The syntheses of δ-NCS-butyl α-L-fucosides and fucobiosides and their clustering to triantennary glycomimetics

Journal of Carbohydrate Chemistry

Volumn 17, Issue 7, 1998, Pages 1131-1149

  Lindhorst, Thisbe K ^a   Ludewig, Michael ^a   Thiem, Joachim ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EUKARYOTA;

EID: 0000351371     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309808001889     Document Type: Article

References (39)

1. A. Varki, Glycobiology, 3, 97 (1993).
2. a) T. W. Rademacher, R. B. Parekh and R. A. Dwek, Ann. Rev. Biochem., 57, 785 (1988);
3. b) T. Feizi, Curr. Opin. Struct. Biol., 3, 701 (1993).
4. A. Giannis, Angew. Chem., 106, 188 (1994), Angew. Chem. Int. Ed. Engl., 33, 178 (1994).
5. A. Giannis, Angew. Chem., 106, 188 (1994), Angew. Chem. Int. Ed. Engl., 33, 178 (1994).
6. a) S. Hakomori, Ann. Rev. Biochem., 50, 733 (1981);
7. b) S. Hakomori, Cancer Res., 45, 2405 (1985);
8. c) T. Feizi, Nature, 314, 53 (1985);
9. d) S. Hakomori, Adv. Cancer Res., 52, 257 (1989).
10. a) K.-A. Karlsson, Curr. Opin. Struct. Biol., 5, 622 (1995);
11. b) E. H. Beachey, J. Infect. Dis., 143, 325 (1981); K. A. Krogfelt, Rev. Infect. Dis., 13, 721 (1991);
12. b) E. H. Beachey, J. Infect. Dis., 143, 325 (1981); K. A. Krogfelt, Rev. Infect. Dis., 13, 721 (1991);
13. c) Bacterial Adhesion to Cells and Tissues (I. Ofek, R. J. Doyle, Eds.), Chapman and Hall, New York 1994.
14. a) N. V. Bovin and H.-J. Gabius, Chem. Soc. Rev., 1995, 413;
15. b) R. Roy, Trends in Glycoscience and Glycotechnology, 8, 79 (1996);
16. c) R. Roy, Curr. Opin. Struct. Biol., 6, 692 (1996);
17. d) R. Roy, Top. Curr. Chem., 187, 241 (1997);
18. e) T. Lindhorst, Nachr. Chem. Techn. Lab., 44, 1073 (1996).
19. a) R. Roy, D. Zanini, S. J. Meunier and A. Romanowska, J. Chem. Soc., Chem. Commun., 1993, 1869;
20. b) M. Mammen, G. Dahmann and G. M. Whitesides, J. Med. Chem., 8, 4179 (1995).
21. a) Y. C. Lee, Carbohydr. Res., 67, 509 (1978);
22. b) R. T. Lee and Y. C. Lee, Glycoconjugate J., 4, 317 (1987).
23. Y. C. Lee and R. T. Lee, Acc. Chem. Res., 28, 321 (1995).
24. a) L. L. Kiessling and N. L. Pohl, Chem. Biol., 3, 71 (1996);
25. b) Th. K. Lindhorst, C. Kieburg, U. Krallmann-Wenzel, Glycoconjugate J., in press;
26. c) K. Bezouška, V. Křen, C. Kieburg and T. K. Lindhorst, FEBS Lett., in press.
27. H. M. Flowers, Adv. Carbohydr. Chem. Biochem., 39, 280 (1981).
28. a) P. Vischer and W. Reutter, Eur. J. Biochem., 84, 363 (1978);
29. b) Ch. H. Bauer, W. G. Reutter, K. P. Erhart, E. Köttgen and W. Gerken, Science, 201, 1232 (1978);
30. c) Ch. H. Bauer, E. Köttgen and W. G. Reutter, Biochem. Biophys. Res. Commun., 76, 488 (1977).
31. C. Kieda and M. Monsigny, Invasion Metastasis, 6, 347 (1986).
32. W. Roszkowski, J. Beuth, H. L. Ko, G. Uhlenbruck and G. Pulverer, Experientia, 45, 584 (1989).
33. a) T. K. Lindhorst and C. Kieburg, Angew. Chem., 108, 2083 (1996); Angew. Chem. Int. Ed. Engl., 35, 1953 (1996);
34. a) T. K. Lindhorst and C. Kieburg, Angew. Chem., 108, 2083 (1996); Angew. Chem. Int. Ed. Engl., 35, 1953 (1996);
35. b) C. Kieburg and T. K. Lindhorst, Tetrahedron Lett., 38, 3885 (1997);
36. c) C. Kieburg, M. Dubber and T. K. Lindhorst, Synlett, 1997, 1447.
37. M. Ludewig and J. Thiem, Synthesis, 1998, 56.
38. B. Schönecker and K. Ponsold, J. Prakt. Chem., 318, 483 (1976).
39. This is a typical NMR behaviour of thiourea bridged glycoclusters, which has often been observed before. When the NMR spectra were recorded at higher temperature, the complete set of signals could be observed.