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

doi:10.1016/j.chemphyslip.2006.01.003

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

University Hospital (not affiliated with any section)

Research output: Contribution to journal › Article › peer-review

2 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 language	English
Pages (from-to)	48-54
Number of pages	7
Journal	Chemistry and Physics of Lipids
Volume	140
Issue number	1-2
DOIs	https://doi.org/10.1016/j.chemphyslip.2006.01.003
Publication status	Published - 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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10.1016/j.chemphyslip.2006.01.003

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title = "Nuclear magnetic resonance spectroscopy of 3β,7β-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 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 = "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",

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

year = "2006",

month = apr,

doi = "10.1016/j.chemphyslip.2006.01.003",

language = "English",

volume = "140",

pages = "48--54",

journal = "Chemistry and Physics of Lipids",

issn = "0009-3084",

publisher = "Elsevier Ireland Ltd",

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TY - JOUR

T1 - Nuclear magnetic resonance spectroscopy of 3β,7β-dihydroxy-5-cholen-24-oic acid multi-conjugates

T2 - unusual bile acid metabolites in human urine

AU - Kakiyama, Genta

AU - Ogawa, Shoujiro

AU - Iida, Takashi

AU - Fujimoto, Yasuo

AU - Mushiake, Kumiko

AU - Goto, Takaaki

AU - Mano, Nariyasu

AU - Goto, Junichi

AU - Nambara, Toshio

PY - 2006/4

Y1 - 2006/4

N2 - 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.

AB - 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.

KW - Bile acid multi-conjugate

KW - C NMR

KW - Glycine-amidated bile acid

KW - H NMR

KW - N-Acetylglucosaminidated bile acid

KW - Sulfated bile acid

KW - Taurine-amidated bile acid

KW - Two-dimensional NMR

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U2 - 10.1016/j.chemphyslip.2006.01.003

DO - 10.1016/j.chemphyslip.2006.01.003

M3 - Article

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AN - SCOPUS:33645890278

SN - 0009-3084

VL - 140

SP - 48

EP - 54

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

IS - 1-2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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