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Issue 5, 2004
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Intramolecular general acid catalysis in the aminolysis of β-lactam antibiotics

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Abstract

The rate of aminolysis of benzylpenicillin and cephaloridine by hydroxylamine, unlike other amines, shows only a first order dependence on amine concentration. The rate enhancement compared with that predicted from a Bronsted plot for other primary amines with benzylpenicillin is greater than 106. This is much more than an α-effect and is compatible with rate-limiting formation of the tetrahedral intermediate due to a rapid intramolecular general acid catalysed breakdown of the intermediate. For cephaloridine, the rate enhancement is greater than 104 which demonstrates that β-lactam C–N bond fission and expulsion of the leaving group at C3′ are not concerted.

Graphical abstract: Intramolecular general acid catalysis in the aminolysis of β-lactam antibiotics

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Article information


Submitted
03 Nov 2003
Accepted
21 Jan 2004
First published
09 Feb 2004

Org. Biomol. Chem., 2004,2, 651-654
Article type
Paper

Intramolecular general acid catalysis in the aminolysis of β-lactam antibiotics

A. Llinás and M. I. Page, Org. Biomol. Chem., 2004, 2, 651
DOI: 10.1039/B313900J

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