Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: Precursors of the [22,23-3H] labelled tracers

Shoujiro Ogawa, Yuuki Adachi, Genta Kakiyama, Miki Simada, Nariyasu Mano, Junichi Goto, Takashi Iida

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

(22E)-3α,6α,7α,12α-Tetrahydroxy-5β-chol-22-en- 24-oic acid and its N-acylamidated conjugates with glycine or taurine were synthesized from cholic acid. The key reactions employed are: 1) degradation of the side chain in intermediary C24 3β,6β,7β,12β- tetrahydroxylated bile acid to the corresponding C22 23,24-dinor-aldehyde, followed by Wittig reaction with methyl (triphenylphosphoranylidene)acetate and 2) N-acylamidation of the unconjugated tetrahydroxy-Δ22-5β-cholenoic acid with glycine (or taurine) in the presence of diethylphosphorocyanide and triethylamine as coupling reagents.

Original languageEnglish
Pages (from-to)1103-1106
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume58
Issue number8
DOIs
Publication statusPublished - 2010 Aug 1

Keywords

  • Bile acid
  • Gycine conjugate
  • N-acylamidation
  • Taurine conjugate
  • Tetrahydroxy-Δ-5β-cholenoic acid
  • Wittig reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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