Analysis of Conjugated Bile Acids in Human Biological Fluids. Synthesis of Hyodeoxycholic Acid 3- and 6-Glycosides and Related Compounds

Takashi Iida, Shinnosuke Tazawa, Yukari Ohshima, Toshifumi Niwa, Junichi Goto, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The glucuronide, glucoside and N-acetylglucosaminide conjugates of hyodeoxycholic acid were synthesized. In addition, murideoxycholic acid 3-glycosides and some of their C-5 epimeric analogs were also prepared. The principal reactions used are 1) the Koenigs-Knorr condensation reaction of 3-oxo-6a-hydroxy and 6-oxo-3a-hydroxy esters with an appropriate a-acetohalosugar catalyzed by cadmium carbonate in benzene under reflux, 2) reduction of the resulting bile acid glycoside methyl ester-acetates with tert-butylamine-borane complex, and 3) subsequent hydrolysis with aqueous lithium hydroxide.

Original languageEnglish
Pages (from-to)1479-1484
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume42
Issue number7
DOIs
Publication statusPublished - 1994

Keywords

  • Koenigs-Knorr condensation reaction
  • N-acetylglucosaminide
  • glucoside
  • glucuronide
  • hyodeoxycholic acid
  • murideoxycholic acid

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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