1H and 13C NMR signal assignments of carboxyl-linked glucosides of bile acids

Takashi Iida; Genta Kakiyama; Akari Shimada; Kumiko Mushiake; Nariyasu Mano; Junichi Goto; Toshio Nambara

doi:10.1002/mrc.1173

¹H and ¹³C NMR signal assignments of carboxyl-linked glucosides of bile acids

Takashi Iida, Genta Kakiyama, Akari Shimada, Kumiko Mushiake, Nariyasu Mano, Junichi Goto, Toshio Nambara

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

6 Citations (Scopus)

Abstract

Complete ¹H and ¹³C resonance assignments were carried out for a new type of carboxyl-linked glucosides of chenodeoxycholic (3α,7α-dihydroxy-5β-cholan-24-oic) and hyodeoxycholic (3α,6α-dihydroxy-5β-cholan24-oic) acids by using several homonuclear (¹H-¹H) and heteronuclear (¹H- ¹³C) 2D NMR techniques. Differences in the ¹H and ¹³C resonances between the α- and β-anomers of the ester glucosides of bile acids were clarified for the first time. A comparison of the ¹H and ¹³C signal shifts induced by β -D-glucosidation at the 24-carboxyl and 3α-hydroxyl groups in the parent 5β-cholanoic acid was also made.

Original language	English
Pages (from-to)	260-264
Number of pages	5
Journal	Magnetic Resonance in Chemistry
Volume	41
Issue number	4
DOIs	https://doi.org/10.1002/mrc.1173
Publication status	Published - 2003 Apr 1

Keywords

Bile acid esters of glucose
C NMR
Carboxyl-linked glucosides of bile acids
Glycosidic conjugates of bile acids
H NMR
H-C shift-correlated 2D NMR
H-H shift-correlated 2D NMR
NMR

ASJC Scopus subject areas

Chemistry(all)
Materials Science(all)

Access to Document

10.1002/mrc.1173

Cite this

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title = "1H and 13C NMR signal assignments of carboxyl-linked glucosides of bile acids",

abstract = "Complete 1H and 13C resonance assignments were carried out for a new type of carboxyl-linked glucosides of chenodeoxycholic (3α,7α-dihydroxy-5β-cholan-24-oic) and hyodeoxycholic (3α,6α-dihydroxy-5β-cholan24-oic) acids by using several homonuclear (1H-1H) and heteronuclear (1H- 13C) 2D NMR techniques. Differences in the 1H and 13C resonances between the α- and β-anomers of the ester glucosides of bile acids were clarified for the first time. A comparison of the 1H and 13C signal shifts induced by β -D-glucosidation at the 24-carboxyl and 3α-hydroxyl groups in the parent 5β-cholanoic acid was also made.",

keywords = "Bile acid esters of glucose, C NMR, Carboxyl-linked glucosides of bile acids, Glycosidic conjugates of bile acids, H NMR, H-C shift-correlated 2D NMR, H-H shift-correlated 2D NMR, NMR",

author = "Takashi Iida and Genta Kakiyama and Akari Shimada and Kumiko Mushiake and Nariyasu Mano and Junichi Goto and Toshio Nambara",

year = "2003",

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doi = "10.1002/mrc.1173",

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T1 - 1H and 13C NMR signal assignments of carboxyl-linked glucosides of bile acids

AU - Iida, Takashi

AU - Kakiyama, Genta

AU - Shimada, Akari

AU - Mushiake, Kumiko

AU - Mano, Nariyasu

AU - Goto, Junichi

AU - Nambara, Toshio

PY - 2003/4/1

Y1 - 2003/4/1

N2 - Complete 1H and 13C resonance assignments were carried out for a new type of carboxyl-linked glucosides of chenodeoxycholic (3α,7α-dihydroxy-5β-cholan-24-oic) and hyodeoxycholic (3α,6α-dihydroxy-5β-cholan24-oic) acids by using several homonuclear (1H-1H) and heteronuclear (1H- 13C) 2D NMR techniques. Differences in the 1H and 13C resonances between the α- and β-anomers of the ester glucosides of bile acids were clarified for the first time. A comparison of the 1H and 13C signal shifts induced by β -D-glucosidation at the 24-carboxyl and 3α-hydroxyl groups in the parent 5β-cholanoic acid was also made.

AB - Complete 1H and 13C resonance assignments were carried out for a new type of carboxyl-linked glucosides of chenodeoxycholic (3α,7α-dihydroxy-5β-cholan-24-oic) and hyodeoxycholic (3α,6α-dihydroxy-5β-cholan24-oic) acids by using several homonuclear (1H-1H) and heteronuclear (1H- 13C) 2D NMR techniques. Differences in the 1H and 13C resonances between the α- and β-anomers of the ester glucosides of bile acids were clarified for the first time. A comparison of the 1H and 13C signal shifts induced by β -D-glucosidation at the 24-carboxyl and 3α-hydroxyl groups in the parent 5β-cholanoic acid was also made.

KW - Bile acid esters of glucose

KW - C NMR

KW - Carboxyl-linked glucosides of bile acids

KW - Glycosidic conjugates of bile acids

KW - H NMR

KW - H-C shift-correlated 2D NMR

KW - H-H shift-correlated 2D NMR

KW - NMR

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DO - 10.1002/mrc.1173

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JO - Magnetic Resonance in Chemistry

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