Beta-sultams-mechanism of reactions and use as inhibitors of serine proteases.
beta-Sultams are reactive sulfonyl analogues of beta-lactams and show enormous rate enhancements over analogous reactions of sulfonamides. N-Acyl beta-sultams undergo S-N rather than C-N fission, although alpha-alkenyl substituents direct nucleophilic attack to the acyl center. They also inactivate serine enzymes such as elastase and beta-lactamase by sulfonylation of the active site serine. Structure-activity relationships are used to identify differences in transition state structures.
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Michael I
MI
Department of Chemical and Biological Sciences, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK.
D006868:Hydrolysis; D015842:Serine Proteinase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000737:chemistry / Q000494:pharmacology*
D015842:Serine Proteinase Inhibitors; D013449:Sulfonamides; C480101:beta-sultam