Stereochemical features of c-methylations on the path to Δ24(28)-Methylene and Δ24(28). Ethylidene sterols: Studies on the recombinant phytosterol methyl transferase from Arabidopsis thaliana

Yusen Tong, Brian S. McCourt, De An Guo, Anil T. Mangla, Wen Xu Zhou, Mark D. Jenkins, Wen Zhou, Monica Lopez, W. David Nes

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Abstract

Using a homogenate prepared from Escherichia coli cells that express the sterol methyl transferase (SMT) gene of Arabidopsis thaliana, migration of the hydrogen atom at C-24 to C-25 from the Re-face of the double bond was demonstrated in the biosynthesis of [27-13C] 24(28)-methylenezymosterol (fecosterol) from [27-13C]zymosterol and the chirality of the C-25 stereocenter (25R) was found to be retained after the stereospecific conversion of [27-13C]24(28)-methylenezymosterol to [27-13C](24(28)Z) -ethylidenecholest-8-en-3β-ol.

Original languageEnglish
Pages (from-to)6115-6118
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number35
DOIs
StatePublished - Sep 1 1997

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