Synthesis of an artificial glycoconjugate polymer carrying P(k)-antigenic trisaccharide and its potent neutralization activity against Shiga-like toxin

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 9, 1999, Pages 2053-2062

  Dohi, Hirofumi ^a   Nishida, Yoshihiro ^a   Mizuno, Mitsuharu ^a   Shinkai, Masashige ^a   Kobayashi, Takeshi ^a   Takeda, Tae ^b   Uzawa, Hirotaka ^c   Kobayashi, Kazukiyo ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b NATIONAL RESEARCH INSTITUTE FOR CHILD HEALTH AND DEVELOPMENT   (Japan)

^c NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLOBOTRIAOSYLCERAMIDE; TRISACCHARIDE; VEROTOXIN;

ARTICLE; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; FLUORESCENCE; HUMAN; HUMAN CELL; NONHUMAN; POLYMERIZATION;

ANTIGENS; BACTERIAL ADHESION; BACTERIAL TOXINS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CELL LINE; ESCHERICHIA COLI O157; FLUORESCENCE; GLYCOCONJUGATES; HUMANS; MOLECULAR SEQUENCE DATA; NEUTRALIZATION TESTS; OLIGOSACCHARIDES; POLYMERS; SHIGA-LIKE TOXIN I; SHIGA-LIKE TOXIN II; SPECTRUM ANALYSIS;

EID: 0032871199     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00129-7     Document Type: Article

References (29)

1. Lee, Y. C.; Lee, R. T. In Neoglycoconjugates: Preparation and Applications; Academic Press: San Diego, 1994.
2. Kobayashi, K.; Kobayashi, A.; Tobe, S.; Akaike, T. In Carbohydrate-Containing Polystyrenes in Neoglycoconjugates: Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic Press: San Diego, 1994; pp 261-282.
3. Bovin N.V., Gabius H.J. Chem. Soc. Rev. 24:1995;413.
4. Rye P.D., Bovin N.V. Glycobiology. 7:1997;179.
5. Rye P.D. Biotechnology. 14:1997;155.
6. Lee, Y. C.; Lee, R. T.; Rice, T. In Enhanced Biochemical Affinities of Multivalent Neoglycoconjugates; Lee, Y. C.; Lee, R. T., Eds.; Academic Press: San Diego, 1994, pp 23-50.
7. Gordon E.G., Sanders W.L., Kiessling L.L. Nature. 392:1998;30.
8. Choi S.K., Mammen M., Whitesides G.M. J. Am. Chem. Soc. 119:1997;4103.
9. Tsuchida A., Akimoto S., Usui T., Kobayashi K. J. Biochem. 123:1998;712.
10. Tsuchida, A.; Kobayashi, K.; Matsubara, N.; Suzuki, T.; Suzuki, Y. Glycoconjugate J. 1999, 15, 1047.
11. Lingwood C.A., Law H., Richardson S., Petric M., Brunton J.L., Grandis S.D., Karmali M. J. Biol. Chem. 262:1987;8834.
12. Lindberg A.A., Brown J.E., Strömberg N., Westling-Ryd M., Schultz J.E., Karlsson K.A. J. Biol. Chem. 262:1987;1779.
13. Arab S., Lingwood C.A. Glycoconjugate J. 13:1996;159.
14. Karlsson K.A. Annu. Rev. Biochem. 58:1989;309.
15. 3 ceramide, see Hashimoto, S.; Sakamoto, H.; Honda, T.; Abe, H.; Nakamura, S.; Ikegami, S. Tetrahedron Lett. 1997, 52, 8969, and the related references therein.
16. Preliminarily communicated, Nishida, Y.; Dohi, H.; Uzawa, H.; Kobayashi, K. Tetrahedron Lett. 1998, 39, 8681.
17. Nishida, Y.; Thiem, J. Carbohydr. Res. 1994, 263, 295.
18. Otera J., Nozaki H. Tetrahedron Lett. 27:1986;5743.
19. Mukaiyama, T.; Murai, Y.; Shouda, T. Chem. Lett. 1981, 431.
20. Van Boeckel C.A.A., Beetz T., van Aelst S.F. Tetrahedron. 40:1984;4097.
21. Fukase T., Yoshimura T., Kotani S., Kusumoto S. Bull. Chem. Soc. Jpn. 67:1994;473.
22. Lee Y.C. J. Biochem. 121:1997;818.
23. Nagata K., Furuike T., Nishimura S. J. Biochem. 118:1995;278.
24. Kamitakahara H., Suzuki T., Nishigori N., Suzuki Y., Kanie O., Wong C.-H. Angew. Chem., Int. Ed. Engl. 37:1998;1524.
25. For recent applications of TBMB carboxylic acid, see Nishida, Y.; Kim, J.-H.; Ohrui, H.; Meguro, H. J. Am. Chem. Soc. 1997, 119, 1484, and the related references therein.
26. Nishida Y., Itoh E., Abe M., Ohrui H., Meguro H. Anal. Sci. 11:1995;213.
27. Hilaire P.M., Boyd M.K., Toone E.J. Biochemistry. 33:1994;14452.
28. Glaudemans C.P.J. Methods Carbohydr. Chem. 8:1980;145.
29. Nishida Y., Thiem J. J. Carbohydr. Chem. 13:1994;1059.