Synthesis of branched tri- to pentasaccharides representative of fragments of Shigella flexneri serotypes 3a and/or X O-antigens

Tetrahedron

Volumn 64, Issue 46, 2008, Pages 10558-10572

  Boutet, Julien ^a,b   Guerreiro, Catherine ^a   Mulard, Laurence A ^a  

^a CNRS   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Glycosylation; N Trichloroacetyl; Oligosaccharide; Shigella

Indexed keywords

GLUCOPYRANOSIDE; LIPOPOLYSACCHARIDE; O ANTIGEN; OLIGOSACCHARIDE; PENTASACCHARIDE; POLYMER; TRICHLOROACETIC ACID; TRICHLOROACETIMIDIC ACID; TRISACCHARIDE;

ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL VIRULENCE; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; GLYCOSYLATION; INNATE IMMUNITY; ISOMERIZATION; KINETICS; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PRIORITY JOURNAL; SEROTYPE; SHIGELLA FLEXNERI; STEREOCHEMISTRY; STEREOSPECIFICITY; THIN LAYER CHROMATOGRAPHY;

SHIGELLA; SHIGELLA FLEXNERI;

EID: 52949135897     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.080     Document Type: Article

References (48)

1. Niyogi S.K. J. Microbiol. 43 (2005) 133-143
2. von Seidlein L., Kim D.R., Ali M., Lee H., Wang X., Thiem V.D., Canh do G., Chaicumpa W., Agtini M.D., Hossain A., Bhutta Z.A., Mason C., Sethabutr O., Talukder K., Nair G.B., Deen J.L., Kotloff K., and Clemens J. PLoS Med. 3 (2006) 1556-1568
3. Levine M.M., Kotloff K.L., Barry E.M., Pasetti M.F., and Sztein M.B. Nat. Rev. Microbiol. 5 (2007) 540-553
4. Kotloff K.L., Winickoff J.P., Ivanoff B., Clemens J.D., Swerdlow D.L., Sansonetti P.J., Adak G.K., and Levine M.M. Bull. World Health Organ. 77 (1999) 651-666
5. Lindberg A.A., Karnell A., and Weintraub A. Rev. Infect. Dis. 13 (1991) S279-S284
6. Mulard L.A., and Ughetto-Monfrin J. J. Carbohydr. Chem. 19 (2000) 193-220
7. Clément M.J., Imberty A., Phalipon A., Perez S., Simenel C., Mulard L.A., and Delepierre M. J. Biol. Chem. 278 (2003) 47928-47936
8. Mulard L.A., Costachel C., and Sansonetti P.J. J. Carbohydr. Chem. 19 (2000) 849-877
9. Bélot F., Wright K., Costachel C., Phalipon A., and Mulard L.A. J. Org. Chem. 69 (2004) 1060-1074
10. West N.P., Sansonetti P., Mounier J., Exley R.M., Parsot C., Guadagnini S., Prevost M.C., Prochnicka-Chalufour A., Delepierre M., Tanguy M., and Tang C.M. Science 307 (2005) 1313-1317
11. Ferreccio C., Prado V., Ojeda A., Cayyazo M., Abrego P., Guers L., and Levine M.M. Am. J. Epidemiol. 134 (1991) 614-627
12. Formal S.B., Oaks E.V., Olsen R.E., Wingfield-Eggleston M., Snoy P.J., and Cogan J.P. J. Infect. Dis. 164 (1991) 533-537
13. Noriega F.R., Liao F.M., Maneval D.R., Ren S., Formal S.B., and Levine M.M. Infect. Immun. 67 (1999) 782-788
14. Pinto B.M., Reimer K.B., Morissette D.G., and Bundle D.R. Carbohydr. Res. 196 (1990) 156-166
15. Tsvetkov Y.E., Bairamova N.E., Bakinovskii L.V., Kochetkov N.K., and Lankina N.F. Bioorg. Khim. 12 (1986) 1213-1224
16. Mulard L.A., and Ughetto-Monfrin J. J. Carbohydr. Chem. 18 (1999) 721-753
17. Schmidt R.R., and Kinzy W. Adv. Carbohydr. Chem. Biochem. 50 (1994) 21-123
18. Blatter G., Beau J.M., and Jacquinet J.C. Carbohydr. Res. 260 (1994) 189-202
19. Boutet J., Kim T.H., Guerreiro C., and Mulard L.A. Tetrahedron Lett. 49 (2008) 5339-5342
20. Bakinovskii L.V., Gomtsyan A.R., Bairamova N.E., and Kochetkov N.K. Bioorg. Khim. 10 (1984) 79-87
21. Wessel H.P., and Bundle D.R. J. Chem. Soc., Perkin Trans. 1 (1985) 2251-2260
22. Mulard L.A., Clément M.J., Segat-Dioury F., and Delepierre M. Tetrahedron 58 (2002) 2593-2604
23. Castro-Palomino J.C., Hernandez Rensoli M., and Verez Bencomo V. J. Carbohydr. Chem. 15 (1996) 137-146
24. Schmidt R.R., Michel J., and Roos M. Liebigs Ann. Chem. (1984) 1343-1357
25. Schmidt R.R., and Michel J. Tetrahedron Lett. 25 (1984) 821-824
26. Pinto B.M., Reimer K.B., and Tixidre A. Carbohydr. Res. 210 (1991) 199-219
27. Gigg J., Payne S., and Conant R. J. Carbohydr. Chem. 2 (1983) 207-223
28. Pinto B.M., Morissette D.G., and Bundle D.R. J. Chem. Soc., Perkin Trans. 1 (1987) 9-14
29. Zhang K.Q., Li S.C., Mao J.M., Chen H.M., and Cai M.S. Chem. J. Chin. Univ. 18 (1997) 1469-1473
30. Lindhorst T.K. Essentials of Carbohydrate Chemistry and Biochemistry (2000), Wiley-VCH, Weinheim p 42
31. Spijker N.M., and van Boeckel C.A.A. Angew. Chem., Int. Ed. Engl. 30 (1991) 180-183
32. Yang F., He H.M., Du Y.G., and Lu M.J. Carbohydr. Res. 337 (2002) 1165-1169
33. Zeng Y., Ning J., and Kong F.Z. Tetrahedron Lett. 43 (2002) 3729-3733
34. Ikeda T., Yamauchi K., Nakano D., Nakanishi K., Miyashita H., Ito S., and Nohara T. Tetrahedron Lett. 47 (2006) 4355-4359
35. Fekete A., Gyergyoi K., Kover K.E., Bajza I., and Liptak A. Carbohydr. Res. 341 (2006) 1312-1321
36. Geyer K., and Seeberger P.H. Helv. Chim. Acta 90 (2007) 395-403
37. Adamo R., and Kovac P. Eur. J. Org. Chem. (2007) 988-1000
38. Whitfield D.M., and Nukada T. Carbohydr. Res. 342 (2007) 1291-1304
39. Segat-Dioury F., and Mulard L.A. Tetrahedron: Asymmetry 13 (2002) 2211-2222
40. Das S.K., and Roy N. J. Carbohydr. Chem. 14 (1995) 417-428
41. Szurmai Z., Liptak A., and Snatzke G. Carbohydr. Res. 200 (1990) 201-208
42. Kitagawa I., Baek N.I., Ohashi K., Sakagami M., Yoshikawa M., and Shibuya H. Chem. Pharm. Bull. 37 (1989) 1131-1133
43. Lubineau A., Basset-Carpentier K., and Augé C. Carbohydr. Res. 300 (1997) 161-167
44. Baeschlin D.K., Green L.G., Hahn M.G., Hinzen B., Ince S.J., and Ley S.V. Tetrahedron: Asymmetry 11 (2000) 173-197
45. Pozsgay V., and Coxon B. Carbohydr. Res. 257 (1994) 189-215
46. Oltvoort J.J., van Boeckel C.A.A., der Koning J.H., and van Boom J.H. Synthesis (1981) 305-308
47. Nashed M.A., and Anderson L. J. Chem. Soc., Chem. Commun. (1982) 1274-1276
48. Donohoe T.J., Logan J.G., and Laffan D.D. Org. Lett. 5 (2003) 4995-4998