Synthesis of a hexasaccharide repeating unit from bacillus anthracis vegetative cell walls

Organic Letters

Volumn 10, Issue 5, 2008, Pages 905-908

  Oberli, Matthias A ^a   Bindschädler, Pascal ^a   Werz, Daniel B ^b   Seeberger, Peter H ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL POLYSACCHARIDE;

ARTICLE; BACILLUS ANTHRACIS; BIOSYNTHESIS; CARBOHYDRATE ANALYSIS; CELL WALL; CHEMICAL STRUCTURE; CHEMISTRY;

BACILLUS ANTHRACIS; CARBOHYDRATE SEQUENCE; CELL WALL; MOLECULAR STRUCTURE; POLYSACCHARIDES, BACTERIAL;

EID: 43549122662     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7030262     Document Type: Article

References (38)

1. Mock, M.; Fouet, A. Anna. Rev. Microbiol. 2001, 55, 647-671.
2. Sylvestre, P.; Couture-Tosi, E.; Mock, M. Mol. Microbiol. 2002, 45, 169-178.
3. Nicholson, W. L.; Munakata, N.; Horneck, G.; Melosh, H. J.; Setlow, P. Microbiol. Mol. Biol. Rev. 2000, 64, 548-572.
4. Daubenspeck, J. M.; Zeng, H.; Chen, P.; Dong, S.; Steichen, C. T.; Krishna, N. R.; Pritchard, D. G.; Turnbough, C. L., Jr. J. Biol. Chem. 2004, 279, 30945-30953.
5. (a) Werz, D. B.; Seeberger, P. H. Angew. Chem., Int. Ed. 2005, 44, 6315-6318.
6. (b) Werz, D. B.; Adibekian, A.; Seeberger, P. H. Eur. J. Org. Chem. 2007, 1976-1982.
7. (c) Adamo, R.; Saksena, R.; Kováč, P. Carbohydr. Res. 2005, 340, 2579-2582.
8. (d) Adamo, R.; Saksena, R.; Kováč, P. Helv. Chim. Acta 2006, 89, 1075-1089.
9. (e) Mehta, A. S.; Saile, E.; Zhong, W.; Buskas, T.; Carlson, R.; Kannenberg, E.; Reed, Y.; Quinn, C. P.; Boons, G.-J. Chem. Eur. J. 2006, 12, 9136-9149.
10. (f) Crich, D.; Vinogradova, O. J. Org. Chem. 2007, 72, 6513 -6520.
11. (g) Guo, H.; O' Doherty, G. A. Angew. Chem., Int. Ed. 2007, 46, 5206-5208.
12. Tamborrini, M.; Werz, D. B.; Frey, J.; Pluschke, G.; Seeberger, P. H. Angew. Chem., Int. Ed. 2006, 45, 6581-6582.
13. Choudhury, B.; Leoff, C; Saile, E.; Wilkins, P.; Quinn, C. P.; Kannenberg, E. L.; Carlson, R. W. J. Biol. Chem. 2006, 281, 27932-27941.
14. Verez-Bencomo, V.; et al. Science 2004, 305, 522-525.
15. (a) Adinolfi, M.; Barone, G.; Iadonisi, A.; Schiattarella, M. Org. Lett. 2003, 5, 987-989.
16. (b) Tanaka, H.; Iwata, Y.; Takahashi, D.; Adachi, M.; Takahashi, T. J. Am. Chem. Soc. 2005, 127, 1630-1631.
17. (a) Garegg, P. J.; Konradsson, P.; Oscarson, S.; Ruda, K. Tetrahedron 1997, 53, 17727-17734.
18. (b) Turek, D.; Sundgren, A.; Lahmann, M.; Oscarson, S. Org. Biomol. Chem. 2006, 4, 1236-1241.
19. (a) Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211-214.
20. (b) Hewitt, M. C.; Seeberger, P. H. Org. Lett. 2001, 3, 3699-3702.
21. (c) Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Fan, H.-F.; Pai, C.-L.; Yang, W.-C.; Lu, L.-D.; Hung, S.-C. Angew. Chem., Int. Ed. 2002, 41, 2360-2362.
22. (d) Werz, D. B.; Ranzinger, R.; Herget, S.; Adibekian, A.; von der Lieth, C.-W.; Seeberger, P. H. ACS Chem. Biol. 2007, 2, 685-691.
23. (a) Buskas, T.; Söderberg, E.; Konradsson, P.; Fraser-Reid, B. J. Org. Chem. 2000, 65, 958-963.
24. (b) Wang, Z.-G.; Williams, L. J.; Zhang, X.-F.; Zatorski, A.; Kudryashov, V.; Ragupathi, G.; Spassova, M.; Born-mann, W.; Slovin, S. F.; Scher, H. I.; Livingston, P. O.; Lloyd, K. O.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 2719-2724.
25. (a) Yamada, A.; Hatano, K.; Koyama, T.; Matsuoka, K.; Esumi, Y.; Terunuma, D. Carbohydr. Res. 2006, 341, 467-473.
26. (b) Isobe, H.; Cho, K.; Solin, N.; Werz, D. B.; Seeberger, P. H.; Nakamura, E. Org. Lett. 2007, 9, 4611-4614.
27. Melean, L. G.; Love, K. R.; Seeberger, P. H. Carbohydr. Res. 2002, 337, 1893-1916.
28. (a) Zuurmond, H. M.; van der Klein, P. A. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1992, 33, 2063-2066.
29. (b) Veselý, J.; Rohlenová, A.; Džoganová, M.; Trnka, T.; Tišlerová, I.; Šaman, D.; Ledvina, M. Synthesis 2006, 699-705.
30. (a) Grathwohl, M.; Schmidt, R. R. Synthesis 2001, 2263-2272.
31. (b) Love, K. R.; Seeberger, P. H. Angew. Chem., Int. Ed. 2004, 43, 602-605.
32. (a) David, S.; Malleron, A.; Dini, C. Carbohydr. Res. 1989, 188, 193-200.
33. (b) Classon, B.; Garegg, P. J.; Oscarson, S.; Tidén, A.-K. Carbohydr. Res. 1991, 216, 187-196.
34. Yu, B.; Tao, H. Tetrahedron Lett. 2001, 42, 2405-2407.
35. Schmidt, R. R.; Michel, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 731-732.
36. (a) Zhu, T.; Boons, G.-J. Tetrahedron: Asymmetry 2000, 11, 199-205.
37. (b) Roussel, F.; Takhi, M.; Schmidt, R. R. J. Org. Chem. 2001, 66, 8540-8548.
38. For detailed comparison of 1 and 3 see the Supporting Information.