Parasite glycoconjugates. Part 9.1 Synthesis of dec-9-enyl β-D-galactopyranosyl-(1→4)-α-D-mannopyranosyl phosphate and its epimers at the D-galactose moiety, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania

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Irina A. Ivanova, Andrew J. Ross, Michael A. J. Ferguson and Andrei V. Nikolaev


Abstract

A set of phosphodisaccharides, substrate analogues, which will be used to study the acceptor substrate specificity of the Leishmania biosynthetic enzymes, have been synthesized using the trichloroacetimidate method for the glycosylation reactions, SN2 nucleophilic displacement of triflic esters for epimerization and the glycosyl hydrogenphosphonate method for phosphorylation.


References

  1. Part 8, A. P. Higson, Yu. E. Tsvetkov, M. A. J. Ferguson and A. V. Nikolaev, J. Chem. Soc., Perkin Trans. 1, 1998, 2587 Search PubMed.
  2. M. J. McConville and M. A. J. Ferguson, Biochem. J., 1993, 294, 305 CAS.
  3. M. J. McConville, L. F. Schnur, C. Jaffe and P. Schneider, Biochem. J., 1995, 310, 807 CAS.
  4. T. Ilg, R. Etges, P. Overath, M. J. McConville, J. E. Thomas-Oates, J. Thomas, S. W. Homans and M. A. J. Ferguson, J. Biol. Chem., 1992, 267, 6834 CAS.
  5. T. Ilg, P. O. Overath, M. A. J. Ferguson, T. Rutherford, D. G. Campbell and M. J. McConville, J. Biol. Chem., 1994, 269, 24073 CAS.
  6. Y.-D. Stierhof, M. Wiese, T. Ilg, P. Overath, M. Haener and U. Aebi, J. Mol. Biol., 1998, 282, 137 CrossRef CAS.
  7. T. Ilg, Y.-D. Stierhof, D. Craik, R. Simpson, E. Handman and A. Bacic, J. Biol. Chem., 1996, 271, 21583 CrossRef CAS.
  8. T. Ilg, D. Craik, G. Currie, G. Multhaup and A. Bacic, J. Biol. Chem., 1998, 273, 13509 CrossRef CAS.
  9. C. Peters, Y.-D. Stierhof and T. Ilg, Infect. Immun., 1997, 65, 783 CAS.
  10. C. Peters, M. Kawakami, M. Kaul, T. Ilg, P. Overath and T. Aebischer, Eur. J. Immunol., 1997, 27, 2666 Search PubMed.
  11. A. V. Nikolaev, T. J. Rutherford, M. A. J. Ferguson and J. S. Brimacombe, J. Chem. Soc., Perkin Trans. 1, 1995, 1977 RSC.
  12. A. V. Nikolaev, T. J. Rutherford, M. A. J. Ferguson and J. S. Brimacombe, J. Chem. Soc., Perkin Trans. 1, 1996, 1559 RSC.
  13. A. V. Nikolaev, G. M. Watt, M. A. J. Ferguson and J. S. Brimacombe, J. Chem. Soc., Perkin Trans. 1, 1997, 969 RSC.
  14. A. V. Nikolaev, J. A. Chudek and M. A. J. Ferguson, Carbohydr. Res., 1995, 272, 179 CrossRef CAS.
  15. G. M. Brown, A. R. Millar, C. Masterson, J. S. Brimacombe, A. V. Nikolaev and M. A. J. Ferguson, Eur. J. Biochem., 1996, 242, 410 CrossRef CAS.
  16. A. V. Nikolaev, I. A. Ivanova, V. N. Shibaev and N. K. Kochetkov, Carbohydr. Res., 1990, 204, 65 CrossRef CAS.
  17. A. Hasegawa, K. Adachi, M. Yoshida and M. Kiso, Carbohydr. Res., 1992, 230, 273 CrossRef CAS.
  18. B. Lou, H. K. Huynh and S. Hanessian, in Preparative Carbohydrate Chemistry, ed. S. Hanessian, Marcel Dekker, New York, 1997, pp. 431–448 Search PubMed.
  19. N. E. Byramova, M. V. Ovchinnikov, L. V. Backinowsky and N. K. Kochetkov, Carbohydr. Res., 1983, 124, c8 CrossRef CAS.
  20. I. A. Ivanova and A. V. Nikolaev, J. Chem. Soc., Perkin Trans. 1, 1998, 3093 RSC.
  21. G. I. Eliseeva, I. A. Ivanova, A. V. Nikolaev and V. N. Shibaev, Sov. J. Bioorg. Chem.(Engl. Transl.), 1991, 17, 808 Search PubMed.
  22. J. V. O'Connor, H. A. Nunez and R. Barker, Biochemistry, 1979, 18, 500 CrossRef.
  23. J. O. Defferary and V. Deulofeu, J. Org. Chem., 1952, 17, 1097 CrossRef.
  24. N. S. Utkina, A. V. Nikolaev and V. N. Shibaev, Sov. J. Bioorg. Chem.(Engl. Transl.), 1991, 17, 303 Search PubMed.
  25. R. K. Ness, H. G. Fletcher, Jr. and C. S. Hudson, J. Am. Chem. Soc., 1950, 72, 2200 CrossRef CAS.
  26. R. K. Ness, H. G. Fletcher, Jr. and C. S. Hudson, J. Am. Chem. Soc., 1951, 73, 959 CrossRef CAS.
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