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1 H and 13 C NMR signal assignments of carboxyl‐linked glucosides of bile acids
Author(s) -
Iida Takashi,
Kakiyama Genta,
Shimada Akari,
Mushiake Kumiko,
Mano Nariyasu,
Goto Junichi,
Nambara Toshio
Publication year - 2003
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1173
Subject(s) - chemistry , heteronuclear molecule , homonuclear molecule , stereochemistry , nuclear magnetic resonance spectroscopy , anomer , organic chemistry , molecule
Complete 1 H and 13 C 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‐cholan‐24‐oic) acids by using several homonuclear ( 1 H– 1 H) and heteronuclear ( 1 H– 13 C) 2D NMR techniques. Differences in the 1 H and 13 C resonances between the α‐ and β‐anomers of the ester glucosides of bile acids were clarified for the first time. A comparison of the 1 H and 13 C signal shifts induced by β‐ D ‐glucosidation at the 24‐carboxyl and 3α‐hydroxyl groups in the parent 5β‐cholanoic acid was also made. Copyright © 2003 John Wiley & Sons, Ltd.