id sid tid token lemma pos kh04dn4272j 1 1 β β X kh04dn4272j 1 2 - - PUNCT kh04dn4272j 1 3 lactam lactam NOUN kh04dn4272j 1 4 antibiotics antibiotic NOUN kh04dn4272j 1 5 are be AUX kh04dn4272j 1 6 arguably arguably ADV kh04dn4272j 1 7 the the DET kh04dn4272j 1 8 most most ADV kh04dn4272j 1 9 important important ADJ kh04dn4272j 1 10 discovery discovery NOUN kh04dn4272j 1 11 in in ADP kh04dn4272j 1 12 the the DET kh04dn4272j 1 13 history history NOUN kh04dn4272j 1 14 of of ADP kh04dn4272j 1 15 modern modern ADJ kh04dn4272j 1 16 medicine medicine NOUN kh04dn4272j 1 17 . . PUNCT kh04dn4272j 2 1 because because SCONJ kh04dn4272j 2 2 of of ADP kh04dn4272j 2 3 these these DET kh04dn4272j 2 4 small small ADJ kh04dn4272j 2 5 molecules molecule NOUN kh04dn4272j 2 6 , , PUNCT kh04dn4272j 2 7 minor minor ADJ kh04dn4272j 2 8 infections infection NOUN kh04dn4272j 2 9 are be AUX kh04dn4272j 2 10 no no ADV kh04dn4272j 2 11 longer long ADV kh04dn4272j 2 12 necessarily necessarily ADV kh04dn4272j 2 13 considered consider VERB kh04dn4272j 2 14 a a DET kh04dn4272j 2 15 death death NOUN kh04dn4272j 2 16 sentence sentence NOUN kh04dn4272j 2 17 . . PUNCT kh04dn4272j 3 1 however however ADV kh04dn4272j 3 2 , , PUNCT kh04dn4272j 3 3 in in ADP kh04dn4272j 3 4 recent recent ADJ kh04dn4272j 3 5 years year NOUN kh04dn4272j 3 6 , , PUNCT kh04dn4272j 3 7 the the DET kh04dn4272j 3 8 prevalence prevalence NOUN kh04dn4272j 3 9 of of ADP kh04dn4272j 3 10 resistance resistance NOUN kh04dn4272j 3 11 to to ADP kh04dn4272j 3 12 these these DET kh04dn4272j 3 13 life life NOUN kh04dn4272j 3 14 - - PUNCT kh04dn4272j 3 15 saving save VERB kh04dn4272j 3 16 compounds compound NOUN kh04dn4272j 3 17 has have AUX kh04dn4272j 3 18 dramatically dramatically ADV kh04dn4272j 3 19 increased increase VERB kh04dn4272j 3 20 . . PUNCT kh04dn4272j 4 1 one one NUM kh04dn4272j 4 2 way way NOUN kh04dn4272j 4 3 to to PART kh04dn4272j 4 4 combat combat VERB kh04dn4272j 4 5 resistance resistance NOUN kh04dn4272j 4 6 is be AUX kh04dn4272j 4 7 to to PART kh04dn4272j 4 8 generate generate VERB kh04dn4272j 4 9 both both PRON kh04dn4272j 4 10 new new ADJ kh04dn4272j 4 11 antibiotic antibiotic ADJ kh04dn4272j 4 12 compounds compound NOUN kh04dn4272j 4 13 and and CCONJ kh04dn4272j 4 14 new new ADJ kh04dn4272j 4 15 synthetic synthetic ADJ kh04dn4272j 4 16 strategies strategy NOUN kh04dn4272j 4 17 to to PART kh04dn4272j 4 18 make make VERB kh04dn4272j 4 19 these these DET kh04dn4272j 4 20 chemical chemical ADJ kh04dn4272j 4 21 entities entity NOUN kh04dn4272j 4 22 . . PUNCT kh04dn4272j 5 1 oxamazins oxamazin NOUN kh04dn4272j 5 2 , , PUNCT kh04dn4272j 5 3 heteroatom heteroatom NOUN kh04dn4272j 5 4 - - PUNCT kh04dn4272j 5 5 activated activate VERB kh04dn4272j 5 6 β β PROPN kh04dn4272j 5 7 - - PUNCT kh04dn4272j 5 8 lactams lactams NOUN kh04dn4272j 5 9 , , PUNCT kh04dn4272j 5 10 have have AUX kh04dn4272j 5 11 demonstrated demonstrate VERB kh04dn4272j 5 12 activity activity NOUN kh04dn4272j 5 13 similar similar ADJ kh04dn4272j 5 14 to to ADP kh04dn4272j 5 15 traditional traditional ADJ kh04dn4272j 5 16 β β NOUN kh04dn4272j 5 17 - - PUNCT kh04dn4272j 5 18 lactams lactams NOUN kh04dn4272j 5 19 , , PUNCT kh04dn4272j 5 20 and and CCONJ kh04dn4272j 5 21 thus thus ADV kh04dn4272j 5 22 are be AUX kh04dn4272j 5 23 of of ADP kh04dn4272j 5 24 interest interest NOUN kh04dn4272j 5 25 . . PUNCT kh04dn4272j 6 1 herein herein ADV kh04dn4272j 6 2 , , PUNCT kh04dn4272j 6 3 we we PRON kh04dn4272j 6 4 report report VERB kh04dn4272j 6 5 different different ADJ kh04dn4272j 6 6 strategies strategy NOUN kh04dn4272j 6 7 for for ADP kh04dn4272j 6 8 the the DET kh04dn4272j 6 9 syntheses synthesis NOUN kh04dn4272j 6 10 of of ADP kh04dn4272j 6 11 bicyclic bicyclic NOUN kh04dn4272j 6 12 and and CCONJ kh04dn4272j 6 13 monocyclic monocyclic ADJ kh04dn4272j 6 14 oxamazins oxamazin NOUN kh04dn4272j 6 15 . . PUNCT kh04dn4272j 7 1 in in ADP kh04dn4272j 7 2 chapter chapter NOUN kh04dn4272j 7 3 1 1 NUM kh04dn4272j 7 4 , , PUNCT kh04dn4272j 7 5 a a DET kh04dn4272j 7 6 broad broad ADJ kh04dn4272j 7 7 overview overview NOUN kh04dn4272j 7 8 of of ADP kh04dn4272j 7 9 β β PROPN kh04dn4272j 7 10 - - PUNCT kh04dn4272j 7 11 lactam lactam NOUN kh04dn4272j 7 12 antibiotics antibiotic NOUN kh04dn4272j 7 13 will will AUX kh04dn4272j 7 14 be be AUX kh04dn4272j 7 15 given give VERB kh04dn4272j 7 16 including include VERB kh04dn4272j 7 17 the the DET kh04dn4272j 7 18 discovery discovery NOUN kh04dn4272j 7 19 of of ADP kh04dn4272j 7 20 these these DET kh04dn4272j 7 21 life life NOUN kh04dn4272j 7 22 - - PUNCT kh04dn4272j 7 23 saving save VERB kh04dn4272j 7 24 compounds compound NOUN kh04dn4272j 7 25 and and CCONJ kh04dn4272j 7 26 their their PRON kh04dn4272j 7 27 historical historical ADJ kh04dn4272j 7 28 syntheses synthesis NOUN kh04dn4272j 7 29 . . PUNCT kh04dn4272j 8 1 several several ADJ kh04dn4272j 8 2 synthetic synthetic ADJ kh04dn4272j 8 3 strategies strategy NOUN kh04dn4272j 8 4 for for ADP kh04dn4272j 8 5 the the DET kh04dn4272j 8 6 closure closure NOUN kh04dn4272j 8 7 of of ADP kh04dn4272j 8 8 the the DET kh04dn4272j 8 9 β β PROPN kh04dn4272j 8 10 - - PUNCT kh04dn4272j 8 11 lactam lactam NOUN kh04dn4272j 8 12 ring ring NOUN kh04dn4272j 8 13 and and CCONJ kh04dn4272j 8 14 subsequent subsequent ADJ kh04dn4272j 8 15 elaboration elaboration NOUN kh04dn4272j 8 16 will will AUX kh04dn4272j 8 17 be be AUX kh04dn4272j 8 18 discussed discuss VERB kh04dn4272j 8 19 . . PUNCT kh04dn4272j 9 1 the the DET kh04dn4272j 9 2 rapidly rapidly ADV kh04dn4272j 9 3 growing grow VERB kh04dn4272j 9 4 concern concern NOUN kh04dn4272j 9 5 of of ADP kh04dn4272j 9 6 bacterial bacterial ADJ kh04dn4272j 9 7 resistance resistance NOUN kh04dn4272j 9 8 development development NOUN kh04dn4272j 9 9 and and CCONJ kh04dn4272j 9 10 the the DET kh04dn4272j 9 11 means mean NOUN kh04dn4272j 9 12 by by ADP kh04dn4272j 9 13 which which PRON kh04dn4272j 9 14 bacteria bacteria NOUN kh04dn4272j 9 15 maintain maintain VERB kh04dn4272j 9 16 their their PRON kh04dn4272j 9 17 resistance resistance NOUN kh04dn4272j 9 18 will will AUX kh04dn4272j 9 19 also also ADV kh04dn4272j 9 20 be be AUX kh04dn4272j 9 21 presented present VERB kh04dn4272j 9 22 . . PUNCT kh04dn4272j 10 1 in in ADP kh04dn4272j 10 2 chapter chapter NOUN kh04dn4272j 10 3 2 2 NUM kh04dn4272j 10 4 , , PUNCT kh04dn4272j 10 5 initial initial ADJ kh04dn4272j 10 6 studies study NOUN kh04dn4272j 10 7 incorporating incorporate VERB kh04dn4272j 10 8 pd pd PROPN kh04dn4272j 10 9 ( ( PUNCT kh04dn4272j 10 10 0 0 NUM kh04dn4272j 10 11 ) ) PUNCT kh04dn4272j 10 12 methodology methodology NOUN kh04dn4272j 10 13 will will AUX kh04dn4272j 10 14 be be AUX kh04dn4272j 10 15 discussed discuss VERB kh04dn4272j 10 16 . . PUNCT kh04dn4272j 11 1 in in ADP kh04dn4272j 11 2 an an DET kh04dn4272j 11 3 attempt attempt NOUN kh04dn4272j 11 4 to to PART kh04dn4272j 11 5 take take VERB kh04dn4272j 11 6 advantage advantage NOUN kh04dn4272j 11 7 of of ADP kh04dn4272j 11 8 π π PROPN kh04dn4272j 11 9 - - PUNCT kh04dn4272j 11 10 allyl allyl NOUN kh04dn4272j 11 11 chemistry chemistry NOUN kh04dn4272j 11 12 , , PUNCT kh04dn4272j 11 13 several several ADJ kh04dn4272j 11 14 acyclic acyclic NOUN kh04dn4272j 11 15 substrates substrate NOUN kh04dn4272j 11 16 were be AUX kh04dn4272j 11 17 generated generate VERB kh04dn4272j 11 18 to to PART kh04dn4272j 11 19 test test VERB kh04dn4272j 11 20 the the DET kh04dn4272j 11 21 utility utility NOUN kh04dn4272j 11 22 of of ADP kh04dn4272j 11 23 π π PROPN kh04dn4272j 11 24 - - PUNCT kh04dn4272j 11 25 allyl allyl NOUN kh04dn4272j 11 26 chemistry chemistry NOUN kh04dn4272j 11 27 for for ADP kh04dn4272j 11 28 the the DET kh04dn4272j 11 29 formation formation NOUN kh04dn4272j 11 30 of of ADP kh04dn4272j 11 31 monocyclic monocyclic ADJ kh04dn4272j 11 32 and and CCONJ kh04dn4272j 11 33 bicyclic bicyclic NOUN kh04dn4272j 11 34 oxamazins oxamazin NOUN kh04dn4272j 11 35 . . PUNCT kh04dn4272j 12 1 the the DET kh04dn4272j 12 2 syntheses synthesis NOUN kh04dn4272j 12 3 of of ADP kh04dn4272j 12 4 the the DET kh04dn4272j 12 5 substrates substrate NOUN kh04dn4272j 12 6 and and CCONJ kh04dn4272j 12 7 the the DET kh04dn4272j 12 8 challenges challenge NOUN kh04dn4272j 12 9 associated associate VERB kh04dn4272j 12 10 with with ADP kh04dn4272j 12 11 the the DET kh04dn4272j 12 12 pd pd PROPN kh04dn4272j 12 13 ( ( PUNCT kh04dn4272j 12 14 0 0 NUM kh04dn4272j 12 15 ) ) PUNCT kh04dn4272j 12 16 chemistry chemistry NOUN kh04dn4272j 12 17 are be AUX kh04dn4272j 12 18 discussed discuss VERB kh04dn4272j 12 19 . . PUNCT kh04dn4272j 13 1 additionally additionally ADV kh04dn4272j 13 2 , , PUNCT kh04dn4272j 13 3 an an DET kh04dn4272j 13 4 interesting interesting ADJ kh04dn4272j 13 5 new new ADJ kh04dn4272j 13 6 route route NOUN kh04dn4272j 13 7 to to ADP kh04dn4272j 13 8 cephalosporins cephalosporin NOUN kh04dn4272j 13 9 through through ADP kh04dn4272j 13 10 the the DET kh04dn4272j 13 11 use use NOUN kh04dn4272j 13 12 of of ADP kh04dn4272j 13 13 pd(0 pd(0 PROPN kh04dn4272j 13 14 ) ) PUNCT kh04dn4272j 13 15 chemistry chemistry NOUN kh04dn4272j 13 16 will will AUX kh04dn4272j 13 17 be be AUX kh04dn4272j 13 18 proposed propose VERB kh04dn4272j 13 19 . . PUNCT kh04dn4272j 14 1 finally finally ADV kh04dn4272j 14 2 , , PUNCT kh04dn4272j 14 3 a a DET kh04dn4272j 14 4 new new ADJ kh04dn4272j 14 5 synthetic synthetic ADJ kh04dn4272j 14 6 strategy strategy NOUN kh04dn4272j 14 7 for for ADP kh04dn4272j 14 8 the the DET kh04dn4272j 14 9 rapid rapid ADJ kh04dn4272j 14 10 access access NOUN kh04dn4272j 14 11 of of ADP kh04dn4272j 14 12 carbocyclic carbocyclic ADJ kh04dn4272j 14 13 nucleosides nucleoside NOUN kh04dn4272j 14 14 utilizing utilize VERB kh04dn4272j 14 15 the the DET kh04dn4272j 14 16 protocols protocol NOUN kh04dn4272j 14 17 discussed discuss VERB kh04dn4272j 14 18 in in ADP kh04dn4272j 14 19 this this DET kh04dn4272j 14 20 chapter chapter NOUN kh04dn4272j 14 21 will will AUX kh04dn4272j 14 22 be be AUX kh04dn4272j 14 23 hypothesized hypothesize VERB kh04dn4272j 14 24 . . PUNCT kh04dn4272j 15 1 in in ADP kh04dn4272j 15 2 chapter chapter NOUN kh04dn4272j 15 3 3 3 NUM kh04dn4272j 15 4 , , PUNCT kh04dn4272j 15 5 ring ring NOUN kh04dn4272j 15 6 - - PUNCT kh04dn4272j 15 7 closing closing NOUN kh04dn4272j 15 8 olefin olefin NOUN kh04dn4272j 15 9 metathesis metathesis NOUN kh04dn4272j 15 10 will will AUX kh04dn4272j 15 11 be be AUX kh04dn4272j 15 12 introduced introduce VERB kh04dn4272j 15 13 and and CCONJ kh04dn4272j 15 14 the the DET kh04dn4272j 15 15 utility utility NOUN kh04dn4272j 15 16 of of ADP kh04dn4272j 15 17 this this DET kh04dn4272j 15 18 versatile versatile ADJ kh04dn4272j 15 19 chemistry chemistry NOUN kh04dn4272j 15 20 for for ADP kh04dn4272j 15 21 the the DET kh04dn4272j 15 22 synthesis synthesis NOUN kh04dn4272j 15 23 of of ADP kh04dn4272j 15 24 the the DET kh04dn4272j 15 25 bicyclic bicyclic NOUN kh04dn4272j 15 26 oxamazin oxamazin PROPN kh04dn4272j 15 27 core core NOUN kh04dn4272j 15 28 will will AUX kh04dn4272j 15 29 be be AUX kh04dn4272j 15 30 explored explore VERB kh04dn4272j 15 31 . . PUNCT kh04dn4272j 16 1 the the DET kh04dn4272j 16 2 core core ADJ kh04dn4272j 16 3 backbone backbone NOUN kh04dn4272j 16 4 of of ADP kh04dn4272j 16 5 bicyclic bicyclic NOUN kh04dn4272j 16 6 oxamazins oxamazin NOUN kh04dn4272j 16 7 were be AUX kh04dn4272j 16 8 synthesized synthesize VERB kh04dn4272j 16 9 and and CCONJ kh04dn4272j 16 10 used use VERB kh04dn4272j 16 11 in in ADP kh04dn4272j 16 12 intramolecular intramolecular ADJ kh04dn4272j 16 13 ring ring NOUN kh04dn4272j 16 14 - - PUNCT kh04dn4272j 16 15 closing close VERB kh04dn4272j 16 16 olefin olefin NOUN kh04dn4272j 16 17 metathesis metathesis NOUN kh04dn4272j 16 18 reactions reaction NOUN kh04dn4272j 16 19 . . PUNCT kh04dn4272j 17 1 the the DET kh04dn4272j 17 2 results result NOUN kh04dn4272j 17 3 of of ADP kh04dn4272j 17 4 those those DET kh04dn4272j 17 5 studies study NOUN kh04dn4272j 17 6 will will AUX kh04dn4272j 17 7 be be AUX kh04dn4272j 17 8 presented present VERB kh04dn4272j 17 9 . . PUNCT kh04dn4272j 18 1 finally finally ADV kh04dn4272j 18 2 , , PUNCT kh04dn4272j 18 3 the the DET kh04dn4272j 18 4 potential potential NOUN kh04dn4272j 18 5 of of ADP kh04dn4272j 18 6 this this DET kh04dn4272j 18 7 chemistry chemistry NOUN kh04dn4272j 18 8 to to PART kh04dn4272j 18 9 generate generate VERB kh04dn4272j 18 10 fully fully ADV kh04dn4272j 18 11 realized realize VERB kh04dn4272j 18 12 antibiotics antibiotic NOUN kh04dn4272j 18 13 will will AUX kh04dn4272j 18 14 be be AUX kh04dn4272j 18 15 discussed discuss VERB kh04dn4272j 18 16 . . PUNCT kh04dn4272j 19 1 in in ADP kh04dn4272j 19 2 chapter chapter NOUN kh04dn4272j 19 3 4 4 NUM kh04dn4272j 19 4 , , PUNCT kh04dn4272j 19 5 the the DET kh04dn4272j 19 6 incorporation incorporation NOUN kh04dn4272j 19 7 of of ADP kh04dn4272j 19 8 peripheral peripheral PROPN kh04dn4272j 19 9 c-3 c-3 PROPN kh04dn4272j 19 10 acylamine acylamine PROPN kh04dn4272j 19 11 and and CCONJ kh04dn4272j 19 12 ionizable ionizable ADJ kh04dn4272j 19 13 group group NOUN kh04dn4272j 19 14 functionalization functionalization NOUN kh04dn4272j 19 15 on on ADP kh04dn4272j 19 16 the the DET kh04dn4272j 19 17 bicyclic bicyclic NOUN kh04dn4272j 19 18 oxamazin oxamazin PROPN kh04dn4272j 19 19 core core NOUN kh04dn4272j 19 20 generated generate VERB kh04dn4272j 19 21 from from ADP kh04dn4272j 19 22 the the DET kh04dn4272j 19 23 use use NOUN kh04dn4272j 19 24 of of ADP kh04dn4272j 19 25 ring ring NOUN kh04dn4272j 19 26 - - PUNCT kh04dn4272j 19 27 closing closing NOUN kh04dn4272j 19 28 olefin olefin NOUN kh04dn4272j 19 29 metathesis metathesis NOUN kh04dn4272j 19 30 will will AUX kh04dn4272j 19 31 be be AUX kh04dn4272j 19 32 presented present VERB kh04dn4272j 19 33 . . PUNCT kh04dn4272j 20 1 the the DET kh04dn4272j 20 2 synthesis synthesis NOUN kh04dn4272j 20 3 of of ADP kh04dn4272j 20 4 the the DET kh04dn4272j 20 5 fully fully ADV kh04dn4272j 20 6 functionalized functionalize VERB kh04dn4272j 20 7 bicyclic bicyclic NOUN kh04dn4272j 20 8 oxamazin oxamazin PROPN kh04dn4272j 20 9 was be AUX kh04dn4272j 20 10 addressed address VERB kh04dn4272j 20 11 through through ADP kh04dn4272j 20 12 three three NUM kh04dn4272j 20 13 pathways pathway NOUN kh04dn4272j 20 14 . . PUNCT kh04dn4272j 21 1 the the DET kh04dn4272j 21 2 first first ADJ kh04dn4272j 21 3 focused focus VERB kh04dn4272j 21 4 on on ADP kh04dn4272j 21 5 the the DET kh04dn4272j 21 6 generation generation NOUN kh04dn4272j 21 7 two two NUM kh04dn4272j 21 8 subunits subunit NOUN kh04dn4272j 21 9 : : PUNCT kh04dn4272j 21 10 and and CCONJ kh04dn4272j 21 11 amino amino NOUN kh04dn4272j 21 12 acid acid NOUN kh04dn4272j 21 13 and and CCONJ kh04dn4272j 21 14 an an DET kh04dn4272j 21 15 aminooxy aminooxy PROPN kh04dn4272j 21 16 acid acid PROPN kh04dn4272j 21 17 ester ester NOUN kh04dn4272j 21 18 . . PUNCT kh04dn4272j 22 1 two two NUM kh04dn4272j 22 2 other other ADJ kh04dn4272j 22 3 strategies strategy NOUN kh04dn4272j 22 4 employing employ VERB kh04dn4272j 22 5 later later ADV kh04dn4272j 22 6 stage stage NOUN kh04dn4272j 22 7 synthetic synthetic ADJ kh04dn4272j 22 8 intermediates intermediate NOUN kh04dn4272j 22 9 as as ADP kh04dn4272j 22 10 scaffolds scaffold NOUN kh04dn4272j 22 11 for for ADP kh04dn4272j 22 12 further further ADJ kh04dn4272j 22 13 functionalization functionalization NOUN kh04dn4272j 22 14 were be AUX kh04dn4272j 22 15 also also ADV kh04dn4272j 22 16 explored explore VERB kh04dn4272j 22 17 . . PUNCT kh04dn4272j 23 1 compounds compound NOUN kh04dn4272j 23 2 generated generate VERB kh04dn4272j 23 3 through through ADP kh04dn4272j 23 4 these these DET kh04dn4272j 23 5 pathways pathway NOUN kh04dn4272j 23 6 were be AUX kh04dn4272j 23 7 tested test VERB kh04dn4272j 23 8 for for ADP kh04dn4272j 23 9 their their PRON kh04dn4272j 23 10 biological biological ADJ kh04dn4272j 23 11 activity activity NOUN kh04dn4272j 23 12 and and CCONJ kh04dn4272j 23 13 those those DET kh04dn4272j 23 14 data datum NOUN kh04dn4272j 23 15 are be AUX kh04dn4272j 23 16 presented present VERB kh04dn4272j 23 17 as as ADV kh04dn4272j 23 18 well well ADV kh04dn4272j 23 19 . . PUNCT