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Mechanism of clerosterol biosynthesis in Ajuga hairy roots: stereochemistry of C-28 methylation of 24-methylene sterol

✍ Scribed by Takeshi Koami; Kiyoshi Ohyama; Yoshinori Fujimoto

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 82 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01061-4

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✦ Synopsis

Biosynthesis of clerosterol, (24S)-ethylcholesta-5,25-dien-3b-ol (1), involves transfer of the methyl group from S-adenosylmethionine to the C-28 position of a 24-methylene-sterol precursor. The resulting C-24 cationic species undergoes migration of hydrogen from C-25 to C-24, followed by deprotonation from C-26 to form 1. We have now investigated the steric course of the methylation in hairy roots of Ajuga reptans var. atropurpurea. Feeding of [28E-2 H]-and [28Z-2 H]-24-methylenecholesterols and 2 H NMR analysis of clionasterol obtained by partial hydrogenation of the biosynthesized clerosterol have revealed that the methylation takes place from the 28-si face.

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