Chemical synthesis of 24-β-d-galactopyranosides of bile acids: A new type of bile acid conjugates in human urine

Genta Kakiyama, Shinji Sadakiyo, Takashi Iida, Kumiko Mushiake, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A method is reported for the preparation of the C-24 carboxyl-linked β-d-galactopyranosides of lithocholic, deoxycholic, chenodeoxycholic, ursodeoxycholic, and cholic acids, two of which were recently identified as a novel type of the metabolites of bile acids excreted in human urine. Direct esterification (galactosidation) of the unprotected bile acids with 2,3,4,6-tetra-O-benzyl-d-galactopyranose in the presence of 2-chloro-1,3,5- trinitrobenzene as a coupling agent and subsequent hydrogenolysis of the resulting benzyloxy-protected bile acid 24-β-d-galactopyranosides over 10% palladium on charcoal under atmospheric pressure afforded the title compounds. The structures of the bile acid acyl galactosides were confirmed by measuring several 1H-1H and 1H-13C shift correlated 2D NMR.

Original languageEnglish
Pages (from-to)141-150
Number of pages10
JournalChemistry and Physics of Lipids
Volume134
Issue number2
DOIs
Publication statusPublished - 2005 Apr

Keywords

  • 2-Chloro-1,3,5-trinitrobenzene
  • 2D NMR
  • Bile acid
  • Bile acid acyl 24-galactoside
  • Ester galactosidation
  • Hydrogenolysis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

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