The mechanism of reactions catalysed by the serine β-lactamases

Laws, Andrew P., Page, Michael I. and Slater, Martin J. (1993) The mechanism of reactions catalysed by the serine β-lactamases. Bioorganic & Medicinal Chemistry Letters, 3 (11). pp. 2317-2322. ISSN 0960-894X

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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 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.

Item Type:	Article
Subjects:	Q Science > Q Science (General) Q Science > QD Chemistry
Schools:	School of Applied Sciences
Related URLs:	Author Author
Depositing User:	Sharon Beastall
Date Deposited:	05 Nov 2009 14:26
Last Modified:	28 Aug 2021 10:52
URI:	http://eprints.hud.ac.uk/id/eprint/6105

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