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 journalArticle

6 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 languageEnglish
Pages (from-to)341-344
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number2
DOIs
Publication statusPublished - 2003 Jan 6

Fingerprint

Desmosterol
Stereochemistry
Cholesterol
Bombyx
Cell-Free System
Deuterium
Liver
Rats
Hydrogen
Cultured Cells
Cells
Nuclear magnetic resonance
Atoms

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol. / Takahashi, Kyoko; Hashimoto, Kenichiro; Fujiyama, Ayako; Yamada, Junko; Kobayashi, Noriko; Morisaki, Masuo; Nakano, Sayaka; Hara, Noriyuki; Fujimoto, Yoshinori.

In: Tetrahedron Letters, Vol. 44, No. 2, 06.01.2003, p. 341-344.

Research output: Contribution to journalArticle

Takahashi, Kyoko ; Hashimoto, Kenichiro ; Fujiyama, Ayako ; Yamada, Junko ; Kobayashi, Noriko ; Morisaki, Masuo ; Nakano, Sayaka ; Hara, Noriyuki ; Fujimoto, Yoshinori. / Stereochemistry of reduction of the C-24,25 double bond in the conversion of desmosterol into cholesterol. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 2. pp. 341-344.
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