New solid-phase oligosaccharide synthesis on glycopeptides bound to a solid phase

Abstract

A solid-phase oligosaccharide synthesis has been developed which utilises glycopeptides bound to the solid phase. The products are glycopeptides elongated at the saccharide chain. The glycosyl acceptors, which are assembled by simple solid-phase glycopeptide synthesis, contain 2-azido-2-deoxy-α-D-galactose with unsubstituted 3-OH or 6-OH groups, which can be glycosylated. Suitable glycosyl donors are perbenzoylated trichloroacetimidates of D-galactose or 2-amino-2-deoxy-D-glucose, although the 2-amino group must be protected with Teoc. A corresponding additional saccharide unit is added with a β-glycosidic linkage. With disaccharide donors, glycopeptides with linear trisaccharide side chains are obtained. By performing the solid-phase glycosylation synthesis twice in succession glycopeptides with branched trisaccharide chains have been obtained.

References

1. B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149.
2. J. S. Früchtel and G. Jung, Angew. Chem., 1996, 108, 19; Angew. Chem., Int. Ed. Engl., 1996, 35, 17.
3. J. M. Frechet and C. Schuerch, J. Am. Chem. Soc., 1971, 93, 492; Carbohydr. Res., 1972, 22, 399.
4. S. J. Danishefsky, K. F. McClure, J. T. Randolph and R. B. Ruggeri, Science, 1993, 260, 1307.
5. K. Suzuki, G. A. Sulikowski, R. W. Friesen and S. J. Danishefsky, J. Am. Chem. Soc., 1990, 112, 8895.
6. J. T. Randolph, K. F. McClure and S. J. Danishefsky, J. Am. Chem. Soc., 1995, 117, 5712.
7. C. M. Timmers, G. A. van der Marel and J. H. van Boom, Recl. Trav. Chim. Pays-Bas, 1993, 112, 609.
8. L. Yan, L. C. M. Taylor, R. Goodnow, Jr. and D. Khane, J. Am. Chem. Soc., 1994, 116, 6953.
9. M. Schuster, P. Wang, J. C. Paulson and C.-H. Wong, J. Am. Chem. Soc., 1994, 116, 1135.
10. S. P. Douglas, D. M. Whitefield and J. J. Krepinsky, J. Am. Chem. Soc., 1991, 113, 5095; 1995, 117, 2116.
11. J. J. Krepinsky, in Modern Methods in Carbohydrate Synthesis, ed. S. H. Khan and R. A. O'Neill, Harwood Academic, Amsterdam, 1996, p. 194.
12. R. R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 1994, 50, 21.
13. R. Verduyn, P. A. M. van der Klein, M. Douwes, G. A. van der Marel and J. H. van Boom, Recl. Trav. Chim. Pays-Bas, 1993, 112, 464.
14. S. Peters, T. Bielfeldt, M. Meldal, K. Bock and H. Paulsen, J. Chem. Soc., Perkin Trans. 1, 1992, 1163.
15. H. Paulsen, T. Bielfeldt, S. Peters, M. Meldal and K. Bock, Liebigs Ann. Chem., 1994, 369, 381.
16. H. Paulsen, S. Peters, T. Bielfeldt, M. Meldal and K. Bock, Carbohydr. Res., 1995, 268, 17.
17. I. Brockhausen, in Glycoproteins, ed. J. Montreuil, H. Schachter and J. F. G. Vliegenthart, Elsevier, Amsterdam, 1995, p. 201.
18. M. Verma and E. A. Davidson, Glycoconjugate J., 1994, 11, 172.
19. J. Taylor-Papadimetriou and A. A. Epenetos, TIB TECH, 1994, 12, 227.
20. E. Meinjohanns, M. Meldal, A. Schleyer, H. Paulsen and K. Bock, J. Chem. Soc., Perkin Trans. 1, 1996, 985.
21. L. R. Cameron, J. Holder, M. Meldal and R. C. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1988, 2895.
22. H. Rink, Tetrahedron Lett., 1987, 28, 3787.
23. S. Rio, J.-M. Beau and J.-C. Jacquinet, Carbohydr. Res., 1991, 219, 71.
24. G. Grundler and R. R. Schmidt, Liebigs Ann. Chem., 1984, 1826.
25. S. Rio, J.-M. Beau and J.-C. Jacquinet, Carbohydr. Res., 1993, 244, 295.
26. H. Paulsen, Angew. Chem., 1982, 94, 184; Angew. Chem., Int. Ed. Engl., 1982, 21, 155.
27. R. U. Lemieux, T. Takeda and B. Y. Chung, ACS Symposium Series, 1976, vol. 39, p. 90.
28. T. M. Windholz and B. R. Jonston, Tetrahedron Lett., 1967, 2555.
29. H. Paulsen and B. Helpap, Carbohydr. Res., 1991, 216, 289.
30. E. Meinjohanns, M. Meldal, H. Paulsen and K. Bock, J. Chem. Soc., Perkin Trans. 1, 1995, 405.
31. A. Vargas-Berenguel, M. Meldal, H. Paulsen and K. Bock, J. Chem. Soc., Perkin Trans. 1, 1994, 2615.
32. M. Mori, Y. Ito and T. Ogawa, Carbohydr. Res., 1990, 195, 199.
33. X.-B. Han and R. R. Schmidt, Liebigs Ann. Chem., 1992, 817.