Stereospecific intramolecular proton transfer in the cyclization of geranylgeranyl diphosphate to (–)-abietadiene catalyzed by recombinant cyclase from grand fir (Abies grandis)

Abstract

The cyclization–rearrangement of deuterated geranylgeranyl diphosphate (GGPP) and (+)-copalyl diphosphate (CPP) catalyzed by recombinant (–)-abietadiene synthase from grand fir proceeds with intramolecular proton transfer from C-19 of GGPP, and from the C-17 pro-E position of CPP, to form the C-16 pro-S methyl group of (–)-abietadiene.