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Synthesis of oligosaccharide fragments of the Streptococcus pneumoniae type 14 capsular polysaccharide and their neoglycoconjugates with bovine serum albumin

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Abstract

2-Aminoethyl glycosides of tetra-, hexa- and octasaccharide fragments of the bacteria Streptococcus pneumoniae type 14 capsular polysaccharide were synthesized within a project directed to the development of pneumococcal conjugated vaccine based on synthetic carbohydrate ligands. Squarate method was used to obtain neoglycoconjugates of the synthesized oligosaccharides with bovine serum albumin.

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References

  1. V. K. Tatochenko, Zh. Det. Infekts. [J. Child Infections], 2008, 2, 13 (in Russian).

    Google Scholar 

  2. V. K. Tatochenko, Zh. Mikrobiol. [Microbiol. J.], 2010, 5, 90 (in Russian).

    Google Scholar 

  3. L. A. Vishnyakova, Pul’monologiya [Pulmonology], 1993, 3, 17 (in Russian).

    Google Scholar 

  4. K. L. O’Brien, L. J. Wolfson, J. P. Watt, E. Henkle, M. Deloria-Knoll, N. McCall, E. Lee, K. Mulholland, O. S Levine, T. Cherian, Lancet, 2009, 374, 893.

    Article  Google Scholar 

  5. D. M. Weinberger, Z. B. Harboe, E. A. Sanders, M. Ndiritu, K. P. Klugman, S. Rückinger, R. Dagan, R. Adegbola, F. Cutts, H. L. Johnson, K. L. O’Brien, A. Scott, M. Lipsitch, Clin. Infect. Dis., 2010, 51, 692.

    Article  Google Scholar 

  6. J. P. Kamerling, in Streptococcus pneumoniae molecular biology and mechanism of disease, Eds A. Tomasz, Mary Ann Libert, 2000, p. 81.

  7. R. S. Kozlov, A. N. Chagaryan, L. V. Kozlova, A. A. Murav’ev, Klin. Mikrobiol. Antimikrob. Khimioter. [Clin. Microbiol. Antimicrob.Chemiother.], 2011, 13, 177 (in Russian).

    Google Scholar 

  8. E. C. Beuvery, F. Van Rossem, J. Nagel, Infect. Immun., 1982, 37, 15.

    CAS  Google Scholar 

  9. G. Ada, D. Isaacs, Clin. Microbiol. Infect., 2003, 9, 79–85.

    Article  CAS  Google Scholar 

  10. M. B. Rennels, K. M. Edwards, H. L. Keyserling, K. S. Reisinger, D. A. Hogerman, D. V. Madore, I. Chang, P. R. Paradiso, F. J. Malinoski, A. Kimura, Pediatrics, 1998, 101, 604.

    Article  CAS  Google Scholar 

  11. J. Niggemann, J. P. Kamerling, J. F. G. Vliegenthart, J. Chem. Soc., Perkin Trans. 1, 1998, 3011.

    Google Scholar 

  12. J. Niggemann, J. P. Kamerling, J. F. G. Vliegenthart, Bioorg. Med. Chem., 1998, 6, 1605.

    Article  CAS  Google Scholar 

  13. D. Michalik, J. F. G. Vliegenthart, J. P. Kamerling, J. Chem. Soc., Perkin Trans. 1, 2002, 1973.

    Google Scholar 

  14. J. A. F. Joosten, J. P. Kamerling, J. F.G. Vliegenthart, Carbohydr. Res., 2003, 338, 2611.

    Article  CAS  Google Scholar 

  15. J. A. F. Joosten, B. J. Lazet, J. P. Kamerling, J. F.G. Vliegenthart, Carbohydr. Res., 2003, 338, 2629.

    Article  CAS  Google Scholar 

  16. A. Sundgren, M. Lahmann, S. Oscarson, J. Carbohydr. Chem., 2005, 24, 379.

    Article  CAS  Google Scholar 

  17. F. Mawas, J. Niggemann, C. Jones, M. J. Corbel, J. P. Kamerling, J. F. G. Vliegenthart, Infect. Immun., 2002, 70, 5107.

    Article  CAS  Google Scholar 

  18. D. Safari, H. A. T. Dekker, J. A. F. Joosten, D. Michalik, A. Carvalho de Souza, R. Adamo, M. Lahmann, A. Sundgren, S. Oscarson, J. P. Kamerling, H. Snippe, Infect. Immun., 2008, 76, 4615.

    Article  CAS  Google Scholar 

  19. B. Lindberg, J. Lönngren, D.A. Powel, Carbohydr. Res., 1977, 58, 177.

    Article  CAS  Google Scholar 

  20. P. E. Cheshev, E.A. Khatuntseva, Y. E. Tsvetkov, A. S. Shashkov, N. E. Nifantiev, Russ. J. Bioorg. Chem., 2004, 30, 60 [Bioorg. Khim., 2004, 30, 68].

    Article  CAS  Google Scholar 

  21. A. Sundgren, M. Lahmann, S. Oscarson, J. Carbohydr. Chem., 2005, 24, 379.

    Article  CAS  Google Scholar 

  22. F. A. W. Koeman, J. W. G. Meissner, H. R. P. van Ritter, J. P. Kamerling, J. F. G. Vliegenthart, J. Carbohydr. Chem., 1994, 13, 1.

    Article  CAS  Google Scholar 

  23. L. Lay, R. Windmüller, S. Reinhardt, R. R. Schmidt, Carbohydr. Res., 1997, 303, 39.

    Article  CAS  Google Scholar 

  24. G.-W. Xing, L. Chen, F.-F. Liang, Eur. J. Org. Chem., 2009, 5963.

    Google Scholar 

  25. R. H. Youssef, B. A. Silwanis, R. I. El-Sokkary, A. S. Nematalla, M. A. Nashed, Carbohydr. Res., 1993, 240, 287.

    Article  CAS  Google Scholar 

  26. C. Yong-Xiang, Z. Wei, Z. Lei, Z. Yu-Fen, L. Yan-Mei, Carbohydr. Res., 2008, 343, 607.

    Article  Google Scholar 

  27. J. Xue, J. Zhu, R. E. Marchant, Z. Guo, Org. Lett., 2005, 7, 3753.

    Article  CAS  Google Scholar 

  28. L. F. Tietze, M. Arlt, M. Beller, K.-H. GlЩsenkamp, E. Jähde, M. Rajewsky, Chem. Ber., 1991, 124, 1215.

    Article  CAS  Google Scholar 

  29. V. P. Kamath, P. Diedrich, O. Hindsgaul, Glycoconjugate J., 1996, 13, 315.

    Article  CAS  Google Scholar 

  30. A. Chernyak, A. Karavanov, Y. Ogawa, P. Kováè, Carbohydr. Res., 2001, 330, 479.

    Article  CAS  Google Scholar 

  31. S.-J. Hou, R. Saksena, P. Kováè, Carbohydr. Res., 2008, 343, 196.

    Article  CAS  Google Scholar 

  32. N. K. Kochetkov, N. E. Nifant’ev, L. V. Backinowsky, Tetrahedron, 1987, 43, 3109.

    Article  CAS  Google Scholar 

  33. N. E. Nifant’ev, L. V. Backinowsky, N. K. Kochetkov, Carbohydr. Res., 1988, 174, 61.

    Article  Google Scholar 

  34. A. A. Sherman, O. N. Yudina, Y. V. Mironov, E. V. Sukhova, A. S. Shashkov, V. M. Menshov, N. E. Nifantiev, Carbohydr. Res., 2001, 336, 13.

    Article  CAS  Google Scholar 

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Correspondence to N. E. Nifantiev.

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On the occasion of the 80th anniversary of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0511–0521, February, 2014.

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Sukhova, E.V., Yashunsky, D.V., Tsvetkov, Y.E. et al. Synthesis of oligosaccharide fragments of the Streptococcus pneumoniae type 14 capsular polysaccharide and their neoglycoconjugates with bovine serum albumin. Russ Chem Bull 63, 511–521 (2014). https://doi.org/10.1007/s11172-014-0462-5

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  • DOI: https://doi.org/10.1007/s11172-014-0462-5

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