THE MECHANISM OF REACTIONS CATALYZED BY THE SERINE BETA-LACTAMASES

Authors
LAWS AP PAGE MI SLATER MJ
Citation
Ap. Laws et al., THE MECHANISM OF REACTIONS CATALYZED BY THE SERINE BETA-LACTAMASES, Bioorganic & medicinal chemistry letters, 3(11), 1993, pp. 2317-2322
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
11
Year of publication
1993
Pages
2317 - 2322
Database
ISI
SICI code
0960-894X(1993)3:11<2317:TMORCB>2.0.ZU;2-V
Abstract
Nucleophilic substitution at the beta-lactam carbonyl of penicillins u sually requires general base and acid catalysis and proceeds via the f ormation of a tetrahedral intermediate. A class C serine beta-lactamas e is inhibited by phosphonamidates, shows diastereoselectivity in P-N and P-0 bond fission and exhibits enzyme catalysed nucleophilic displa cement of proline. The requirements for general acid catalysed expulsi on of proline have interesting stereochemical consequences.