The mechanism of reactions catalysed by the serine β-lactamases

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 PO and PO bond fission and e...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1993-11, Vol.3 (11), p.2317-2322
Main Authors: Laws, Andrew P, Page, Michael I, Slater, Martin J
Format: Article
Language:English
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Summary: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 PO and PO bond fission and exhibits enzyme catalysed nucleophilic displacement of proline. The requirements for general acid catalysed expulsion of proline have interesting stereochemical consequences. Necleophilic 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 PN and PO bond fission and exhibits enzyme catalysed nucleophilic displacement of proline. The requirements for general acid catalysed expulsion of proline have interesting stereochemical consequences.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)80947-1