The mechanism of reactions catalysed by the serine β-lactamases

Andrew P. Laws, Michael I. Page, Martin J. Slater

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Nucleophilic substitution at the β-lactam carbonyl of penicillins usually requires general base and acid catalysis and proceeds via the formation of a tetrahedral intermediate. A class C serine β-lactamase is inhibited by phosphonamidates, shows diastereoselectivity in PO and PO bond fission and exhibits enzyme catalysed nucleophilic displacement of proline. The requirements for general acid catalysed expulsion of proline have interesting stereochemical consequences.

Original languageEnglish
Pages (from-to)2317-2322
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume3
Issue number11
DOIs
Publication statusPublished - Nov 1993

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