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Lipids. 1980 Oct;15(10):805-10. doi: 10.1007/BF02534369.

Bile acids: LXI. Synthesis and properties of conjugates of 5α-bile acids.

Lipids

R Shaw, W H Elliott

Affiliations

  1. Edward A. Doisy Department of Biochemistry, Saint Louis University School of Medicine, 63104, St. Louis, MO.

PMID: 27520782 DOI: 10.1007/BF02534369

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.

References

  1. J Chem Educ. 1967 Dec;44(12):724-8 - PubMed
  2. Steroids. 1972 Sep;20(3):279-94 - PubMed
  3. J Lipid Res. 1978 Aug;19(6):783-7 - PubMed
  4. J Lipid Res. 1977 May;18(3):339-62 - PubMed
  5. J Lipid Res. 1973 May;14(3):367-70 - PubMed
  6. J Chromatogr. 1969 Nov 11;44(3):452-64 - PubMed
  7. J Lipid Res. 1960 Apr;1:250-1 - PubMed
  8. J Chem Soc Perkin 1. 1974;0(12):1438-9 - PubMed
  9. Lipids. 1978 Dec;13(12):971-5 - PubMed
  10. Anal Biochem. 1976 Aug;74(2):273-81 - PubMed
  11. Biomed Mass Spectrom. 1978 Jul;5(7):433-8 - PubMed
  12. Anal Biochem. 1978 Jun 1;86(2):450-6 - PubMed
  13. J Steroid Biochem. 1977 Oct;8(10):1077-84 - PubMed
  14. J Org Chem. 1968 Jul;33(7):2814-8 - PubMed
  15. J Lipid Res. 1976 Jan;17(1):21-4 - PubMed
  16. J Lipid Res. 1968 Mar;9(2):288-90 - PubMed
  17. J Lipid Res. 1978 Feb;19(2):177-86 - PubMed
  18. Steroids. 1974 Feb;23(2):221-8 - PubMed
  19. J Lipid Res. 1977 May;18(3):404-7 - PubMed
  20. FEBS Lett. 1974 May 1;41(2):223-6 - PubMed
  21. J Biol Chem. 1964 Sep;239:2813-21 - PubMed

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