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Bile acids: LXI. Synthesis and properties of conjugates of 5α-bile acids
1Edward A. Doisy Department of Biochemistry, Saint Louis University School of Medicine, 63104, St. Louis, MO.
Abstract:
Allo bile acids and their taurine- and glycine-conjugates were synthesized by modification of existing procedures. Their chromatographic and spectral properties were investigated and compared with the 5β-analogs. Some of the naturally occurring 5α- and 5β-conjugates were separable by high performance liquid chromatography via straight-phase (Corasil II column) or reverse-phase systems (μBondapak/C18 column), though unsuccessful with thin layer or gas liquid chromatography. Differences between the C-5 epimers in the infrared and proton magnetic resonance spectra could be attributed to the configurations at the A/B ring junction and the configuration of the 3-hydroxyl group. The calcium salts of the allo compounds were generally less soluble in water than the 5β-isomers.
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