An isotopic probe to follow the stereochemical course of dehydratase reactions in polyketide and fatty acid biosynthesis

Four stereoisomeric and isotopically labelled probes that are suitable to easily follow the stereochemical course of dehydratases have been synthesised. The synthesis made use of an epoxide opening through catalytic hydrogenation that was shown to proceed with inversion of configuration. The obtained labelled probes were applied to study the stereochemical courses of several dehydratases involved in the biosynthesis of selected antibiotics and of fatty acids.