Premium
1 H and 13 C NMR characterization and stereochemical assignments of bile acids in aqueous media
Author(s) -
Ijare Omkar B.,
Somashekar B. S.,
Jadegoud Y.,
Nagana Gowda G. A.
Publication year - 2005
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-005-1466-1
Subject(s) - glycocholic acid , deoxycholic acid , cholic acid , tauroursodeoxycholic acid , chenodeoxycholic acid , chemistry , taurocholic acid , taurine , bile acid , ursodeoxycholic acid , heteronuclear molecule , nuclear magnetic resonance spectroscopy , amino acid , stereochemistry , biochemistry , unfolded protein response , endoplasmic reticulum
The unconjugated bile acids cholic acid, deoxycholic acid, and chenodeoxycholic acid; their glycine and taurine conjugated glycocholic acid, glycodeoxycholic acid, glycochenodeoxycholic acid, taurocholic acid, taurodeoxycholic acid, and taurochenodeoxycholic acid; and a taurine conjugated ursodeoxycholic acid, tauroursodeoxycholic acid, were characterized through 1 H and 13 C NMR in aqueous media under the physiological pH region (7.4±0.1). Assignments of 1 H and 13 C signals of all the bile acids were made using a combination of several one‐ and two‐dimensional, homonuclear ( 1 H− 1 H) and heteronuclear ( 1 H− 13 C) correlations as well as spectral editing NMR methods. Stereochemical assignment of the five‐membered ring of the bile acids is reported here for the first time. The complete characterization of various bile acids in aqueous media presented here may have implications in the study of the pathophysiology of biliary diseases through human biliary fluids using NMR spectroscopy.