Bile acid sulfates. III. Synthesis of 7- and 12-monosulfates of bile acids and their conjugates using a sulfur trioxide-triethylamine complex
The 7- and 12-monosulfates of chenodeoxycholic acid, deoxycholic acid, and cholic acid were prepared by sulfation of the protected bile acids with sulfur trioxide-triethylamine in pyridine overnight and were isolated by precipitation as the p-toluidinium salt after removing the protection group(s). The taurine conjugates were obtained by conjugating the bile acid sulfates with taurine in hot dimethylformamide (DMF) in the presence of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ). A new procedure of preparing glycine conjugated bile acid sulfates by direct conjugation of the bile acid sulfate triethylammonium salt with ethyl glycinate in boiling chloroform in the presence of EEDQ is also described. The advantages of these procedures over other procedures are their simplicity and their higher yields (typically above 90%). The thin layer chromatographic mobilities of these sulfates are presented. The influence of side chain and hydroxyl group configurations on the properties of bile acid sulfates is briefly discussed.
- Research Organization:
- Argonne National Lab., IL
- OSTI ID:
- 5707758
- Journal Information:
- Steroids; (United States), Journal Name: Steroids; (United States) Vol. 33:2; ISSN STEDA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
59 BASIC BIOLOGICAL SCIENCES
AMINES
AMINO ACIDS
AZINES
BILE ACIDS
CARBOXYLIC ACIDS
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CHOLIC ACID
CHROMATOGRAPHY
GLYCINE
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PYRIDINE
PYRIDINES
SEPARATION PROCESSES
STEROIDS
STEROLS
SULFATES
SULFONIC ACIDS
SULFUR COMPOUNDS
SYNTHESIS
TAURINE
THIN-LAYER CHROMATOGRAPHY
TOLUIDINES