A concise synthesis of the 6-O- and 6'-O-sulfated analogues of the sialyl Lewis X tetrasaccharide

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 14, 2000, Pages 1505-1509

  Misra, Anup Kumar ^a   Ding, Yili ^a   Lowe, John B ^a,b   Hindsgaul, Ole ^a  

^a BURNHAM INSTITUTE   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLYCOSIDE;

ARTICLE; CHEMICAL MODIFICATION; DRUG TRANSFORMATION; PARTIAL DRUG SYNTHESIS; PROTEIN BINDING; REACTION ANALYSIS; SIALYLATION;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CATALYSIS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; SULFATES;

EID: 0034679646     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00207-9     Document Type: Article

References (44)

1. (a) Lawrence, M. B.; Springer, T. A. Cell 1991, 65, 859.
2. (b) Watson, S. R.; Fennie, C.; Lasky, L. A. Nature 1991, 349, 164.
3. (c) Lowe, J. B.; Stoolman, L. M.; Nair, R. P.; Larsen, R. D.; Berhend, T. L.; Marks, R. M. Cell 1990, 63, 475.
4. (d) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.-I., Paulsen, J. C. Science 1990, 250, 1130.
5. (a) Drickamer, K. J. Biol. Chem. 1988, 263, 9557.
6. (b) Varki, A. Proc. Natl. Acad. Sci. USA 1994, 91, 7390.
7. (c) Crocker, P. R.; Feizi, T. Curr. Opin. Struct. Biol. 1996, 6, 679.
8. (d) Kansas, G. S. Blood 1996, 88, 3259.
9. (a) Bevilacque, M. P.; Pober, J. S.; Mendrick, D. L.; Cotran, R. S.; Gimbrone, M. A. Proc. Natl. Acad. Sci, USA 1987, 84, 9238.
10. (b) Lasky, L. A. Annu. Rev. Biochem. 1995, 64, 113.
11. (c) Pigott, R.; Dillon, L. P.; Hemingway, L. H.; Gearing, A. J. H. Biochem. Biophys. Res. Commun. 1992, 187, 584.
12. Johnston G.I., Kurosky A., McEver R.P. J. Biol. Chem. 264:1989;1816.
13. (a) Rosen, S. D. Semin, Immunol. 1993, 5, 237.
14. (b) Imai, Y.; Lasky, L. A.; Rosen, S. D. Nature 1993, 361, 555.
15. (a) Hemmerich, S.; Bertozzi, C. R.; Leffler, H.; Rosen, S. D. Biochemistry 1994, 33, 4820.
16. (b) Hemmerich, S.; Leffler, H.; Rosen, S. D. J. Biol. Chem. 1995, 270, 12035.
17. (a) Simanek, E. E.; McGarver, G. J.; Jablonowski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833.
18. (b) Varki, A. Curr. Opin. Cell. Biol. 1992, 4, 257.
19. Fukushima K., Hirota M., Terasaki P.I., Wakisaka A., Togashi H., Chia D., Suyama N., Fukushi Y., Nudelman E., Hakomori S. Cancer Res. 44:1984;5279.
20. Galustian C., Lawson A.M., Komba S., Ishida H., Kiso M., Feizi T. Biochem. Biophys. Res. Commun. 240:1997;748.
21. (a) Mitsuoka, C.; Kawakami-Kimura, N.; Kasugai-Sawada, M.; Hiraiwa, N.; Toda, K.; Ishida, H.; Kiso, M.; Hasegawa, A.; Kannagi, R. Biochem. Biophys. Res. Commun. 1997, 230, 546.
22. (b) Mitsuoka, C.; Sawada-Kasugai, M.; Ando-Furui, K.; Izawa, M.; Nakanishi, H.; Nakamura, S.; Ishida, H.; Kiso, M.; Kannagi, R. J. Biol. Chem. 1998, 273, 11225.
23. (a) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314; Ellervik, U.; Grundberg, H.; Magnusson, G. J. Org. Chem. 1998, 63, 9323 and the references cited therein.
24. (a) Ellervik, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314; Ellervik, U.; Grundberg, H.; Magnusson, G. J. Org. Chem. 1998, 63, 9323 and the references cited therein.
25. (b) Tsukida, T.; Yoshida, M.; Kurokawa, K.; Nakai, Y.; Achiha, T.; Kiyoi, T.; Kondo, H. J. Org. Chem. 1997, 62, 6876 and the references cited therein.
26. (c) Kiyoi, T.; Inone, y.; Ohmoto, H.; Yoshida, M.; Kiso, M.; Kondo, H. Bioorg. Med. Chem. 1998, 6, 587.
27. (d) Dumas, D. P.; Ichikawa, Y.; Wong, C.-H.; Lowe, J. B.; Nair, R. P. Bioorg. Med. Chem. Lett. 1991, 1, 425.
28. (e) Kondo, H.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 8748.
29. (f) Halcomb, R. L.; Huang, H.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 11315.
30. (g) Seitz, O.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8766.
31. (h) Blixt, O.; Norberg, T. J. Org. Chem. 1998, 63, 2705.
32. Lönn H. Carbohydr. Res. 139:1985;105.
33. Sato S., Mori M., Ito Y., Ogawa T. Carbohydr. Res. 155, C6-C10. 1986.
34. Garegg, P. J.; Hultberg, H.; Oscarson, S. J. Chem. Soc., Perkin Trans. 1, 1982, 2395.
35. Kameyama A., Ishida H., Kiso M., Hasegawa A. Carbohydr. Res. 200:1990;269.
36. (a) Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
37. (b) Veenemann, G. H.; vanLeeuwen, S. H.; vanBoom, J. H. Tetrahedron Lett. 1990, 31, 1331.
38. (a) Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16.
39. (b) Marra, A.; Sinaÿ, P. Carbohydr. Res. 1990, 195, 303.
40. (c) Kanie, O.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 7, 501.
41. Pearlman, W. M. Tetrahedron Lett. 1967, 1663.
42. Nashed E.M., Glaudemans C.P.J. J. Org. Chem. 52:1987;5255.
43. Nicolaou K.C., Randall J.L., Furst G.T. J. Am. Chem. Soc. 107:1985;5556.
44. +) 1079.9862; found 1079.9858.