Journal of Lipid Research, Vol 36, 628-638, Copyright © 1995 by Lipid Research, Inc.
Potential bile acid metabolites. 23. Syntheses of 3-glucosides of nonamidated and glycine- and taurine-amidated bile acids
T Iida, S Nishida, Y Yamaguchi, M Kodake, FC Chang, T Niwa, J Goto and T Nambara
College of Engineering, Nihon University, Fukushima, Japan.
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.
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