Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates

Steroids. 1977 Nov;30(5):583-90. doi: 10.1016/0039-128x(77)90049-6.


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.

MeSH terms

  • Bile Acids and Salts / chemical synthesis*
  • Chenodeoxycholic Acid / chemical synthesis
  • Chromatography, Thin Layer
  • Deoxycholic Acid / chemical synthesis
  • Glycochenodeoxycholic Acid / chemical synthesis
  • Glycodeoxycholic Acid / chemical synthesis
  • Methods
  • Sulfates / chemical synthesis
  • Taurochenodeoxycholic Acid / chemical synthesis
  • Taurodeoxycholic Acid / chemical synthesis


  • Bile Acids and Salts
  • Sulfates
  • Deoxycholic Acid
  • Chenodeoxycholic Acid
  • Glycodeoxycholic Acid
  • Taurochenodeoxycholic Acid
  • Taurodeoxycholic Acid
  • Glycochenodeoxycholic Acid