Chemistry of Natural Compounds

, Volume 21, Issue 5, pp 582–584 | Cite as

Some aspects of the stereochemistry and nomenclature of polyunsaturated hydroxy fatty acids

  • A. G. Panosyan


When the D, L (but not the R, S) nomenclature is used, general laws are observed in the stereochemistry of lipoxygenase oxidation reactions and in the formation of epoxides from hydroperoxides of polysaturated hydroxy fatty acids. In both cases the formation of a C-O bond is coupled with the stereoselective elimination of a hydrogen atom, and the chiral and prochiral carbon atoms have identical configurations. The use of the D, L nomenclature in the polyenic hydroxy fatty acid series appears preferable to that of the R, S nomenclature.


Epoxide Hydroxy Fatty Acid Asymmetric Center Asymmetric Carbon Atom Tritium Atom 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    M. Hamberg and G. Hamberg, Biochem. Biophys. Res. Communs.,95, 1090 (1980).CrossRefGoogle Scholar
  2. 2.
    M. Hamberg and B. Samuelsson, Biochim. Biophys. Acta,617, 545 (1980).CrossRefGoogle Scholar
  3. 3.
    M. Hamberg and B. Samuelsson, J. Biol. Chem.,242, 5329 (1967).PubMedGoogle Scholar
  4. 4.
    M. R. Egmond, J. F. G. Vliegenthart, and J. Boldingh, Biochem. Biophys. Res. Communs.,48, 1055 (1972).CrossRefGoogle Scholar
  5. 5.
    E. J. Corey and R. T. Lansbury, Jr., J. Am. Chem. Soc.,105, 4093 (1983).CrossRefGoogle Scholar
  6. 6.
    A. G. Panossian, M. Hamberg, and B. Samuelsson, FEBS Lett.,150, 511 (1982).CrossRefGoogle Scholar
  7. 7.
    R. L. Mass, C. D. Ingram, D. F. Taber, J. A. Oates, and A. R. Brash, J. Biol. Chem.,257, 13525 (1982).Google Scholar
  8. 8.
    S. Hammarström, J. Biol. Chem.,258, 1427 (1983).PubMedGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • A. G. Panosyan

There are no affiliations available

Personalised recommendations