Computing and Library Services - delivering an inspiring information environment

Metal-ion catalysed hydrolysis of some ?-lactam antibiotics

Gensmantel, Nigel P., Proctor, Philip and Page, Michael I. (1980) Metal-ion catalysed hydrolysis of some ?-lactam antibiotics. Journal of the Chemical Society, Perkin Transactions 2 (11). pp. 1725-1732. ISSN 1472-779X

Metadata only available from this repository.


The metal(II)-ion catalysed hydrolysis of some pencillin and cephalosporin derivatives in water at 30° shows saturation kinetics. A 1 : 1 complex is formed between the metal ion and penicillin which is attacked by hydroxide ion up to 108 fold faster than the unco-ordinated compound. The site of co-ordination of the penicillins and copper(II) ions is the -lactam nitrogen and the carboxylate group. The association constants for the cephalosporins and metal ions are greater than those for the penicillins but the transition states for the cephalosporin reaction with hydroxide ion bind less tightly to metal ions. The order of rate enhancement brought about by the metal ion is CuII > ZnII > NiII CoII. The metal ions are thought to stabilise the tetrahedral intermediate formed by hydroxide ion attack on the -lactam. Some comments are made about metal ions as electrophilic catalysts in enzymes.

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
Related URLs:
Depositing User: Sharon Beastall
Date Deposited: 11 Nov 2009 13:53
Last Modified: 28 Aug 2021 10:52


Downloads per month over past year

Repository Staff Only: item control page

View Item View Item

University of Huddersfield, Queensgate, Huddersfield, HD1 3DH Copyright and Disclaimer All rights reserved ©