Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids

Niwa Toshifumi, Koshiyama Tomoyoshi, Goto Junichi, Nambara Toshio

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

3-N-Acetylglucosaminides of unconjugated, glycine- and taurine-conjugated bile acids have been synthesized. Bile acids appropriately protected were condensed with acetochloroglucosamine through the 3α-hydroxyl group by means of the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. Subsequent borohydride reduction and/or alkaline hydrolysis provided desired 3-N-acetylglucosaminides of unconjugated bile acids. Glycine-conjugates were obtained from N-acetylglucosaminides of unconjugated bile acids and ethyl glycinate by the carbodiimide method. The preparation of N-acetylglucosaminides of taurine-conjugates was attained by the Koenigs-Knorr reaction of bile acid p-nitrophenyl esters followed by condensation with taurine. 7-N-Acetylglucosaminides of ursodeoxycholates were prepared in a similar fashion. The convenient synthesis of 3-N-acetylglucosaminides of unconjugated bile acids is also described.

Original languageEnglish
Pages (from-to)522-529
Number of pages8
JournalSteroids
Volume57
Issue number11
DOIs
Publication statusPublished - 1992 Nov

Keywords

  • Koenigs-Knorr reaction
  • N-acetylglucosaminide
  • bile acid
  • glycine-conjugate
  • p-nilrophenyl ester method
  • taurine-conjugate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids'. Together they form a unique fingerprint.

Cite this