First synthesis of C. difficile PS-II cell wall polysaccharide repeating unit

Organic Letters

Volumn 13, Issue 3, 2011, Pages 378-381

  Danieli, Elisa ^a   Lay, Luigi ^b   Proietti, Daniela ^a   Berti, Francesco ^a   Costantino, Paolo ^a   Adamo, Roberto ^a  

^a NOVARTIS VACCINES AND DIAGNOSTICS   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL POLYSACCHARIDE; POLYSACCHARIDE II, CLOSTRIDIUM DIFFICILE;

AGED; ARTICLE; CARBOHYDRATE ANALYSIS; CELL WALL; CHEMISTRY; CLOSTRIDIUM DIFFICILE; DIARRHEA; HUMAN;

AGED; CARBOHYDRATE SEQUENCE; CELL WALL; CLOSTRIDIUM DIFFICILE; DIARRHEA; HUMANS; POLYSACCHARIDES, BACTERIAL;

EID: 79851474622     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1026188     Document Type: Article

References (29)

1. Koo, H. L.; Garey, K. W.; DuPont, H. L. Expert Opin. Invest. Drugs 2010, 825.
2. Knoop, F. C.; Owens, M.; Crocker, I. C. Clin. Microbiol. Rev. 1993, 6, 251.
3. Freeman, J.; Bauer, M. P.; Baines, S. D.; Corver, J.; Fawley, W. N.; Goorhuis, B.; Kuijper, E. J.; Wilcox, M. H. Clin. Microbiol. Rev. 2010, 23, 529.
4. Pepin, J.; Valiquette, L.; Alary, M.-E.; Villemure, P.; Pelletier, A.; Forget, K.; Pepin, K.; Chouinard, D. Can. Med. Assoc. J. 2004, 171, 466.
5. Loo, V. G.; Poirier, L.; Miller, M. A.; Oughton, M.; Libman, M. D.; Michaud, S.; Bourgault, A.-M.; Nguyen, T.; Frenette, C.; Kelly, M.; Vibien, A.; Brassard, P.; Fenn, S.; Dewar, K.; Hudson, T. J.; Horn, R.; Rene, P.; Monczak, Y.; Dascal, A. N. Engl. J. Med. 2005, 353, 2442.
6. Redelings, M. D.; Sorvillo, F.; Mascola, L. Emerg. Infect. Dis. 2007, 13, 1417.
7. Kyne, L.; Hamel, M. B.; Polavaram, R.; Kelly, C. P. Clin. Infect. Dis. 2002, 34, 346.
8. (a) Gerding, D. N.; Muto, C. A.; Owens, R. C. Clin. Infect. Dis. 2008, 46, S32.
9. (b) Sun, X.; Savidge, T.; Feng, H. Toxins 2010, 2, 1848.
10. Ganeshapillai, J.; Vinogradov, E.; Rousseau, J.; Scott Weesec, J.; Monteiro, M. A. Carbohydr. Res. 2008, 343, 703.
11. For reviews on oligosaccharide-based glycoconjugate vaccines, see: (a) Astronomo, R. D.; Burton, D. R. Nat. Rev. Drug. Discov. 2010, 9, 308.
12. (b) Hecht, M.-L.; Stallforth, P.; Varon Silva, D.; Adibekiany, A.; Seeberger, P. H. Curr. Opin. Chem. Biol. 2009, 13, 354.
13. (c) Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046.
14. (d) Vliegenthart, J. F. G. FEBS Lett. 2003, 580, 2945.
15. Bardotti, A.; Averani, G.; Berti, F.; Berti, S.; Carinci, V.; D'Ascenzi, S.; Fabbri, B.; Giannini, S.; Giannozzi, A.; Magagnoli, C.; Proietti, D.; Norelli, F.; Rappuoli, R.; Ricci, S.; Costantino, P. Vaccine 2009, 26, 2284.
16. Z. Zhang, G. M. Carbohydr. Res. 1996, 280, 251.
17. Ellervik, U.; Magnusson, H. G., G. J. Org. Chem. 1998, 63, 9323.
18. Wang, Y.; Yan, Q.; Wu, J.; Zhang, L.-H.; Ye, X.-S. Tetrahedron 2005, 61, 4313.
19. The moderate yield of 11 is due to the formation of variable amounts of the orthoester which besides rearranging to the desired product 11 was partially hydrolyzed during the reaction course.
20. Evans, M. Carbohydr. Res. 1977, 54, 105.
21. Handa, V.; Barlow, J. J.; Maita, K. Carbohydr. Res. 1979, 73, C1.
22. Nitz, M.; Bundle, D. R. J. Org. Chem. 2000, 65, 3064.
23. Wu X.; Lipinski T.; Carrel F. R.; Baileya J. J.; Bundle D. R. Org. Biomol. Chem. 2007, 5, 3477.
24. Lay, L.; Manzoni, L.; Schmidt, R. R. Carbohydr. Res. 1998, 310, 157.
25. Haag, T.; Hughes, R. A.; Ritter, G.; Schmidt, R. R. Eur. J. Org. Chem. 2007, 6016.
26. (a) Oikawa, M.; Liu, W.-C.; Nakai, Y.; Koshida, S.; Fukase, K.; Kusumoto, S. Synlett 1996, 1179.
27. (b) Baumann, K.; Kowalczyk, D.; Kunz, H. Angew. Chem., Int. Ed. 2008, 47, 3445.
28. Mandal M.; Dudkin V. Y.; Geng X.; Danishefsky S. J. Angew. Chem., Int. Ed. 2004, 43, 2557.
29. Zhang Y.; M. A. Wolfert J. G.; Boons G.-J. Chem.-Eur. J. 2008 14 558.