Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol

Kyoko Takahashi; Kenichiro Hashimoto; Ayako Fujiyama; Junko Yamada; Noriko Kobayashi; Masuo Morisaki; Sayaka Nakano; Noriyuki Hara; Yoshinori Fujimoto

doi:10.1016/S0040-4039(02)02567-4

Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol

Kyoko Takahashi, Kenichiro Hashimoto, Ayako Fujiyama, Junko Yamada, Noriko Kobayashi, Masuo Morisaki, Sayaka Nakano, Noriyuki Hara, Yoshinori Fujimoto

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

Feeding of the chemically prepared [24-¹³C, 24-²H]desmosterol to cell-free systems derived from rat liver and silkworm gut and to cultured cells of Oryza sativa followed by deuterium-decoupled ¹H, ¹³C shift correlation NMR analysis of the biosynthesized cholesterol revealed the stereospecific incorporation of hydrogen atoms from the re-face of the C-24 position of desmosterol.

Original language	English
Pages (from-to)	341-344
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4039(02)02567-4
Publication status	Published - 2003 Jan 6

Keywords

3β-hydroxysterol Δ-reductase
Cholesterol biosynthesis
Desmosterol
Stereochemistry
Steroids and sterols

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)02567-4

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title = "Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol",

abstract = "Feeding of the chemically prepared [24-13C, 24-2H]desmosterol to cell-free systems derived from rat liver and silkworm gut and to cultured cells of Oryza sativa followed by deuterium-decoupled 1H, 13C shift correlation NMR analysis of the biosynthesized cholesterol revealed the stereospecific incorporation of hydrogen atoms from the re-face of the C-24 position of desmosterol.",

keywords = "3β-hydroxysterol Δ-reductase, Cholesterol biosynthesis, Desmosterol, Stereochemistry, Steroids and sterols",

author = "Kyoko Takahashi and Kenichiro Hashimoto and Ayako Fujiyama and Junko Yamada and Noriko Kobayashi and Masuo Morisaki and Sayaka Nakano and Noriyuki Hara and Yoshinori Fujimoto",

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T1 - Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol

AU - Takahashi, Kyoko

AU - Hashimoto, Kenichiro

AU - Fujiyama, Ayako

AU - Yamada, Junko

AU - Kobayashi, Noriko

AU - Morisaki, Masuo

AU - Nakano, Sayaka

AU - Hara, Noriyuki

AU - Fujimoto, Yoshinori

PY - 2003/1/6

Y1 - 2003/1/6

N2 - Feeding of the chemically prepared [24-13C, 24-2H]desmosterol to cell-free systems derived from rat liver and silkworm gut and to cultured cells of Oryza sativa followed by deuterium-decoupled 1H, 13C shift correlation NMR analysis of the biosynthesized cholesterol revealed the stereospecific incorporation of hydrogen atoms from the re-face of the C-24 position of desmosterol.

AB - Feeding of the chemically prepared [24-13C, 24-2H]desmosterol to cell-free systems derived from rat liver and silkworm gut and to cultured cells of Oryza sativa followed by deuterium-decoupled 1H, 13C shift correlation NMR analysis of the biosynthesized cholesterol revealed the stereospecific incorporation of hydrogen atoms from the re-face of the C-24 position of desmosterol.

KW - 3β-hydroxysterol Δ-reductase

KW - Cholesterol biosynthesis

KW - Desmosterol

KW - Stereochemistry

KW - Steroids and sterols

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol

Abstract

Keywords

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