rvjk 307 13 which which WDT cord-003318-abs9rvjk 307 14 , , , cord-003318-abs9rvjk 307 15 UDP UDP NNP cord-003318-abs9rvjk 307 16 - - HYPH cord-003318-abs9rvjk 307 17 Dglucose Dglucose NNP cord-003318-abs9rvjk 307 18 ( ( -LRB- cord-003318-abs9rvjk 307 19 UDP UDP NNP cord-003318-abs9rvjk 307 20 - - HYPH cord-003318-abs9rvjk 307 21 Glc Glc NNP cord-003318-abs9rvjk 307 22 ) ) -RRB- cord-003318-abs9rvjk 307 23 , , , cord-003318-abs9rvjk 307 24 UDP udp NN cord-003318-abs9rvjk 307 25 - - HYPH cord-003318-abs9rvjk 307 26 D d NN cord-003318-abs9rvjk 307 27 - - HYPH cord-003318-abs9rvjk 307 28 galactose galactose NN cord-003318-abs9rvjk 307 29 ( ( -LRB- cord-003318-abs9rvjk 307 30 UDP UDP NNP cord-003318-abs9rvjk 307 31 - - HYPH cord-003318-abs9rvjk 307 32 Gal Gal NNP cord-003318-abs9rvjk 307 33 ) ) -RRB- cord-003318-abs9rvjk 307 34 , , , cord-003318-abs9rvjk 307 35 UDP udp NN cord-003318-abs9rvjk 307 36 - - HYPH cord-003318-abs9rvjk 307 37 D- d- NN cord-003318-abs9rvjk 308 1 glucuronic glucuronic NNP cord-003318-abs9rvjk 308 2 acid acid NNP cord-003318-abs9rvjk 309 1 ( ( -LRB- cord-003318-abs9rvjk 309 2 UDP UDP NNP cord-003318-abs9rvjk 309 3 - - HYPH cord-003318-abs9rvjk 309 4 GlcA GlcA NNP cord-003318-abs9rvjk 309 5 ) ) -RRB- cord-003318-abs9rvjk 309 6 and and CC cord-003318-abs9rvjk 309 7 UDP UDP NNP cord-003318-abs9rvjk 309 8 - - HYPH cord-003318-abs9rvjk 309 9 N N NNP cord-003318-abs9rvjk 309 10 - - HYPH cord-003318-abs9rvjk 309 11 acetylglucosamine acetylglucosamine NNP cord-003318-abs9rvjk 309 12 ( ( -LRB- cord-003318-abs9rvjk 309 13 UDP UDP NNP cord-003318-abs9rvjk 309 14 - - HYPH cord-003318-abs9rvjk 309 15 GlcNAc GlcNAc NNP cord-003318-abs9rvjk 309 16 ) ) -RRB- cord-003318-abs9rvjk 309 17 were be VBD cord-003318-abs9rvjk 309 18 obtained obtain VBN cord-003318-abs9rvjk 309 19 from from IN cord-003318-abs9rvjk 309 20 Sigma Sigma NNP cord-003318-abs9rvjk 309 21 - - HYPH cord-003318-abs9rvjk 309 22 Aldrich Aldrich NNP cord-003318-abs9rvjk 309 23 Co. Co. NNP cord-003318-abs9rvjk 309 24 , , , cord-003318-abs9rvjk 309 25 LLC LLC NNP cord-003318-abs9rvjk 309 26 . . . cord-003318-abs9rvjk 310 1 ( ( -LRB- cord-003318-abs9rvjk 310 2 St. St. NNP cord-003318-abs9rvjk 310 3 Louis Louis NNP cord-003318-abs9rvjk 310 4 , , , cord-003318-abs9rvjk 310 5 MO MO NNP cord-003318-abs9rvjk 310 6 , , , cord-003318-abs9rvjk 310 7 USA USA NNP cord-003318-abs9rvjk 310 8 ) ) -RRB- cord-003318-abs9rvjk 310 9 . . . cord-003318-abs9rvjk 311 1 UDP udp NN cord-003318-abs9rvjk 311 2 - - HYPH cord-003318-abs9rvjk 311 3 D d NN cord-003318-abs9rvjk 311 4 - - HYPH cord-003318-abs9rvjk 311 5 xylose xylose NN cord-003318-abs9rvjk 312 1 ( ( -LRB- cord-003318-abs9rvjk 312 2 UDP UDP NNP cord-003318-abs9rvjk 312 3 - - HYPH cord-003318-abs9rvjk 312 4 Xyl Xyl NNP cord-003318-abs9rvjk 312 5 ) ) -RRB- cord-003318-abs9rvjk 312 6 , , , cord-003318-abs9rvjk 312 7 UDP UDP NNP cord-003318-abs9rvjk 312 8 - - HYPH cord-003318-abs9rvjk 312 9 L l NN cord-003318-abs9rvjk 312 10 - - HYPH cord-003318-abs9rvjk 312 11 arabinose arabinose JJ cord-003318-abs9rvjk 312 12 ( ( -LRB- cord-003318-abs9rvjk 312 13 UDP UDP NNP cord-003318-abs9rvjk 312 14 - - HYPH cord-003318-abs9rvjk 312 15 Ara Ara NNP cord-003318-abs9rvjk 312 16 ) ) -RRB- cord-003318-abs9rvjk 312 17 and and CC cord-003318-abs9rvjk 312 18 UDP udp NN cord-003318-abs9rvjk 312 19 - - HYPH cord-003318-abs9rvjk 312 20 D d NN cord-003318-abs9rvjk 312 21 - - HYPH cord-003318-abs9rvjk 312 22 galacturonic galacturonic NN cord-003318-abs9rvjk 312 23 acid acid NN cord-003318-abs9rvjk 312 24 ( ( -LRB- cord-003318-abs9rvjk 312 25 UDP UDP NNP cord-003318-abs9rvjk 312 26 - - HYPH cord-003318-abs9rvjk 312 27 GalA GalA NNP cord-003318-abs9rvjk 312 28 ) ) -RRB- cord-003318-abs9rvjk 312 29 was be VBD cord-003318-abs9rvjk 312 30 synthesized synthesize VBN cord-003318-abs9rvjk 312 31 by by IN cord-003318-abs9rvjk 312 32 enzymemediated enzymemediated JJ cord-003318-abs9rvjk 312 33 reactions reaction NNS cord-003318-abs9rvjk 312 34 in in IN cord-003318-abs9rvjk 312 35 our -PRON- PRP$ cord-003318-abs9rvjk 312 36 laboratory laboratory NN cord-003318-abs9rvjk 312 37 [ [ -LRB- cord-003318-abs9rvjk 312 38 27 27 CD cord-003318-abs9rvjk 312 39 ] ] -RRB- cord-003318-abs9rvjk 313 1 [ [ -LRB- cord-003318-abs9rvjk 313 2 28 28 CD cord-003318-abs9rvjk 313 3 ] ] -RRB- cord-003318-abs9rvjk 313 4 [ [ -LRB- cord-003318-abs9rvjk 313 5 29 29 CD cord-003318-abs9rvjk 313 6 ] ] -RRB- cord-003318-abs9rvjk 313 7 . . . cord-003318-abs9rvjk 314 1 The the DT cord-003318-abs9rvjk 314 2 acyl acyl NN cord-003318-abs9rvjk 314 3 acceptor acceptor NN cord-003318-abs9rvjk 314 4 library library NN cord-003318-abs9rvjk 314 5 is be VBZ cord-003318-abs9rvjk 314 6 made make VBN cord-003318-abs9rvjk 314 7 up up RP cord-003318-abs9rvjk 314 8 of of IN cord-003318-abs9rvjk 314 9 10 10 CD cord-003318-abs9rvjk 314 10 steroidal steroidal JJ cord-003318-abs9rvjk 314 11 glucosides glucoside NNS cord-003318-abs9rvjk 314 12 ( ( -LRB- cord-003318-abs9rvjk 314 13 1a-10a 1a-10a CD cord-003318-abs9rvjk 314 14 ) ) -RRB- cord-003318-abs9rvjk 314 15 and and CC cord-003318-abs9rvjk 314 16 13 13 CD cord-003318-abs9rvjk 314 17 other other JJ cord-003318-abs9rvjk 314 18 glucosides glucoside NNS cord-003318-abs9rvjk 314 19 ( ( -LRB- cord-003318-abs9rvjk 314 20 50 50 CD cord-003318-abs9rvjk 314 21 - - SYM cord-003318-abs9rvjk 314 22 62 62 CD cord-003318-abs9rvjk 314 23 ) ) -RRB- cord-003318-abs9rvjk 314 24 listed list VBN cord-003318-abs9rvjk 314 25 in in IN cord-003318-abs9rvjk 314 26 Supplementary Supplementary NNP cord-003318-abs9rvjk 314 27 Information Information NNP cord-003318-abs9rvjk 314 28 Fig Fig NNP cord-003318-abs9rvjk 314 29 . . . cord-003318-abs9rvjk 315 1 S58 S58 NNP cord-003318-abs9rvjk 315 2 . . . cord-003318-abs9rvjk 316 1 The the DT cord-003318-abs9rvjk 316 2 acyl acyl NN cord-003318-abs9rvjk 316 3 donor donor NN cord-003318-abs9rvjk 316 4 library library NN cord-003318-abs9rvjk 316 5 includes include VBZ cord-003318-abs9rvjk 316 6 acetyl acetyl NN cord-003318-abs9rvjk 316 7 - - HYPH cord-003318-abs9rvjk 316 8 CoA CoA NNP cord-003318-abs9rvjk 316 9 , , , cord-003318-abs9rvjk 316 10 succinyl succinyl NNP cord-003318-abs9rvjk 316 11 - - HYPH cord-003318-abs9rvjk 316 12 CoA CoA NNP cord-003318-abs9rvjk 316 13 , , , cord-003318-abs9rvjk 316 14 arachidonoyl arachidonoyl NNP cord-003318-abs9rvjk 316 15 - - HYPH cord-003318-abs9rvjk 316 16 CoA CoA NNP cord-003318-abs9rvjk 316 17 , , , cord-003318-abs9rvjk 316 18 palmitoyl palmitoyl NNP cord-003318-abs9rvjk 316 19 - - HYPH cord-003318-abs9rvjk 316 20 CoA CoA NNP cord-003318-abs9rvjk 316 21 and and CC cord-003318-abs9rvjk 316 22 acetoacetyl acetoacetyl NNP cord-003318-abs9rvjk 316 23 - - HYPH cord-003318-abs9rvjk 316 24 CoA CoA NNP cord-003318-abs9rvjk 316 25 , , , cord-003318-abs9rvjk 316 26 all all DT cord-003318-abs9rvjk 316 27 of of IN cord-003318-abs9rvjk 316 28 which which WDT cord-003318-abs9rvjk 316 29 were be VBD cord-003318-abs9rvjk 316 30 purchased purchase VBN cord-003318-abs9rvjk 316 31 from from IN cord-003318-abs9rvjk 316 32 Sigma Sigma NNP cord-003318-abs9rvjk 316 33 - - HYPH cord-003318-abs9rvjk 316 34 Aldrich Aldrich NNP cord-003318-abs9rvjk 316 35 Co. Co. NNP cord-003318-abs9rvjk 316 36 , , , cord-003318-abs9rvjk 316 37 LLC LLC NNP cord-003318-abs9rvjk 316 38 . . . cord-003318-abs9rvjk 317 1 The the DT cord-003318-abs9rvjk 317 2 other other JJ cord-003318-abs9rvjk 317 3 chemicals chemical NNS cord-003318-abs9rvjk 317 4 were be VBD cord-003318-abs9rvjk 317 5 either either CC cord-003318-abs9rvjk 317 6 reagent reagent JJ cord-003318-abs9rvjk 317 7 or or CC cord-003318-abs9rvjk 317 8 analytic analytic JJ cord-003318-abs9rvjk 317 9 grade grade NN cord-003318-abs9rvjk 317 10 when when WRB cord-003318-abs9rvjk 317 11 available available JJ cord-003318-abs9rvjk 317 12 . . . cord-003318-abs9rvjk 317 13 _SP cord-003318-abs9rvjk 318 1 The the DT cord-003318-abs9rvjk 318 2 resulting result VBG cord-003318-abs9rvjk 318 3 raw raw JJ cord-003318-abs9rvjk 318 4 reads read NNS cord-003318-abs9rvjk 318 5 from from IN cord-003318-abs9rvjk 318 6 sequence sequence NN cord-003318-abs9rvjk 318 7 library library NN cord-003318-abs9rvjk 318 8 of of IN cord-003318-abs9rvjk 318 9 O. O. NNP cord-003318-abs9rvjk 318 10 saundersiae saundersiae NNP cord-003318-abs9rvjk 318 11 was be VBD cord-003318-abs9rvjk 318 12 firstly firstly RB cord-003318-abs9rvjk 318 13 filtered filter VBN cord-003318-abs9rvjk 318 14 to to TO cord-003318-abs9rvjk 318 15 obtain obtain VB cord-003318-abs9rvjk 318 16 clean clean JJ cord-003318-abs9rvjk 318 17 reads read NNS cord-003318-abs9rvjk 318 18 , , , cord-003318-abs9rvjk 318 19 discarding discard VBG cord-003318-abs9rvjk 318 20 dirty dirty JJ cord-003318-abs9rvjk 318 21 reads read NNS cord-003318-abs9rvjk 318 22 with with IN cord-003318-abs9rvjk 318 23 adaptors adaptor NNS cord-003318-abs9rvjk 318 24 , , , cord-003318-abs9rvjk 318 25 unknown unknown JJ cord-003318-abs9rvjk 318 26 or or CC cord-003318-abs9rvjk 318 27 low low JJ cord-003318-abs9rvjk 318 28 quality quality NN cord-003318-abs9rvjk 318 29 bases basis NNS cord-003318-abs9rvjk 318 30 . . . cord-003318-abs9rvjk 319 1 These these DT cord-003318-abs9rvjk 319 2 clean clean JJ cord-003318-abs9rvjk 319 3 reads read NNS cord-003318-abs9rvjk 319 4 were be VBD cord-003318-abs9rvjk 319 5 subsequently subsequently RB cord-003318-abs9rvjk 319 6 combined combine VBN cord-003318-abs9rvjk 319 7 to to TO cord-003318-abs9rvjk 319 8 form form VB cord-003318-abs9rvjk 319 9 longer long JJR cord-003318-abs9rvjk 319 10 unigenes unigene NNS cord-003318-abs9rvjk 319 11 by by IN cord-003318-abs9rvjk 319 12 assembling assemble VBG cord-003318-abs9rvjk 319 13 program program NN cord-003318-abs9rvjk 319 14 trinity trinity NN cord-003318-abs9rvjk 319 15 . . . cord-003318-abs9rvjk 320 1 These these DT cord-003318-abs9rvjk 320 2 unigenes unigene NNS cord-003318-abs9rvjk 320 3 obtained obtain VBN cord-003318-abs9rvjk 320 4 by by IN cord-003318-abs9rvjk 320 5 de de NNP cord-003318-abs9rvjk 320 6 novo novo NNP cord-003318-abs9rvjk 320 7 assembly assembly NNP cord-003318-abs9rvjk 320 8 can can MD cord-003318-abs9rvjk 320 9 not not RB cord-003318-abs9rvjk 320 10 be be VB cord-003318-abs9rvjk 320 11 extended extend VBN cord-003318-abs9rvjk 320 12 on on IN cord-003318-abs9rvjk 320 13 either either DT cord-003318-abs9rvjk 320 14 end end NN cord-003318-abs9rvjk 320 15 . . . cord-003318-abs9rvjk 321 1 Next next RB cord-003318-abs9rvjk 321 2 , , , cord-003318-abs9rvjk 321 3 these these DT cord-003318-abs9rvjk 321 4 unigenes unigene NNS cord-003318-abs9rvjk 321 5 were be VBD cord-003318-abs9rvjk 321 6 aligned align VBN cord-003318-abs9rvjk 321 7 by by IN cord-003318-abs9rvjk 321 8 Blast blast NN cord-003318-abs9rvjk 321 9 X X NNP cord-003318-abs9rvjk 321 10 algorithm algorithm NN cord-003318-abs9rvjk 321 11 to to IN cord-003318-abs9rvjk 321 12 protein protein NN cord-003318-abs9rvjk 321 13 databases database NNS cord-003318-abs9rvjk 321 14 , , , cord-003318-abs9rvjk 321 15 such such JJ cord-003318-abs9rvjk 321 16 as as IN cord-003318-abs9rvjk 321 17 NR NR NNP cord-003318-abs9rvjk 321 18 , , , cord-003318-abs9rvjk 321 19 Swiss Swiss NNP cord-003318-abs9rvjk 321 20 - - HYPH cord-003318-abs9rvjk 321 21 Prot Prot NNP cord-003318-abs9rvjk 321 22 , , , cord-003318-abs9rvjk 321 23 KEGG KEGG NNP cord-003318-abs9rvjk 321 24 and and CC cord-003318-abs9rvjk 321 25 COG cog NN cord-003318-abs9rvjk 321 26 ( ( -LRB- cord-003318-abs9rvjk 321 27 e e NN cord-003318-abs9rvjk 321 28 - - HYPH cord-003318-abs9rvjk 321 29 valueo0.00001 valueo0.00001 NNP cord-003318-abs9rvjk 321 30 ) ) -RRB- cord-003318-abs9rvjk 321 31 for for IN cord-003318-abs9rvjk 321 32 functional functional JJ cord-003318-abs9rvjk 321 33 annotation annotation NN cord-003318-abs9rvjk 321 34 . . . cord-003318-abs9rvjk 322 1 The the DT cord-003318-abs9rvjk 322 2 unigenes unigene NNS cord-003318-abs9rvjk 322 3 displaying display VBG cord-003318-abs9rvjk 322 4 similarity similarity NN cord-003318-abs9rvjk 322 5 to to IN cord-003318-abs9rvjk 322 6 SGTs sgt NNS cord-003318-abs9rvjk 322 7 were be VBD cord-003318-abs9rvjk 322 8 retrieved retrieve VBN cord-003318-abs9rvjk 322 9 for for IN cord-003318-abs9rvjk 322 10 further further JJ cord-003318-abs9rvjk 322 11 ORF ORF NNP cord-003318-abs9rvjk 322 12 analysis analysis NN cord-003318-abs9rvjk 322 13 . . . cord-003318-abs9rvjk 323 1 In in IN cord-003318-abs9rvjk 323 2 a a DT cord-003318-abs9rvjk 323 3 word word NN cord-003318-abs9rvjk 323 4 , , , cord-003318-abs9rvjk 323 5 those those DT cord-003318-abs9rvjk 323 6 unigenes unigene NNS cord-003318-abs9rvjk 323 7 with with IN cord-003318-abs9rvjk 323 8 a a DT cord-003318-abs9rvjk 323 9 complete complete JJ cord-003318-abs9rvjk 323 10 ORF ORF NNP cord-003318-abs9rvjk 323 11 and and CC cord-003318-abs9rvjk 323 12 displaying display VBG cord-003318-abs9rvjk 323 13 high high JJ cord-003318-abs9rvjk 323 14 similarity similarity NN cord-003318-abs9rvjk 323 15 to to IN cord-003318-abs9rvjk 323 16 SGTs sgt NNS cord-003318-abs9rvjk 323 17 were be VBD cord-003318-abs9rvjk 323 18 selected select VBN cord-003318-abs9rvjk 323 19 as as IN cord-003318-abs9rvjk 323 20 the the DT cord-003318-abs9rvjk 323 21 candidate candidate NN cord-003318-abs9rvjk 323 22 for for IN cord-003318-abs9rvjk 323 23 further further JJ cord-003318-abs9rvjk 323 24 investigation investigation NN cord-003318-abs9rvjk 323 25 . . . cord-003318-abs9rvjk 324 1 To to TO cord-003318-abs9rvjk 324 2 verify verify VB cord-003318-abs9rvjk 324 3 the the DT cord-003318-abs9rvjk 324 4 authenticity authenticity NN cord-003318-abs9rvjk 324 5 of of IN cord-003318-abs9rvjk 324 6 the the DT cord-003318-abs9rvjk 324 7 candidate candidate NN cord-003318-abs9rvjk 324 8 unigene unigene NN cord-003318-abs9rvjk 324 9 , , , cord-003318-abs9rvjk 324 10 cDNA cdna NN cord-003318-abs9rvjk 324 11 isolation isolation NN cord-003318-abs9rvjk 324 12 was be VBD cord-003318-abs9rvjk 324 13 performed perform VBN cord-003318-abs9rvjk 324 14 using use VBG cord-003318-abs9rvjk 324 15 gene gene NN cord-003318-abs9rvjk 324 16 - - HYPH cord-003318-abs9rvjk 324 17 specific specific JJ cord-003318-abs9rvjk 324 18 primers primer NNS cord-003318-abs9rvjk 324 19 by by IN cord-003318-abs9rvjk 324 20 a a DT cord-003318-abs9rvjk 324 21 nested nest VBN cord-003318-abs9rvjk 324 22 PCR PCR NNP cord-003318-abs9rvjk 324 23 assay assay NN cord-003318-abs9rvjk 324 24 as as IN cord-003318-abs9rvjk 324 25 previously previously RB cord-003318-abs9rvjk 324 26 described describe VBN cord-003318-abs9rvjk 324 27 ( ( -LRB- cord-003318-abs9rvjk 324 28 Supplementary Supplementary NNP cord-003318-abs9rvjk 324 29 Information Information NNP cord-003318-abs9rvjk 324 30 _SP cord-003318-abs9rvjk 324 31 Table Table NNP cord-003318-abs9rvjk 324 32 S1 S1 NNP cord-003318-abs9rvjk 324 33 ) ) -RRB- cord-003318-abs9rvjk 324 34 [ [ -LRB- cord-003318-abs9rvjk 324 35 28 28 CD cord-003318-abs9rvjk 324 36 ] ] -RRB- cord-003318-abs9rvjk 324 37 [ [ -LRB- cord-003318-abs9rvjk 324 38 29 29 CD cord-003318-abs9rvjk 324 39 ] ] -RRB- cord-003318-abs9rvjk 325 1 [ [ -LRB- cord-003318-abs9rvjk 325 2 30 30 CD cord-003318-abs9rvjk 325 3 ] ] -RRB- cord-003318-abs9rvjk 325 4 [ [ -LRB- cord-003318-abs9rvjk 325 5 31 31 CD cord-003318-abs9rvjk 325 6 ] ] -RRB- cord-003318-abs9rvjk 325 7 . . . cord-003318-abs9rvjk 326 1 The the DT cord-003318-abs9rvjk 326 2 obtained obtain VBN cord-003318-abs9rvjk 326 3 amplicon amplicon NN cord-003318-abs9rvjk 326 4 was be VBD cord-003318-abs9rvjk 326 5 inserted insert VBN cord-003318-abs9rvjk 326 6 into into IN cord-003318-abs9rvjk 326 7 pEASY peasy JJ cord-003318-abs9rvjk 326 8 TM TM NNP cord-003318-abs9rvjk 326 9 -Blunt -blunt NN cord-003318-abs9rvjk 326 10 plasmid plasmid NNP cord-003318-abs9rvjk 326 11 ( ( -LRB- cord-003318-abs9rvjk 326 12 TransGen TransGen NNP cord-003318-abs9rvjk 326 13 Co. Co. NNP cord-003318-abs9rvjk 326 14 , , , cord-003318-abs9rvjk 326 15 Ltd. Ltd. NNP cord-003318-abs9rvjk 326 16 , , , cord-003318-abs9rvjk 326 17 Beijing Beijing NNP cord-003318-abs9rvjk 326 18 , , , cord-003318-abs9rvjk 326 19 China China NNP cord-003318-abs9rvjk 326 20 ) ) -RRB- cord-003318-abs9rvjk 326 21 and and CC cord-003318-abs9rvjk 326 22 then then RB cord-003318-abs9rvjk 326 23 transformed transform VBN cord-003318-abs9rvjk 326 24 into into IN cord-003318-abs9rvjk 326 25 E. E. NNP cord-003318-abs9rvjk 326 26 coli coli VBZ cord-003318-abs9rvjk 326 27 Trans1-T1 Trans1-T1 NNP cord-003318-abs9rvjk 326 28 competent competent JJ cord-003318-abs9rvjk 326 29 cells cell NNS cord-003318-abs9rvjk 326 30 for for IN cord-003318-abs9rvjk 326 31 recombinant recombinant JJ cord-003318-abs9rvjk 326 32 plasmid plasmid NN cord-003318-abs9rvjk 326 33 selection selection NN cord-003318-abs9rvjk 326 34 ( ( -LRB- cord-003318-abs9rvjk 326 35 Supplementary Supplementary NNP cord-003318-abs9rvjk 326 36 Information information NN cord-003318-abs9rvjk 326 37 Table table NN cord-003318-abs9rvjk 326 38 _SP cord-003318-abs9rvjk 326 39 S2 S2 NNP cord-003318-abs9rvjk 326 40 ) ) -RRB- cord-003318-abs9rvjk 326 41 . . . cord-003318-abs9rvjk 327 1 The the DT cord-003318-abs9rvjk 327 2 resultant resultant JJ cord-003318-abs9rvjk 327 3 recombinant recombinant JJ cord-003318-abs9rvjk 327 4 plasmid plasmid NN cord-003318-abs9rvjk 327 5 was be VBD cord-003318-abs9rvjk 327 6 isolated isolate VBN cord-003318-abs9rvjk 327 7 and and CC cord-003318-abs9rvjk 327 8 subjected subject VBN cord-003318-abs9rvjk 327 9 to to IN cord-003318-abs9rvjk 327 10 nucleotide nucleotide JJ cord-003318-abs9rvjk 327 11 sequencing sequencing NN cord-003318-abs9rvjk 327 12 . . . cord-003318-abs9rvjk 328 1 The the DT cord-003318-abs9rvjk 328 2 obtained obtain VBN cord-003318-abs9rvjk 328 3 cDNA cdna NN cord-003318-abs9rvjk 328 4 was be VBD cord-003318-abs9rvjk 328 5 thus thus RB cord-003318-abs9rvjk 328 6 designated designate VBN cord-003318-abs9rvjk 328 7 as as IN cord-003318-abs9rvjk 328 8 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 328 9 for for IN cord-003318-abs9rvjk 328 10 convenience convenience NN cord-003318-abs9rvjk 328 11 . . . cord-003318-abs9rvjk 329 1 The the DT cord-003318-abs9rvjk 329 2 bioinformatics bioinformatics NN cord-003318-abs9rvjk 329 3 analyses analysis NNS cord-003318-abs9rvjk 329 4 of of IN cord-003318-abs9rvjk 329 5 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 329 6 , , , cord-003318-abs9rvjk 329 7 like like IN cord-003318-abs9rvjk 329 8 prediction prediction NN cord-003318-abs9rvjk 329 9 of of IN cord-003318-abs9rvjk 329 10 physiochemical physiochemical JJ cord-003318-abs9rvjk 329 11 properties property NNS cord-003318-abs9rvjk 329 12 , , , cord-003318-abs9rvjk 329 13 multiple multiple JJ cord-003318-abs9rvjk 329 14 sequence sequence NN cord-003318-abs9rvjk 329 15 alignment alignment NN cord-003318-abs9rvjk 329 16 and and CC cord-003318-abs9rvjk 329 17 phylogenetic phylogenetic JJ cord-003318-abs9rvjk 329 18 analysis analysis NN cord-003318-abs9rvjk 329 19 , , , cord-003318-abs9rvjk 329 20 were be VBD cord-003318-abs9rvjk 329 21 performed perform VBN cord-003318-abs9rvjk 329 22 as as IN cord-003318-abs9rvjk 329 23 detailed detail VBN cord-003318-abs9rvjk 329 24 in in IN cord-003318-abs9rvjk 329 25 our -PRON- PRP$ cord-003318-abs9rvjk 329 26 previous previous JJ cord-003318-abs9rvjk 329 27 reports report NNS cord-003318-abs9rvjk 329 28 [ [ -LRB- cord-003318-abs9rvjk 329 29 27 27 CD cord-003318-abs9rvjk 329 30 ] ] -RRB- cord-003318-abs9rvjk 329 31 [ [ -LRB- cord-003318-abs9rvjk 329 32 28 28 CD cord-003318-abs9rvjk 329 33 ] ] -RRB- cord-003318-abs9rvjk 329 34 [ [ -LRB- cord-003318-abs9rvjk 329 35 29 29 CD cord-003318-abs9rvjk 329 36 ] ] -RRB- cord-003318-abs9rvjk 330 1 [ [ -LRB- cord-003318-abs9rvjk 330 2 30 30 CD cord-003318-abs9rvjk 330 3 ] ] -RRB- cord-003318-abs9rvjk 330 4 32 32 CD cord-003318-abs9rvjk 330 5 . . . cord-003318-abs9rvjk 331 1 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 331 2 was be VBD cord-003318-abs9rvjk 331 3 amplified amplify VBN cord-003318-abs9rvjk 331 4 using use VBG cord-003318-abs9rvjk 331 5 gene gene NN cord-003318-abs9rvjk 331 6 - - HYPH cord-003318-abs9rvjk 331 7 specific specific JJ cord-003318-abs9rvjk 331 8 primers primer NNS cord-003318-abs9rvjk 331 9 ( ( -LRB- cord-003318-abs9rvjk 331 10 Supplementary Supplementary NNP cord-003318-abs9rvjk 331 11 Information Information NNP cord-003318-abs9rvjk 331 12 Table Table NNP cord-003318-abs9rvjk 331 13 S1 S1 NNP cord-003318-abs9rvjk 331 14 ) ) -RRB- cord-003318-abs9rvjk 331 15 and and CC cord-003318-abs9rvjk 332 1 the the DT cord-003318-abs9rvjk 332 2 resulting result VBG cord-003318-abs9rvjk 332 3 PCR PCR NNP cord-003318-abs9rvjk 332 4 product product NN cord-003318-abs9rvjk 332 5 was be VBD cord-003318-abs9rvjk 332 6 ligated ligate VBN cord-003318-abs9rvjk 332 7 into into IN cord-003318-abs9rvjk 332 8 EcoRI EcoRI NNP cord-003318-abs9rvjk 332 9 and and CC cord-003318-abs9rvjk 332 10 Hind Hind NNP cord-003318-abs9rvjk 332 11 III III NNP cord-003318-abs9rvjk 332 12 sites site NNS cord-003318-abs9rvjk 332 13 within within IN cord-003318-abs9rvjk 332 14 the the DT cord-003318-abs9rvjk 332 15 pET-28a(þ pet-28a(þ NN cord-003318-abs9rvjk 332 16 ) ) -RRB- cord-003318-abs9rvjk 332 17 vector vector NN cord-003318-abs9rvjk 333 1 ( ( -LRB- cord-003318-abs9rvjk 333 2 Novagen Novagen NNP cord-003318-abs9rvjk 333 3 , , , cord-003318-abs9rvjk 333 4 Madison Madison NNP cord-003318-abs9rvjk 333 5 , , , cord-003318-abs9rvjk 333 6 USA USA NNP cord-003318-abs9rvjk 333 7 ) ) -RRB- cord-003318-abs9rvjk 333 8 using use VBG cord-003318-abs9rvjk 333 9 seamless seamless JJ cord-003318-abs9rvjk 333 10 assembly assembly NN cord-003318-abs9rvjk 333 11 cloning cloning NN cord-003318-abs9rvjk 333 12 kit kit NN cord-003318-abs9rvjk 333 13 ( ( -LRB- cord-003318-abs9rvjk 333 14 CloneSmarter CloneSmarter NNP cord-003318-abs9rvjk 333 15 Technologies Technologies NNP cord-003318-abs9rvjk 333 16 Inc. Inc. NNP cord-003318-abs9rvjk 333 17 , , , cord-003318-abs9rvjk 333 18 Houston Houston NNP cord-003318-abs9rvjk 333 19 , , , cord-003318-abs9rvjk 333 20 TX TX NNP cord-003318-abs9rvjk 333 21 , , , cord-003318-abs9rvjk 333 22 USA USA NNP cord-003318-abs9rvjk 333 23 ) ) -RRB- cord-003318-abs9rvjk 333 24 as as IN cord-003318-abs9rvjk 333 25 described describe VBN cord-003318-abs9rvjk 333 26 previously previously RB cord-003318-abs9rvjk 333 27 33 33 CD cord-003318-abs9rvjk 333 28 . . . cord-003318-abs9rvjk 334 1 The the DT cord-003318-abs9rvjk 334 2 generated generate VBN cord-003318-abs9rvjk 334 3 construct construct VBP cord-003318-abs9rvjk 334 4 pET28a pet28a JJ cord-003318-abs9rvjk 334 5 - - HYPH cord-003318-abs9rvjk 334 6 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 334 7 was be VBD cord-003318-abs9rvjk 334 8 transformed transform VBN cord-003318-abs9rvjk 334 9 into into IN cord-003318-abs9rvjk 334 10 E. E. NNP cord-003318-abs9rvjk 334 11 coli coli NNS cord-003318-abs9rvjk 334 12 strain strain VBP cord-003318-abs9rvjk 334 13 Transetta Transetta NNP cord-003318-abs9rvjk 334 14 ( ( -LRB- cord-003318-abs9rvjk 334 15 DE3 DE3 NNP cord-003318-abs9rvjk 334 16 ) ) -RRB- cord-003318-abs9rvjk 334 17 for for IN cord-003318-abs9rvjk 334 18 expression expression NN cord-003318-abs9rvjk 334 19 as as IN cord-003318-abs9rvjk 334 20 described describe VBN cord-003318-abs9rvjk 334 21 previously previously RB cord-003318-abs9rvjk 334 22 34 34 CD cord-003318-abs9rvjk 334 23 . . . cord-003318-abs9rvjk 335 1 Also also RB cord-003318-abs9rvjk 335 2 , , , cord-003318-abs9rvjk 335 3 to to TO cord-003318-abs9rvjk 335 4 improve improve VB cord-003318-abs9rvjk 335 5 heterologous heterologous JJ cord-003318-abs9rvjk 335 6 expression expression NN cord-003318-abs9rvjk 335 7 of of IN cord-003318-abs9rvjk 335 8 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 335 9 , , , cord-003318-abs9rvjk 335 10 pET28a pet28a JJ cord-003318-abs9rvjk 335 11 - - HYPH cord-003318-abs9rvjk 335 12 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 335 13 was be VBD cord-003318-abs9rvjk 335 14 cotransformed cotransforme VBN cord-003318-abs9rvjk 335 15 into into IN cord-003318-abs9rvjk 335 16 E. E. NNP cord-003318-abs9rvjk 335 17 coli coli NNS cord-003318-abs9rvjk 335 18 BL21(DE3 BL21(DE3 NNP cord-003318-abs9rvjk 335 19 ) ) -RRB- cord-003318-abs9rvjk 335 20 strain strain VBP cord-003318-abs9rvjk 335 21 with with IN cord-003318-abs9rvjk 335 22 a a DT cord-003318-abs9rvjk 335 23 chaperone chaperone NN cord-003318-abs9rvjk 335 24 plasmid plasmid NN cord-003318-abs9rvjk 335 25 pGro7 pgro7 NN cord-003318-abs9rvjk 336 1 ( ( -LRB- cord-003318-abs9rvjk 336 2 Takara Takara NNP cord-003318-abs9rvjk 336 3 Biotechnology Biotechnology NNP cord-003318-abs9rvjk 336 4 Co. Co. NNP cord-003318-abs9rvjk 336 5 , , , cord-003318-abs9rvjk 336 6 Ltd. Ltd. NNP cord-003318-abs9rvjk 336 7 , , , cord-003318-abs9rvjk 336 8 Dalian Dalian NNP cord-003318-abs9rvjk 336 9 , , , cord-003318-abs9rvjk 336 10 China China NNP cord-003318-abs9rvjk 336 11 ) ) -RRB- cord-003318-abs9rvjk 336 12 as as IN cord-003318-abs9rvjk 336 13 introduced introduce VBN cord-003318-abs9rvjk 336 14 by by IN cord-003318-abs9rvjk 336 15 Yin Yin NNP cord-003318-abs9rvjk 336 16 et et NNP cord-003318-abs9rvjk 336 17 al al NNP cord-003318-abs9rvjk 336 18 . . . cord-003318-abs9rvjk 337 1 27 27 CD cord-003318-abs9rvjk 338 1 The the DT cord-003318-abs9rvjk 338 2 expression expression NN cord-003318-abs9rvjk 338 3 of of IN cord-003318-abs9rvjk 338 4 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 338 5 was be VBD cord-003318-abs9rvjk 338 6 induced induce VBN cord-003318-abs9rvjk 338 7 by by IN cord-003318-abs9rvjk 338 8 IPTG IPTG NNP cord-003318-abs9rvjk 338 9 at at IN cord-003318-abs9rvjk 338 10 a a DT cord-003318-abs9rvjk 338 11 final final JJ cord-003318-abs9rvjk 338 12 concentration concentration NN cord-003318-abs9rvjk 338 13 of of IN cord-003318-abs9rvjk 338 14 0.3 0.3 CD cord-003318-abs9rvjk 338 15 mmol mmol JJ cord-003318-abs9rvjk 338 16 / / SYM cord-003318-abs9rvjk 338 17 L. L. NNP cord-003318-abs9rvjk 338 18 The the DT cord-003318-abs9rvjk 338 19 expressed express VBN cord-003318-abs9rvjk 338 20 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 338 21 was be VBD cord-003318-abs9rvjk 338 22 checked check VBN cord-003318-abs9rvjk 338 23 by by IN cord-003318-abs9rvjk 338 24 SDS SDS NNP cord-003318-abs9rvjk 338 25 - - HYPH cord-003318-abs9rvjk 338 26 PAGE PAGE NNP cord-003318-abs9rvjk 338 27 and and CC cord-003318-abs9rvjk 338 28 Western western JJ cord-003318-abs9rvjk 338 29 - - HYPH cord-003318-abs9rvjk 338 30 blot blot NN cord-003318-abs9rvjk 338 31 analyses analysis NNS cord-003318-abs9rvjk 338 32 as as IN cord-003318-abs9rvjk 338 33 described describe VBN cord-003318-abs9rvjk 338 34 by by IN cord-003318-abs9rvjk 338 35 Guo Guo NNP cord-003318-abs9rvjk 338 36 et et FW cord-003318-abs9rvjk 338 37 al al NNP cord-003318-abs9rvjk 338 38 . . . cord-003318-abs9rvjk 339 1 31 31 CD cord-003318-abs9rvjk 340 1 Next next RB cord-003318-abs9rvjk 340 2 , , , cord-003318-abs9rvjk 340 3 the the DT cord-003318-abs9rvjk 340 4 BL21(DE3 BL21(DE3 NNP cord-003318-abs9rvjk 340 5 ) ) -RRB- cord-003318-abs9rvjk 341 1 [ [ -LRB- cord-003318-abs9rvjk 341 2 pET28a pET28a NNP cord-003318-abs9rvjk 341 3 - - HYPH cord-003318-abs9rvjk 341 4 OsSGT1þpGro7 OsSGT1þpGro7 NNP cord-003318-abs9rvjk 341 5 ] ] -RRB- cord-003318-abs9rvjk 341 6 suspension suspension NN cord-003318-abs9rvjk 341 7 cells cell NNS cord-003318-abs9rvjk 341 8 were be VBD cord-003318-abs9rvjk 341 9 disrupted disrupt VBN cord-003318-abs9rvjk 341 10 in in IN cord-003318-abs9rvjk 341 11 a a DT cord-003318-abs9rvjk 341 12 high high JJ cord-003318-abs9rvjk 341 13 - - HYPH cord-003318-abs9rvjk 341 14 pressure pressure NN cord-003318-abs9rvjk 341 15 homogeniser homogeniser NN cord-003318-abs9rvjk 341 16 ( ( -LRB- cord-003318-abs9rvjk 341 17 APV-2000 APV-2000 NNP cord-003318-abs9rvjk 341 18 , , , cord-003318-abs9rvjk 341 19 Albertslund Albertslund NNP cord-003318-abs9rvjk 341 20 , , , cord-003318-abs9rvjk 341 21 Denmark Denmark NNP cord-003318-abs9rvjk 341 22 ) ) -RRB- cord-003318-abs9rvjk 341 23 operated operate VBD cord-003318-abs9rvjk 341 24 at at IN cord-003318-abs9rvjk 341 25 800 800 CD cord-003318-abs9rvjk 341 26 bar bar NN cord-003318-abs9rvjk 341 27 . . . cord-003318-abs9rvjk 342 1 Disrupted disrupt VBN cord-003318-abs9rvjk 342 2 cells cell NNS cord-003318-abs9rvjk 342 3 were be VBD cord-003318-abs9rvjk 342 4 centrifuged centrifuge VBN cord-003318-abs9rvjk 342 5 at at IN cord-003318-abs9rvjk 342 6 12,000 12,000 CD cord-003318-abs9rvjk 342 7 rpm rpm NN cord-003318-abs9rvjk 342 8 for for IN cord-003318-abs9rvjk 342 9 30 30 CD cord-003318-abs9rvjk 342 10 min min NN cord-003318-abs9rvjk 342 11 to to TO cord-003318-abs9rvjk 342 12 discard discard VB cord-003318-abs9rvjk 342 13 the the DT cord-003318-abs9rvjk 342 14 pellet pellet NN cord-003318-abs9rvjk 342 15 . . . cord-003318-abs9rvjk 343 1 The the DT cord-003318-abs9rvjk 343 2 resultant resultant JJ cord-003318-abs9rvjk 343 3 supernatant supernatant NN cord-003318-abs9rvjk 343 4 , , , cord-003318-abs9rvjk 343 5 namely namely RB cord-003318-abs9rvjk 343 6 the the DT cord-003318-abs9rvjk 343 7 membrane membrane NN cord-003318-abs9rvjk 343 8 - - HYPH cord-003318-abs9rvjk 343 9 free free JJ cord-003318-abs9rvjk 343 10 crude crude NN cord-003318-abs9rvjk 343 11 extract extract NN cord-003318-abs9rvjk 343 12 , , , cord-003318-abs9rvjk 343 13 was be VBD cord-003318-abs9rvjk 343 14 used use VBN cord-003318-abs9rvjk 343 15 as as IN cord-003318-abs9rvjk 343 16 the the DT cord-003318-abs9rvjk 343 17 biocatalyst biocatalyst NN cord-003318-abs9rvjk 343 18 for for IN cord-003318-abs9rvjk 343 19 steroidal steroidal JJ cord-003318-abs9rvjk 343 20 glycosylation glycosylation NN cord-003318-abs9rvjk 343 21 . . . cord-003318-abs9rvjk 344 1 After after IN cord-003318-abs9rvjk 344 2 verification verification NN cord-003318-abs9rvjk 344 3 of of IN cord-003318-abs9rvjk 344 4 heterologous heterologous JJ cord-003318-abs9rvjk 344 5 expression expression NN cord-003318-abs9rvjk 344 6 of of IN cord-003318-abs9rvjk 344 7 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 344 8 , , , cord-003318-abs9rvjk 344 9 the the DT cord-003318-abs9rvjk 344 10 crude crude JJ cord-003318-abs9rvjk 344 11 extract extract NN cord-003318-abs9rvjk 344 12 containing contain VBG cord-003318-abs9rvjk 344 13 the the DT cord-003318-abs9rvjk 344 14 recombinant recombinant JJ cord-003318-abs9rvjk 344 15 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 344 16 was be VBD cord-003318-abs9rvjk 344 17 applied apply VBN cord-003318-abs9rvjk 344 18 as as IN cord-003318-abs9rvjk 344 19 the the DT cord-003318-abs9rvjk 344 20 biocatalyst biocatalyst NN cord-003318-abs9rvjk 344 21 to to TO cord-003318-abs9rvjk 344 22 react react VB cord-003318-abs9rvjk 344 23 with with IN cord-003318-abs9rvjk 344 24 various various JJ cord-003318-abs9rvjk 344 25 sugar sugar NN cord-003318-abs9rvjk 344 26 acceptors acceptor NNS cord-003318-abs9rvjk 344 27 and and CC cord-003318-abs9rvjk 344 28 donors donor NNS cord-003318-abs9rvjk 344 29 ( ( -LRB- cord-003318-abs9rvjk 344 30 Fig Fig NNP cord-003318-abs9rvjk 344 31 . . NNP cord-003318-abs9rvjk 344 32 1 1 CD cord-003318-abs9rvjk 344 33 and and CC cord-003318-abs9rvjk 344 34 Supplementary Supplementary NNP cord-003318-abs9rvjk 344 35 Information Information NNP cord-003318-abs9rvjk 344 36 Fig Fig NNP cord-003318-abs9rvjk 344 37 . . . cord-003318-abs9rvjk 344 38 S4 S4 NNP cord-003318-abs9rvjk 344 39 ) ) -RRB- cord-003318-abs9rvjk 344 40 . . . cord-003318-abs9rvjk 345 1 The the DT cord-003318-abs9rvjk 345 2 total total JJ cord-003318-abs9rvjk 345 3 reaction reaction NN cord-003318-abs9rvjk 345 4 mixture mixture NN cord-003318-abs9rvjk 345 5 was be VBD cord-003318-abs9rvjk 345 6 100 100 CD cord-003318-abs9rvjk 346 1 μL μL NNP cord-003318-abs9rvjk 346 2 contained contain VBD cord-003318-abs9rvjk 346 3 20 20 CD cord-003318-abs9rvjk 346 4 mmol mmol JJ cord-003318-abs9rvjk 346 5 / / SYM cord-003318-abs9rvjk 346 6 L l NN cord-003318-abs9rvjk 346 7 phosphate phosphate NN cord-003318-abs9rvjk 346 8 buffer buffer NN cord-003318-abs9rvjk 346 9 ( ( -LRB- cord-003318-abs9rvjk 346 10 pH pH NNP cord-003318-abs9rvjk 346 11 8.0 8.0 CD cord-003318-abs9rvjk 346 12 ) ) -RRB- cord-003318-abs9rvjk 346 13 , , , cord-003318-abs9rvjk 346 14 a a DT cord-003318-abs9rvjk 346 15 sugar sugar NN cord-003318-abs9rvjk 346 16 acceptor acceptor NN cord-003318-abs9rvjk 346 17 ( ( -LRB- cord-003318-abs9rvjk 346 18 1 1 CD cord-003318-abs9rvjk 346 19 mmol mmol NNP cord-003318-abs9rvjk 346 20 / / SYM cord-003318-abs9rvjk 346 21 L L NNP cord-003318-abs9rvjk 346 22 ) ) -RRB- cord-003318-abs9rvjk 346 23 , , , cord-003318-abs9rvjk 346 24 a a DT cord-003318-abs9rvjk 346 25 sugar sugar NN cord-003318-abs9rvjk 346 26 donor donor NN cord-003318-abs9rvjk 346 27 ( ( -LRB- cord-003318-abs9rvjk 346 28 1 1 CD cord-003318-abs9rvjk 346 29 mmol mmol NNP cord-003318-abs9rvjk 346 30 / / SYM cord-003318-abs9rvjk 346 31 L L NNP cord-003318-abs9rvjk 346 32 ) ) -RRB- cord-003318-abs9rvjk 346 33 and and CC cord-003318-abs9rvjk 346 34 20 20 CD cord-003318-abs9rvjk 346 35 μL μl CD cord-003318-abs9rvjk 346 36 crude crude JJ cord-003318-abs9rvjk 346 37 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 346 38 proteins protein NNS cord-003318-abs9rvjk 346 39 . . . cord-003318-abs9rvjk 347 1 The the DT cord-003318-abs9rvjk 347 2 reaction reaction NN cord-003318-abs9rvjk 347 3 mixture mixture NN cord-003318-abs9rvjk 347 4 was be VBD cord-003318-abs9rvjk 347 5 incubated incubate VBN cord-003318-abs9rvjk 347 6 at at IN cord-003318-abs9rvjk 347 7 50 50 CD cord-003318-abs9rvjk 347 8 1C 1c CD cord-003318-abs9rvjk 347 9 for for IN cord-003318-abs9rvjk 347 10 1 1 CD cord-003318-abs9rvjk 347 11 h. h. NN cord-003318-abs9rvjk 348 1 The the DT cord-003318-abs9rvjk 348 2 formation formation NN cord-003318-abs9rvjk 348 3 of of IN cord-003318-abs9rvjk 348 4 glycosylated glycosylated JJ cord-003318-abs9rvjk 348 5 products product NNS cord-003318-abs9rvjk 348 6 was be VBD cord-003318-abs9rvjk 348 7 Table table NN cord-003318-abs9rvjk 348 8 6 6 CD cord-003318-abs9rvjk 349 1 The the DT cord-003318-abs9rvjk 349 2 cytotoxic cytotoxic JJ cord-003318-abs9rvjk 349 3 activities activity NNS cord-003318-abs9rvjk 349 4 of of IN cord-003318-abs9rvjk 349 5 monoacylates monoacylate NNS cord-003318-abs9rvjk 349 6 against against IN cord-003318-abs9rvjk 349 7 human human JJ cord-003318-abs9rvjk 349 8 tumor tumor NN cord-003318-abs9rvjk 349 9 cell cell NN cord-003318-abs9rvjk 349 10 lines line NNS cord-003318-abs9rvjk 349 11 . . . cord-003318-abs9rvjk 350 1 unambiguously unambiguously RB cord-003318-abs9rvjk 350 2 determined determine VBN cord-003318-abs9rvjk 350 3 by by IN cord-003318-abs9rvjk 350 4 a a DT cord-003318-abs9rvjk 350 5 combination combination NN cord-003318-abs9rvjk 350 6 of of IN cord-003318-abs9rvjk 350 7 HPLC HPLC NNP cord-003318-abs9rvjk 350 8 - - HYPH cord-003318-abs9rvjk 350 9 UV UV NNP cord-003318-abs9rvjk 350 10 , , , cord-003318-abs9rvjk 350 11 HPLC HPLC NNP cord-003318-abs9rvjk 350 12 - - HYPH cord-003318-abs9rvjk 350 13 MS MS NNP cord-003318-abs9rvjk 350 14 and and CC cord-003318-abs9rvjk 350 15 NMR NMR NNP cord-003318-abs9rvjk 350 16 as as IN cord-003318-abs9rvjk 350 17 described describe VBN cord-003318-abs9rvjk 350 18 previously previously RB cord-003318-abs9rvjk 350 19 35 35 CD cord-003318-abs9rvjk 350 20 , , , cord-003318-abs9rvjk 350 21 36 36 CD cord-003318-abs9rvjk 350 22 . . . cord-003318-abs9rvjk 351 1 The the DT cord-003318-abs9rvjk 351 2 determination determination NN cord-003318-abs9rvjk 351 3 conditions condition NNS cord-003318-abs9rvjk 351 4 for for IN cord-003318-abs9rvjk 351 5 HPLC HPLC NNP cord-003318-abs9rvjk 351 6 - - HYPH cord-003318-abs9rvjk 351 7 UV UV NNP cord-003318-abs9rvjk 351 8 were be VBD cord-003318-abs9rvjk 351 9 summarized summarize VBN cord-003318-abs9rvjk 351 10 in in IN cord-003318-abs9rvjk 351 11 Supplementary Supplementary NNP cord-003318-abs9rvjk 351 12 Information Information NNP cord-003318-abs9rvjk 351 13 Table Table NNP cord-003318-abs9rvjk 351 14 S3 S3 NNP cord-003318-abs9rvjk 351 15 . . . cord-003318-abs9rvjk 352 1 The the DT cord-003318-abs9rvjk 352 2 genome genome NN cord-003318-abs9rvjk 352 3 DNA dna NN cord-003318-abs9rvjk 352 4 was be VBD cord-003318-abs9rvjk 352 5 extracted extract VBN cord-003318-abs9rvjk 352 6 from from IN cord-003318-abs9rvjk 352 7 E. E. NNP cord-003318-abs9rvjk 352 8 coli coli NNS cord-003318-abs9rvjk 352 9 strain strain NN cord-003318-abs9rvjk 352 10 BL21(DE3 bl21(de3 IN cord-003318-abs9rvjk 352 11 ) ) -RRB- cord-003318-abs9rvjk 352 12 using use VBG cord-003318-abs9rvjk 352 13 BacteriaGen BacteriaGen NNP cord-003318-abs9rvjk 352 14 DNA dna NN cord-003318-abs9rvjk 352 15 kit kit NN cord-003318-abs9rvjk 352 16 ( ( -LRB- cord-003318-abs9rvjk 352 17 CWBio CWBio NNP cord-003318-abs9rvjk 352 18 Co. Co. NNP cord-003318-abs9rvjk 352 19 , , , cord-003318-abs9rvjk 352 20 Ltd. Ltd. NNP cord-003318-abs9rvjk 352 21 , , , cord-003318-abs9rvjk 352 22 Beijing Beijing NNP cord-003318-abs9rvjk 352 23 , , , cord-003318-abs9rvjk 352 24 China China NNP cord-003318-abs9rvjk 352 25 ) ) -RRB- cord-003318-abs9rvjk 352 26 according accord VBG cord-003318-abs9rvjk 352 27 to to IN cord-003318-abs9rvjk 352 28 the the DT cord-003318-abs9rvjk 352 29 supplier supplier NN cord-003318-abs9rvjk 352 30 recommendation recommendation NN cord-003318-abs9rvjk 352 31 . . . cord-003318-abs9rvjk 353 1 The the DT cord-003318-abs9rvjk 353 2 resulting result VBG cord-003318-abs9rvjk 353 3 genome genome NN cord-003318-abs9rvjk 353 4 DNA dna NN cord-003318-abs9rvjk 353 5 was be VBD cord-003318-abs9rvjk 353 6 then then RB cord-003318-abs9rvjk 353 7 used use VBN cord-003318-abs9rvjk 353 8 as as IN cord-003318-abs9rvjk 353 9 the the DT cord-003318-abs9rvjk 353 10 template template NN cord-003318-abs9rvjk 353 11 of of IN cord-003318-abs9rvjk 353 12 PCR PCR NNP cord-003318-abs9rvjk 353 13 amplification amplification NN cord-003318-abs9rvjk 353 14 to to TO cord-003318-abs9rvjk 353 15 isolate isolate VB cord-003318-abs9rvjk 353 16 these these DT cord-003318-abs9rvjk 353 17 candidate candidate NN cord-003318-abs9rvjk 353 18 SGA SGA NNP cord-003318-abs9rvjk 353 19 genes gene NNS cord-003318-abs9rvjk 353 20 using use VBG cord-003318-abs9rvjk 353 21 gene gene NN cord-003318-abs9rvjk 353 22 - - HYPH cord-003318-abs9rvjk 353 23 specific specific JJ cord-003318-abs9rvjk 353 24 primers primer NNS cord-003318-abs9rvjk 353 25 ( ( -LRB- cord-003318-abs9rvjk 353 26 Supplementary Supplementary NNP cord-003318-abs9rvjk 353 27 Information Information NNP cord-003318-abs9rvjk 353 28 Table Table NNP cord-003318-abs9rvjk 353 29 S1 S1 NNP cord-003318-abs9rvjk 353 30 ) ) -RRB- cord-003318-abs9rvjk 353 31 . . . cord-003318-abs9rvjk 354 1 The the DT cord-003318-abs9rvjk 354 2 amplified amplify VBN cord-003318-abs9rvjk 354 3 PCR PCR NNP cord-003318-abs9rvjk 354 4 products product NNS cord-003318-abs9rvjk 354 5 were be VBD cord-003318-abs9rvjk 354 6 inserted insert VBN cord-003318-abs9rvjk 354 7 into into IN cord-003318-abs9rvjk 354 8 pEASY peasy JJ cord-003318-abs9rvjk 354 9 TM TM NNP cord-003318-abs9rvjk 354 10 -Blunt -blunt NN cord-003318-abs9rvjk 354 11 plasmid plasmid NN cord-003318-abs9rvjk 354 12 to to TO cord-003318-abs9rvjk 354 13 generate generate VB cord-003318-abs9rvjk 354 14 recombinant recombinant JJ cord-003318-abs9rvjk 354 15 vectors vector NNS cord-003318-abs9rvjk 354 16 for for IN cord-003318-abs9rvjk 354 17 sequencing sequence VBG cord-003318-abs9rvjk 354 18 verification verification NN cord-003318-abs9rvjk 354 19 . . . cord-003318-abs9rvjk 355 1 Next next RB cord-003318-abs9rvjk 355 2 , , , cord-003318-abs9rvjk 355 3 these these DT cord-003318-abs9rvjk 355 4 Oacetyltransferase Oacetyltransferase NNP cord-003318-abs9rvjk 355 5 - - HYPH cord-003318-abs9rvjk 355 6 encoding encode VBG cord-003318-abs9rvjk 355 7 genes gene NNS cord-003318-abs9rvjk 355 8 were be VBD cord-003318-abs9rvjk 355 9 heterologously heterologously NNP cord-003318-abs9rvjk 355 10 expressed express VBN cord-003318-abs9rvjk 355 11 in in IN cord-003318-abs9rvjk 355 12 BL21(DE3 BL21(DE3 NNP cord-003318-abs9rvjk 355 13 ) ) -RRB- cord-003318-abs9rvjk 355 14 as as IN cord-003318-abs9rvjk 355 15 described describe VBN cord-003318-abs9rvjk 355 16 above above RB cord-003318-abs9rvjk 355 17 . . . cord-003318-abs9rvjk 356 1 SDS SDS NNP cord-003318-abs9rvjk 356 2 - - HYPH cord-003318-abs9rvjk 356 3 PAGE PAGE NNP cord-003318-abs9rvjk 356 4 and and CC cord-003318-abs9rvjk 356 5 Western western JJ cord-003318-abs9rvjk 356 6 - - HYPH cord-003318-abs9rvjk 356 7 blot blot NN cord-003318-abs9rvjk 356 8 of of IN cord-003318-abs9rvjk 356 9 these these DT cord-003318-abs9rvjk 356 10 recombinant recombinant JJ cord-003318-abs9rvjk 356 11 proteins protein NNS cord-003318-abs9rvjk 356 12 were be VBD cord-003318-abs9rvjk 356 13 conducted conduct VBN cord-003318-abs9rvjk 356 14 as as IN cord-003318-abs9rvjk 356 15 that that DT cord-003318-abs9rvjk 356 16 of of IN cord-003318-abs9rvjk 356 17 OsSGT1 OsSGT1 NNP cord-003318-abs9rvjk 356 18 ( ( -LRB- cord-003318-abs9rvjk 356 19 see see VB cord-003318-abs9rvjk 356 20 above above RB cord-003318-abs9rvjk 356 21 ) ) -RRB- cord-003318-abs9rvjk 356 22 . . . cord-003318-abs9rvjk 357 1 The the DT cord-003318-abs9rvjk 357 2 recombinant recombinant JJ cord-003318-abs9rvjk 357 3 O o NN cord-003318-abs9rvjk 357 4 - - HYPH cord-003318-abs9rvjk 357 5 acetyltransferase acetyltransferase NN cord-003318-abs9rvjk 357 6 proteins protein NNS cord-003318-abs9rvjk 357 7 were be VBD cord-003318-abs9rvjk 357 8 subjected subject VBN cord-003318-abs9rvjk 357 9 to to IN cord-003318-abs9rvjk 357 10 purification purification NN cord-003318-abs9rvjk 357 11 with with IN cord-003318-abs9rvjk 357 12 Ni Ni NNP cord-003318-abs9rvjk 357 13 - - HYPH cord-003318-abs9rvjk 357 14 NTA NTA NNP cord-003318-abs9rvjk 357 15 agarose agarose NN cord-003318-abs9rvjk 357 16 columns column NNS cord-003318-abs9rvjk 357 17 according accord VBG cord-003318-abs9rvjk 357 18 to to IN cord-003318-abs9rvjk 357 19 the the DT cord-003318-abs9rvjk 357 20 manufacture manufacture NN cord-003318-abs9rvjk 357 21 's 's POS cord-003318-abs9rvjk 357 22 protocol protocol NN cord-003318-abs9rvjk 357 23 . . . cord-003318-abs9rvjk 358 1 Purified purify VBN cord-003318-abs9rvjk 358 2 protein protein NN cord-003318-abs9rvjk 358 3 concentrations concentration NNS cord-003318-abs9rvjk 358 4 were be VBD cord-003318-abs9rvjk 358 5 determined determine VBN cord-003318-abs9rvjk 358 6 using use VBG cord-003318-abs9rvjk 358 7 Bradford Bradford NNP cord-003318-abs9rvjk 358 8 protein protein NN cord-003318-abs9rvjk 358 9 assay assay NN cord-003318-abs9rvjk 358 10 ( ( -LRB- cord-003318-abs9rvjk 358 11 Bio Bio NNP cord-003318-abs9rvjk 358 12 - - HYPH cord-003318-abs9rvjk 358 13 Rad Rad NNP cord-003318-abs9rvjk 358 14 , , , cord-003318-abs9rvjk 358 15 Hercules Hercules NNP cord-003318-abs9rvjk 358 16 , , , cord-003318-abs9rvjk 358 17 CA CA NNP cord-003318-abs9rvjk 358 18 , , , cord-003318-abs9rvjk 358 19 USA USA NNP cord-003318-abs9rvjk 358 20 ) ) -RRB- cord-003318-abs9rvjk 358 21 . . . cord-003318-abs9rvjk 359 1 The the DT cord-003318-abs9rvjk 359 2 enzymatic enzymatic JJ cord-003318-abs9rvjk 359 3 activities activity NNS cord-003318-abs9rvjk 359 4 of of IN cord-003318-abs9rvjk 359 5 EcSGAs EcSGAs NNP cord-003318-abs9rvjk 359 6 were be VBD cord-003318-abs9rvjk 359 7 determined determine VBN cord-003318-abs9rvjk 359 8 in in IN cord-003318-abs9rvjk 359 9 100 100 CD cord-003318-abs9rvjk 359 10 μL μL NFP cord-003318-abs9rvjk 359 11 citrate citrate NN cord-003318-abs9rvjk 359 12 buffer buffer NN cord-003318-abs9rvjk 359 13 solution solution NN cord-003318-abs9rvjk 359 14 ( ( -LRB- cord-003318-abs9rvjk 359 15 pH pH NNP cord-003318-abs9rvjk 359 16 5.0 5.0 CD cord-003318-abs9rvjk 359 17 ) ) -RRB- cord-003318-abs9rvjk 359 18 containing contain VBG cord-003318-abs9rvjk 359 19 an an DT cord-003318-abs9rvjk 359 20 acyl acyl NN cord-003318-abs9rvjk 359 21 acceptor acceptor NN cord-003318-abs9rvjk 359 22 ( ( -LRB- cord-003318-abs9rvjk 359 23 1 1 CD cord-003318-abs9rvjk 359 24 mmol mmol NNP cord-003318-abs9rvjk 359 25 / / SYM cord-003318-abs9rvjk 359 26 L L NNP cord-003318-abs9rvjk 359 27 ) ) -RRB- cord-003318-abs9rvjk 359 28 listed list VBN cord-003318-abs9rvjk 359 29 in in IN cord-003318-abs9rvjk 359 30 Supplementary Supplementary NNP cord-003318-abs9rvjk 359 31 Information Information NNP cord-003318-abs9rvjk 359 32 Fig Fig NNP cord-003318-abs9rvjk 359 33 . . . cord-003318-abs9rvjk 360 1 S58 S58 NNP cord-003318-abs9rvjk 360 2 , , , cord-003318-abs9rvjk 360 3 an an DT cord-003318-abs9rvjk 360 4 acyl acyl NN cord-003318-abs9rvjk 360 5 donor donor NN cord-003318-abs9rvjk 360 6 ( ( -LRB- cord-003318-abs9rvjk 360 7 1 1 CD cord-003318-abs9rvjk 360 8 mmol mmol NNP cord-003318-abs9rvjk 360 9 / / SYM cord-003318-abs9rvjk 360 10 L L NNP cord-003318-abs9rvjk 360 11 ) ) -RRB- cord-003318-abs9rvjk 360 12 summarized summarize VBD cord-003318-abs9rvjk 360 13 in in IN cord-003318-abs9rvjk 360 14 Chemicals Chemicals NNP cord-003318-abs9rvjk 360 15 section section NN cord-003318-abs9rvjk 360 16 and and CC cord-003318-abs9rvjk 360 17 the the DT cord-003318-abs9rvjk 360 18 purified purify VBN cord-003318-abs9rvjk 360 19 protein protein NN cord-003318-abs9rvjk 360 20 ( ( -LRB- cord-003318-abs9rvjk 360 21 2.97 2.97 CD cord-003318-abs9rvjk 360 22 μg μg NNP cord-003318-abs9rvjk 360 23 ) ) -RRB- cord-003318-abs9rvjk 360 24 . . . cord-003318-abs9rvjk 361 1 The the DT cord-003318-abs9rvjk 361 2 reactions reaction NNS cord-003318-abs9rvjk 361 3 were be VBD cord-003318-abs9rvjk 361 4 incubated incubate VBN cord-003318-abs9rvjk 361 5 at at IN cord-003318-abs9rvjk 361 6 37 37 CD cord-003318-abs9rvjk 361 7 1C 1c CD cord-003318-abs9rvjk 361 8 for for IN cord-003318-abs9rvjk 361 9 1 1 CD cord-003318-abs9rvjk 361 10 h. h. NN cord-003318-abs9rvjk 362 1 Then then RB cord-003318-abs9rvjk 362 2 100 100 CD cord-003318-abs9rvjk 362 3 μL μL NFP cord-003318-abs9rvjk 362 4 methanol methanol NN cord-003318-abs9rvjk 362 5 was be VBD cord-003318-abs9rvjk 362 6 added add VBN cord-003318-abs9rvjk 362 7 to to TO cord-003318-abs9rvjk 362 8 terminate terminate VB cord-003318-abs9rvjk 362 9 the the DT cord-003318-abs9rvjk 362 10 reaction reaction NN cord-003318-abs9rvjk 362 11 . . . cord-003318-abs9rvjk 363 1 The the DT cord-003318-abs9rvjk 363 2 reaction reaction NN cord-003318-abs9rvjk 363 3 mixture mixture NN cord-003318-abs9rvjk 363 4 was be VBD cord-003318-abs9rvjk 363 5 monitored monitor VBN cord-003318-abs9rvjk 363 6 by by IN cord-003318-abs9rvjk 363 7 HPLC HPLC NNP cord-003318-abs9rvjk 363 8 - - HYPH cord-003318-abs9rvjk 363 9 UV UV NNP cord-003318-abs9rvjk 363 10 ( ( -LRB- cord-003318-abs9rvjk 363 11 Supplementary Supplementary NNP cord-003318-abs9rvjk 363 12 Information information NN cord-003318-abs9rvjk 363 13 Table Table NNP cord-003318-abs9rvjk 363 14 S3 S3 NNP cord-003318-abs9rvjk 363 15 ) ) -RRB- cord-003318-abs9rvjk 363 16 and and CC cord-003318-abs9rvjk 363 17 the the DT cord-003318-abs9rvjk 363 18 structure structure NN cord-003318-abs9rvjk 363 19 of of IN cord-003318-abs9rvjk 363 20 the the DT cord-003318-abs9rvjk 363 21 generated generate VBN cord-003318-abs9rvjk 363 22 product product NN cord-003318-abs9rvjk 363 23 was be VBD cord-003318-abs9rvjk 363 24 determined determine VBN cord-003318-abs9rvjk 363 25 by by IN cord-003318-abs9rvjk 363 26 a a DT cord-003318-abs9rvjk 363 27 combination combination NN cord-003318-abs9rvjk 363 28 of of IN cord-003318-abs9rvjk 363 29 HPLC HPLC NNP cord-003318-abs9rvjk 363 30 - - HYPH cord-003318-abs9rvjk 363 31 MS MS NNP cord-003318-abs9rvjk 363 32 and and CC cord-003318-abs9rvjk 363 33 NMR NMR NNP cord-003318-abs9rvjk 363 34 as as IN cord-003318-abs9rvjk 363 35 reported report VBN cord-003318-abs9rvjk 363 36 by by IN cord-003318-abs9rvjk 363 37 Liu Liu NNP cord-003318-abs9rvjk 363 38 et et NNP cord-003318-abs9rvjk 363 39 al al NNP cord-003318-abs9rvjk 363 40 . . . cord-003318-abs9rvjk 364 1 35 35 CD cord-003318-abs9rvjk 364 2 5.10 5.10 CD cord-003318-abs9rvjk 364 3 . . . cord-003318-abs9rvjk 365 1 Biotransformation Biotransformation NNP cord-003318-abs9rvjk 365 2 of of IN cord-003318-abs9rvjk 365 3 testosterone testosterone NN cord-003318-abs9rvjk 365 4 and and CC cord-003318-abs9rvjk 365 5 testosterone-17-Oβ testosterone-17-oβ CD cord-003318-abs9rvjk 365 6 - - HYPH cord-003318-abs9rvjk 365 7 glucoside glucoside NN cord-003318-abs9rvjk 365 8 using use VBG cord-003318-abs9rvjk 365 9 the the DT cord-003318-abs9rvjk 365 10 whole whole JJ cord-003318-abs9rvjk 365 11 cell cell NN cord-003318-abs9rvjk 365 12 system system NN cord-003318-abs9rvjk 365 13 After after IN cord-003318-abs9rvjk 365 14 IPTG IPTG NNP cord-003318-abs9rvjk 365 15 induction induction NN cord-003318-abs9rvjk 365 16 , , , cord-003318-abs9rvjk 365 17 the the DT cord-003318-abs9rvjk 365 18 engineered engineer VBN cord-003318-abs9rvjk 365 19 BL21(DE3)[pET28a BL21(DE3)[pET28a NNP cord-003318-abs9rvjk 365 20 - - HYPH cord-003318-abs9rvjk 365 21 OsSGT1þpGro7 OsSGT1þpGro7 NNP cord-003318-abs9rvjk 365 22 ] ] -RRB- cord-003318-abs9rvjk 365 23 cells cell NNS cord-003318-abs9rvjk 365 24 were be VBD cord-003318-abs9rvjk 365 25 harvested harvest VBN cord-003318-abs9rvjk 365 26 by by IN cord-003318-abs9rvjk 365 27 centrifugation centrifugation NN cord-003318-abs9rvjk 365 28 at at IN cord-003318-abs9rvjk 365 29 12,000 12,000 CD cord-003318-abs9rvjk 365 30 rpm rpm NN cord-003318-abs9rvjk 365 31 for for IN cord-003318-abs9rvjk 365 32 10 10 CD cord-003318-abs9rvjk 365 33 min min NN cord-003318-abs9rvjk 365 34 and and CC cord-003318-abs9rvjk 365 35 then then RB cord-003318-abs9rvjk 365 36 resuspended resuspend VBD cord-003318-abs9rvjk 365 37 in in IN cord-003318-abs9rvjk 365 38 M9 M9 NNP cord-003318-abs9rvjk 365 39 medium medium NN cord-003318-abs9rvjk 365 40 37 37 CD cord-003318-abs9rvjk 365 41 with with IN cord-003318-abs9rvjk 365 42 cell cell NN cord-003318-abs9rvjk 365 43 density density NN cord-003318-abs9rvjk 365 44 of of IN cord-003318-abs9rvjk 365 45 OD OD NNP cord-003318-abs9rvjk 365 46 600 600 CD cord-003318-abs9rvjk 365 47 value value NN cord-003318-abs9rvjk 365 48 of of IN cord-003318-abs9rvjk 365 49 0.6 0.6 CD cord-003318-abs9rvjk 365 50 . . . cord-003318-abs9rvjk 366 1 The the DT cord-003318-abs9rvjk 366 2 substrate substrate JJ cord-003318-abs9rvjk 366 3 testosterone testosterone NN cord-003318-abs9rvjk 366 4 ( ( -LRB- cord-003318-abs9rvjk 366 5 8) 8) NN cord-003318-abs9rvjk 366 6 or or CC cord-003318-abs9rvjk 366 7 testosterone-17-O testosterone-17-O NNS cord-003318-abs9rvjk 366 8 - - HYPH cord-003318-abs9rvjk 366 9 β β NN cord-003318-abs9rvjk 366 10 - - HYPH cord-003318-abs9rvjk 366 11 glucoside glucoside NN cord-003318-abs9rvjk 366 12 ( ( -LRB- cord-003318-abs9rvjk 366 13 T-17-O t-17-o NN cord-003318-abs9rvjk 366 14 - - HYPH cord-003318-abs9rvjk 366 15 β β NN cord-003318-abs9rvjk 366 16 - - HYPH cord-003318-abs9rvjk 366 17 G G NNP cord-003318-abs9rvjk 366 18 , , , cord-003318-abs9rvjk 366 19 8a 8a NN cord-003318-abs9rvjk 366 20 ) ) -RRB- cord-003318-abs9rvjk 366 21 with with IN cord-003318-abs9rvjk 366 22 the the DT cord-003318-abs9rvjk 366 23 final final JJ cord-003318-abs9rvjk 366 24 concentration concentration NN cord-003318-abs9rvjk 366 25 of of IN cord-003318-abs9rvjk 366 26 0.3 0.3 CD cord-003318-abs9rvjk 366 27 mmol mmol NNP cord-003318-abs9rvjk 366 28 / / SYM cord-003318-abs9rvjk 366 29 L L NNP cord-003318-abs9rvjk 366 30 was be VBD cord-003318-abs9rvjk 366 31 added add VBN cord-003318-abs9rvjk 366 32 into into IN cord-003318-abs9rvjk 366 33 the the DT cord-003318-abs9rvjk 366 34 M9 M9 NNP cord-003318-abs9rvjk 366 35 medium medium NN cord-003318-abs9rvjk 366 36 and and CC cord-003318-abs9rvjk 366 37 continued continue VBD cord-003318-abs9rvjk 366 38 to to TO cord-003318-abs9rvjk 366 39 incubate incubate VB cord-003318-abs9rvjk 366 40 at at IN cord-003318-abs9rvjk 366 41 37 37 CD cord-003318-abs9rvjk 366 42 1C 1c NN cord-003318-abs9rvjk 366 43 overnight overnight RB cord-003318-abs9rvjk 366 44 . . . cord-003318-abs9rvjk 367 1 The the DT cord-003318-abs9rvjk 367 2 formation formation NN cord-003318-abs9rvjk 367 3 of of IN cord-003318-abs9rvjk 367 4 products product NNS cord-003318-abs9rvjk 367 5 was be VBD cord-003318-abs9rvjk 367 6 monitored monitor VBN cord-003318-abs9rvjk 367 7 by by IN cord-003318-abs9rvjk 367 8 HPLC HPLC NNP cord-003318-abs9rvjk 367 9 analysis analysis NN cord-003318-abs9rvjk 367 10 as as IN cord-003318-abs9rvjk 367 11 mentioned mention VBN cord-003318-abs9rvjk 367 12 above above RB cord-003318-abs9rvjk 367 13 . . . cord-003318-abs9rvjk 368 1 The the DT cord-003318-abs9rvjk 368 2 effects effect NNS cord-003318-abs9rvjk 368 3 of of IN cord-003318-abs9rvjk 368 4 pH ph NN cord-003318-abs9rvjk 368 5 and and CC cord-003318-abs9rvjk 368 6 temperature temperature NN cord-003318-abs9rvjk 368 7 on on IN cord-003318-abs9rvjk 369 1 OsSGT1-and ossgt1-and NN cord-003318-abs9rvjk 369 2 EcSGA1catalyzed ecsga1catalyzed JJ cord-003318-abs9rvjk 369 3 reactions reaction NNS cord-003318-abs9rvjk 369 4 were be VBD cord-003318-abs9rvjk 369 5 investigated investigate VBN cord-003318-abs9rvjk 369 6 . . . cord-003318-abs9rvjk 370 1 The the DT cord-003318-abs9rvjk 370 2 crude crude JJ cord-003318-abs9rvjk 370 3 extract extract NN cord-003318-abs9rvjk 370 4 of of IN cord-003318-abs9rvjk 370 5 BL21(DE3)[pET28a BL21(DE3)[pET28a NNP cord-003318-abs9rvjk 370 6 - - HYPH cord-003318-abs9rvjk 370 7 OsSGT1þpGro7 OsSGT1þpGro7 NNP cord-003318-abs9rvjk 370 8 ] ] -RRB- cord-003318-abs9rvjk 370 9 and and CC cord-003318-abs9rvjk 370 10 the the DT cord-003318-abs9rvjk 370 11 purified purify VBN cord-003318-abs9rvjk 370 12 EcSGA1 EcSGA1 NNP cord-003318-abs9rvjk 370 13 protein protein NN cord-003318-abs9rvjk 370 14 were be VBD cord-003318-abs9rvjk 370 15 applied apply VBN cord-003318-abs9rvjk 370 16 as as IN cord-003318-abs9rvjk 370 17 the the DT cord-003318-abs9rvjk 370 18 biocatalyst biocatalyst NN cord-003318-abs9rvjk 370 19 in in IN cord-003318-abs9rvjk 370 20 their -PRON- PRP$ cord-003318-abs9rvjk 370 21 respective respective JJ cord-003318-abs9rvjk 370 22 reactions reaction NNS cord-003318-abs9rvjk 370 23 . . . cord-003318-abs9rvjk 371 1 The the DT cord-003318-abs9rvjk 371 2 effects effect NNS cord-003318-abs9rvjk 371 3 of of IN cord-003318-abs9rvjk 371 4 pH ph NN cord-003318-abs9rvjk 371 5 on on IN cord-003318-abs9rvjk 371 6 both both DT cord-003318-abs9rvjk 371 7 reactions reaction NNS cord-003318-abs9rvjk 371 8 were be VBD cord-003318-abs9rvjk 371 9 determined determine VBN cord-003318-abs9rvjk 371 10 at at IN cord-003318-abs9rvjk 371 11 varied varied JJ cord-003318-abs9rvjk 371 12 buffers buffer NNS cord-003318-abs9rvjk 371 13 including include VBG cord-003318-abs9rvjk 371 14 citric citric JJ cord-003318-abs9rvjk 371 15 acid acid NN cord-003318-abs9rvjk 371 16 / / SYM cord-003318-abs9rvjk 371 17 sodium sodium NN cord-003318-abs9rvjk 371 18 citrate citrate NN cord-003318-abs9rvjk 371 19 buffer buffer NN cord-003318-abs9rvjk 371 20 ( ( -LRB- cord-003318-abs9rvjk 371 21 0.1 0.1 CD cord-003318-abs9rvjk 371 22 mol mol NN cord-003318-abs9rvjk 371 23 / / SYM cord-003318-abs9rvjk 371 24 L L NNP cord-003318-abs9rvjk 371 25 , , , cord-003318-abs9rvjk 371 26 pH pH NNP cord-003318-abs9rvjk 371 27 3.0 3.0 NNP cord-003318-abs9rvjk 371 28 - - HYPH cord-003318-abs9rvjk 371 29 6.6 6.6 CD cord-003318-abs9rvjk 371 30 ) ) -RRB- cord-003318-abs9rvjk 371 31 , , , cord-003318-abs9rvjk 371 32 Na Na NNP cord-003318-abs9rvjk 371 33 2 2 CD cord-003318-abs9rvjk 371 34 HPO HPO NNP cord-003318-abs9rvjk 371 35 4 4 CD cord-003318-abs9rvjk 372 1 /NaH /NaH NFP cord-003318-abs9rvjk 372 2 2 2 CD cord-003318-abs9rvjk 372 3 PO po NN cord-003318-abs9rvjk 372 4 4 4 CD cord-003318-abs9rvjk 372 5 ( ( -LRB- cord-003318-abs9rvjk 372 6 0.1 0.1 CD cord-003318-abs9rvjk 372 7 mol mol NN cord-003318-abs9rvjk 372 8 / / SYM cord-003318-abs9rvjk 372 9 L L NNP cord-003318-abs9rvjk 372 10 , , , cord-003318-abs9rvjk 372 11 pH pH NNP cord-003318-abs9rvjk 372 12 5.8 5.8 CD cord-003318-abs9rvjk 372 13 - - HYPH cord-003318-abs9rvjk 372 14 9.0 9.0 CD cord-003318-abs9rvjk 372 15 ) ) -RRB- cord-003318-abs9rvjk 372 16 , , , cord-003318-abs9rvjk 372 17 Na Na NNP cord-003318-abs9rvjk 372 18 2 2 CD cord-003318-abs9rvjk 372 19 HPO HPO NNP cord-003318-abs9rvjk 372 20 4 4 CD cord-003318-abs9rvjk 372 21 / / SYM cord-003318-abs9rvjk 372 22 NaOH NaOH NNP cord-003318-abs9rvjk 372 23 buffer buffer NN cord-003318-abs9rvjk 372 24 ( ( -LRB- cord-003318-abs9rvjk 372 25 0.1 0.1 CD cord-003318-abs9rvjk 372 26 mol mol NN cord-003318-abs9rvjk 372 27 / / SYM cord-003318-abs9rvjk 372 28 L L NNP cord-003318-abs9rvjk 372 29 , , , cord-003318-abs9rvjk 372 30 pH pH NNP cord-003318-abs9rvjk 372 31 9.0 9.0 CD cord-003318-abs9rvjk 372 32 - - HYPH cord-003318-abs9rvjk 372 33 12 12 CD cord-003318-abs9rvjk 372 34 ) ) -RRB- cord-003318-abs9rvjk 372 35 . . . cord-003318-abs9rvjk 373 1 The the DT cord-003318-abs9rvjk 373 2 influences influence NNS cord-003318-abs9rvjk 373 3 of of IN cord-003318-abs9rvjk 373 4 temperature temperature NN cord-003318-abs9rvjk 373 5 were be VBD cord-003318-abs9rvjk 373 6 explored explore VBN cord-003318-abs9rvjk 373 7 in in IN cord-003318-abs9rvjk 373 8 a a DT cord-003318-abs9rvjk 373 9 range range NN cord-003318-abs9rvjk 373 10 of of IN cord-003318-abs9rvjk 373 11 20 20 CD cord-003318-abs9rvjk 373 12 to to TO cord-003318-abs9rvjk 373 13 80 80 CD cord-003318-abs9rvjk 373 14 1C 1c NN cord-003318-abs9rvjk 373 15 with with IN cord-003318-abs9rvjk 373 16 intervals interval NNS cord-003318-abs9rvjk 373 17 of of IN cord-003318-abs9rvjk 373 18 15 15 CD cord-003318-abs9rvjk 373 19 1C 1c NN cord-003318-abs9rvjk 373 20 ( ( -LRB- cord-003318-abs9rvjk 373 21 OsSGT1-mediated OsSGT1-mediated NNP cord-003318-abs9rvjk 373 22 glycosylation glycosylation NN cord-003318-abs9rvjk 373 23 ) ) -RRB- cord-003318-abs9rvjk 373 24 or or CC cord-003318-abs9rvjk 373 25 10 10 CD cord-003318-abs9rvjk 373 26 1C 1c NN cord-003318-abs9rvjk 373 27 ( ( -LRB- cord-003318-abs9rvjk 373 28 EcSGA1-catalyzed ecsga1-catalyze VBN cord-003318-abs9rvjk 373 29 acylation acylation NN cord-003318-abs9rvjk 373 30 ) ) -RRB- cord-003318-abs9rvjk 373 31 in in IN cord-003318-abs9rvjk 373 32 the the DT cord-003318-abs9rvjk 373 33 standard standard JJ cord-003318-abs9rvjk 373 34 reaction reaction NN cord-003318-abs9rvjk 373 35 mixture mixture NN cord-003318-abs9rvjk 373 36 as as IN cord-003318-abs9rvjk 373 37 described describe VBN cord-003318-abs9rvjk 373 38 above above RB cord-003318-abs9rvjk 373 39 . . . cord-003318-abs9rvjk 374 1 Scale scale NN cord-003318-abs9rvjk 374 2 - - HYPH cord-003318-abs9rvjk 374 3 up up NN cord-003318-abs9rvjk 374 4 of of IN cord-003318-abs9rvjk 374 5 OsSGT1-and ossgt1-and NN cord-003318-abs9rvjk 374 6 EcSGA1-catalyzed ecsga1-catalyzed JJ cord-003318-abs9rvjk 374 7 reactions reaction NNS cord-003318-abs9rvjk 374 8 was be VBD cord-003318-abs9rvjk 374 9 performed perform VBN cord-003318-abs9rvjk 374 10 to to TO cord-003318-abs9rvjk 374 11 obtain obtain VB cord-003318-abs9rvjk 374 12 sufficient sufficient JJ cord-003318-abs9rvjk 374 13 AT-17β AT-17β NNP cord-003318-abs9rvjk 374 14 - - HYPH cord-003318-abs9rvjk 374 15 Gs Gs NNP cord-003318-abs9rvjk 374 16 for for IN cord-003318-abs9rvjk 374 17 structural structural JJ cord-003318-abs9rvjk 374 18 characterization characterization NN cord-003318-abs9rvjk 374 19 and and CC cord-003318-abs9rvjk 374 20 further further JJ cord-003318-abs9rvjk 374 21 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 374 22 assay assay NN cord-003318-abs9rvjk 374 23 . . . cord-003318-abs9rvjk 375 1 Initially initially RB cord-003318-abs9rvjk 375 2 , , , cord-003318-abs9rvjk 375 3 the the DT cord-003318-abs9rvjk 375 4 100 100 CD cord-003318-abs9rvjk 375 5 μL μl CD cord-003318-abs9rvjk 375 6 OsSGT1catalyzed ossgt1catalyzed JJ cord-003318-abs9rvjk 375 7 reaction reaction NN cord-003318-abs9rvjk 375 8 was be VBD cord-003318-abs9rvjk 375 9 directly directly RB cord-003318-abs9rvjk 375 10 scaled scale VBN cord-003318-abs9rvjk 375 11 to to IN cord-003318-abs9rvjk 375 12 53 53 CD cord-003318-abs9rvjk 375 13 mL ml NN cord-003318-abs9rvjk 375 14 , , , cord-003318-abs9rvjk 375 15 in in IN cord-003318-abs9rvjk 375 16 which which WDT cord-003318-abs9rvjk 375 17 152 152 CD cord-003318-abs9rvjk 375 18 mg mg NNP cord-003318-abs9rvjk 375 19 testosterone testosterone NN cord-003318-abs9rvjk 375 20 ( ( -LRB- cord-003318-abs9rvjk 375 21 8) 8) NNP cord-003318-abs9rvjk 375 22 were be VBD cord-003318-abs9rvjk 375 23 added add VBN cord-003318-abs9rvjk 375 24 into into IN cord-003318-abs9rvjk 375 25 and and CC cord-003318-abs9rvjk 375 26 then then RB cord-003318-abs9rvjk 375 27 incubated incubate VBN cord-003318-abs9rvjk 375 28 with with IN cord-003318-abs9rvjk 375 29 crude crude JJ cord-003318-abs9rvjk 375 30 cell cell NN cord-003318-abs9rvjk 375 31 extract extract NN cord-003318-abs9rvjk 375 32 at at IN cord-003318-abs9rvjk 375 33 optimal optimal JJ cord-003318-abs9rvjk 375 34 pH ph NN cord-003318-abs9rvjk 375 35 and and CC cord-003318-abs9rvjk 375 36 temperature temperature NN cord-003318-abs9rvjk 375 37 for for IN cord-003318-abs9rvjk 375 38 1 1 CD cord-003318-abs9rvjk 375 39 h. h. NN cord-003318-abs9rvjk 376 1 The the DT cord-003318-abs9rvjk 376 2 resultant resultant JJ cord-003318-abs9rvjk 376 3 reaction reaction NN cord-003318-abs9rvjk 376 4 mixture mixture NN cord-003318-abs9rvjk 376 5 was be VBD cord-003318-abs9rvjk 376 6 applied apply VBN cord-003318-abs9rvjk 376 7 to to IN cord-003318-abs9rvjk 376 8 preparative preparative JJ cord-003318-abs9rvjk 376 9 HPLC HPLC NNP cord-003318-abs9rvjk 376 10 to to TO cord-003318-abs9rvjk 376 11 isolate isolate VB cord-003318-abs9rvjk 376 12 pure pure JJ cord-003318-abs9rvjk 376 13 T-17β T-17β NNS cord-003318-abs9rvjk 376 14 - - HYPH cord-003318-abs9rvjk 376 15 G g NN cord-003318-abs9rvjk 376 16 , , , cord-003318-abs9rvjk 376 17 which which WDT cord-003318-abs9rvjk 376 18 was be VBD cord-003318-abs9rvjk 376 19 then then RB cord-003318-abs9rvjk 376 20 used use VBN cord-003318-abs9rvjk 376 21 as as IN cord-003318-abs9rvjk 376 22 the the DT cord-003318-abs9rvjk 376 23 substrate substrate NN cord-003318-abs9rvjk 376 24 in in IN cord-003318-abs9rvjk 376 25 135 135 CD cord-003318-abs9rvjk 376 26 mL ml NN cord-003318-abs9rvjk 376 27 EcSGA1-catalyzed ecsga1-catalyze VBN cord-003318-abs9rvjk 376 28 reaction reaction NN cord-003318-abs9rvjk 376 29 for for IN cord-003318-abs9rvjk 376 30 AT-17β AT-17β NNP cord-003318-abs9rvjk 376 31 - - HYPH cord-003318-abs9rvjk 376 32 Gs Gs NNP cord-003318-abs9rvjk 376 33 production production NN cord-003318-abs9rvjk 376 34 . . . cord-003318-abs9rvjk 377 1 Structure structure NN cord-003318-abs9rvjk 377 2 characterization characterization NN cord-003318-abs9rvjk 377 3 of of IN cord-003318-abs9rvjk 377 4 AT-17β AT-17β NNP cord-003318-abs9rvjk 377 5 - - HYPH cord-003318-abs9rvjk 377 6 Gs Gs NNP cord-003318-abs9rvjk 377 7 was be VBD cord-003318-abs9rvjk 377 8 performed perform VBN cord-003318-abs9rvjk 377 9 using use VBG cord-003318-abs9rvjk 377 10 HPLC HPLC NNP cord-003318-abs9rvjk 377 11 - - HYPH cord-003318-abs9rvjk 377 12 SPE SPE NNP cord-003318-abs9rvjk 377 13 - - HYPH cord-003318-abs9rvjk 377 14 NMR NMR NNP cord-003318-abs9rvjk 377 15 technique technique NN cord-003318-abs9rvjk 377 16 as as IN cord-003318-abs9rvjk 377 17 described describe VBN cord-003318-abs9rvjk 377 18 by by IN cord-003318-abs9rvjk 377 19 Liu Liu NNP cord-003318-abs9rvjk 377 20 et et NNP cord-003318-abs9rvjk 377 21 al al NNP cord-003318-abs9rvjk 377 22 . . . cord-003318-abs9rvjk 378 1 35 35 CD cord-003318-abs9rvjk 378 2 except except IN cord-003318-abs9rvjk 378 3 some some DT cord-003318-abs9rvjk 378 4 modifications modification NNS cord-003318-abs9rvjk 378 5 on on IN cord-003318-abs9rvjk 378 6 chromatographic chromatographic JJ cord-003318-abs9rvjk 378 7 conditions condition NNS cord-003318-abs9rvjk 378 8 . . . cord-003318-abs9rvjk 379 1 HPLC HPLC NNP cord-003318-abs9rvjk 379 2 separation separation NN cord-003318-abs9rvjk 379 3 was be VBD cord-003318-abs9rvjk 379 4 carried carry VBN cord-003318-abs9rvjk 379 5 out out RP cord-003318-abs9rvjk 379 6 on on IN cord-003318-abs9rvjk 379 7 an an DT cord-003318-abs9rvjk 379 8 YMC YMC NNP cord-003318-abs9rvjk 379 9 - - HYPH cord-003318-abs9rvjk 379 10 Pack Pack NNP cord-003318-abs9rvjk 379 11 Ph Ph NNP cord-003318-abs9rvjk 379 12 column column NN cord-003318-abs9rvjk 379 13 ( ( -LRB- cord-003318-abs9rvjk 379 14 5 5 CD cord-003318-abs9rvjk 379 15 μm μm NN cord-003318-abs9rvjk 379 16 , , , cord-003318-abs9rvjk 379 17 12 12 CD cord-003318-abs9rvjk 379 18 nm nm NN cord-003318-abs9rvjk 379 19 , , , cord-003318-abs9rvjk 379 20 250 250 CD cord-003318-abs9rvjk 379 21 mm mm NN cord-003318-abs9rvjk 379 22 Â â CD cord-003318-abs9rvjk 379 23 4.6 4.6 CD cord-003318-abs9rvjk 379 24 mm mm NNP cord-003318-abs9rvjk 379 25 ) ) -RRB- cord-003318-abs9rvjk 379 26 with with IN cord-003318-abs9rvjk 379 27 an an DT cord-003318-abs9rvjk 379 28 isocratic isocratic JJ cord-003318-abs9rvjk 379 29 elution elution NN cord-003318-abs9rvjk 379 30 of of IN cord-003318-abs9rvjk 379 31 50 50 CD cord-003318-abs9rvjk 379 32 % % NN cord-003318-abs9rvjk 379 33 water water NN cord-003318-abs9rvjk 379 34 - - HYPH cord-003318-abs9rvjk 379 35 trifluoroacetic trifluoroacetic NN cord-003318-abs9rvjk 379 36 acid acid NN cord-003318-abs9rvjk 379 37 ( ( -LRB- cord-003318-abs9rvjk 379 38 A A NNP cord-003318-abs9rvjk 379 39 , , , cord-003318-abs9rvjk 379 40 99.9%:0.1 99.9%:0.1 CD cord-003318-abs9rvjk 379 41 % % NN cord-003318-abs9rvjk 379 42 , , , cord-003318-abs9rvjk 379 43 v v NN cord-003318-abs9rvjk 379 44 / / SYM cord-003318-abs9rvjk 379 45 v v NN cord-003318-abs9rvjk 379 46 ) ) -RRB- cord-003318-abs9rvjk 379 47 and and CC cord-003318-abs9rvjk 379 48 50 50 CD cord-003318-abs9rvjk 379 49 % % NN cord-003318-abs9rvjk 379 50 methanol methanol NN cord-003318-abs9rvjk 379 51 ( ( -LRB- cord-003318-abs9rvjk 379 52 B b NN cord-003318-abs9rvjk 379 53 ) ) -RRB- cord-003318-abs9rvjk 379 54 at at IN cord-003318-abs9rvjk 379 55 a a DT cord-003318-abs9rvjk 379 56 flow flow NN cord-003318-abs9rvjk 379 57 rate rate NN cord-003318-abs9rvjk 379 58 of of IN cord-003318-abs9rvjk 379 59 1 1 CD cord-003318-abs9rvjk 379 60 mL ml NN cord-003318-abs9rvjk 379 61 / / SYM cord-003318-abs9rvjk 379 62 min min NN cord-003318-abs9rvjk 379 63 . . . cord-003318-abs9rvjk 380 1 Seven seven CD cord-003318-abs9rvjk 380 2 human human JJ cord-003318-abs9rvjk 380 3 cancer cancer NN cord-003318-abs9rvjk 380 4 cell cell NN cord-003318-abs9rvjk 380 5 lines line NNS cord-003318-abs9rvjk 380 6 , , , cord-003318-abs9rvjk 380 7 HCT-116 HCT-116 NNP cord-003318-abs9rvjk 380 8 ( ( -LRB- cord-003318-abs9rvjk 380 9 human human JJ cord-003318-abs9rvjk 380 10 colon colon NN cord-003318-abs9rvjk 380 11 cancer cancer NN cord-003318-abs9rvjk 380 12 cell cell NN cord-003318-abs9rvjk 380 13 line line NN cord-003318-abs9rvjk 380 14 ) ) -RRB- cord-003318-abs9rvjk 380 15 , , , cord-003318-abs9rvjk 380 16 Bel7402 Bel7402 NNP cord-003318-abs9rvjk 380 17 ( ( -LRB- cord-003318-abs9rvjk 380 18 human human JJ cord-003318-abs9rvjk 380 19 hepatocellular hepatocellular JJ cord-003318-abs9rvjk 380 20 carcinoma carcinoma NN cord-003318-abs9rvjk 380 21 cell cell NN cord-003318-abs9rvjk 380 22 line line NN cord-003318-abs9rvjk 380 23 ) ) -RRB- cord-003318-abs9rvjk 380 24 , , , cord-003318-abs9rvjk 380 25 MGC803 MGC803 NNP cord-003318-abs9rvjk 380 26 ( ( -LRB- cord-003318-abs9rvjk 380 27 human human JJ cord-003318-abs9rvjk 380 28 gastric gastric JJ cord-003318-abs9rvjk 380 29 carcinoma carcinoma NN cord-003318-abs9rvjk 380 30 cell cell NN cord-003318-abs9rvjk 380 31 line line NN cord-003318-abs9rvjk 380 32 ) ) -RRB- cord-003318-abs9rvjk 380 33 , , , cord-003318-abs9rvjk 380 34 Capan Capan NNP cord-003318-abs9rvjk 380 35 2 2 CD cord-003318-abs9rvjk 380 36 ( ( -LRB- cord-003318-abs9rvjk 380 37 human human JJ cord-003318-abs9rvjk 380 38 pancreatic pancreatic JJ cord-003318-abs9rvjk 380 39 cancer cancer NN cord-003318-abs9rvjk 380 40 cell cell NN cord-003318-abs9rvjk 380 41 line line NN cord-003318-abs9rvjk 380 42 ) ) -RRB- cord-003318-abs9rvjk 380 43 , , , cord-003318-abs9rvjk 380 44 NCI NCI NNP cord-003318-abs9rvjk 380 45 - - HYPH cord-003318-abs9rvjk 380 46 H1650 H1650 NNP cord-003318-abs9rvjk 380 47 , , , cord-003318-abs9rvjk 380 48 NCI NCI NNP cord-003318-abs9rvjk 380 49 - - HYPH cord-003318-abs9rvjk 380 50 H460 H460 NNP cord-003318-abs9rvjk 380 51 and and CC cord-003318-abs9rvjk 380 52 A549 a549 JJ cord-003318-abs9rvjk 380 53 ( ( -LRB- cord-003318-abs9rvjk 380 54 human human JJ cord-003318-abs9rvjk 380 55 lung lung NN cord-003318-abs9rvjk 380 56 cancer cancer NN cord-003318-abs9rvjk 380 57 cell cell NN cord-003318-abs9rvjk 380 58 lines line NNS cord-003318-abs9rvjk 380 59 ) ) -RRB- cord-003318-abs9rvjk 380 60 were be VBD cord-003318-abs9rvjk 380 61 used use VBN cord-003318-abs9rvjk 380 62 in in IN cord-003318-abs9rvjk 380 63 the the DT cord-003318-abs9rvjk 380 64 cytotoxicity cytotoxicity NN cord-003318-abs9rvjk 380 65 assay assay NN cord-003318-abs9rvjk 380 66 . . . cord-003318-abs9rvjk 381 1 The the DT cord-003318-abs9rvjk 381 2 viability viability NN cord-003318-abs9rvjk 381 3 of of IN cord-003318-abs9rvjk 381 4 the the DT cord-003318-abs9rvjk 381 5 cells cell NNS cord-003318-abs9rvjk 381 6 after after IN cord-003318-abs9rvjk 381 7 treated treat VBN cord-003318-abs9rvjk 381 8 with with IN cord-003318-abs9rvjk 381 9 various various JJ cord-003318-abs9rvjk 381 10 chemicals chemical NNS cord-003318-abs9rvjk 381 11 was be VBD cord-003318-abs9rvjk 381 12 evaluated evaluate VBN cord-003318-abs9rvjk 381 13 using use VBG cord-003318-abs9rvjk 381 14 the the DT cord-003318-abs9rvjk 381 15 MTT MTT NNP cord-003318-abs9rvjk 381 16 ( ( -LRB- cord-003318-abs9rvjk 381 17 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl CD cord-003318-abs9rvjk 381 18 tetrazolium tetrazolium NNP cord-003318-abs9rvjk 381 19 bromide bromide NN cord-003318-abs9rvjk 381 20 ) ) -RRB- cord-003318-abs9rvjk 381 21 assay assay NN cord-003318-abs9rvjk 381 22 performed perform VBN cord-003318-abs9rvjk 381 23 as as IN cord-003318-abs9rvjk 381 24 previously previously RB cord-003318-abs9rvjk 381 25 reported report VBN cord-003318-abs9rvjk 381 26 7 7 CD cord-003318-abs9rvjk 381 27 , , , cord-003318-abs9rvjk 381 28 38 38 CD cord-003318-abs9rvjk 381 29 . . . cord-003318-abs9rvjk 382 1 The the DT cord-003318-abs9rvjk 382 2 inhibitory inhibitory JJ cord-003318-abs9rvjk 382 3 effects effect NNS cord-003318-abs9rvjk 382 4 of of IN cord-003318-abs9rvjk 382 5 these these DT cord-003318-abs9rvjk 382 6 tested test VBN cord-003318-abs9rvjk 382 7 compounds compound NNS cord-003318-abs9rvjk 382 8 on on IN cord-003318-abs9rvjk 382 9 the the DT cord-003318-abs9rvjk 382 10 proliferation proliferation NN cord-003318-abs9rvjk 382 11 of of IN cord-003318-abs9rvjk 382 12 cancer cancer NN cord-003318-abs9rvjk 382 13 cells cell NNS cord-003318-abs9rvjk 382 14 were be VBD cord-003318-abs9rvjk 382 15 reflected reflect VBN cord-003318-abs9rvjk 382 16 by by IN cord-003318-abs9rvjk 382 17 their -PRON- PRP$ cord-003318-abs9rvjk 382 18 respective respective JJ cord-003318-abs9rvjk 382 19 IC IC NNP cord-003318-abs9rvjk 382 20 50 50 CD cord-003318-abs9rvjk 382 21 ( ( -LRB- cord-003318-abs9rvjk 382 22 50 50 CD cord-003318-abs9rvjk 382 23 % % NN cord-003318-abs9rvjk 382 24 inhibitory inhibitory JJ cord-003318-abs9rvjk 382 25 concentration concentration NN cord-003318-abs9rvjk 382 26 ) ) -RRB- cord-003318-abs9rvjk 382 27 . . . cord-003318-abs9rvjk 383 1 Steryl Steryl NNP cord-003318-abs9rvjk 383 2 glycosides glycoside NNS cord-003318-abs9rvjk 383 3 and and CC cord-003318-abs9rvjk 383 4 acylated acylated JJ cord-003318-abs9rvjk 383 5 steryl steryl NNS cord-003318-abs9rvjk 383 6 glycosides glycoside NNS cord-003318-abs9rvjk 383 7 in in IN cord-003318-abs9rvjk 383 8 plant plant NN cord-003318-abs9rvjk 383 9 foods food NNS cord-003318-abs9rvjk 383 10 reflect reflect VBP cord-003318-abs9rvjk 383 11 unique unique JJ cord-003318-abs9rvjk 383 12 sterol sterol NN cord-003318-abs9rvjk 383 13 patterns pattern NNS cord-003318-abs9rvjk 383 14 Rice Rice NNP cord-003318-abs9rvjk 383 15 bran bran NN cord-003318-abs9rvjk 383 16 extract extract NN cord-003318-abs9rvjk 383 17 containing contain VBG cord-003318-abs9rvjk 383 18 acylated acylated NNP cord-003318-abs9rvjk 383 19 steryl steryl NNPS cord-003318-abs9rvjk 383 20 glucoside glucoside NNP cord-003318-abs9rvjk 383 21 fraction fraction NN cord-003318-abs9rvjk 383 22 decreases decrease VBZ cord-003318-abs9rvjk 383 23 elevated elevate VBD cord-003318-abs9rvjk 383 24 blood blood NN cord-003318-abs9rvjk 383 25 LDL ldl NN cord-003318-abs9rvjk 383 26 cholesterol cholesterol NN cord-003318-abs9rvjk 383 27 level level NN cord-003318-abs9rvjk 383 28 in in IN cord-003318-abs9rvjk 383 29 obese obese JJ cord-003318-abs9rvjk 383 30 Japanese japanese JJ cord-003318-abs9rvjk 383 31 men man NNS cord-003318-abs9rvjk 383 32 Structural structural JJ cord-003318-abs9rvjk 383 33 analysis analysis NN cord-003318-abs9rvjk 383 34 of of IN cord-003318-abs9rvjk 383 35 novel novel JJ cord-003318-abs9rvjk 383 36 bioactive bioactive JJ cord-003318-abs9rvjk 383 37 acylated acylated NNP cord-003318-abs9rvjk 383 38 steryl steryl NNP cord-003318-abs9rvjk 383 39 glucosides glucosides NNP cord-003318-abs9rvjk 383 40 in in IN cord-003318-abs9rvjk 383 41 pre pre JJ cord-003318-abs9rvjk 383 42 - - JJ cord-003318-abs9rvjk 383 43 germinated germinate VBN cord-003318-abs9rvjk 383 44 brown brown JJ cord-003318-abs9rvjk 383 45 rice rice NN cord-003318-abs9rvjk 383 46 bran bran NN cord-003318-abs9rvjk 383 47 A a DT cord-003318-abs9rvjk 383 48 potent potent JJ cord-003318-abs9rvjk 383 49 anticomplementary anticomplementary JJ cord-003318-abs9rvjk 383 50 acylated acylated JJ cord-003318-abs9rvjk 383 51 sterol sterol NN cord-003318-abs9rvjk 383 52 glucoside glucoside NN cord-003318-abs9rvjk 383 53 from from IN cord-003318-abs9rvjk 383 54 Orostachys Orostachys NNP cord-003318-abs9rvjk 383 55 japonicus japonicus NN cord-003318-abs9rvjk 383 56 Therapeutic therapeutic JJ cord-003318-abs9rvjk 383 57 potential potential NN cord-003318-abs9rvjk 383 58 of of IN cord-003318-abs9rvjk 383 59 cholesteryl cholesteryl NNP cord-003318-abs9rvjk 383 60 O O NNP cord-003318-abs9rvjk 383 61 - - HYPH cord-003318-abs9rvjk 383 62 acyl acyl NNP cord-003318-abs9rvjk 383 63 alpha alpha NN cord-003318-abs9rvjk 383 64 - - HYPH cord-003318-abs9rvjk 383 65 glucoside glucoside NN cord-003318-abs9rvjk 383 66 found find VBD cord-003318-abs9rvjk 383 67 in in IN cord-003318-abs9rvjk 383 68 Helicobacter Helicobacter NNP cord-003318-abs9rvjk 383 69 pylori pylori NN cord-003318-abs9rvjk 383 70 Immunological immunological JJ cord-003318-abs9rvjk 383 71 functions function NNS cord-003318-abs9rvjk 383 72 of of IN cord-003318-abs9rvjk 383 73 steryl steryl NNS cord-003318-abs9rvjk 383 74 glycosides glycoside VBZ cord-003318-abs9rvjk 383 75 Cholestane Cholestane NNP cord-003318-abs9rvjk 383 76 glycosides glycoside NNS cord-003318-abs9rvjk 383 77 with with IN cord-003318-abs9rvjk 383 78 potent potent JJ cord-003318-abs9rvjk 383 79 cytostatic cytostatic JJ cord-003318-abs9rvjk 383 80 activities activity NNS cord-003318-abs9rvjk 383 81 on on IN cord-003318-abs9rvjk 383 82 various various JJ cord-003318-abs9rvjk 383 83 tumor tumor NN cord-003318-abs9rvjk 383 84 cells cell NNS cord-003318-abs9rvjk 383 85 from from IN cord-003318-abs9rvjk 383 86 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 383 87 saundersiae saundersiae NN cord-003318-abs9rvjk 383 88 bulbs bulb NNS cord-003318-abs9rvjk 384 1 A a DT cord-003318-abs9rvjk 384 2 new new JJ cord-003318-abs9rvjk 384 3 rearranged rearrange VBN cord-003318-abs9rvjk 384 4 cholestane cholestane NN cord-003318-abs9rvjk 384 5 glycoside glycoside NN cord-003318-abs9rvjk 384 6 from from IN cord-003318-abs9rvjk 384 7 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 384 8 saundersiae saundersiae NN cord-003318-abs9rvjk 384 9 bulbs bulb NNS cord-003318-abs9rvjk 384 10 exhibiting exhibit VBG cord-003318-abs9rvjk 384 11 potent potent JJ cord-003318-abs9rvjk 384 12 cytostatic cytostatic JJ cord-003318-abs9rvjk 384 13 activities activity NNS cord-003318-abs9rvjk 384 14 on on IN cord-003318-abs9rvjk 384 15 leukemia leukemia NN cord-003318-abs9rvjk 384 16 HL-60 HL-60 NNP cord-003318-abs9rvjk 384 17 and and CC cord-003318-abs9rvjk 384 18 molt-4 molt-4 NNP cord-003318-abs9rvjk 384 19 cells cell NNS cord-003318-abs9rvjk 384 20 Acylated Acylated NNP cord-003318-abs9rvjk 384 21 cholestane cholestane NN cord-003318-abs9rvjk 384 22 glycosides glycoside NNS cord-003318-abs9rvjk 384 23 from from IN cord-003318-abs9rvjk 384 24 the the DT cord-003318-abs9rvjk 384 25 bulbs bulb NNS cord-003318-abs9rvjk 384 26 of of IN cord-003318-abs9rvjk 384 27 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 384 28 saundersiae saundersiae NN cord-003318-abs9rvjk 384 29 Synthesis Synthesis NNP cord-003318-abs9rvjk 384 30 of of IN cord-003318-abs9rvjk 384 31 a a DT cord-003318-abs9rvjk 384 32 cholestane cholestane NN cord-003318-abs9rvjk 384 33 glycoside glycoside NN cord-003318-abs9rvjk 384 34 OSW-1 OSW-1 NNP cord-003318-abs9rvjk 384 35 with with IN cord-003318-abs9rvjk 384 36 potent potent JJ cord-003318-abs9rvjk 384 37 cytostatic cytostatic JJ cord-003318-abs9rvjk 384 38 activity activity NN cord-003318-abs9rvjk 385 1 First first JJ cord-003318-abs9rvjk 385 2 total total JJ cord-003318-abs9rvjk 385 3 synthesis synthesis NN cord-003318-abs9rvjk 385 4 of of IN cord-003318-abs9rvjk 385 5 an an DT cord-003318-abs9rvjk 385 6 exceptionally exceptionally RB cord-003318-abs9rvjk 385 7 potent potent JJ cord-003318-abs9rvjk 385 8 antitumor antitumor JJ cord-003318-abs9rvjk 385 9 saponin saponin NN cord-003318-abs9rvjk 385 10 , , , cord-003318-abs9rvjk 385 11 OSW-1 OSW-1 NNP cord-003318-abs9rvjk 385 12 Improved Improved NNP cord-003318-abs9rvjk 385 13 enzyme enzyme NN cord-003318-abs9rvjk 385 14 - - HYPH cord-003318-abs9rvjk 385 15 mediated mediate VBN cord-003318-abs9rvjk 385 16 synthesis synthesis NN cord-003318-abs9rvjk 385 17 and and CC cord-003318-abs9rvjk 385 18 supramolecular supramolecular NNP cord-003318-abs9rvjk 385 19 selfassembly selfassembly RB cord-003318-abs9rvjk 385 20 of of IN cord-003318-abs9rvjk 385 21 naturally naturally RB cord-003318-abs9rvjk 385 22 occurring occur VBG cord-003318-abs9rvjk 385 23 conjugates conjugate NNS cord-003318-abs9rvjk 385 24 of of IN cord-003318-abs9rvjk 385 25 β β NN cord-003318-abs9rvjk 385 26 - - HYPH cord-003318-abs9rvjk 385 27 sitosterol sitosterol NNP cord-003318-abs9rvjk 386 1 Simple simple JJ cord-003318-abs9rvjk 386 2 method method NN cord-003318-abs9rvjk 386 3 for for IN cord-003318-abs9rvjk 386 4 high high JJ cord-003318-abs9rvjk 386 5 purity purity NN cord-003318-abs9rvjk 386 6 acylated acylated NNP cord-003318-abs9rvjk 386 7 steryl steryl NNP cord-003318-abs9rvjk 386 8 glucosides glucoside VBZ cord-003318-abs9rvjk 386 9 synthesis synthesis NN cord-003318-abs9rvjk 386 10 Regioselective Regioselective NNP cord-003318-abs9rvjk 386 11 diversification diversification NN cord-003318-abs9rvjk 386 12 of of IN cord-003318-abs9rvjk 386 13 a a DT cord-003318-abs9rvjk 386 14 cardiac cardiac JJ cord-003318-abs9rvjk 386 15 glycoside glycoside NN cord-003318-abs9rvjk 386 16 , , , cord-003318-abs9rvjk 386 17 lanatoside lanatoside NNP cord-003318-abs9rvjk 386 18 C C NNP cord-003318-abs9rvjk 386 19 , , , cord-003318-abs9rvjk 386 20 by by IN cord-003318-abs9rvjk 386 21 organocatalysis organocatalysis NN cord-003318-abs9rvjk 386 22 Sterol Sterol NNP cord-003318-abs9rvjk 386 23 glycosyltransferases- glycosyltransferases- XX cord-003318-abs9rvjk 387 1 the the DT cord-003318-abs9rvjk 387 2 enzymes enzyme NNS cord-003318-abs9rvjk 387 3 that that WDT cord-003318-abs9rvjk 387 4 modify modify VBP cord-003318-abs9rvjk 387 5 sterols sterol NNS cord-003318-abs9rvjk 387 6 The the DT cord-003318-abs9rvjk 387 7 functions function NNS cord-003318-abs9rvjk 387 8 of of IN cord-003318-abs9rvjk 387 9 steryl steryl NNS cord-003318-abs9rvjk 387 10 glycosides glycoside NNS cord-003318-abs9rvjk 387 11 come come VBP cord-003318-abs9rvjk 387 12 to to IN cord-003318-abs9rvjk 387 13 those those DT cord-003318-abs9rvjk 387 14 who who WP cord-003318-abs9rvjk 387 15 wait wait VBP cord-003318-abs9rvjk 387 16 : : : cord-003318-abs9rvjk 387 17 recent recent JJ cord-003318-abs9rvjk 387 18 advances advance NNS cord-003318-abs9rvjk 387 19 in in IN cord-003318-abs9rvjk 387 20 plants plant NNS cord-003318-abs9rvjk 387 21 , , , cord-003318-abs9rvjk 387 22 fungi fungus NNS cord-003318-abs9rvjk 387 23 , , , cord-003318-abs9rvjk 387 24 bacteria bacteria NNS cord-003318-abs9rvjk 387 25 and and CC cord-003318-abs9rvjk 387 26 animals animal NNS cord-003318-abs9rvjk 388 1 Sterol Sterol NNP cord-003318-abs9rvjk 388 2 3β 3β NN cord-003318-abs9rvjk 388 3 - - HYPH cord-003318-abs9rvjk 388 4 glucosyltransferase glucosyltransferase NNP cord-003318-abs9rvjk 388 5 biocatalysts biocatalyst NNS cord-003318-abs9rvjk 388 6 with with IN cord-003318-abs9rvjk 388 7 a a DT cord-003318-abs9rvjk 388 8 range range NN cord-003318-abs9rvjk 388 9 of of IN cord-003318-abs9rvjk 388 10 selectivities selectivity NNS cord-003318-abs9rvjk 388 11 , , , cord-003318-abs9rvjk 388 12 including include VBG cord-003318-abs9rvjk 388 13 selectivity selectivity NN cord-003318-abs9rvjk 388 14 for for IN cord-003318-abs9rvjk 388 15 testosterone testosterone NN cord-003318-abs9rvjk 388 16 Molecular molecular JJ cord-003318-abs9rvjk 388 17 cloning clone VBG cord-003318-abs9rvjk 388 18 and and CC cord-003318-abs9rvjk 388 19 biochemical biochemical JJ cord-003318-abs9rvjk 388 20 characterization characterization NN cord-003318-abs9rvjk 388 21 of of IN cord-003318-abs9rvjk 388 22 a a DT cord-003318-abs9rvjk 388 23 recombinant recombinant JJ cord-003318-abs9rvjk 388 24 sterol sterol NN cord-003318-abs9rvjk 388 25 3-O 3-o CD cord-003318-abs9rvjk 388 26 - - HYPH cord-003318-abs9rvjk 388 27 glucosyltransferase glucosyltransferase NN cord-003318-abs9rvjk 388 28 from from IN cord-003318-abs9rvjk 388 29 Gymnema Gymnema NNP cord-003318-abs9rvjk 388 30 sylvestre sylvestre NNP cord-003318-abs9rvjk 388 31 R.Br R.Br NNP cord-003318-abs9rvjk 388 32 . . . cord-003318-abs9rvjk 389 1 catalyzing catalyze VBG cord-003318-abs9rvjk 389 2 biosynthesis biosynthesis NN cord-003318-abs9rvjk 389 3 of of IN cord-003318-abs9rvjk 389 4 steryl steryl NNP cord-003318-abs9rvjk 389 5 glucosides glucoside VBZ cord-003318-abs9rvjk 389 6 Cloning clone VBG cord-003318-abs9rvjk 389 7 and and CC cord-003318-abs9rvjk 389 8 functional functional JJ cord-003318-abs9rvjk 389 9 expression expression NN cord-003318-abs9rvjk 389 10 of of IN cord-003318-abs9rvjk 389 11 UGT UGT NNP cord-003318-abs9rvjk 389 12 genes gene NNS cord-003318-abs9rvjk 389 13 encoding encode VBG cord-003318-abs9rvjk 389 14 sterol sterol NN cord-003318-abs9rvjk 389 15 glucosyltransferases glucosyltransferase NNS cord-003318-abs9rvjk 389 16 from from IN cord-003318-abs9rvjk 389 17 Saccharomyces Saccharomyces NNP cord-003318-abs9rvjk 389 18 cerevisiae cerevisiae NNS cord-003318-abs9rvjk 389 19 , , , cord-003318-abs9rvjk 389 20 Candida Candida NNP cord-003318-abs9rvjk 389 21 albicans albican NNS cord-003318-abs9rvjk 389 22 , , , cord-003318-abs9rvjk 389 23 Pichia Pichia NNP cord-003318-abs9rvjk 389 24 pastoris pastoris NN cord-003318-abs9rvjk 389 25 , , , cord-003318-abs9rvjk 389 26 and and CC cord-003318-abs9rvjk 389 27 Dictyostelium Dictyostelium NNP cord-003318-abs9rvjk 389 28 discoideum discoideum NN cord-003318-abs9rvjk 389 29 Glycosyltransferases Glycosyltransferases NNP cord-003318-abs9rvjk 389 30 in in IN cord-003318-abs9rvjk 389 31 plant plant NN cord-003318-abs9rvjk 389 32 natural natural JJ cord-003318-abs9rvjk 389 33 product product NN cord-003318-abs9rvjk 389 34 synthesis synthesis NN cord-003318-abs9rvjk 389 35 : : : cord-003318-abs9rvjk 389 36 characterization characterization NN cord-003318-abs9rvjk 389 37 of of IN cord-003318-abs9rvjk 389 38 a a DT cord-003318-abs9rvjk 389 39 supergene supergene JJ cord-003318-abs9rvjk 389 40 family family NN cord-003318-abs9rvjk 389 41 Chaperone Chaperone NNP cord-003318-abs9rvjk 389 42 coexpression coexpression NN cord-003318-abs9rvjk 389 43 plasmids plasmid NNS cord-003318-abs9rvjk 389 44 : : : cord-003318-abs9rvjk 389 45 differential differential JJ cord-003318-abs9rvjk 389 46 and and CC cord-003318-abs9rvjk 389 47 synergistic synergistic JJ cord-003318-abs9rvjk 389 48 roles role NNS cord-003318-abs9rvjk 389 49 of of IN cord-003318-abs9rvjk 389 50 DnaK DnaK NNP cord-003318-abs9rvjk 389 51 - - HYPH cord-003318-abs9rvjk 389 52 DnaJ DnaJ NNP cord-003318-abs9rvjk 389 53 - - HYPH cord-003318-abs9rvjk 389 54 GrpE GrpE NNP cord-003318-abs9rvjk 389 55 and and CC cord-003318-abs9rvjk 389 56 GroEL groel NN cord-003318-abs9rvjk 389 57 - - HYPH cord-003318-abs9rvjk 389 58 GroES GroES NNP cord-003318-abs9rvjk 389 59 in in IN cord-003318-abs9rvjk 389 60 assisting assist VBG cord-003318-abs9rvjk 389 61 folding folding NN cord-003318-abs9rvjk 389 62 of of IN cord-003318-abs9rvjk 389 63 an an DT cord-003318-abs9rvjk 389 64 allergen allergen NN cord-003318-abs9rvjk 389 65 of of IN cord-003318-abs9rvjk 389 66 Japanese japanese JJ cord-003318-abs9rvjk 389 67 cedar cedar NN cord-003318-abs9rvjk 389 68 pollen pollen NN cord-003318-abs9rvjk 389 69 , , , cord-003318-abs9rvjk 389 70 Cryj2 Cryj2 NNS cord-003318-abs9rvjk 389 71 , , , cord-003318-abs9rvjk 389 72 in in IN cord-003318-abs9rvjk 389 73 Escherichia Escherichia NNP cord-003318-abs9rvjk 389 74 coli coli VBZ cord-003318-abs9rvjk 389 75 Regioselective Regioselective NNP cord-003318-abs9rvjk 389 76 enzymatic enzymatic JJ cord-003318-abs9rvjk 389 77 acylation acylation NN cord-003318-abs9rvjk 389 78 of of IN cord-003318-abs9rvjk 389 79 complex complex JJ cord-003318-abs9rvjk 389 80 natural natural JJ cord-003318-abs9rvjk 389 81 products product NNS cord-003318-abs9rvjk 389 82 : : : cord-003318-abs9rvjk 389 83 expanding expand VBG cord-003318-abs9rvjk 389 84 molecular molecular JJ cord-003318-abs9rvjk 389 85 diversity diversity NN cord-003318-abs9rvjk 389 86 Structure Structure NNP cord-003318-abs9rvjk 389 87 , , , cord-003318-abs9rvjk 389 88 bioactivity bioactivity NN cord-003318-abs9rvjk 389 89 , , , cord-003318-abs9rvjk 389 90 and and CC cord-003318-abs9rvjk 389 91 chemical chemical JJ cord-003318-abs9rvjk 389 92 synthesis synthesis NN cord-003318-abs9rvjk 389 93 of of IN cord-003318-abs9rvjk 389 94 OSW-1 OSW-1 NNP cord-003318-abs9rvjk 389 95 and and CC cord-003318-abs9rvjk 389 96 other other JJ cord-003318-abs9rvjk 389 97 steroidal steroidal JJ cord-003318-abs9rvjk 389 98 glycosides glycoside NNS cord-003318-abs9rvjk 389 99 in in IN cord-003318-abs9rvjk 389 100 the the DT cord-003318-abs9rvjk 389 101 genus genus NN cord-003318-abs9rvjk 389 102 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 389 103 Functional functional JJ cord-003318-abs9rvjk 389 104 diversification diversification NN cord-003318-abs9rvjk 389 105 of of IN cord-003318-abs9rvjk 389 106 two two CD cord-003318-abs9rvjk 389 107 UGT80 UGT80 NNP cord-003318-abs9rvjk 389 108 enzymes enzyme NNS cord-003318-abs9rvjk 389 109 required require VBN cord-003318-abs9rvjk 389 110 for for IN cord-003318-abs9rvjk 389 111 steryl steryl NNP cord-003318-abs9rvjk 389 112 glucoside glucoside NN cord-003318-abs9rvjk 389 113 synthesis synthesis NN cord-003318-abs9rvjk 389 114 in in IN cord-003318-abs9rvjk 389 115 Arabidopsis Arabidopsis NNP cord-003318-abs9rvjk 389 116 lac lac NNP cord-003318-abs9rvjk 389 117 operon operon NN cord-003318-abs9rvjk 389 118 induction induction NN cord-003318-abs9rvjk 389 119 in in IN cord-003318-abs9rvjk 389 120 Escherichia Escherichia NNP cord-003318-abs9rvjk 389 121 coli coli NNS cord-003318-abs9rvjk 389 122 : : : cord-003318-abs9rvjk 389 123 systematic systematic JJ cord-003318-abs9rvjk 389 124 comparison comparison NN cord-003318-abs9rvjk 389 125 of of IN cord-003318-abs9rvjk 389 126 IPTG IPTG NNP cord-003318-abs9rvjk 389 127 and and CC cord-003318-abs9rvjk 389 128 TMG TMG NNP cord-003318-abs9rvjk 389 129 induction induction NN cord-003318-abs9rvjk 389 130 and and CC cord-003318-abs9rvjk 389 131 influence influence NN cord-003318-abs9rvjk 389 132 of of IN cord-003318-abs9rvjk 389 133 the the DT cord-003318-abs9rvjk 389 134 transacetylase transacetylase NN cord-003318-abs9rvjk 390 1 LacA LacA NNP cord-003318-abs9rvjk 391 1 The the DT cord-003318-abs9rvjk 391 2 lac lac NNP cord-003318-abs9rvjk 391 3 operon operon NN cord-003318-abs9rvjk 391 4 galactoside galactoside NNP cord-003318-abs9rvjk 391 5 acetyltransferase acetyltransferase NNP cord-003318-abs9rvjk 391 6 cDNA cDNA NNP cord-003318-abs9rvjk 391 7 Isolation Isolation NNP cord-003318-abs9rvjk 391 8 and and CC cord-003318-abs9rvjk 391 9 functional functional JJ cord-003318-abs9rvjk 391 10 characterization characterization NN cord-003318-abs9rvjk 391 11 of of IN cord-003318-abs9rvjk 391 12 UDP udp NN cord-003318-abs9rvjk 391 13 - - HYPH cord-003318-abs9rvjk 391 14 D D NNP cord-003318-abs9rvjk 391 15 - - HYPH cord-003318-abs9rvjk 391 16 glucuronic glucuronic JJ cord-003318-abs9rvjk 391 17 acid acid NN cord-003318-abs9rvjk 391 18 4-epimerase 4-epimerase CD cord-003318-abs9rvjk 391 19 family family NN cord-003318-abs9rvjk 391 20 from from IN cord-003318-abs9rvjk 391 21 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 391 22 caudatum caudatum NN cord-003318-abs9rvjk 391 23 Transcriptome Transcriptome NNP cord-003318-abs9rvjk 391 24 - - HYPH cord-003318-abs9rvjk 391 25 guided guide VBN cord-003318-abs9rvjk 391 26 discovery discovery NN cord-003318-abs9rvjk 391 27 and and CC cord-003318-abs9rvjk 391 28 functional functional JJ cord-003318-abs9rvjk 391 29 characterization characterization NN cord-003318-abs9rvjk 391 30 of of IN cord-003318-abs9rvjk 391 31 two two CD cord-003318-abs9rvjk 391 32 UDP udp NN cord-003318-abs9rvjk 391 33 - - HYPH cord-003318-abs9rvjk 391 34 sugar sugar NN cord-003318-abs9rvjk 391 35 4-epimerase 4-epimerase CD cord-003318-abs9rvjk 391 36 families family NNS cord-003318-abs9rvjk 391 37 involved involve VBN cord-003318-abs9rvjk 391 38 in in IN cord-003318-abs9rvjk 391 39 the the DT cord-003318-abs9rvjk 391 40 biosynthesis biosynthesis NN cord-003318-abs9rvjk 391 41 of of IN cord-003318-abs9rvjk 391 42 anti anti JJ cord-003318-abs9rvjk 391 43 - - JJ cord-003318-abs9rvjk 391 44 tumor tumor JJ cord-003318-abs9rvjk 391 45 polysaccharides polysaccharide NNS cord-003318-abs9rvjk 391 46 in in IN cord-003318-abs9rvjk 391 47 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 391 48 caudatum caudatum NN cord-003318-abs9rvjk 391 49 Transcriptome Transcriptome NNP cord-003318-abs9rvjk 391 50 - - HYPH cord-003318-abs9rvjk 391 51 guided guide VBN cord-003318-abs9rvjk 391 52 gene gene NN cord-003318-abs9rvjk 391 53 isolation isolation NN cord-003318-abs9rvjk 391 54 and and CC cord-003318-abs9rvjk 391 55 functional functional JJ cord-003318-abs9rvjk 391 56 characterization characterization NN cord-003318-abs9rvjk 391 57 of of IN cord-003318-abs9rvjk 391 58 UDP udp NN cord-003318-abs9rvjk 391 59 - - HYPH cord-003318-abs9rvjk 391 60 xylose xylose NN cord-003318-abs9rvjk 391 61 synthase synthase NN cord-003318-abs9rvjk 391 62 and and CC cord-003318-abs9rvjk 391 63 UDP udp NN cord-003318-abs9rvjk 391 64 - - HYPH cord-003318-abs9rvjk 391 65 D d NN cord-003318-abs9rvjk 391 66 - - HYPH cord-003318-abs9rvjk 391 67 apiose apiose NN cord-003318-abs9rvjk 391 68 / / SYM cord-003318-abs9rvjk 391 69 UDP udp NN cord-003318-abs9rvjk 391 70 - - HYPH cord-003318-abs9rvjk 391 71 Dxylose Dxylose NNP cord-003318-abs9rvjk 391 72 synthase synthase NN cord-003318-abs9rvjk 391 73 families family NNS cord-003318-abs9rvjk 391 74 from from IN cord-003318-abs9rvjk 391 75 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 391 76 caudatum caudatum NN cord-003318-abs9rvjk 392 1 Ait Ait NNP cord-003318-abs9rvjk 392 2 Transcriptome Transcriptome NNP cord-003318-abs9rvjk 392 3 - - HYPH cord-003318-abs9rvjk 392 4 wide wide JJ cord-003318-abs9rvjk 392 5 identification identification NN cord-003318-abs9rvjk 392 6 of of IN cord-003318-abs9rvjk 392 7 sucrose sucrose NN cord-003318-abs9rvjk 392 8 synthase synthase NN cord-003318-abs9rvjk 392 9 genes gene NNS cord-003318-abs9rvjk 392 10 in in IN cord-003318-abs9rvjk 392 11 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 392 12 caudatum caudatum NN cord-003318-abs9rvjk 393 1 Transcriptomeenabled transcriptomeenable VBN cord-003318-abs9rvjk 393 2 discovery discovery NN cord-003318-abs9rvjk 393 3 and and CC cord-003318-abs9rvjk 393 4 functional functional JJ cord-003318-abs9rvjk 393 5 characterization characterization NN cord-003318-abs9rvjk 393 6 of of IN cord-003318-abs9rvjk 393 7 enzymes enzyme NNS cord-003318-abs9rvjk 393 8 related relate VBN cord-003318-abs9rvjk 393 9 to to IN cord-003318-abs9rvjk 393 10 ( ( -LRB- cord-003318-abs9rvjk 393 11 2S)-pinocembrin 2s)-pinocembrin JJ cord-003318-abs9rvjk 393 12 biosynthesis biosynthesis NN cord-003318-abs9rvjk 393 13 from from IN cord-003318-abs9rvjk 393 14 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 393 15 caudatum caudatum NN cord-003318-abs9rvjk 393 16 and and CC cord-003318-abs9rvjk 393 17 their -PRON- PRP$ cord-003318-abs9rvjk 393 18 application application NN cord-003318-abs9rvjk 393 19 for for IN cord-003318-abs9rvjk 393 20 metabolic metabolic JJ cord-003318-abs9rvjk 393 21 engineering engineering NN cord-003318-abs9rvjk 393 22 Functional functional JJ cord-003318-abs9rvjk 393 23 analyses analysis NNS cord-003318-abs9rvjk 393 24 of of IN cord-003318-abs9rvjk 393 25 OcRhS1 OcRhS1 NNP cord-003318-abs9rvjk 393 26 and and CC cord-003318-abs9rvjk 393 27 OcUER1 ocuer1 NN cord-003318-abs9rvjk 393 28 involved involve VBN cord-003318-abs9rvjk 393 29 in in IN cord-003318-abs9rvjk 393 30 UDP UDP NNP cord-003318-abs9rvjk 393 31 - - HYPH cord-003318-abs9rvjk 393 32 L l NN cord-003318-abs9rvjk 393 33 - - HYPH cord-003318-abs9rvjk 393 34 rhamnose rhamnose JJ cord-003318-abs9rvjk 393 35 biosynthesis biosynthesis NN cord-003318-abs9rvjk 393 36 in in IN cord-003318-abs9rvjk 393 37 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 393 38 caudatum caudatum NN cord-003318-abs9rvjk 393 39 Interactions Interactions NNPS cord-003318-abs9rvjk 393 40 among among IN cord-003318-abs9rvjk 393 41 SARS SARS NNP cord-003318-abs9rvjk 393 42 - - HYPH cord-003318-abs9rvjk 393 43 CoV CoV NNP cord-003318-abs9rvjk 393 44 accessory accessory NN cord-003318-abs9rvjk 393 45 proteins protein NNS cord-003318-abs9rvjk 393 46 revealed reveal VBN cord-003318-abs9rvjk 393 47 by by IN cord-003318-abs9rvjk 393 48 bimolecular bimolecular NNP cord-003318-abs9rvjk 393 49 fluorescence fluorescence NN cord-003318-abs9rvjk 393 50 complementation complementation NN cord-003318-abs9rvjk 393 51 assay assay NN cord-003318-abs9rvjk 393 52 cDNA cdna NN cord-003318-abs9rvjk 393 53 isolation isolation NN cord-003318-abs9rvjk 393 54 and and CC cord-003318-abs9rvjk 393 55 functional functional JJ cord-003318-abs9rvjk 393 56 characterization characterization NN cord-003318-abs9rvjk 393 57 of of IN cord-003318-abs9rvjk 393 58 squalene squalene NN cord-003318-abs9rvjk 393 59 synthase synthase NN cord-003318-abs9rvjk 393 60 gene gene NN cord-003318-abs9rvjk 393 61 from from IN cord-003318-abs9rvjk 393 62 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 393 63 caudatum caudatum NN cord-003318-abs9rvjk 393 64 Probing probe VBG cord-003318-abs9rvjk 393 65 steroidal steroidal JJ cord-003318-abs9rvjk 393 66 substrate substrate NN cord-003318-abs9rvjk 393 67 specificity specificity NN cord-003318-abs9rvjk 393 68 of of IN cord-003318-abs9rvjk 393 69 cytochrome cytochrome NN cord-003318-abs9rvjk 393 70 P450 p450 NN cord-003318-abs9rvjk 393 71 BM3 BM3 NNP cord-003318-abs9rvjk 393 72 variants variant VBZ cord-003318-abs9rvjk 393 73 Steroids steroid NNS cord-003318-abs9rvjk 393 74 hydroxylation hydroxylation NN cord-003318-abs9rvjk 393 75 catalyzed catalyze VBN cord-003318-abs9rvjk 393 76 by by IN cord-003318-abs9rvjk 393 77 the the DT cord-003318-abs9rvjk 393 78 monooxygenase monooxygenase NN cord-003318-abs9rvjk 393 79 mutant mutant NN cord-003318-abs9rvjk 393 80 139 139 CD cord-003318-abs9rvjk 393 81 - - SYM cord-003318-abs9rvjk 393 82 3 3 CD cord-003318-abs9rvjk 393 83 from from IN cord-003318-abs9rvjk 393 84 Bacillus Bacillus NNP cord-003318-abs9rvjk 393 85 megaterium megaterium NN cord-003318-abs9rvjk 394 1 BM3 BM3 NNP cord-003318-abs9rvjk 394 2 Metabolic Metabolic NNP cord-003318-abs9rvjk 394 3 engineering engineering NN cord-003318-abs9rvjk 394 4 of of IN cord-003318-abs9rvjk 394 5 Escherichia Escherichia NNP cord-003318-abs9rvjk 394 6 coli coli NNS cord-003318-abs9rvjk 394 7 for for IN cord-003318-abs9rvjk 394 8 1-butanol 1-butanol CD cord-003318-abs9rvjk 394 9 production production NN cord-003318-abs9rvjk 394 10 Cytotoxic Cytotoxic NNP cord-003318-abs9rvjk 394 11 cholestane cholestane VBD cord-003318-abs9rvjk 394 12 glycosides glycoside NNS cord-003318-abs9rvjk 394 13 from from IN cord-003318-abs9rvjk 394 14 the the DT cord-003318-abs9rvjk 394 15 bulbs bulb NNS cord-003318-abs9rvjk 394 16 of of IN cord-003318-abs9rvjk 394 17 Ornithogalum Ornithogalum NNP cord-003318-abs9rvjk 395 1 saundersiae saundersiae NNP cord-003318-abs9rvjk 395 2 Supplementary Supplementary NNP cord-003318-abs9rvjk 395 3 data datum NNS cord-003318-abs9rvjk 395 4 associated associate VBN cord-003318-abs9rvjk 395 5 with with IN cord-003318-abs9rvjk 395 6 this this DT cord-003318-abs9rvjk 395 7 article article NN cord-003318-abs9rvjk 395 8 can can MD cord-003318-abs9rvjk 395 9 be be VB cord-003318-abs9rvjk 395 10 found find VBN cord-003318-abs9rvjk 395 11 in in IN cord-003318-abs9rvjk 395 12 the the DT cord-003318-abs9rvjk 395 13 online online JJ cord-003318-abs9rvjk 395 14 version version NN cord-003318-abs9rvjk 395 15 at at IN cord-003318-abs9rvjk 395 16 doi:10.1016 doi:10.1016 NNP cord-003318-abs9rvjk 395 17 / / SYM cord-003318-abs9rvjk 395 18 j.apsb.2018.04.006 j.apsb.2018.04.006 NNP cord-003318-abs9rvjk 395 19 . . .