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

Michael I. Page

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

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

Original languageEnglish
Pages (from-to)297-303
Number of pages7
JournalAccounts of Chemical Research
Volume37
Issue number5
Early online date24 Feb 2004
DOIs
Publication statusPublished - May 2004

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