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, T. Niwa, J. Goto, T. Nambara

研究成果: Article査読

18 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)628-638
ページ数11
ジャーナルJournal of lipid research
36
3
出版ステータスPublished - 1995
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 内分泌学
  • 細胞生物学

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