Stereochemistry of hydrogen migration from C-24 to C-25 during biomethylation in ergosterol biosynthesis

Wen Zhou, De An Guo, W. David Nes

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

[methyl-2H3]Methionine and zymosterol, [27-13C]lanosterol, [24-2H]lanosterol and lanosterol were separately incubated with the sterol auxotroph Saccharomyces cerevisiae strain GL7. Spectral evidence (1H and 13C-NMR) obtained on three different isotopically labeled ergosterol samples indicated that C-28 was derived from AdoMet, H-24 migrated to C-25 and the C-25 hydrogen on (27-)-methyl 13C-labeled ergosterol was introduced from the Re-face to produce the 25R-stereochemistry.

Original languageEnglish
Pages (from-to)1339-1342
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number9
DOIs
StatePublished - Feb 26 1996

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