Positions of conjugation of bile acids with glucose and N-acetylglucosamine in vitro.
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.
Marschall
H U
HU
Department of Internal Medicine III, Aachen University of Technology, Germany.
Griffiths
W J
WJ
Zhang
J
J
Wietholtz
H
H
Matern
H
H
Matern
S
S
Sjövall
J
J
D000117:Acetylglucosamine / Q000737:chemistry; D001647:Bile Acids and Salts / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D002635:Chenodeoxycholic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D003840:Deoxycholic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D066298:In Vitro Techniques; D015394:Molecular Structure; D016339:Spectrometry, Mass, Fast Atom Bombardment
D001647:Bile Acids and Salts; D006001:Glycoconjugates; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; C010471:hyodeoxycholic acid; D005947:Glucose; D000117:Acetylglucosamine