Sugar mimics: An artificial receptor for cholera toxin

Journal of the American Chemical Society

Volumn 121, Issue 10, 1999, Pages 2032-2036

  Bernardi, Anna ^a   Checchia, Anna ^a   Brocca, Paola ^a   Sonnino, Sandro ^a   Zuccotto, Fabio ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLERA TOXIN; GALACTOSE; GANGLIOSIDE;

ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ENANTIOMER; GLYCOSYLATION; MOLECULAR MODEL; RECEPTOR BINDING; SIALYLATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033577261     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983567c     Document Type: Article

References (36)

1. Topics in Current Chemistry: Driguez, H., Thiem, J., Eds.: Springer-Verlag: Berlin, 1997; Vol. 187; Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: New York, 1998.
2. Topics in Current Chemistry: Driguez, H., Thiem, J., Eds.: Springer-Verlag: Berlin, 1997; Vol. 187; Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: New York, 1998.
3. Kolb, H. C.; Ernst, B. Chem. Eur. J. 1997, 3, 1571-1578.
4. Hakomiri, S.-I. Biochem. Soc. Trans. 1993, 21, 583-585.
5. Spangler, B. D. Microbiol. Rev. 1992, 56, 622-647 and references therein Masserini, M.; Freire, E.; Palestini, P.; Calappi, E.; Tettamanti, G. Biochemistry 1992, 31, 2422-2426.
6. Spangler, B. D. Microbiol. Rev. 1992, 56, 622-647 and references therein Masserini, M.; Freire, E.; Palestini, P.; Calappi, E.; Tettamanti, G. Biochemistry 1992, 31, 2422-2426.
7. Lanne, B.; Schierbeck, B.; Karlsson, K. A. J. Biochem. 1994, 116, 1269-1274; Fukuta, S.; Magnani, J. L.; Twiddy, E. M.; Holmes, R. K.; Ginsburg, V. Infect. Immun. 1988, 56, 1748-1753; Ångstrøm, J.; Tenenberg, S.; Karlsson, K. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11859-11863; Schengrund, C.-L.; Ringler, N. J. J. Biol. Chem. 1989, 264, 13233-13237.
8. Lanne, B.; Schierbeck, B.; Karlsson, K. A. J. Biochem. 1994, 116, 1269-1274; Fukuta, S.; Magnani, J. L.; Twiddy, E. M.; Holmes, R. K.; Ginsburg, V. Infect. Immun. 1988, 56, 1748-1753; Ångstrøm, J.; Tenenberg, S.; Karlsson, K. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11859-11863; Schengrund, C.-L.; Ringler, N. J. J. Biol. Chem. 1989, 264, 13233-13237.
9. Lanne, B.; Schierbeck, B.; Karlsson, K. A. J. Biochem. 1994, 116, 1269-1274; Fukuta, S.; Magnani, J. L.; Twiddy, E. M.; Holmes, R. K.; Ginsburg, V. Infect. Immun. 1988, 56, 1748-1753; Ångstrøm, J.; Tenenberg, S.; Karlsson, K. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11859-11863; Schengrund, C.-L.; Ringler, N. J. J. Biol. Chem. 1989, 264, 13233-13237.
10. Lanne, B.; Schierbeck, B.; Karlsson, K. A. J. Biochem. 1994, 116, 1269-1274; Fukuta, S.; Magnani, J. L.; Twiddy, E. M.; Holmes, R. K.; Ginsburg, V. Infect. Immun. 1988, 56, 1748-1753; Ångstrøm, J.; Tenenberg, S.; Karlsson, K. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11859-11863; Schengrund, C.-L.; Ringler, N. J. J. Biol. Chem. 1989, 264, 13233-13237.
11. (a) Merritt, E. A.; Sarfaty, S.; v. d. Akker, F.; L'Hoir, C.; Martial, J. A.; Hol, W. G. J. Protein Sci. 1994, 3, 166-175.
12. (b) Merritt, E. A.; Sarfaty, S.; Jobling, M. G.; Chang, T.; Holmes, R. K.; Hirst, T. R.; Hol, W. G. J. Protein Sci. 1997, 6, 1516-1528.
13. (c) Merritt, E. A.; Hol, W. G. J. Curr. Opin. Struct. Biol. 1995, 5, 165-171 and references therein.
14. Bernardi, A.; Raimondi, L.; Zuccotto, F. J. Med. Chem. 1997, 40, 1855-1862.
15. Acquotti, D.; Poppe, L.; Dahrowski, J.; v. d. Lieth, C.-W.; Sonnino, S.; Tettamanti, G. J. Am. Chem. Soc. 1990, 112, 7772-7778.
16. Bernardi, A.; Raimondi, L. J. Org. Chem. 1995, 60, 3370-3377.
17. Both the unbranched carbohydrates asialo-GM1 (ref 11) and GM4 (NeuAc(α2,3)Gal-βOMe) (ref 12) were shown to be considerably more flexible than GM1 by NMR spectroscopy.
18. Scarsdale, N. J.; Prestegard, J. H.; Yu, R. K. Biochemistry 1990, 29, 9843-9855 and references therein.
19. Poppe, L.; Dabrowski, J.; v. d. Lieth, C.-W.; Numata, M.; Ogawa, T. Eur. J. Biochem. 1989, 180, 337-342.
20. Acquotti, D., Cantú, L., Ragg, E.; Sonnino, S. Eur. J. Biochem. 1994, 225, 271-288
21. Tettamanti, G.; Bonali, F.; Marchesini, S.; Zambotti, V. Biochim. Biophys. Acta 1973, 296, 160-170
22. Wiegandt, H.; Bucking, H. W. Eur. J. Biochem. 1970, 15, 287-292.
23. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
24. Still, W. C.; Tempzyk, A.; Hawley, R.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
25. Farmer, H. B. T.; Macura, S.; Brown, L. R. J. Magn. Res. 1987, 72, 347-352.
26. Wu, G.; Leeden, R. Anal. Biochem. 1988, 173, 368-375; Carpo, M.; Nobile-Orario, E.; Chigorno, V.; Sonnino, S. Glycoconjugate J. 1995, 12, 729-731.
27. Wu, G.; Leeden, R. Anal. Biochem. 1988, 173, 368-375; Carpo, M.; Nobile-Orario, E.; Chigorno, V.; Sonnino, S. Glycoconjugate J. 1995, 12, 729-731.
28. Merritt, E. A.; Sarfaty, S.; Feil, I. K.; Hol W. G. J. Structure 1997, 5, 1485-1499 and references therein.
29. Analytical data for compounds 2 and 3 are given in the Supporting Information. Details of the synthetic procedure will be reported elsewhere.
30. Hartmann, H.; Hady, A. F. A.; Sartor, K.; Weetman, J.; Heimchen, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 1143-1144. The desired (S,S)-diacid was obtained as a 6:1 mixture with the (R,R)-enantiomer and purified via crystallization of its quinine salt, following a published procedure (ref 23).
31. Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333-2351.
32. Okamoto, K.; Goto, T. Tetrahedron 1990, 17, 5835-5857.
33. Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123-6126; Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconj. J. 1993, 10, 16-25.
34. Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123-6126; Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconj. J. 1993, 10, 16-25.
35. Bax, A.; Davis, D. G. J. Magn. Res. 1985, 64, 533-535.
36. 2O solution, which may suggest a different distribution of the H-bonding network for the NeuAc side chain of 2 in the two solvents.