Bile acid sulfates. II. Synthesis of 3-monosulfates of bile acids and their conjugates
Bile acid 3-monosulfates were synthesized by the sulfation of 3-hydroxy formyloxy bile acids with sulfur trioxide-triethylamine in dimethylformamide at 25 C for 0.5 h. The protecting formyl groups were then hydrolyzed under mild alkaline conditions, and the deformylated products were isolated as p-toluidinium salts. These p-toluidinium salts were converted easily to the corresponding disodium salts by methanolic sodium hydroxide. Disodium salts were then isolated by precipitation from methanol-ether. The corresponding glycine conjugates were similarly synthesized by the sulfation of ethyl esters of 3-hydroxy formyloxy bile acid glycine conjugates. However, the taurine-conjugated bile acid sulfates were obtained by conjugating bile acid 3-monosulfates, either as triethylammonium salt or as disodium salt, with taurine in dimethylformamide in the presence of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. These procedures produced the desired bile acid sulfates in high yield (typically above 90%) with minimum manipulation. No time-consuming and capacity-limited chromatographic purification was needed to isolate the pure sulfates. The thin layer chromatographic mobilities, the ir spectra, and some of the preliminary studies of the properties of these synthesized 3-monosulfates are also discussed. 3 figures, 2 tables.
- Research Organization:
- Argonne National Lab., IL
- OSTI ID:
- 5163403
- Journal Information:
- Lipids; (United States), Journal Name: Lipids; (United States) Vol. 13:7; ISSN LPDSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
59 BASIC BIOLOGICAL SCIENCES
BILE ACIDS
CARBOXYLIC ACIDS
CHEMICAL PREPARATION
CHROMATOGRAPHY
HYDROXY COMPOUNDS
INFRARED SPECTRA
MOBILITY
ORGANIC ACIDS
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
SEPARATION PROCESSES
SPECTRA
STEROIDS
STEROLS
SULFATES
SULFUR COMPOUNDS
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY