With our current antibiotic arsenal dwindling, the need for new antibiotics with novel mechanisms is needed. Described herein are the syntheses of sets of hydroxamate containing monobactams, bicyclic β-lactams, and cephalosporins in addition to their biological evaluations.Chapter 1 provides a general introduction to antibiotics and the β-lactam family with an emphasis on utilizing the β-lactam core for delivery of medicinal agents. The Chapter then concludes with a preview of the present work in addition to key literature precedent. Chapters 2-4 detail studies on the syntheses of monobactams, bicyclic hydroxamate containing β-lactams, and cephalosporins bearing hydroxamate functionality. As reported, a number of compounds exhibited notable antibacterial activity and/or β-lactamase inhibitory activity. Chapter 5 discusses the synthesis of hydroxamate containing β-lactam systems bearing an alkylthio linkage between hydroxamate and β-lactam. Chapter 6 presents the syntheses of an intriguing library of hydroxamate containing, N-methylthiolated monobactams. A number of compounds exhibited significant anti-TB and β-lactamase inhibitory activity, with MIC values in the range of 25 to <0.19 μM against TB, and Ki values in the range of 25-0.03 μM against purified NDM-1 and VIM-1 lysate metallo β-lactamases. Chapter 7 then focuses on the syntheses and biological evaluations of penicillins and cephalosporins possessing O-substituted hydroxamates as alternative "ionizable" groups in place for the carboxylate. Many of these compounds have potent activity against a variety of Gram-positive bacteria. Lastly, Chapter 8 discusses the design, syntheses, and anti-tuberculosis activities for a number of cephalosproin-pBTZ conjugates. These conjugates showed notable anti-tuberculosis activity with MIC values in the range of 4.6 to 1.5 μM.