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

Wen Xu Zhou; W. David Nes

doi:10.1016/S0040-4039(00)00265-3

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

Wen Xu Zhou, W. David Nes

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2791-2795
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4039(00)00265-3
State	Published - Apr 15 2000

Keywords

Biosynthesis
Ergosterol
Non-mevalonate pathway
Prototheca wickerhamii

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

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.",

keywords = "Biosynthesis, Ergosterol, Non-mevalonate pathway, Prototheca wickerhamii",

author = "Zhou, {Wen Xu} and Nes, {W. David}",

year = "2000",

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doi = "10.1016/S0040-4039(00)00265-3",

language = "English",

volume = "41",

pages = "2791--2795",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Stereochemistry of hydrogen introduction at C-25 in ergosterol synthesized by the mevalonate-independent pathway

AU - Zhou, Wen Xu

AU - Nes, W. David

PY - 2000/4/15

Y1 - 2000/4/15

N2 - 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.

AB - 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.

KW - Biosynthesis

KW - Ergosterol

KW - Non-mevalonate pathway

KW - Prototheca wickerhamii

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U2 - 10.1016/S0040-4039(00)00265-3

DO - 10.1016/S0040-4039(00)00265-3

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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