Potential bile acid metabolites. 23. Syntheses of 3-glucosides of nonamidated and glycine- and taurine-amidated bile acids

T. Iida, S. Nishida, Y. Yamaguchi, M. Kodake, F. C. Chang, Toshifumi Niwa, J. Goto, T. Nambara

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The 3-glucosides of nonamidated lithocholic, chenodeoxycholic, ursodeoxycholic, deoxycholic, and cholic acids, and their double conjugate forms with glycine and taurine were synthesized. The key reactions used were 1) β-D- glucosidation at C-3 by the Koenigs-Knorr condensation reaction of 3α-hydroxylated bile acid methyl (or p-nitrophenyl) esters with 1α-bromo- 1-deoxy-2, 3, 4, 6-tetra-O-acetyl-D-glucopyranose in the presence of cadmium carbonate in refluxing benzene; 2) indirect and direct amidations at C-24 by the activated p-nitrophenyl ester and by the diethylphosphorylcyanide methods, respectively, using glycinate ester and taurine as coupling agents; and 3) simultaneous alkaline hydrolysis of the hydroxyl-protecting and ester groups in both the sugar and aglycone moieties.

Original languageEnglish
Pages (from-to)628-638
Number of pages11
JournalJournal of Lipid Research
Volume36
Issue number3
Publication statusPublished - 1995 Jan 1
Externally publishedYes

Keywords

  • HNMR
  • amidation
  • bile acid 3-glucoside
  • diethylphosphorylcyanide method
  • glucosidation
  • glycine conjugate
  • Koenigs-Knorr reaction
  • p-nitrophenyl ester method
  • taurine conjugate

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology

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