Chemical synthesis of 24-beta-D-galactopyranosides of bile acids: a new type of bile acid conjugates in human urine.
A method is reported for the preparation of the C-24 carboxyl-linked beta-D-galactopyranosides of lithocholic, deoxycholic, chenodeoxycholic, ursodeoxycholic, and cholic acids, two of which were recently identified as a novel type of the metabolites of bile acids excreted in human urine. Direct esterification (galactosidation) of the unprotected bile acids with 2,3,4,6-tetra-O-benzyl-D-galactopyranose in the presence of 2-chloro-1,3,5-trinitrobenzene as a coupling agent and subsequent hydrogenolysis of the resulting benzyloxy-protected bile acid 24-beta-D-galactopyranosides over 10% palladium on charcoal under atmospheric pressure afforded the title compounds. The structures of the bile acid acyl galactosides were confirmed by measuring several (1)H-(1)H and (1)H-(13)C shift correlated 2D NMR.
Kakiyama
Genta
G
Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, Japan.
Sadakiyo
Shinji
S
Iida
Takashi
T
Mushiake
Kumiko
K
Goto
Takaaki
T
Mano
Nariyasu
N
Goto
Junichi
J
Nambara
Toshio
T
D001647:Bile Acids and Salts / Q000138:chemical synthesis* / Q000652:urine*; D002635:Chenodeoxycholic Acid / Q000737:chemistry; D019826:Cholic Acid / Q000737:chemistry; D003840:Deoxycholic Acid / Q000737:chemistry; D005690:Galactose / Q000138:chemical synthesis* / Q000652:urine*; D006031:Glycosylation; D006801:Humans; D008095:Lithocholic Acid / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D014580:Ursodeoxycholic Acid / Q000737:chemistry
D001647:Bile Acids and Salts; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; D008095:Lithocholic Acid; D014580:Ursodeoxycholic Acid; D019826:Cholic Acid; D005690:Galactose