title: Nuclear magnetic resonance spectroscopy of 3 beta,7 beta-dihydroxy-5-cholen-24-oic acid multi-conjugates: unusual bile acid metabolites in human urine.
abstract: Complete 1H and 13C resonance assignments were made for a new type of 3 beta,7 beta-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.
authors.affiliation: Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajousui, Tokyo 156-8550, Japan.
authors.forename: Genta
authors.initials: G
authors.lastname: Kakiyama
authors.forename: Shoujiro
authors.initials: S
authors.lastname: Ogawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Iida
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Fujimoto
authors.forename: Kumiko
authors.initials: K
authors.lastname: Mushiake
authors.forename: Takaaki
authors.initials: T
authors.lastname: Goto
authors.forename: Nariyasu
authors.initials: N
authors.lastname: Mano
authors.forename: Junichi
authors.initials: J
authors.lastname: Goto
authors.forename: Toshio
authors.initials: T
authors.lastname: Nambara
mesh_terms: D001647:Bile Acids and Salts / Q000737:chemistry* / Q000378:metabolism / Q000652:urine; D002247:Carbon Isotopes; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002793:Cholic Acids / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D011522:Protons; D012015:Reference Standards; D012680:Sensitivity and Specificity; D013464:Sulfuric Acids / Q000737:chemistry; D014556:Urine / Q000737:chemistry*
chemical_list: C511396:3beta,7beta-dihydroxy-5-cholen-24-oic acid; D001647:Bile Acids and Salts; D002247:Carbon Isotopes; D002793:Cholic Acids; D011522:Protons; D013464:Sulfuric Acids; C033158:sulfuric acid