35 イソプレノイド生合成における鎖延長反応の立体化学

概要

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In order to study the stereochemical course of the C-C bond formation in the chain elongation of isoprenoid biosynthesis, we improved the Cornforth's method so that it could be applied more widely and directly to prenyltransferases. In contrast to the original method that requires chirally labelled deutero-mevalonic acids and an enzyme system containing several enzymes in addition to prenyltransferase, our method requires easily obtainable E- or z-4-deutero-isopentenyl pyrophosphate and prenyltransferase. The applicability was warranted by the observation that the chirally labelled 4,8-dideutero-farnesol derived in a good yield from E- or z-4-deutero-isopentenyl pyrophosphate by the reaction with dimethyl-allyl pyrophosphate and pig liver farnesyl pyrophosphate synthetase was converted by ozonolysis into S-(+) or R-(-)levulinic acid. We separated from Bacillus subtilis undecaprenyl pyrophosphate synthetase which catalyzed the cis condensation of isopentenyl pyrophosphate with elimination of the pro-S hydrogen at C-2. The configuration of the deutero-levulinic acid obtained by the new method is being determined.
天然有機化合物討論会の論文
1983-09-15