Stereochemistry of the methyl→methylene elimination in the enzyme-catalysed cyclization of geranyl diphosphate to (4S)-limonene
Abstract
The cyclization of (R)-[9-2H1,3H1]geranyl diphosphate catalysed by a recombinant form of (4S)-limonene synthase from spearmint leaf (Mentha spicata) is terminated predominantly by re-facial, anti proton elimination at the cis methyl group, producing (4S, 8E)-[8-2H1,3H1]limonene.