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 language | English |
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Pages (from-to) | 297-303 |
Number of pages | 7 |
Journal | Accounts of Chemical Research |
Volume | 37 |
Issue number | 5 |
Early online date | 24 Feb 2004 |
DOIs | |
Publication status | Published - May 2004 |