Journal of Lipid Research, Vol 35, 1599-1610, Copyright © 1994 by Lipid Research, Inc.

ARTICLES

Positions of conjugation of bile acids with glucose and N- acetylglucosamine in vitro

HU Marschall, WJ Griffiths, J Zhang, H Wietholtz, H Matern, S Matern and J Sjovall
Department of Internal Medicine III, Aachen University of Technology, Germany.

In order to establish the position of conjugation of bile acids with glucose or N-acetylglucosamine, glucosides of chenodeoxycholic and hyodeoxycholic acids and of 13C-labeled cholic, lithocholic, chenodeoxycholic, hyodeoxycholic, and ursodeoxycholic acids, and N- acetylglucosaminides of ursodeoxycholic, isoursodeoxycholic, 3-dehydro- ursodeoxycholic, and ursodeoxycholylglycine were synthesized in vitro. The conjugates were purified by anion-exchange chromatography and reversed-phase HLPC and were analyzed by gas chromatography-mass spectrometry. The glucosides of chenodeoxycholic and hyodeoxycholic acids were also analyzed after periodate and chronic acid oxidation. All conjugates were analyzed by fast atom bombardment mass spectrometry with collision-induced dissociation. Glucose conjugation was shown to occur at C-3 in all bile acid glucosides studied. In contrast, the selective N-acetylglucosaminidation of 7 beta-hydroxy bile acids was shown to occur at the 7 beta-position.
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