View PDF Version
 
DOI: 10.1039/A700353F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1845-1850

Phospholipase-A2-mediated stereoselective synthesis of (R)-1-O-alkylglycero-3-phosphate and alkyl-acyl analogues: application for synthesis of radiolabelled biosynthetic precursors of cell surface glycoconjugates of Leishmania donovani

(Note: The full text of this document is currently only available in the PDF Version )

Parmeshwari Sahai and Ram A. Vishwakarma

Abstract

Stereoselective syntheses of (R)-1-O-alkylglycero-3-phosphate and alkyl-acyl analogues have been achieved using glycerol as starting material by an efficient application of Phospholipase-A2 enzyme from Naja mocambique mocambique. This synthetic strategy allows a high yielding preparation of radiolabelled [14C] and chirally pure biosynthetic precursors of GIPLs and LPG cell surface molecules of promastigote and amastigote forms of the protozoan parasite Leishmania donovani.

References

  1. K.-P. Chang and R. S. Bray, Leishmaniasis, Human Parasitic Diseases Vol. 1, Elsevier Science Publishing Co., New York, 1985 Search PubMed.
  2. M. J. McConville and M. A. J. Ferguson, Biochem. J., 1993, 294, 305 CAS; S. J. Turco and A. Descoteaux, Annu. Rev. Microbiol, 1992, 46, 65 CrossRef CAS; V. L. Stevens, Biochem. J., 1995, 310, 361 CAS; P. T. Englund, Annu. Rev. Biochem., 1993, 62, 121 CrossRef CAS.
  3. M. A. Carver and S. J. Turco, J. Biol. Chem., 1991, 266, 10 974 CAS.
  4. K. A. Ryan, L. A. Garraway, A. Descoteaux, S. J. Turco and S. M. Beverley, Proc. Natl. Acad. Sci. USA, 1993, 90, 8609 CAS; A. Descoteaux, Ya Luo, S. J. Turco and S. M. Beverley, Science, 1995, 269, 1869 CAS.
  5. A. V. Nikolaev, T. J. Rutherford, M. A. J. Ferguson and J. S. Brimacombe, J. Chem. Soc., Perkin Trans. 1, 1996, 1559 RSC; 1995, 1977; S. Cottaz, J. S. Brimacombe and M. A. J. Ferguson, J. Chem. Soc., Perkin Trans. 1, 1995, 1673 Search PubMed; Carbohydr. Res., 1995, 270, 85 RSC; J. Chem. Soc., Perkin Trans. 1, 1993, 2945 RSC; A. V. Nikolaev, T. J. Rutherford, M. A. J. Ferguson and J. S. Brimacombe, Bioorg. Med. Chem. Lett., 1994, 4, 785 RSC; A. Arasappan and B. Fraser-Reid, J. Org. Chem., 1996, 61, 2401 Search PubMed; Tetrahedron Lett., 1995, 36, 7967 Search PubMed.
  6. R. Bittman, Chemical Preparation of Glycerolipids: A Review recent Syntheses, in Phospholipids Handbook, ed. Gregor Cevc, Marcel Dekker Inc., New York, 1993, ch. 6 Search PubMed; H. Eibl, Angew. Chem., Int. Ed. Engl., 1984, 23, 257 Search PubMed; F. Ramirej and J. F. Marecek, Synthesis, 1985, 449 CrossRef.
  7. E. Bare and M. Kates, J. Am. Chem. Soc., 1950, 72, 942 CrossRef; H. Eibl and P. Woolley, Chem. Phys. Lipids, 1988, 47, 47 CrossRef CAS.
  8. K. Aggarwal, A. Bali and C. M. Gupta, Chem. Phys. Lipids, 1984, 36, 169 CrossRef; H. Eibl and P. Woolley, Chem. Phys. Lipids, 1986, 41, 53 CrossRef CAS.
  9. B. Rattay, G. Brezesinski, B. Dobner, G. Föster and P. Nuhn, Chem. Phys. Lipids, 1995, 75, 81 CrossRef CAS.
  10. E. Eibl and P. Woolley, Chem. Phys. Lipids, 1988, 47, 63 CrossRef; Chem. Phys. Lipids, 1988, 47, 55 Search PubMed; S. F. Martin, J. A. Josey, Y.-L. Wong and D. W. Dean, J. Org. Chem., 1994, 59, 4805 Search PubMed; S. F. Martin, Y.-L. Wong and S. A. Wagman, J. Org. Chem., 1994, 59, 4821 CrossRef CAS.
  11. K. Fugita, H. Nakai, S. Kobayashi, K. Inoue, S. Nojima and M. Ohno, Tetrahedron Lett., 1982, 23, 3507 CrossRef.
  12. V. Achterber, H. Fricke and G. Gerken, Chem. Phys. Lipids, 1986, 41, 137 CrossRef.
  13. B. V. L. Potter and D. Lampe, Angew. Chem., Int. Ed. Engl., 1995, 34, 1933 CrossRef CAS; W. H. Moolenaar, J. Biol. Chem., 1995, 270, 12 949 CAS.
  14. M. Renoll and M. S. Newman, Org. Synth., 1955, Coll. Vol. 3, p. 502.
  15. C. I. Hong, A. Nachaev, A. J. Kiristis, R. Vig, S.-W. Hui and C. R. West, J. Med. Chem., 1995, 38, 1629 CrossRef CAS.
  16. J. Kotting and H. Eibl, Lipases and Phospholipases in Organic Synthesis, in Lipases: Their Structure, Biochemistry, and Applications, ed. P. Woolley and S. B. Petersen, Cambridge University Press, Great Britain, 1994, ch. 14 Search PubMed.
  17. L. M. van Deenen and G. H. de Haas, Biochim. Biophys. Acta, 1963, 70, 538 CrossRef; A. J. Slotbloom, R. Verger, H. M. Verheij, P. H. M. Baartmans and L. L. M. van Deenen, Chem. Phys. Lipids, 1976, 17, 128 CrossRef CAS; A. Hermetter and F. Paltauf, Biochim. Biophys. Acta, 1983, 752, 444 CrossRef CAS.
  18. C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry (Tetrahedron Organic Chemistry Series, Vol. 12), Pergamon, Elsevier Science Ltd., UK, 1994, ch. 2, p. 69 Search PubMed.
  19. B. Kleuser, A. Meister, L. Sternfeld and G. Gerken, Chem. Phys. Lipids, 1996, 79, 29 CrossRef CAS.
  20. D. L. Scot, S. P. White, Z. Otwinowski, W. Yuan, M. H. Gelb and P. B. Sigler, Science, 1990, 250, 1541 CrossRef.
  21. X. Han and R. W. Gross, Proc. Natl. Acad. Sci. USA, 1994, 91, 10 635 CAS; J. Am. Chem. Soc., 1996, 118, 451 Search PubMed.
  22. H. Eibl, J. O. McIntyre, E. A. M. Fleer and S. Fleischer, Methods Enzymol., 1983, 98, 623 CrossRef CAS; S. Palitzsch, Biochem. Z., 1915, 70, 333 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.