Stereochemistry of hydrogen introduction at C-25 in ergosterol synthesized by the mevalonate-independent pathway

Wen Xu Zhou, W. David Nes

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Feeding of [1-13C]glucose to Prototheca wickerhamii followed by 13C NMR analysis of the resulting 13C-labeled ergosterol demonstrated this yeast-like alga operates the mevalonate-independent pathway. Based on the 13C NMR signal assignment of [2,6,11,12,16,18,19, 21,23,27-13C10] ergosterol synthesized from [1-13C]glucose indicated the pro-Z methyl group of cycloartenol is derived from C-5 of IPP and that protonation at C-25 of the Δ(25(27))-sterol intermediate takes place from the Si-face of Δ25 to form the isopropyl pro-R methyl group. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)2791-2795
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number16
DOIs
StatePublished - Apr 15 2000

Keywords

  • Biosynthesis
  • Ergosterol
  • Non-mevalonate pathway
  • Prototheca wickerhamii

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