Biosynthesis of carbapenem antibiotics: new carbapenam substrates for carbapenem synthase (CarC).

A non-haem iron and 2-oxoglutarate oxygenase, CarC catalyses the highly unusual epimerisation and desaturation of a (3S,5S)-carbapenam 2 to give a (5R)-carbapenem 1. All stereoisomers of 2 were synthesised and analysed as CarC substrates. The results imply that the (3S,5S)-carbapenam is an intermedi...

Full description

Bibliographic Details
Main Authors: Sleeman, M, Smith, P, Kellam, B, Chhabra, SR, Bycroft, B, Schofield, C
Format: Journal article
Language:English
Published: 2004
Description
Summary:A non-haem iron and 2-oxoglutarate oxygenase, CarC catalyses the highly unusual epimerisation and desaturation of a (3S,5S)-carbapenam 2 to give a (5R)-carbapenem 1. All stereoisomers of 2 were synthesised and analysed as CarC substrates. The results imply that the (3S,5S)-carbapenam is an intermediate in carbapenem biosynthesis and that CarC is able to accept unnatural stereoisomers of its carbapenam substrate.