Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates.
The isomeric monosulfates of chenodeoxycholate, deoxycholate, and their taurine or glycine conjugates, were synthesized and characterized. Reaction with chlorosulfonic acid in pyridine for 2 minutes mainly afforded the 3-monosulfates. To prepare the 7- or the 12-monosulfates, the 3-hydroxyl group was protected by carbethoxylation prior to sulfation of the 7- or 12-hydroxyl group for 24 h to 5 days; after sulfation, the protecting 3-carbethoxy function was removed by mild alkaline hydrolysis. The crude bile salt monosulfates were purified by chromatography on silica gel and on Sephadex LH-20 and were crystallized from methanolethanol-ethyl acetate. The results of elemental analysis demonstrated that the compounds were disodium dihydroxy bile salt monosulfates. Thin layer chromatography of the sulfates, and gas-liquid chromatography after oxidation and solvolysis, showed that the substances were pure and that the sulfate group was at the expected position.
D001647:Bile Acids and Salts / Q000138:chemical synthesis*; D002635:Chenodeoxycholic Acid / Q000138:chemical synthesis; D002855:Chromatography, Thin Layer; D003840:Deoxycholic Acid / Q000138:chemical synthesis; D005999:Glycochenodeoxycholic Acid / Q000138:chemical synthesis; D006002:Glycodeoxycholic Acid / Q000138:chemical synthesis; D008722:Methods; D013431:Sulfates / Q000138:chemical synthesis; D013655:Taurochenodeoxycholic Acid / Q000138:chemical synthesis; D013657:Taurodeoxycholic Acid / Q000138:chemical synthesis
D001647:Bile Acids and Salts; D013431:Sulfates; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; D006002:Glycodeoxycholic Acid; D013655:Taurochenodeoxycholic Acid; D013657:Taurodeoxycholic Acid; D005999:Glycochenodeoxycholic Acid