Nuclear magnetic resonance spectroscopy of 3β,7β-dihydroxy-5-cholen-24-oic acid multi-conjugates: unusual bile acid metabolites in human urine

Genta Kakiyama, Shoujiro Ogawa, Takashi Iida, Yasuo Fujimoto, Kumiko Mushiake, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Complete 1H and 13C resonance assignments were made for a new type of 3β,7β-dihydroxy-5-cholen-24-oic acid doubly conjugated with sulfuric acid at C-3 and N-acetylglucosamine at C-7 and its glycine- and taurine-amidated triple-conjugates by the combined use of several homonuclear and heteronuclear shift-correlated 2D NMR techniques. The effects of sulfation at C-3, N-acetylglucosaminidation at C-7, and aminoacyl amidation at C-24 on the 1H and 13C chemical shifts and signal multiplicity were clarified. The shielding data serving to characterize each of the bile acid multi-conjugates are also discussed.

Original languageEnglish
Pages (from-to)48-54
Number of pages7
JournalChemistry and Physics of Lipids
Volume140
Issue number1-2
DOIs
Publication statusPublished - 2006 Apr

Keywords

  • Bile acid multi-conjugate
  • C NMR
  • Glycine-amidated bile acid
  • H NMR
  • N-Acetylglucosaminidated bile acid
  • Sulfated bile acid
  • Taurine-amidated bile acid
  • Two-dimensional NMR

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Cell Biology

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