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Phospholipids — Natural, Semisynthetic, Synthetic

  • F. Paltauf
  • A. Hermetter

Abstract

Nature was remarkably inventive in creating the variety of polar lipids which form the matrix of biological membranes. The rationale for the variability of membrane lipids is not clear, it might simply be that these amphiphilic structures have in common the capability to arrange as bilayers in an aqueous environment. However, lipids are not only the plaster which holds the membrane together; there is ample evidence that distinct phospholipid classes or species serve additional tasks which make them indispensable for the functioning of membrane-linked pocesses. For example, phosphatidylinositols are involved in signal transduction and are therefore essential for the viability of eukaryotic cells. Most likely adaptation of polar lipid structures to specific requirements has occurred during evolution. The cell envelope of thermoacidophilic archaebacteria consists of chemically stable tetraether glyceroglyco-(or phospho-) lipids19 that might be essential for these organisms to survive at the extremes of high temperature and low pH. The pulmonary surfactant coating the mammalian alveolus contains dipalmitoylphosphatidylcholine (DPPC) as a major constituent. Together with other phospholipids and specific proteins DPPC reduces the surface tension at the air-liquid interface26. Reversible changes in the membrane phospholipid pattern in response to environmental stress, e.g., temperature or solvents, have repeatedly been observed (see respective chapters in ref.17).

Keywords

Phosphatidic Acid Phospholipid Class Ether Lipid Tetraether Lipid Aliphatic Moiety 
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.
    Aneja, R., and Chadha, J. S., 1971, A total synthesis of phosphatidylcholines, Biochim. Biophys. Acta 248:455–457.CrossRefGoogle Scholar
  2. 2.
    Benveniste, J., and Vargaftig, B. B., 1983, Platelet activating factor: An ether lipid with biological activity, in: “Ether Lipids. Biochemical and Biomedical Aspects”, H. K. Mangold and F. Paltauf, eds., Academic Press, New York, pp. 355–376.Google Scholar
  3. 3.
    Comfurius, P., and Zwaal, R. F. A., 1977, The enzymatic synthesis of phosphatidylserine and purification by CM — cellulose column chromatography, Biochim. Biophys. Acta 488:36–42.PubMedCrossRefGoogle Scholar
  4. 4.
    Cunningham, J., and Gigg, R., 1965, The preparation of 1 — O — alk — 1′ — enyl ethers of glycerol, J. Chem. Soc. 2968-2975.Google Scholar
  5. 5.
    Eibl, H., 1978, Phospholipid synthesis: Oxazaphospholanes and dioxaphospholanes as intermediates, Proc. Natl. Acad. Sci. USA 75:4074–4077.PubMedCrossRefGoogle Scholar
  6. 6.
    Eibl, H., 1980, Synthesis of glycerophospholipids, Chem. Phys. Lipids 26:405–429.PubMedCrossRefGoogle Scholar
  7. 7.
    Eibl, H., and Woolley, P., 1986, Synthesis of enantiomerically pure glyceryl esters and ethers. I. Methods employing the precursor 1,2 — isopropylidene — sn — glycerol, Chem. Phys. Lipids 41:53–63.CrossRefGoogle Scholar
  8. 8.
    Eibl, H., and Woolley, P., 1988, Synthesis of enantiomerically pure glyceryl esters and ethers. II. Methods employing the precursor 3,4 — isopropylidene — D — mannitol, Chem. Phys. Lipids 47:47–53.CrossRefGoogle Scholar
  9. 9.
    El-Tarras, M. F., Abdel Moety, E. M., Ahmad, A. K. S., and Amer, M. M., 1976, Studies on rancidity of oils and fats. On the autoxidation of phospholipids, Oleagineux 31:229; Chem. Abstr. 85:122107.Google Scholar
  10. 10.
    Goldfine, H., and Hagen, P.-O., 1972, Bacterial plasmalogens, in: “Ether Lipids. Chemistry and Biology,” F. Snyder, ed., Academic Press, New York, pp. 329–350.CrossRefGoogle Scholar
  11. 11.
    Hermetter, A., and Paltauf, F., 1981, A facile procedure for the synthesis of saturated phosphatidylcholines, Chem. Phys. Lipids 28:111–115.CrossRefGoogle Scholar
  12. 12.
    Hermetter, A., and Paltauf, F., 1987, Partial synthesis of glycerophospholipids, in: “Lecithin. Technological, Biological and Therapeutic Aspects,” I. Hanin and G. B. Ansell, eds., Plenum Press, New York, pp. 37–45.Google Scholar
  13. 13.
    Hermetter, A., Paltauf, F., and Hauser, H., 1982, Synthesis of diacyl and alkylacyl glycerophosphoserines, Chem. Phys. Lipids 30:35–45.CrossRefGoogle Scholar
  14. 14.
    Hermetter, A., Stütz, H., Franzmair, R., and Paltauf, F., 1989, 1 — O — Trityl — sn — glycero — 3 — phosphocholine: a new intermediate for the facile preparation of mixed — acid 1,2 — diacylglycerophosphocholines, Chem. Phys. Lipids, 50: 57–62.CrossRefGoogle Scholar
  15. 15.
    Horrocks, L. A., 1972, Content composition and metabolism of mammalian and avian lipids that contain ether groups, in: “Ether Lipids. Chemistry and Biology,” F. Snyder, ed., Academic Press, New York, pp. 177–272.CrossRefGoogle Scholar
  16. 16.
    Kates, M., 1972, Ether — linked lipids in extremely halophilic bacteria, in: “Ether Lipids. Chemistry and Biology,” F. Snyder, ed., Academic Press, New York, pp. 351–398.CrossRefGoogle Scholar
  17. 17.
    Kates, M., and Kuksis, A., eds., “Membrane Fluidity. Biophysical Techniques and Cellular Regulation”, 1980, The Humana Press Inc., Clifton.Google Scholar
  18. 18.
    Kudo, S., 1988, Biosurfactants as food additives, in: “Proceedings World Conference on Biotechnology for the Fats and Oils Industry,” T. H. Applewhite, ed., Amer. Oil Chem. Soc, pp. 195-201.Google Scholar
  19. 19.
    Langworthy, T. A., 1983, Dialkyldiglyceroltetraethers, in: “Ether Lipids. Biochemical and Biomedical Aspects,” H. K. Mangold and F. Paltauf, eds., Academic Press, New York, pp. 161–175.Google Scholar
  20. 20.
    Mangold, H. K., 1972, The search for alkoxylipids in plants, in: “Ether Lipids. Chemistry and Biology,” F. Snyder, ed., Academic Press, New York, pp. 399–405.CrossRefGoogle Scholar
  21. 21.
    Nielsen, N. C., and Wilcox, J. R., 1988, Biotechnology for soybean improvement, in: “Proceedings. World Conference on Biotechnology for the Fats and Oils Industry,” T. H. Applewhite, ed., Amer. Oil Chem. Soc, pp. 58-64.Google Scholar
  22. 22.
    Paltauf, F., 1983, Biosynthesis of 1 — O — (1’alkenyl) glycerolipids (plasmalogens), in: “Ether Lipids. Biochemical and Biomedical Aspects,” H. K. Mangold and F. Paltauf, eds., Academic Press, New York, pp. 107–128.Google Scholar
  23. 23.
    Pardun, H., 1982, Progress in productions and processing of vegetable lecithins, Fette Seifen. Anstrichm. 84:1–11.CrossRefGoogle Scholar
  24. 24.
    Pardun, H., 1982, An empiric method to determine the emulsifiability of vegetable lecithins in O/W — systems, Fette Seifen. Anstrichm. 84:291–299.CrossRefGoogle Scholar
  25. 25.
    Patton, G. M., Fasulo, J. M., and Robins, S. J., 1982, Separation of phospholipids and individual molecular species of phospholipids by high — performance liquid chromatography, J. Lipid Res. 23:190–196.PubMedGoogle Scholar
  26. 26.
    Possmayer, F., Metcalfe, I. L., and Enhorning, G., 1980, The pulmonary surfactant, in: “Membrane Fluidity. Biophysical Techniques and Cellular Regulation”, M. Kates and A. Kuksis, eds., The Humana Press Inc., Clifton, pp. 57–67.Google Scholar
  27. 27.
    Ratledge, C., 1987, Microorganisms as sources of phospholipids, in: Lecithin. Technological, Biological and Therapeutic Aspects,” I. Hanin and G. B. Ansell, eds., Plenum Press, New York, pp. 17–35.Google Scholar
  28. 28.
    Stepanov, A. E., and Shvets, V. I., 1980, Formation of phosphoester bonds in phosphoglyceride synthesis, Chem. Phys. Lipids 41:1–51.CrossRefGoogle Scholar
  29. 29.
    Warner, T. G., and Benson, A., 1977, An improved method for the preparation of unsaturated phosphatidylcholines: Acylation of sn — glycero — 3 — phosphocholine in the presence of sodium methylsulfinylmethide, J.Lipid Res. 18:548–552.PubMedGoogle Scholar
  30. 30.
    Woolley, P., and Eibl, H., 1988, Synthesis of enantiomerically pure phospholipids including phosphatidylserine and phosphatidylglycerol, Chem. Phys.Lipids 47:55–62.CrossRefGoogle Scholar
  31. 31.
    Yamane, T., 1988, Enzyme technology for the lipids industry: an engineering overview, in: “Proceedings. World Conference on Biotechnology for the Fats and Oils Industry,” T. H. Applewhite, ed., Amer. Oil Chem. Soc., pp. 17-22.Google Scholar

Copyright information

© Springer Science+Business Media New York 1990

Authors and Affiliations

  • F. Paltauf
    • 1
  • A. Hermetter
    • 1
  1. 1.Department of Biochemistry and Food ChemistryGraz University of TechnologyGrazAustria

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