Potential bile acid metabolites. 23. Syntheses of 3-glucosides of nonamidated and glycine- and taurine-amidated bile acids.
The 3-glucosides of nonamidated lithocholic, chenodeoxycholic, ursodeoxycholic, deoxycholic, and cholic acids, and their double conjugate forms with glycine and taurine were synthesized. The key reactions used were 1) beta-D- glucosidation at C-3 by the Koenigs-Knorr condensation reaction of 3 alpha-hydroxylated bile acid methyl (or p-nitrophenyl) esters with 1 alpha-bromo-1-deoxy-2, 3, 4, 6-tetra-O-acetyl-D-glucopyranose in the presence of cadmium carbonate in refluxing benzene; 2) indirect and direct amidations at C-24 by the activated p-nitrophenyl ester and by the diethylphosphorylcyanide methods, respectively, using glycinate ester and taurine as coupling agents; and 3) simultaneous alkaline hydrolysis of the hydroxyl-protecting and ester groups in both the sugar and aglycone moieties.
Iida
T
T
College of Engineering, Nihon University, Fukushima, Japan.
Nishida
S
S
Yamaguchi
Y
Y
Kodake
M
M
Chang
F C
FC
Niwa
T
T
Goto
J
J
Nambara
T
T
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D001647:Bile Acids and Salts / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry; D005998:Glycine / Q000737:chemistry; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013654:Taurine / Q000737:chemistry
D000577:Amides; D001647:Bile Acids and Salts; D005960:Glucosides; D013654:Taurine; D005998:Glycine