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

Wen Zhou; De An Guo; W. David Nes

doi:10.1016/0040-4039(96)00017-2

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

Wen Zhou, De An Guo, W. David Nes

Chemistry and Biochemistry

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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 language	English
Pages (from-to)	1339-1342
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	9
DOIs	https://doi.org/10.1016/0040-4039(96)00017-2
State	Published - Feb 26 1996

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title = "Stereochemistry of hydrogen migration from C-24 to C-25 during biomethylation in ergosterol biosynthesis",

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.",

author = "Wen Zhou and Guo, {De An} and Nes, {W. David}",

note = "Funding Information: Acknowledgements. We thank the Welch Foundation for financial support. References and Notes 1. (a) Barton, D.H.R.; Harrison, D.M.; Moss, G.P. Chem. Commun. 1966, 595-596;",

year = "1996",

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doi = "10.1016/0040-4039(96)00017-2",

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T1 - Stereochemistry of hydrogen migration from C-24 to C-25 during biomethylation in ergosterol biosynthesis

AU - Zhou, Wen

AU - Guo, De An

AU - Nes, W. David

N1 - Funding Information: Acknowledgements. We thank the Welch Foundation for financial support. References and Notes 1. (a) Barton, D.H.R.; Harrison, D.M.; Moss, G.P. Chem. Commun. 1966, 595-596;

PY - 1996/2/26

Y1 - 1996/2/26

N2 - [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.

AB - [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.

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DO - 10.1016/0040-4039(96)00017-2

M3 - Article

AN - SCOPUS:0030010226

SN - 0040-4039

VL - 37

SP - 1339

EP - 1342

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

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

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