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.
|Number of pages||6|
|Journal||Bioorganic and Medicinal Chemistry Letters|
|Publication status||Published - Nov 1993|