Skip to main content
Log in

The total synthesis of phosphatidyl(Dioleoyl)hydroxy-l-proline and its activity in blood-clotting systems

  • Published:
Lipids

Abstract

The phthalimidomethyl ester ofN-anisyloxycarbonyl-hydroxy-l-proline was combined with phosphorus oxychloride andrac-1,2-diolein. The diolein was made by large-scale preparative application of the method of Krabisch and Borgström (1). The protected phosphatide, obtained by the phosphorylation reaction, was stripped of its protective groups under mild conditions. The phosphatidyl(dioleoyl)-hydroxy-l-proline was purified by TEAE cellulose (acetate) chromatography, as developed by Rouser (6), also by silicic acid chromatography. Aqueous dispersions of the material were tested for anticoagulant activity in the antithrom-boplastin test and the Hicks-Pitney test. The new phosphatide had about one-tenth of the activity of beef brain phosphatidylserine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Krabisch, L., and B. Borgström, J. Lipid Res.6, 156–157 (1965).

    PubMed  CAS  Google Scholar 

  2. Baer, E., and A. Zschocke, J. Biol. Chem.236, 1273–1276 (1961).

    PubMed  CAS  Google Scholar 

  3. Turner, D. L., M. J. Silver, E. Baczynski, N. Giordano and I. Rodalewicz, J. Lipid Res.5, 616–623 (1964).

    PubMed  CAS  Google Scholar 

  4. Turner, D. L., M. J. Silver and E. Baczynski, Lipids1, 439–443 (1968).

    Google Scholar 

  5. Sen, Subha, R. R. Smeby and F. M. Bumpus, Biochem.6, 1572–1581 (1967).

    Article  Google Scholar 

  6. Rouser, G., G. Kritchevsky, D. Heller and E. Lieber, JAOCS40, 425–454 (1963).

    Google Scholar 

  7. Turner, D. L., in “Blood Coagulation. Hemorrhage, and Thrombosis. Methods of Study,” Tocantins, L. M. and L. A. Kazal eds., New York, Grune and Stratton, 1964, p. 368.

    Google Scholar 

  8. Barry, P. J., and B. M. Craig, Canad. J. Chem.33, 716–721 (1955).

    Article  CAS  Google Scholar 

  9. Crossley, A., I. P. Freeman, B. J. F. Hudson and J. F. Pierce, J. Chem. Soc. 760–764 (1959).

  10. Baer, E., and D. Buchnea, J. Biol. Chem.230, 447–456 (1958).

    PubMed  CAS  Google Scholar 

  11. Thomas, A. E., J. E. Scharoun and H. Ralston, JAOCS42, 789–792 (1965).

    CAS  Google Scholar 

  12. Morris, L. J., in “Metabolism and Physiological Significance of Lipids,” eds., R. M. C. Dawson and D. N. Rhodes, John Wiley and Sons Inc., New York, 1964, p. 641–650.

    Google Scholar 

  13. Weygand, F., and K. Hunger, Chem. Ber.95, 1–6 (1962).

    CAS  Google Scholar 

  14. Grisdale, P. J., and A. Okany, Canad. J. Biochem.43, 781–786 (1965).

    CAS  Google Scholar 

  15. Pataki, G., J. Chromatogr.12, 541 (1963).

    Article  CAS  Google Scholar 

  16. Dawson, R. M. C., D. C. Elliott, W. H. Elliott and K. M. Jones, “Data for Biochemical Research,” Oxford University Press, London, 1959, p. 231.

    Google Scholar 

  17. Long, C., R. Odavic and E. J. Sargent, Biochem. J.102, 216–220 (1967).

    PubMed  CAS  Google Scholar 

  18. Marinetti, G. V., J. Lipid Res.3, 1–20 (1962).

    CAS  Google Scholar 

  19. Silver, M. J., D. L. Turner, I. Rodalewicz, N. Giordano, R. Holburn, S. F. Herb, and F. E. Luddy, Thromb. Diath. Haemorr.10, 164–189 (1963).

    CAS  Google Scholar 

  20. Abramson, M. B., R. Katzman and H. P. Gregor, J. Biol. Chem.239, 70–76 (1964).

    PubMed  CAS  Google Scholar 

  21. McCay, P. B., Ibid.241, 2333–2339 (1968).

    Google Scholar 

  22. Fenster, L. J., and J. H. Copenhaver Jr., Biochim. Biophys. Acta137, 406–408 (1967).

    PubMed  CAS  Google Scholar 

  23. Tobias, J. M., Nature203, 13–17 (1964).

    Article  PubMed  CAS  Google Scholar 

  24. Breyer, U., and G. Quadbeck, J. Neurochem.13 493–500 (1968).

    Article  Google Scholar 

  25. Gigg, R., and J. Gigg, J. Chem. Soc. 431–434 (1967).

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

Turner, D.L., Silver, M.J., Holburn, R.R. et al. The total synthesis of phosphatidyl(Dioleoyl)hydroxy-l-proline and its activity in blood-clotting systems. Lipids 3, 228–233 (1968). https://doi.org/10.1007/BF02531192

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02531192

Keywords

Navigation