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Title: Bile acid sulfates. III. Synthesis of 7- and 12-monosulfates of bile acids and their conjugates using a sulfur trioxide-triethylamine complex

Abstract

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.

Authors:
;
Publication Date:
Research Org.:
Argonne National Lab., IL
OSTI Identifier:
5707758
Resource Type:
Journal Article
Journal Name:
Steroids; (United States)
Additional Journal Information:
Journal Volume: 33:2
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; BILE ACIDS; SULFATES; CHLOROFORM; CHOLIC ACID; GLYCINE; PYRIDINE; SYNTHESIS; TAURINE; THIN-LAYER CHROMATOGRAPHY; TOLUIDINES; AMINES; AMINO ACIDS; AZINES; CARBOXYLIC ACIDS; CHLORINATED ALIPHATIC HYDROCARBONS; CHROMATOGRAPHY; 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; PYRIDINES; SEPARATION PROCESSES; STEROIDS; STEROLS; SULFONIC ACIDS; SULFUR COMPOUNDS; 550200* - Biochemistry

Citation Formats

Tserng, K.Y., and Klein, P.D. Bile acid sulfates. III. Synthesis of 7- and 12-monosulfates of bile acids and their conjugates using a sulfur trioxide-triethylamine complex. United States: N. p., 1979. Web. doi:10.1016/0039-128X(79)90024-2.
Tserng, K.Y., & Klein, P.D. Bile acid sulfates. III. Synthesis of 7- and 12-monosulfates of bile acids and their conjugates using a sulfur trioxide-triethylamine complex. United States. doi:10.1016/0039-128X(79)90024-2.
Tserng, K.Y., and Klein, P.D. Thu . "Bile acid sulfates. III. Synthesis of 7- and 12-monosulfates of bile acids and their conjugates using a sulfur trioxide-triethylamine complex". United States. doi:10.1016/0039-128X(79)90024-2.
@article{osti_5707758,
title = {Bile acid sulfates. III. Synthesis of 7- and 12-monosulfates of bile acids and their conjugates using a sulfur trioxide-triethylamine complex},
author = {Tserng, K.Y. and Klein, P.D.},
abstractNote = {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.},
doi = {10.1016/0039-128X(79)90024-2},
journal = {Steroids; (United States)},
number = ,
volume = 33:2,
place = {United States},
year = {1979},
month = {2}
}