18 イソペンテニルピロリン酸ホモログの酵素反応 : Juvenile Hormoneの生合成へのアプローチ

概要

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It is known that the structural requirement for the allylic pyrophosphates (2 and 3) to condense with isopentenyl pyrophosphate (1a) by the action of farnesyl pyrophosphate synthetase is not very stringent with respect to the alkyl groups R_1 and R_2 in 2, but that certain homologs of type 3 and 4 where R_3 is CH_3 can be synthesized enzymatically from proper artificial substrates. As to isopentenyl pyrophosphate homologs, only 3-ethyl-3-butenyl pyrophosphate (1c) acts as a substrate for the enzyme in place of isopentenyl pyrophosphate (1a) to give new farnesyl pyrophosphate homologs, the stereochemical course of the condensation of 1c being exclusively trans. trans, trans, cis-3,11-Dimethyl-7-ethyltrideca-2,6,10-trien-1-ol (bishomofarnesol) and its pyrophosphate, possible precursors for the biosynthesis of insect juvenile hormone were synthesized enzymatically from cis-3-methyl-2-pentenyl pyrophosphate (18), 1c and 1a.
天然有機化合物討論会の論文
1972-10-01