Synthesis of a spore surface pentasaccharide of Bacillus anthracis

European Journal of Organic Chemistry

Volumn , Issue 12, 2007, Pages 1976-1982

  Werz, Daniel B ^a,b   Adibekian, Alexander ^a   Seeberger, Peter H ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Anthrose; Bacillus anthracis; Carbohydrates; Oligosaccharides; Total synthesis

Indexed keywords

EID: 34250651326     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601082     Document Type: Article

References (30)

1. M. Mock, A. Fouet, Annu. Rev. Microbiol. 2001, 55, 647-671.
2. P. Sylvestre, E. Couture-Tosi, M. Mock, Mol. Microbiol. 2002, 45, 169-178.
3. W. L. Nicholson, N. Munakata, G. Horneck, H. J. Melosh, P. Setlow, Microbiol. Mol. Biol. Rev. 2000, 64, 548-572.
4. J. M. Daubenspeck, H. Zeng, P. Chen, S. Dong, C. T. Steichen, N. R. Krishna, D. G. Pritchard, C. L. Turnbough Jr, J. Biol. Chem. 2004, 279, 30945-30953.
5. D. B. Werz, P. H. Seeberger, Angew. Chem. 2005, 117, 6474-6476;
6. Angew. Chem. Int. Ed. 2005, 44, 6315-6318.
7. M. Tamborrini, D. B. Werz, J. Frey, G. Pluschke, P. H. Seeberger, Angew. Chem. 2006, 118, 6731-6732;
8. Angew. Chem. Int. Ed. 2006, 45, 6581-6582.
9. a) R. Saksena, R. Adamo, P. Kováč, Carbohydr. Res. 2005, 340, 1591-1600;
10. b) R. Adamo, R. Saksena, P. Kováč, Carbohydr. Res. 2005, 340, 2579-3582;
11. c) R. Saksena, R. Adamo, P. Kováč, Bioorg. Med. Chem. Lett. 2006, 16, 615-617;
12. d) R. Adamo, R. Saksena, P. Kováč, Helv. Chim. Acta 2006, 89, 1075-1089.
13. A. S. Mehta, E. Saile, W. Zhong, T. Buskas, R. Carlson, E. Kannenberg, Y. Reed, C. P. Quinn, G.-J. Boons, Chem. Eur. J. 2006, 12, 9136-9149.
14. C. L. Turnbough Jr, personal communication.
15. a) A. H. Haines, Adv. Carbohydr. Chem. Biochem. 1976, 33, 11-109;
16. b) T. Nukada, A. Berces, D. M. Whitfield, J. Org. Chem. 1999, 64, 9030-9045;
17. c) M. Chandrasekhar, K. L. Chandra, V. K. Singh, J. Org. Chem. 2003, 68, 4039-4045.
18. F. Roussel, L. Knerr, M. Grathwohl, R. R. Schmidt, Org. Lett. 2000, 2, 3043-3046.
19. a) R. R. Schmidt, J. Michel, Angew. Chem. 1980, 92, 763-764;
20. Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732;
21. b) R. R. Schmidt, J. Michel, M. Roos, Liebigs Ann. Chem. 1984, 1343-1357.
22. H. J. Koeners, J. Verhoeven, J. H. van Boom, Tetrahedron Lett. 1980, 21, 381-382.
23. B. Castagner, D. B. Werz, P. H. Seeberger, manuscript in preparation.
24. A. Ravida, X. Liu, L. Kovacs, P. H. Seeberger, Org. Lett. 2006, 8, 1815-1818.
25. R. M. Rowell, Carbohydr. Res. 1972, 23, 417-424.
26. L. A. Carpino, Acc. Chem. Res. 1987, 20, 401-407.
27. H. H. Wasserman, R. K. Brunner, J. D. Buynak, C. G. Carter, T. Oku, R. P. Robinson, J. Am. Chem. Soc. 1985, 107, 519-521.
28. L. A. Carpino, A. El-Faham, J. Org. Chem. 1995, 60, 3561-3564.
29. The non-reducing terminal sugars are commonly most relevant to induce a specific immune response. The mixture of anomers at the carbon carrying the linker is not expected to influence subsequent immunological studies: a) R. Roy, Drug Discov. Today: Technol 2004, 1, 327-336;
30. b) B. Kuberan, R. J. Linhardt, Curr. Org. Chem. 2000, 4, 653-677.