Parasite glycoconjugates. Part 6.1 Chemical synthesis of phosphorylated penta- and hepta-saccharide fragments of Leishmania major antigenic lipophosphoglycan

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

Andrei V. Nikolaev, Gregory M. Watt, Michael A. J. Ferguson and John S. Brimacombe


Abstract

The phosphorylated branched oligosaccharides 1 and 2, fragments of the phosphoglycan portion of Leishmania major lipophosphoglycan, have been synthesized using the trichloroacetimidate method for the glycosylation reactions and the phosphoramidite and hydrogenphosphonate methods for phosphorylation.


References

  1. Part 5, A. V. Nikolaev, T. J. Rutherford, M. A. J. Ferguson and J. S. Brimacombe, J. Chem. Soc., Perkin Trans. 1, 1996, 1559 Search PubMed.
  2. A. V. Nikolaev, T. J. Rutherford, M. A. J. Ferguson and J. S. Brimacombe, J. Chem. Soc., Perkin Trans. 1, 1995, 1977 RSC.
  3. A. V. Nikolaev, J. A. Chudek and M. A. J. Ferguson, Carbohydr. Res., 1995, 272, 179 CrossRef CAS.
  4. M. J. McConville, J. E. Thomas-Oates, M. A. J. Ferguson and S. W. Homans, J. Biol. Chem., 1990, 265, 19611 CAS.
  5. M. J. McConville, S. J. Turco, M. A. J. Ferguson and D. L. Sacks, EMBO J., 1992, 11, 3593 CAS.
  6. P. F. P. Pimenta, S. J. Turco, M. J. McConville, P. G. Lawyer, P. V. Perkins and D. L. Sacks, Science, 1992, 256, 1812 CAS.
  7. P. F. P. Pimenta, E. M. B. Saraiva, E. Rowton, G. B. Modi, L. A. Garraway, S. M. Beverley, S. J. Truco and D. L. Sacks, Proc. Natl. Acad. Sci. USA, 1994, 91, 9155 CAS.
  8. M. Kelleher, A. Bacic and E. Handman, Proc. Natl. Acad. Sci. USA, 1992, 89, 6 CAS.
  9. R. R. Schmidt, Angew. Chem., Int. Ed. Engl., 1986, 25, 212 CrossRef.
  10. R. R. Schmidt, in Carbohydrates—Synthetic Methods and Application in Medicinal Chemistry, ed. H. Ogura, A. Hasegawa and T. Suami, Kodansha (Tokyo)/VCH (Weinheim), 1992, pp. 66–88 Search PubMed.
  11. V. V. Bencomo, J.-C. Jacquinet and P. Sinaij, Carbohydr. Res., 1982, 110, c9 CrossRef.
  12. P. Kováč, R. B. Taylor and C. P. J. Glaudemans, J. Org. Chem., 1985, 50, 5323 CrossRef CAS.
  13. T. Ziegler, B. Adams, P. Kováč and C. P. J. Glaudemans, J. Carbohydr. Chem., 1990, 9, 135 CAS.
  14. J. M. Williams and A. C. Richardson, Tetrahedron, 1967, 23, 1369 CrossRef CAS.
  15. A. V. Nikolaev, I. A. Ivanova and V. N. Shibaev, Carbohydr. Res., 1993, 242, 91 CrossRef CAS.
  16. A. Hasegawa, K. Adachi, M. Yoshida and M. Kiso, Carbohydr. Res., 1992, 230, 273 CrossRef CAS.
  17. C. W. Slife, M. A. Nashed and L. Anderson, Carbohydr. Res., 1981, 93, 219 CrossRef CAS.
  18. G. Yang, F. Kong and S. Zhou, Carbohydr. Res., 1991, 211, 179 CrossRef CAS.
  19. K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg and G. Magnusson, J. Org. Chem., 1988, 53, 5629 CrossRef CAS.
  20. P. Kováč, H. J. C. Yeh and C. P. J. Glaudemans, Carbohydr. Res., 1985, 140, 277 CrossRef CAS.
  21. S. Hanessian and P. Lavallee, Can. J. Chem., 1975, 53, 2975 CAS.
  22. S. L. Beaucage and M. N. Caruthers, Tetrahedron Lett., 1981, 22, 1859 CrossRef CAS.
  23. A. D. Barone, J.-Y. Tang and M. N. Caruthers, Nucleic Acids Res., 1984, 12, 4051 CAS.
  24. T. Tanaka, S. Tamatsukuri and T. Ikehara, Tetrahedron Lett., 1986, 27, 199 CrossRef CAS.
  25. E. Uhlmann and J. Engels, Tetrahedron Lett., 1986, 27, 1023 CrossRef CAS.
  26. B. A. Dmitriev, A. V. Nikolaev, A. S. Shashkov and N. K. Kochetkov, Carbohydr. Res., 1982, 100, 195 CrossRef CAS.
  27. F.-I. Auzanneau, F. Forooghian and B. M. Pinto, Carbohydr. Res., 1996, 291, 21 CAS.
  28. A. V. Nikolaev, I. A. Ivanova, V. N. Shibaev and N. K. Kochetkov, Sov. J. Bioorg. Chem. (Engl. Transl.), 1990, 16, 376 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.