Stereochemistry of the methyl→methylene elimination in the enzyme-catalysed cyclization of geranyl diphosphate to (4S)-limonene

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Robert M. Coates, Charles S. Elmore, Robert M. Coates, Rodney B. Croteau, David C. Williams, Charles S. Elmore, Rodney B. Croteau, Hiromi Morimoto and Philip G. Williams


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.


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