Synthesis of sialyl Le(x) ganglioside analogues modified at C-6 of the galactose residue to elucidate the mechanism of selection recognition

Carbohydrate Research

Volumn 306, Issue 4, 1998, Pages 517-530

  Otsubo, Nobumasa ^a   Ishida, Hideharu ^a   Kiso, Makoto ^a   Hasegawa, Akira ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

Ganglioside; Selectin; Sialyl Le(x)

Indexed keywords

GANGLIOSIDE; SIALIC ACID DERIVATIVE; GALACTOSE; SELECTIN; SIALYL LEWIS(X) GANGLIOSIDE;

ARTICLE; CARBOHYDRATE METABOLISM; CONFORMATIONAL TRANSITION; GLYCOSYLATION; MOLECULAR RECOGNITION; PRIORITY JOURNAL; SIALYLATION; STRUCTURE ANALYSIS; BLOOD GROUP LEWIS SYSTEM; CARBOHYDRATE ANALYSIS; CHEMISTRY; METABOLISM; MOLECULAR GENETICS; MOLECULAR PROBE; PROTEIN BINDING;

CARBOHYDRATE SEQUENCE; GALACTOSE; GANGLIOSIDES; LEWIS BLOOD-GROUP SYSTEM; MOLECULAR PROBES; MOLECULAR SEQUENCE DATA; PROTEIN BINDING; SELECTINS;

EID: 0031990169     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00013-5     Document Type: Article

References (28)

1. [1] K. Baba, N. Iwata, H. Hamajima, T. Ikami, H. Ishida, A. Hsegawa, and M. Kiso, Biosci. Biotech. Biochem., 62 (1998) 590-592.
2. [2] M.P. Bevilacqua, S. Stengelin, M.A. Gimbrone Jr., and B. Seed, Science, 243 (1989) 1160-1165.
3. [3] G.I. Johnston, R.G. Cook, and R.P. McEvrer, Cell, 56 (1989) 1033-1044.
4. [4] L.A. Lasky, M.S. Singer, T.A. Yednock, D. Dowvenko, C. Fennie, H. Rodriguez, T. Nguyen, S. Stachel, and S.D. Rosen, Cell, 56 (1989) 1045-1055.
5. [5] T.F. Tedder, C.M. Isaacs, E.J. Ernst, G.D. Demetri, D.A. Adler, and C.M. Disteche, J. Exp. Med., 170 (1989) 123-133.
6. [6] B.K. Brandley, S. Swiedler, and P.W. Robbins, Cell, 63 (1990) 861-863.
7. [7] C. Foxall, S.R. Watson, D. Dowbenko, C. Fennie, L.A. Lasky, M. Kiso, A. Hasegawa, D. Asa, and B.K. Brandley, J. Cell Biol., 117 (1992) 895-902.
8. [8] A. Varki, Proc. Natl. Acad. Sci. USA., 91 (1994) 7390-7397.
9. [9] A. Kameyama, H. Ishida, M. Kiso, and A. Hasegawa, J. Carbohydr. Chem., 10 (1991) 549-560.
10. [10] A. Hasegawa, K. Ito, H. Ishida, and M. Kiso, J. Carbohydr. Chem., 14 (1995) 353-368.
11. [11] S. Komba, H. Ishida, M. Kiso, and A. Hasegawa, Glycoconjugate J., 13 (1996) 241-254.
12. [12] S. Komba, H. Ishida, M. Kiso, and A. Hasegawa, Bioorg. Med. Chem., 4 (1996) 1833-1847.
13. [13] K. Yoshino, H. Ohmoto, N. Kondo, H. Tsujishita, Y. Hiramatsu, Y. Inoue, H. Kondo, H. Ishida, M. Kiso, and A. Hasegawa, J. Med. Chem., 40 (1997) 455-462.
14. [14] H. Tsujishita, Y. Hiramatsu, N. Kondo, H. Ohmoto, H. Kondo, M. Kiso, and A. Hasegawa, J. Med. Chem., 40 (1997) 362-369.
15. [15] P. Fügedi and J. Kovacs, Abstracts of Papers, XVth International Carbohydrate Symposium, Yokohama, Japan, August 1990, A041.
16. [16] K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Magnusson, J. Dahmen, G. Noori, and K. Stenvall, J. Org. Chem., 53 (1988) 5629-5641.
17. [17] V. Pozsgay and H.J. Jennings, Tetrahedron Lett., 28 (1987) 1375-1376.
18. [18] A. Kameyama, H. Ishida, M. Kiso, and A. Hasegawa, Carbohydr. Res., 200 (1990) 269-285.
19. [19] P. Fugedi and P.J. Garegg, Carbohydr. Res., 149 (1986) c9-c12.
20. [20] T. Akiyama, H. Shima, and S. Ozaki, Synlett, (1992) 415-416.
21. [21] P. Konradsson, U.E. Udodong, and B. Fraser-Reid, Tetrahedron Lett., 31 (1990) 4313-4316.
22. [22] G.H. Veeneman, S.H. van Leeuwen, and J.H. van Boom, Tetrahedron Lett., 31 (1990) 1331-1334.
23. [23] (a) K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Magnusson, J. Dahmen, G. Noori, and K. Stenvall, J. Org. Chem., 53 (1988) 5629-5641;
24. (b) A. Hasegawa, H. Ogawa, and M. Kiso, Carbohydr. Res., 224 (1992) 185-192.
25. [24] R.R. Schmidt and G. Grundler, Synthesis, (1981) 885-887.
26. [25] T. Ehara, A. Kameyama, Y. Yamada, H. Ishida, M. Kiso, and A. Hasegawa, Carbohydr. Res., 281 (1996) 237-252.
27. [26] M. Mori, Y. Ito, and T. Ogawa, Carbohydr. Res., 195 (1990) 199-224.
28. [27] W. Stahl, U. Sprengard, G. Kretzschmar, and H. Kunz, Angew. Chem. Int. Ed. Engl., 33 (1994) 2096-2098.