Mimics of ganglioside GM1 as cholera toxin ligands: Replacement of the GalNAc residue

Organic and Biomolecular Chemistry

Volumn 1, Issue 5, 2003, Pages 785-792

  Bernardi, Anna ^a   Arosio, Daniela ^a   Manzoni, Leonardo ^b   Monti, Diego ^b   Posteri, Helena ^a   Potenza, Donatella ^a   Mari, Silvia ^a   Jiménez Barbero, Jesús ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

^c CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CELL MEMBRANES; CHEMICAL BONDS; CONFORMATIONS; DISEASES; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEINS; SYNTHESIS (CHEMICAL);

CHOLERA TOXIN LIGAND; OLIGOSACCHARIDE; THREE-DIMENSIONAL STRUCTURE;

POLYSACCHARIDES;

BACTERIA (MICROORGANISMS);

CHOLERA TOXIN; GANGLIOSIDE GM1; LIGAND; N ACETYLGALACTOSAMINE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; MOLECULAR GENETICS; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ACETYLGALACTOSAMINE; CARBOHYDRATE SEQUENCE; CHOLERA TOXIN; G(M1) GANGLIOSIDE; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA;

EID: 0042821581     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b210503a     Document Type: Article

References (37)

1. (a) H. Lis and N. Sharon, Chem. Rev., 1998, 98, 637-674
2. (b) R. A. Dwek, Chem. Rev., 1996, 96, 683-720
3. (c) A. Varki, Glycobiology, 1993, 3, 97-130.
4. P. Sears and C. H. Wong, Angew. Chem., Int. Ed., 1999, 111, 2446-2471
5. P. Sears and C. H. Wong, Angew. Chem., Int. Ed., 1999, 38, 2300-2324 and references therein.
6. A. Bernardi, D. Arosio, L. Manzoni, F. Micheli, S. Pasquarello and P. Seneci, J. Org. Chem., 2001, 66, 6209-6216.
7. trans-Cyclohexane-1,2-diol has been used by many authors as an effective replacement for 3,4-disubstituted N-acetylglucosamine in the synthesis of sialyl Lewis x mimics. E. E. Simanek, G. J. McGarvey, J. A. Jablonowski and C.-H. Wong, Chem. Rev., 1998, 98, 833-862.
8. A. Bernardi, A. Checchia, P. Brocca, S. Sonnino and F. Zuccotto, J. Am. Chem. Soc., 1999, 121, 2032-2036.
9. C.-L. Schengrund and N. J. Ringler, J. Biol. Chem., 1989, 264, 13233-13237 and references therein.
10. (a) E. A. Merritt, S. Sarfaty, F. van den Akker, C. L'Hoir, J. A. Martial and W. G. J. Hol, Protein Sci., 1994, 3, 166-175
11. (b) E. A. Merritt, P. Kuhn, S. Safarty, J. L. Erbe, R. K. Holmes and W. G. Z. Hol, J. Mol. Biol., 1998, 282, 1043-1059.
12. A. Bernardi, G. Boschin, A. Checchia, M. Lattanzio, L. Manzoni, D. Potenza and C. Scolastico, Eur. J. Org. Chem., 1999, 6, 1311-1317.
13. A. Bernardi, L. Carrettoni, A. Grosso Ciponte, D. Monti and S. Sonnino, Bioorg. Med. Chem. Lett., 2000, 10, 2197-2200.
14. A. Bernardi, L. Raimondi and F. Zuccotto, J. Med. Chem., 1997, 40, 1855-1862.
15. A. Bernardi, M. Galgano, L. Belvisi and G. Colombo, J. Comput.-Aided Mol. Des., 2001, 15, 117-128.
16. P. Brocca, P. Berthault and S. Sonnino, Biophys. J., 1998, 74, 309-318.
17. A. Bernardi, D. Potenza, A. M. Capelli, A. García-Herrero, F. J. Cañada and J. Jiménez-Barbero, Chem.-Eur. J., 2002, 8, 4597-4612.
18. P. Brocca, A. Bernardi, L. Raimondi and S. Sonnino, Glycoconjugate J., 2000, 17, 283-299.
19. A. A. Bothner-By and R. Gassend, Ann. N. Y. Acad. Sci., 1973, 222, 668-676.
20. P. L. Jackson, H. N. Moseley and N. R. Krishna, J. Magn. Reson., Ser. B, 1995, 107, 289-292
21. V. L. Bevilacqua, D. S. Thomson and J. H. Prestegard, Biochemistry, 1990, 29, 5529-5537
22. V. L. Bevilacqua, Y. Kim and J. H. Prestegard, Biochemistry, 1992, 31, 9339-9349.
23. M. Vogtherr and T. Peters, J. Am. Chem. Soc., 2000, 122, 6093-6099.
24. M. Mayer and B. Meyer, J. Med. Chem., 2000, 43, 2093-2099.
25. A. Schoen and E. Freire, Biochemistry, 1989, 28, 5019-5024.
26. An accurate NMR study of these complexes is in progress, and will be reported in due course.
27. J. A. Mertz, J. A. McCann and W. D. Picking, Biochem. Biophys. Res. Commun., 1996, 226, 140-144.
28. M. Mammen, S.-K. Chio and G. M. Whitesides, Angew. Chem., Int. Ed., 1998, 37, 2755-2794.
29. S. Cattaldo Tesi di Laurea, Universita' di Milano a.a. 2000-2001.
30. E. A. Merritt, T. K. Sixma, K. H. Kalk, B. A. M. van Zanten and W. G. J. Hol, Mol. Microbiol., 1994, 13, 745-753.
31. A. T. Amn, S. Fraser, E. A. Merritt, C. Rodrigherio, M. Kenny, M. Ahn, W. G. J. Hol, N. A. Williams, W. I. Lencer and T. R. Hirst, Proc. Natl. Acad. Sci. USA, 2001, 98, 8536-8541.
32. W. E. Minke, C. Roach, W. G. J. Hol and C. L. M. J. Verlinde, Biochemistry, 1999, 38, 5684-5692.
33. A. Pathiaseril and R. J. Woods, J. Am. Chem. Soc., 2000, 122, 331-338.
34. D. Arosio, unpublished.
35. Generous gift of Mariagrazia Pizza at Chiron Vaccines, Siena.
36. J. Dabrowski, T. Kozár, H. Grosskurth and N. E. Nifant'ev, J. Am. Chem. Soc., 1995, 117, 5534-5539.
37. D. Acquotti, L. Poppe, J. Dabrowski, C.-W. V.d. Lieth, S. Sonnino and G. Tettamanti, J. Am. Chem. Soc., 1990, 112, 7772-7778.