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

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  • Ogawa Shoujiro
    Department of Chemistry, College of Humanities & Sciences, Nihon University
  • Adachi Yuuki
    Department of Chemistry, College of Humanities & Sciences, Nihon University
  • Kakiyama Genta
    Department of Chemistry, College of Humanities & Sciences, Nihon University
  • Shimada Miki
    Department of Pharmaceutical Sciences, Tohoku University Hospital
  • Mano Nariyasu
    Department of Pharmaceutical Sciences, Tohoku University Hospital
  • Goto Junichi
    Department of Pharmaceutical Sciences, Tohoku University Hospital
  • Iida Takashi
    Department of Chemistry, College of Humanities & Sciences, Nihon University

書誌事項

タイトル別名
  • Chemical Synthesis of (22E)-3.ALPHA.,6.ALPHA.,7.ALPHA.,12.ALPHA.-Tetrahydroxy-5.BETA.-chol-22-en-24-oic Acid and Its N-Acylamidated Conjugates with Glycine or Taurine: Precursors of the [22,23-3H] Labelled Tracers
  • Chemical synthesis of 22E 3 a 6 a 7 a 12 a tetrahydroxy 5 v chol 22 en 24 oic acid and its N acylamidated conjugates with glycine or taurine precursors of the 22 23 3H labelled tracers

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(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 3α,6α,7α,12α-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.

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