Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Unusual Chain Elongation at the Reversed Face in the Biosynthesis of (E,E)-Farnesol with the Enzyme System of Pisum sativum
Takayuki SugaRong-yu ZhengShinji OhtaTakamitsu YoshiokaToshifumi Hirata
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1987 Volume 16 Issue 3 Pages 497-500

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Abstract

When (E,E)-farnesol was enzymatically synthesized from an equimolar mixture of 3,3-dimethylallyl pyrophosphate and (E)- or (Z)-[4-2H]isopentenyl pyrophosphate (IPP) in the presence of iodoacetamide with a farnesyl pyrophosphate synthetase fraction prepared from Pisum sativum, the unusual addition of allylic residue to the re-re, face of the carbon-carbon double bond of IPP was found to occur. This finding was the first example of the unusual chain elongation against Cornforth’s stereochemical picture for the biosynthesis of isoprenoids.

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