Issue 20, 2004
From the journal:

Chemical Communications

Penicillins as β-lactamase-dependent prodrugs: enabling role of a vinyl ester exocyclic to the lactam ring†

Carol C. Ruddlea  and  Timothy P. Smyth*a  

* Corresponding authors

a Department of Chemical and Environmental Sciences, University of Limerick, National Technological Park, County Limerick, Ireland
E-mail: timothy.smyth@ul.ie

Abstract

Incorporation of a vinyl ester exocyclic to the β-lactam ring of a penicillin nucleus enables this to act as a β-lactamase-dependent prodrug – rapid release of the (unactivated) alkoxy component of the vinyl ester is triggered by enzyme-catalysed hydrolysis of the β-lactam ring, whilst buffer-catalysed hydrolysis of the structure at neutral pH is particularly slow.

Graphical abstract: Penicillins as β-lactamase-dependent prodrugs: enabling role of a vinyl ester exocyclic to the lactam ring

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Article information

DOI
https://doi.org/10.1039/B409517K
Article type
Communication
Submitted
24 Jun 2004
Accepted
11 Aug 2004
First published
07 Sep 2004

Chem. Commun., 2004, 2332-2333

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Penicillins as β-lactamase-dependent prodrugs: enabling role of a vinyl ester exocyclic to the lactam ring

C. C. Ruddle and T. P. Smyth, Chem. Commun., 2004, 2332 DOI: 10.1039/B409517K

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