Journal of Lipid Research, Vol 36, 901-910, Copyright © 1995 by Lipid Research, Inc.
Synthesis and characterization of novel analogs of conjugated bile acids containing reversed amide bonds
JP Coleman, LC Kirby and RA Klein
Department of Microbiology and Immunology, School of Medicine, East Carolina University, Greenville, NC 27858, USA.
New analogs of amino acid-conjugated bile acids were synthesized in which
the amide bond was reversed from its normal configuration. These structural
isomers of the beta-alanyl conjugates of cholic acid and ursodeoxycholic
acid were synthesized by reaction of succinic anhydride with the
24-nor-23-amine derivatives of cholic acid and ursodeoxycholic acid. The
chemical and physical properties of these reverse amide conjugated bile
acid analogs were compared with those of the normal glycine and
beta-alanine conjugates. The reverse amide analogs comigrated with their
isomeric beta-alanine conjugates during thin- layer chromatography using a
variety of solvent systems. However, the isomeric pairs could be resolved
by reversed-phase high performance liquid chromatography, with the reverse
amides having greater retention times compared to the beta-alanine
conjugates. Critical micelle concentrations, solubility of undissociated
forms, and acid dissociation constants were similar for the isomeric pairs.
Significant differences in melting points were observed, however, While the
isomeric pairs showed no significant differences in sensitivity to base
hydrolysis, the reverse amides were not hydrolyzed by the cholylglycine
hydrolase from Clostridium perfringens, even after long incubation periods.
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