Synthesis of three Salmonella epitopes for biosensor studies of carbohydrate-antibody interactions

Canadian Journal of Chemistry

Volumn 80, Issue 8, 2002, Pages 1131-1140

  Yu, Henry N ^a   Ling, Chang Chun ^a   Bundle, David R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

3,6 dideoxyhexose; Abequose; Deoxygenation; Glycoside tethers; Immobilization via pentenyl glycosides; Lipopolysaccharide; Paratose; Salmonella O antigens; Tyvelose

Indexed keywords

ANTIBODIES; ANTIGENS; BIOSENSORS; MONOLAYERS; SYNTHESIS (CHEMICAL);

TERMINAL THIOLS;

CARBOHYDRATES;

5 (2 AMINOETHANETHIO)PENTYL 3,6 DIDEOXY ALPHA DEXTRO RIBOHEXOPYRANOSYL (1-3) ALPHA DEXTRO MANNOPYRANOSIDE; 5 (2 AMINOETHYLTHIO)PENTYL 3,6 DIDEOXY ALPHA DEXTRO ARABINO HEXOPYRANOSYL(1-3)ALPHA DEXTRO MANNOPYRANOSIDE; 5 (2 AMINOETHYLTHIO)PENTYL 3,6 DIDEOXY ALPHA DEXTRO XYLOHEXOPYRANOSYL (1-3) ALPHA DEXTRO MANNOPYRANOSIDE; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; ETHYL 2,4 DI O ACETYL 3,6 DIDEOXY 1 THIO ALPHA,BETA DEXTRO RIBOHEXOPYRANOSIDE; ETHYL 2,4 DI O BENZOYL 3,6 DIDEOXY 1 THIO BETA DEXTRO ARABINOHEXOPYRANOSIDE; HEXOSE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANTIGEN ANTIBODY REACTION; ARTICLE; BIOSENSOR; CARBOHYDRATE SYNTHESIS; DERIVATIZATION; MOLECULAR INTERACTION; OXYGENATION; SALMONELLA; SEROTYPE;

EID: 0036434883     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v02-121     Document Type: Article

References (33)

1. A. Varki. Glycobiology, 3, 97 (1993).
2. P.I. Kitov, J.M. Sadowska, G. Mulvey, G.D. Armstrong, H. Ling, N.S. Pannu, R.J. Read, and D.R. Bundle. Nature (London), 403, 669 (2000).
3. D.R. Bundle. Recognition of carbohydrate antigens by antibody binding sites. In Carbohydrates. Edited by S. Hecht. Oxford University Press Inc., Oxford. 1995. pp. 370-440.
4. U. Jönsson, L. Fägerstam, B. Ivarssson, B. Johnsson, R. Karlsson, K. Lundh, S. Löfås, B. Persson, H. Roos, I. Rönnberg, S. Sjölander, E. Stenberg, R. Ståhlberg, C. Urbaniczky, H. Östlin, and M. Malmqvist. BioTechniques, 11, 620 (1991).
5. W.M. Mullett, E.P.C. Lai, and J.M. Yeung. Methods - A Companion to Methods Enzymol. 22, 77 (2000).
6. M. Mrksich. Chem. Soc. Rev. 29, 267 (2000), and refs. therein.
7. K.L. Prime and G.M. Whitesides. J. Am. Chem. Soc. 115, 10 714 (1993).
8. M. Mrksich, G.S. Sigal, and G.M. Whitesides. Langmuir, 11, 4383 (1995).
9. N. Horan, L. Yan, H. Isobe, G.M. Whitesides, and D. Kahne. Proc. Natl. Acad. Sci. U.S.A. 96, 11 782 (1999).
10. D.A. Mann, M. Kanai, D.J. Maly, and L.L. Kiessling. J. Am. Chem. Soc. 120, 10 575 (1998).
11. B.T. Houseman and M. Mrksich. Angew. Chem. Int. Ed. 38, 782 (1999).
12. P.I. Kitov, C. Railton, and D.R. Bundle. Carbohydr. Res. 307, 361 (1998).
13. D.R. Bundle. Top. Curr. Chem. 154, 1 (1990), and refs. therein.
14. A.A. Lindberg, R. Wollin, G. Gruse, and S.B. Svenson. Am. Chem. Soc. Symp. Ser. 231, 83 (1983)
15. A. Zdanov, Y. Li, D.R. Bundle, S.-J. Deng, C.R. Mackenzie, S.A. Narang, N.M. Young, and M. Cygler. Biochemistry, 33, 5172 (1994).
16. B.W. Sigurskjold and D.R. Bundle. J. Biol. Chem. 267, 8371 (1992).
17. B.W. Sigurskjold, E. Altman, and D.R. Bundle. Eur. J. Biochem. 197, 239 (1991).
18. C.R. Mackenzie, T. Hirama, S.-J. Deng, D.R. Bundle, S.A. Narang, and N.M. Young. J. Biol. Chem. 271, 1527 (1995).
19. B. Fraser-Reid, U.E. Udodong, A. Wu, H. Ottosson, J.R. Merritt, C.S. Ral, C. Roberts, and R. Madsen. Synlett, 927 (1992), and refs. therein.
20. D.R. Mootoo, P. Konradsson, U. Udodong, and B. Fraser-Reid. J. Am. Chem. Soc. 110, 5583 (1988).
21. H.N. Yu, P. Zhang, C.-C. Ling, and D.R. Bundle. Tetrahedron: Asymmetry, 11, 465 (2000).
22. T.L. Lowary, E. Eichler, and D.R. Bundle. J. Org. Chem. 60, 7316 (1995).
23. B. Classon, P.J. Garegg, and B. Samuelsson. Can. J. Chem. 59, 339 (1981).
24. D.H.R. Barton and S.W. McCombie. J. Chem. Soc. Perkin Trans. 1, 1574 (1975).
25. G. Ekborg and S. Svensson. Acta Chem. Scand. 27, 1437 (1973).
26. M.A. Probert, J. Zhang, and D.R. Bundle. Carbohydr. Res. 296, 149 (1996).
27. S. Oscarson and A. Tiden. Carbohydr. Res. 247, 323 (1993).
28. H.N. Yu, C.-C. Ling, and D.R. Bundle. J. Chem. Soc. Perkin Trans. 1, 832 (2001).
29. C.J. France, I.M. McFarlane, C.G. Newton, P. Pitchen, and D.H.R. Barton. Tetrahedron, 47, 6381 (1991).
30. A.V. Demchenko and G.-J. Boons. J. Org. Chem. 66, 2547 (2001).
31. K. Bock and C. Pedersen. J. Chem. Soc. Perkin Trans. 2, 293 (1974).
32. R.T. Lee and Y.C. Lee. Carbohydr. Res. 37, 193 (1974).
33. R.K. Jain, X.-G. Liu, S.R. Oruganti, E.V. Chandrasekaran, and K.L. Matta. Carbohydr. Res. 271, 185 (1995).