β-sultams-mechanism of reactions and use as inhibitors of serine proteases

β-Sultams are reactive sulfonyl analogues of -lactams and show enormous rate enhancements over analogous reactions of sulfonamides. N-Acyl -sultams undergo S-N rather than C-N fission, although -alkenyl substituents direct nucleophilic attack to the acyl center. They also inactivate serine enzymes such as elastase and -lactamase by sulfonylation of the active site serine. Structure-activity relationships are used to identify differences in transition state structures