Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids.
3-N-Acetylglucosaminides of unconjugated, glycine- and taurine-conjugated bile acids have been synthesized. Bile acids appropriately protected were condensed with acetochloroglucosamine through the 3 alpha-hydroxyl group by means of the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. Subsequent borohydride reduction and/or alkaline hydrolysis provided desired 3-N-acetylglucosaminides of unconjugated bile acids. Glycine-conjugates were obtained from N-acetylglucosaminides of unconjugated bile acids and ethyl glycinate by the carbodiimide method. The preparation of N-acetylglucosaminides of taurine-conjugates was attained by the Koenigs-Knorr reaction of bile acid p-nitrophenyl esters followed by condensation with taurine. 7-N-Acetylglucosaminides of ursodeoxycholates were prepared in a similar fashion. The convenient synthesis of 3-N-acetylglucosaminides of unconjugated bile acids is also described.
Niwa
T
T
Pharmaceutical Institute, Tohoku University, Sendai, Japan.
Koshiyama
T
T
Goto
J
J
Nambara
T
T
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D001647:Bile Acids and Salts / Q000737:chemistry*; D001894:Borohydrides; D002104:Cadmium; D002254:Carbonates; D002384:Catalysis; D005998:Glycine / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D013654:Taurine / Q000378:metabolism; D014580:Ursodeoxycholic Acid / Q000737:chemistry
D001647:Bile Acids and Salts; D001894:Borohydrides; D002254:Carbonates; D002104:Cadmium; D013654:Taurine; C038075:cadmium carbonate; D014580:Ursodeoxycholic Acid; D005998:Glycine; D000117:Acetylglucosamine