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Nuclear magnetic resonance spectroscopy of 3 beta,7 beta-dihydroxy-5-cholen-24-oic acid multi-conjugates: unusual bile acid metabolites in human urine |
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| Authors: | Kakiyama Genta Ogawa Shoujiro Iida Takashi Fujimoto Yasuo Mushiake Kumiko Goto Takaaki Mano Nariyasu Goto Junichi Nambara Toshio |
| Institution: | aDepartment of Chemistry, College of Humanities & Sciences, Nihon University, Setagaya, Sakurajousui, Tokyo 156-8550, Japan bDepartment of General Education, College of Humanities & Sciences, Nihon University, Setagaya, Sakurajousui, Tokyo 156-8550, Japan cLaboratory of Bioanalytical Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-ku, Sendai 980-8578, Japan dDepartment of Pharmaceutical Sciences, Tohoku University Hospital, Seriryou-cho, Aoba-ku, Sendai 980-8574, Japan |
| 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. |
| Keywords: | 1H NMR 13C NMR Two-dimensional NMR Bile acid multi-conjugate Glycine-amidated bile acid Taurine-amidated bile acid Sulfated bile acid N-Acetylglucosaminidated bile acid |
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