34 高等植物におけるイソプレノイドの生合成 : 逆縮合面からのプレニル鎖の延長

概要

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When the (E,E)-farnesol was enzymatically synthesized from an equimolar mixture of 3,3-dimethylallyl pyrophosphate (DMAPP) and (E)- or (Z)-[4-^2H]isopentenyl pyrophosphate (IPP) in the presence of iodoacetamide (IAA) with the cell-free extract of Pisum sativum, occurrence of the unusual addition of allylic residue to the re-re face of the carbon-carbon double bond of IPP was found. This unusual addition was indicated by the chirality of C-4 and C-8 of the deuterated farnesol obtained. The elimination of the pro-2R hydrogen of IPP occurred during the enzymatically formation of farnesol from an equimolar mixture of DMAPP and (R)- or (S)-[2-^2H]IPP by incubation with the same enzyme solution as above in the presence of IAA. These findings indicated occurrence of the anti elimination of the pro-2R hydrogen atom. The addition of the allylic residue to the re-re face of the carbon-carbon double bond of IPP as well as the anti elimination of the pro-2R hydrogen atom are the first unusual examples in E-prenyl chain elongation in the biosynthesis of (E,E)-farnesol and squalene.
天然有機化合物討論会の論文
1986-09-09