The synthesis of a multivalent heterobifunctional ligand for specific interaction with Shiga toxin 2 produced by E. coli O157:H7

Carbohydrate Research

Volumn 378, Issue , 2013, Pages 4-14

  Jacobson, Jared M ^a   Kitov, Pavel I ^a   Bundle, David R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Escherichia coli O157:H7; Heterobifunctional ligand; Shiga toxin 2; Toxin inhibitors; Trisaccharide synthesis

Indexed keywords

BIOSYNTHESIS; CHELATION; LIGANDS; TOXIC MATERIALS;

E.COLI O157:H7; ESCHERICHIA COLI O157:H7; FOOD POISONING; POTENTIALLY FATAL; PREFERENTIAL BINDING; SHIGA TOXIN; SPECIFIC INTERACTION; SUPRAMOLECULAR COMPLEX FORMATION;

ESCHERICHIA COLI;

LIGAND; VEROTOXIN 2;

ARTICLE; COMPLEX FORMATION; ESCHERICHIA COLI O157; LIGAND BINDING; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS;

ESCHERICHIA COLI;

ESCHERICHIA COLI O157:H7; HETEROBIFUNCTIONAL LIGAND; P(K) TRISACCHARIDE; SHIGA TOXIN 2; TOXIN INHIBITORS; TRISACCHARIDE SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; ESCHERICHIA COLI O157; GALACTOSE; HUMANS; LIGANDS; MODELS, MOLECULAR; OLIGOSACCHARIDES; PROTEIN BINDING; PROTEIN CONFORMATION; SHIGA TOXIN 2; SUBSTRATE SPECIFICITY;

EID: 84885019126     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2013.05.010     Document Type: Article

References (27)

1. Karmali, M. A.; Petric, M.; Lim, C.; Fleming, P. C.; Arbus, G. S.; Lior, H. J. Infect. Dis. 1985, 151, 775-782.
2. Tarr, P. I.; Gordon, C. A.; Chandler, W. L. Lancet 2005, 365, 1073-1086.
3. Jackson, M. P.; Neill, R. J.; O' Brien, A. D.; Holmes, R. K. FEMS Microbiol. Lett. 1987, 44, 109-114.
4. Endo, Y.; Mitsui, K.; Motizuki, M.; Tsurugi, K. J. Biol. Chem. 1987, 262, 5908-5912.
5. Obrig, T. G.; Moran, T. P.; Brown, J. E. Biochem. J. 1987, 244, 287-294.
6. Falguières, T.; Mallard, F.; Baron, C.; Hanau, D.; Lingwood, C.; Goud, B.; Salamero, J.; Johannes, L. Mol. Biol. Cell 2001, 12, 2453-2468.
7. Jacewicz, M.; Clausen, H.; Nudelman, E.; Donohue-Rolfe, A.; Keusch, G. T. J. Exp. Med. 1986, 163, 1391-1404.
8. Rutjes, N. W. P.; Binnington, B. A.; Smith, C. R.; Maloney, M. D.; Lingwood, C. A. Kidney Int. 2002, 62, 832-845.
9. Kale, R. R.; McGannon, C. M.; Fuller-Schaefer, C.; Hatch, D. M.; Flagler, M. J.; Gamage, S. D.; Weiss, A. A.; Iyer, S. S. Angew. Chem., Int. Ed. 2008, 47, 1265-1268.
10. Mammen, M.; Choi, S. K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2755-2794.
11. Kitov, P. I.; Sadowska, J. M.; Mulvey, G.; Armstrong, G. D.; Ling, H.; Pannu, N. S.; Read, R. J.; Bundle, D. R. Nature 2000, 403, 669-672.
12. Kitov, P. I.; Lipinski, T.; Paszkiewicz, E.; Solomon, D.; Sadowska, J. M.; Grant, G. A.; Mulvey, G. L.; Kitova, E. N.; Klassen, J. S.; Armstrong, G. D.; Bundle, D. R. Angew. Chem., Int. Ed. 2008, 47, 672-676.
13. Kitov, P. I.; Mulvey, G. L.; Griener, T. P.; Lipinski, T.; Solomon, D.; Paszkiewicz, E.; Jacobson, J. M.; Sadowska, J. M.; Suzuki, M.; Yamamura, K.-i.; Armstrong, G. D.; Bundle, D. R. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 16837-16842.
14. Ho, J. G. S.; Kitov, P. I.; Paszkiewicz, E.; Sadowska, J.; Bundle, D. R.; Ng, K. K.-S. J. Biol. Chem. 2005, 280, 31999-32008.
15. Boerlin, P.; McEwen, S.; Boerlin-Petzold, F.; Wilson, J.; Johnson, R.; Gyles, C. J. Clin. Microbiol. 1999, 37, 497-503.
16. Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1979, 68, C11-C13.
17. Ferro, V.; Mocerino, M.; Stick, R. V.; Tilbrook, D. Aust. J. Chem. 1988, 41, 813-815.
18. DeNinno, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669-672.
19. Ferrier, R. J.; Furneaux, R. H. Carbohydr. Res. 1976, 52, 63-68.
20. Daragics, K.; Fügedi, P. Tetrahedron Lett. 2009, 50, 2914-2916.
21. Fügedi, P.; Garegg, P. J.; Lönn, H.; Norberg, T. Glycoconjugate J. 1987, 4, 97-108.
22. Koeller, K. M.; Smith, M. E.; Wong, C. H. Bioorg. Med. Chem. 2000, 8, 1017-1025.
23. Schmidt, R. R.; Toepfer, A. Tetrahedron Lett. 1991, 32, 3353-3356.
24. Komarova, B. S.; Tsvetkov, Y. E.; Pier, G. B.; Nifantiev, N. E. Carbohydr. Res. 2012, 360, 56-68.
25. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
26. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
27. Kitov, P. I.; Paszkiewicz, E.; Sadowska, J. M.; Deng, Z.; Ahmed, M.; Narain, R.; Griener, T. P.; Mulvey, G. L.; Armstrong, G. D.; Bundle, D. R. Toxins 2011, 3, 1065-1088.