Lecithin pp 37-45 | Cite as

Partial Synthesis of Glycerophospholipids

  • A. Hermetter
  • F. Paltauf
Part of the Advances in Behavioral Biology book series (ABBI, volume 33)

Abstract

Glycerophospholipids obtained from natural sources, that is from plant, animal or microbial cells, are complex mixtures of phospholipid classes, subclasses and species. It is extremely difficult if not impossible to isolate, with available technology, individual phospholipid species from such mixtures. If one needs a chemically defined phospholipid, e.g., for biochemical or biophysical studies, for the preparation of lipid vesicles or liposomes, or as emulsifiers with well defined properties etc., then chemical synthesis is the only way to make these substances available. The use of synthetic methods is even more compulsory if the desired product is a radioactively or otherwise — spin, fluorescent or photoreactive — labeled phospholipid, or if it contains other “unnatural” rests, such as modified head groups or hydrophobic moieties.

Keywords

Phosphatidic Acid Phospholipid Class Acyl Migration Amino Alcohol Partial Synthesis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    H. Eibl, Phospholipide als funktioneile Bausteine biologischer Membranen Angew. Chemie 96:247 (1984).Google Scholar
  2. 2.
    A. Hermetter, H. Stütz, and F. Paltauf, An improved method for the preparation of mixed-chain phosphatidylethanolamines, Chem. Phys. Lipids 32:145 (1983).CrossRefGoogle Scholar
  3. 3.
    R. Aneja, J. S. Chadha, E. Cubero Rubles, and R. Van Daal, Partial synthesis of phosphatidylethanolamines, Biochim. Biophys. Acta 187:439 (1969).PubMedCrossRefGoogle Scholar
  4. 4.
    C. M. Gupta, R. Radhakrishnan, and H. G. Khorana, Glycerophospholipid synthesis: Improved general method and new analogs containing photoactivable groups, Proc. Natl. Acad. Sci. USA 74:4315 (1977).PubMedCrossRefGoogle Scholar
  5. 5.
    H. Brockerhoff, P. C. Schmidt, J. W. Fong, and L. J. Tirri, Introduction of labeled fatty acid in position 1 of phosphoglycerides, Lipids 11:421 (1976).PubMedCrossRefGoogle Scholar
  6. 6.
    P. Comfurius, and R. F. A. Zwaal, The enzymatic synthesis of phosphatidylserine and purification by CM-cellulose column chromatography, Biochim. Biophys. Acta 488:36 (1977).PubMedCrossRefGoogle Scholar
  7. 7.
    Production of primary or secondary alcohol derivatives of phospholipids by the enzymatic technique, JP 63304/83, and JP 63305/83.Google Scholar
  8. 8.
    I. Barzilay, and Y. Lapidot, The modified synthesis of phosphatidyl-ethanolamine, Chem. Phys. Lipids 3:280 (1969).PubMedCrossRefGoogle Scholar
  9. 9.
    F. Paltauf, An improved synthesis of l-0-[3H]alkyl-2-acyl-sn-glycerol-3-phosphoethanolamine with an unsaturated acyl chain, Chem. Phys. Lipids 17:148 (1976).PubMedCrossRefGoogle Scholar
  10. 10.
    R. Aneja, and J. S. Chadha, A total synthesis of phosphatidylcholines, Biochim. Biophys. Acta 248:455 (1971).CrossRefGoogle Scholar
  11. 11.
    A. F. Rosenthal, New, partially hydrolyzable synthetic analogues of lecithin, phosphatidylethanolamine, and phosphatidic acid, J. Lipid Res. 7:779 (1966).PubMedGoogle Scholar
  12. 12.
    A. Hermetter, F. Paltauf, and H. Hauser, Synthesis of diacyl and alkyl-acyl glycerophosphoserines, Chem. Phys. Lipids 30:35 (1982).CrossRefGoogle Scholar
  13. 13.
    M. Bugaut, A. Kuksis, and J. J. Myher, Loss of stereospecificity of phospholipases C and D upon introduction of a 2-alkyl group into rac-l,2-diacyl-glycero-3-phosphocholine, Biochim. Biophys. Acta 835:304 (1985).PubMedCrossRefGoogle Scholar
  14. 14.
    F. Paltauf, and E. Wagner, Stereospecificity of upases. Enzymatic hydrolysis of enantiomeric alkyldiacyl-and dialkylacylglycerols by lipoprotein lipase, Biochim. Biophys. Acta 431:359 (1976).PubMedCrossRefGoogle Scholar
  15. 15.
    N. Weber, H. Benning, and H. K. Mangold, Production of complex ether glycerolipids from exogenous alkylglycerols by cell suspension cultures of rape, Appl. Microbiol. Biotechnol. 20:238 (1984).CrossRefGoogle Scholar
  16. 16.
    T. G. Warner, and A. A. Benson, An improved method for the preparation of unsaturated phosphatidylcholines: acylation of sn-glycero-3-phos-phocholine in the presence of sodium methylsulfinylmethide, J. Lipid Res. 18:548 (1977).PubMedGoogle Scholar
  17. 17.
    A. Hermetter, and F. Paltauf, A facile procedure for the synthesis of saturated phosphatidylcholines, Chem. Phys. Lipids 28:111 (1981).CrossRefGoogle Scholar
  18. 18.
    A. Hermetter, H. Stütz, K. Lohner, and F. Paltauf, 1-0,N-Ditritylgly-cerophosphoethanolamine, a novel intermediate for the facile preparation of mixed-acid phosphatidylethanolamines, Chem. Phys. Lipids, in press.Google Scholar

Copyright information

© Springer Science+Business Media New York 1987

Authors and Affiliations

  • A. Hermetter
    • 1
  • F. Paltauf
    • 1
  1. 1.Institute of Biochemistry and Food ChemistryTechnical University of GrazAustria

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