Cluster mannosides as inhibitors of type 1 fimbriae-mediated adhesion of Escherichia coli: Pentaerythritol derivatives as scaffolds

European Journal of Organic Chemistry

Volumn , Issue 11, 2000, Pages 2027-2034

  Lindhorst, Thisbe K ^a   Dubber, Michael ^a   Krallmann Wenzel, Ulrike ^b   Ehlers, Stefan ^b  

^a UNIVERSITY OF HAMBURG   (Germany)

^b RESEARCH CENTER BORSTEL   (Germany)

Author keywords

Antiadhesives; Cluster mannosides; Glycosylations; Oligosaccharides; Type 1 fimbriae

Indexed keywords

MANNOSIDE;

ARTICLE; BACTERIUM ADHERENCE; ESCHERICHIA COLI; FIMBRIA; GLYCOSYLATION; SYNTHESIS;

EID: 0034045412     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200006)2000:11<2027::AID-EJOC2027>3.0.CO;2-L     Document Type: Article

References (32)

1. [1a] A. Varki, Glycobiology 1993, 3, 97-130.
2. [1b] R. A. Dwek, Chem. Rev. 1996, 96, 683-720.
3. [2a] H. Lis, N. Sharon, Chem. Rev. 1998, 98, 637-674.
4. [2b] E. E. Simanek, G. J. McGarvey, J. A. Jablonowski, C.-H. Wong, Chem. Rev. 1998, 98, 833-862.
5. W. I. Weis, K. Drickamer, Annu. Rev. Biochem. 1996, 65, 441-473.
6. P. Sears, C.-H. Wong, Chem. Commun. 1998, 1161-1170.
7. [5a] D. Zanini, R. Roy in Carbohydrate Mimics (Ed.: Y. Chapleur), Wiley-VCH, Weinheim 1998, p. 385-415.
8. [5b] Y. C. Lee, R. T. Lee, Methods Enzymol. 1987, 138, 424-429.
9. [5c] Th. K. Lindhorst, Nachr. Chem. Techn. Lab. 1996, 44, 1073-1079.
10. H. Conell, W. Agace, P. Klemm, M. Schembri, S. Mårlid, C. Svanborg, Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 9827-9832.
11. I. Ofek, R. J. Doyle (Eds.), Bacterial Adhesion to Cells and Tissues, Chapman & Hall, New York, 1994.
12. [8a] Th. K. Lindhorst, C. Kieburg, U. Krallmann-Wenzel, Glycoconjugate J. 1998, 15, 605-613.
13. [8b] B. König, T. Fricke, A. Waßmann, U. Krallmann-Wenzel, Th. K. Lindhorst, Tetrahedron Lett. 1998, 39, 2307-2310.
14. [8c] S. Kötter, U. Krallmann-Wenzel, S. Ehlers, Th. K. Lindhorst, J. Chem. Soc., Perkin Trans. 1 1998, 2193-2200.
15. N. Sharon, FEBS Lett. 1987, 217, 145-157.
16. [10a] G. R. Newkome, X. Lin, Macromolecules 1991, 24, 1443-1444.
17. [10b] G. R. Newkome, J. K. Young, G. R. Baker, R. L. Potter, L. Audoly, D. Cooper, C. D. Weis, Macromolecules 1993, 26, 2394-2396.
18. S. Hanessian, C. Hoornaert, Carbohydr. Res. 1985, 137, C14-C16.
19. W. H. Binder, W. Schmid, Monatsh. Chem. 1995, 126, 923-931.
20. S. Hanessian, D. Qiu, H. Prabhanjan, G. V. Reddy, B. Lou, Can. J. Chem. 1996, 74, 1738-1747.
21. H. C. Hansen, S. Haatja, J. Finne, G. Magnusson, J. Am. Chem. Soc. 1997, 119, 6974-6979.
22. S. Hanessian, H. Prabhanjan, Synlett 1994, 868-870.
23. J. Lehmann, M. Scheuring, Carbohydr. Res. 1995, 276, 57-74.
24. J. Lehmann, U. P. Weitzel, Carbohydr. Res. 1996, 294, 65-94.
25. S. Jegge, J. Lehmann, Carbohydr. Res. 1984, 133, 247-254.
26. R. M. Nougier, M. Mchich, J. Org. Chem. 1985, 50, 3296-3298.
27. F. Bien, T. Ziegler, Tetrahedron: Asymmmetry 1998, 9, 781-790.
28. P. Klemm, B. J. Jørgensen, I. van Die, H. de Ree, H. Bergmans, Mol. Gen. Genet. 1985, 199, 410-414.
29. [22a] Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321-327.
30. [22b] M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794.
31. [22b] M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794.
32. E. Stahl, U. Kaltenbach, J. Chromatogr. 1961, 5, 351-355.