Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
9757666 | Chemistry and Physics of Lipids | 2005 | 10 Pages |
Abstract
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.
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Physical Sciences and Engineering
Chemistry
Chemistry (General)
Authors
Genta Kakiyama, Shinji Sadakiyo, Takashi Iida, Kumiko Mushiake, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara,