Non-stereoselective Formation of 3α, 7α, 12α, 24-Tetrahydroxy-5β-cholestan-26-oic Acid during Cholic Acid Biosynthesis

Noriko Kobayashi, Chiaki Hagiwara, Masuo Morisaki, Masatoshi Yuri, Izumi Oya, Yoshinori Fujimoto

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Incubation of (25iRS)-, (25R)- and (25S)-3α, 7α, 12v-trihydroxy-5β-cholestan-26-oic acid (THCA, 6, 6a, 6b) and (24E)-3α, 7α, 12α-trihydroxy-5β-cholest-24-en-26-oic acid (7) with rat liver mitochondria gave all four stereoisomers (9a, 9b, 9c, 9d) of 3α, 7α, 12α, 24-Tetrahydroxy-5β-cholestan-26-oic acid (TeHCA). The corresponding 27-nor analogs (10, 11) were also converted non-stereoselectively to a 1:1 mixture of the epimeric 24-hydroxy compounds (12).

Original languageEnglish
Pages (from-to)1028-1035
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume42
Issue number5
DOIs
Publication statusPublished - 1994 Jan 1

Keywords

  • 12α
  • 12α
  • 12α
  • 24-tetrahydroxy- 5β
  • 24-trihydroxy-5β
  • bile acid cholic acid β
  • cholest-24-en-26-oic acid
  • cholestan-26-oic acid 3α
  • cholestan-26-oic acid 3α
  • oxidation 3α
  • trihydroxy-5β

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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