Synthesis of the specific monosulfates of cholic acid.
The three isomeric cholic acid-monosulfates were synthetized and characterized. Cholic acid-3-sulfate was obtained by reacting cholic acid for 2 min with chlorosulfonic acid in pyridine and chromatography of the resulting bile salt mixture on Sephadex LH-20. The 7- and the 12-monosulfate were prepared by sulfation of the corresponding monohydroxy-diacetates followed by removal of the acetyl groups by alkaline hydrolysis and purification by chromatography on Sephadex LH-20. On TLC in n-butanol-acetic acid-water (10:1:1, v/v) the Rf values were 0.59 for cholic acid-3-sulfate, 0.52 for cholic acid-7-sulfate and 0.48 for cholic acid-12-sulfate. The time required for complete solvolysis at 37 degrees C in acid methanol-acetone (1:9) was 3 h for cholic acid-3-sulfate, 12 h for the 12-monosulfate and 18 h for the 7-monosulfate.
D002793:Cholic Acids; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D008722:Methods; D013055:Spectrophotometry, Infrared; D013464:Sulfuric Acids / Q000138:chemical synthesis*
D002793:Cholic Acids; D013464:Sulfuric Acids