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,5R)-carbapenam is an intermediate in carbapenem biosynthesis and that CarC is able to accept unnatural stereoisomers of its carbapenam substrate.
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Sleeman et al. (2004) studied this question.
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