22 ファルネシルピロリン酸合成酵素の不斉合成への応用 : 昆虫フェロモン,Faranalの酵素的合成

概要

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The stereospecificity of farnesyl pyrophosphate synthetase was applied to the synthesis and determination of the chiral structure of faranal, an insect trail pheromone. In the presence of the enzyme, E-(12) and Z isomer (15) of 3-methylpent-3-enyl pyrophosphate reacted stereospecifically with (2E,6Z)-3,7-dimethylnona-2,6-dienyl pyrophosphate (34) to give (4S)-(2E,6E,10Z)-3,4,7,11-tetra-methyltrideca-2,6,10-trienyl pyrophosphate (21) and its R isomer(22), respectively. Each of these two enantiomers was also synthesized enzymatically from (Z)-methylpent-2-enyl pyrophosphate (4), isopentenyl pyrophosphate (2), and 12 or 15. Treatment of 21 (or 22) with alkaline phosphatase afforded the free alcohol 41 (or 43), which was then oxidized to the corresponding aldehyde. Reduction of the double bond at C-2 of the aldehydes derived from 12 and 15 was attempted to obtain 4S-faranals (3S,4S+3R,4S) and 4R-faranals (3R,4R+3S,4R), respectively.
天然有機化合物討論会の論文
1979-09-20