TY - JOUR
T1 - Chemical synthesis of 24-β-d-galactopyranosides of bile acids
T2 - A new type of bile acid conjugates in human urine
AU - Kakiyama, Genta
AU - Sadakiyo, Shinji
AU - Iida, Takashi
AU - Mushiake, Kumiko
AU - Goto, Takaaki
AU - Mano, Nariyasu
AU - Goto, Junichi
AU - Nambara, Toshio
N1 - Funding Information:
This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture of Japan.
PY - 2005/4
Y1 - 2005/4
N2 - A method is reported for the preparation of the C-24 carboxyl-linked β-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-β-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 1H-1H and 1H-13C shift correlated 2D NMR.
AB - A method is reported for the preparation of the C-24 carboxyl-linked β-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-β-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 1H-1H and 1H-13C shift correlated 2D NMR.
KW - 2-Chloro-1,3,5-trinitrobenzene
KW - 2D NMR
KW - Bile acid
KW - Bile acid acyl 24-galactoside
KW - Ester galactosidation
KW - Hydrogenolysis
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U2 - 10.1016/j.chemphyslip.2005.01.002
DO - 10.1016/j.chemphyslip.2005.01.002
M3 - Article
C2 - 15784232
AN - SCOPUS:14844316418
SN - 0009-3084
VL - 134
SP - 141
EP - 150
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
IS - 2
ER -