TY - JOUR
T1 - Potential bile acid metabolites. 23. Syntheses of 3-glucosides of nonamidated and glycine- and taurine-amidated bile acids
AU - Iida, T.
AU - Nishida, S.
AU - Yamaguchi, Y.
AU - Kodake, M.
AU - Chang, F. C.
AU - Niwa, Toshifumi
AU - Goto, J.
AU - Nambara, T.
PY - 1995/1/1
Y1 - 1995/1/1
N2 - 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) β-D- glucosidation at C-3 by the Koenigs-Knorr condensation reaction of 3α-hydroxylated bile acid methyl (or p-nitrophenyl) esters with 1α-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.
AB - 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) β-D- glucosidation at C-3 by the Koenigs-Knorr condensation reaction of 3α-hydroxylated bile acid methyl (or p-nitrophenyl) esters with 1α-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.
KW - HNMR
KW - amidation
KW - bile acid 3-glucoside
KW - diethylphosphorylcyanide method
KW - glucosidation
KW - glycine conjugate
KW - Koenigs-Knorr reaction
KW - p-nitrophenyl ester method
KW - taurine conjugate
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M3 - Article
C2 - 7775874
AN - SCOPUS:0028939754
VL - 36
SP - 628
EP - 638
JO - Journal of Lipid Research
JF - Journal of Lipid Research
SN - 0022-2275
IS - 3
ER -