Skip to main content

Advertisement

Log in

Synthesis of oligosaccharides structurally related to fragments of Streptococcus pneumoniae type 3 capsular polysaccharide

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

3-Aminopropyl glycosides of di-, tri-, and tetrasaccharide structurally related to fragments of Streptococcus pneumoniae type 3 bacteria capsular polysaccharide were synthesized.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. M. Kharit, in Vaktsini i vactsinatsiya: natsionalnoe rukovodstvo [Vaccines and Vaccination: National Guidelines] Ed. V. V. Zverev, B. F. Semenov, and R. M. Khaitov, GEOTAR-Media, Moscow, 2011, 880 p. (in Russian).

  2. J. P. Kamerling, Pneumococcal polysaccharides: a chemical view, in Streptococcus pneumoniae: molecular biology and mechanism of disease, Eds A. Tomasz, Mary Ann Libert, Inc., Larchmont, New York, 2000, p.81.

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

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. 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 

  6. M. L. Gening, E. A. Kurbatova, Yu. E. Tsvetkov, N. E. Nifantiev, Russ. Chem. Rev., 2015, 84, 1100 (Engl. Transl.), [Uspekhi Khimii, 2015, 84, 1100].

    Article  CAS  Google Scholar 

  7. L. Morelli, L. Poletti, L. Lay, Eur. J. Org. Chem., 2011, 5723.

    Google Scholar 

  8. E. V. Sukhova, D. V. Yashunsky, Y. E. Tsvetkov, E. A. Kurbatova, N. E. Nifantiev, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 511 [Izv. Acad. Nauk, Ser. Khim. 2014, 511].

    Article  CAS  Google Scholar 

  9. E. A. Kurbatova, D. S. Vorobyov, N. B. Egorova, I. B. Semenova, E. V. Sukhova, D. V. Yashunsky, Yu. E. Tsvetkov, N. E. Nifantiev, Zhurn. Mikrobiol. Epidemiol. Immunobiol., 2012, 36 (in Russian).

  10. E. A. Kurbatova, N. K. Akhmatova, N. B. Egorova, I. B. Semenova, N. E. Yastrebova, Yu. E. Tsvetkov, E. V. Sukhova, D. V. Yashunsky, N. E. Nifantiev, Zhurn. Mikrobiol. Epidemiol. Immunobiol., 2015, 46 (in Russian).

    Google Scholar 

  11. E. A. Kurbatova, D. S. Vorob´ev, E. A. Akhmatov, N. K. Akhmatova, N. B. Egorova, Y. E. Tsvetkov, E. V. Sukhova, D. V. Yashunskii, N. E. Nifant´ev. Bull. Exp. Biol. Med., 2014, 157, 612 [Bull. Experim. Biologii i Meditsini, 2014, 157, 630].

    Article  CAS  Google Scholar 

  12. N. K. Akhmatova, E. A. Kurbatova, E. A. Akhmatov, N. B. Egorova, D. Y. Logunov, M. L. Gening, E. V. Sukhova, D. V. Yashunsky, Y. E. Tsvetkov, N. E. Nifantiev, Front. Immunol., 2016, 7,248.

    Article  Google Scholar 

  13. V. P. Ananikov, E. A. Khokhlova, M. P. Egorov, A. M. Sakharov, S. G. Zlotin, A. V. Kucherov, L. M. Kustov, M. L. Gening, N. E. Nifantiev, Mendeleev Commun., 2015, 25,75.

    Article  CAS  Google Scholar 

  14. A. Ya. Chernyak, K. V. Antonov, N. K. Kochetkov, Russ. J. Bioorg. Chem. (Engl. Transl.), 1987, 13 [Bioorgan. Khimiya, 987, 13, 958].

  15. D. J. Lefeber, J. P. Kamerling, J. F. G. Vliegenthart, Chem. Eur. J., 2001, 7, 4411.

    Article  CAS  Google Scholar 

  16. D. J. Lefeber, E. A. Arévalo, J. P. Kamerling, J. F. G. Vliegenthart, Can. J. Chem., 2002, 80,76.

    Article  CAS  Google Scholar 

  17. A.-R. de Jong, B. Hagen, V. van der Ark, H. S. Overkleeft, J. D. C. Codée, G. A. Van der Marel, J. Org. Chem., 2012, 77,108.

    Article  Google Scholar 

  18. D. V. Yashunsky, Y. E. Tsvetkov, A. A. Grachev, A. O. Chizhov, N. E. Nifantiev, Carbohydr. Res., 2016, 419,8.

    Article  CAS  Google Scholar 

  19. H. Paulsen, Angew. Chem., Int. Ed., 1982, 21,155.

    Article  Google Scholar 

  20. Y. Wang, Q. Yan, J. Wu, L.-H. Zhang, X.-S. Ye, Tetrahedron, 2005, 61, 4313.

    Article  CAS  Google Scholar 

  21. P. J. Garegg, I. Kvarnstrom, A. Niklasson, G. Niklasson, S. C. T. Svensson, J. Carbohydr. Chem., 1993, 12,933.

    Article  CAS  Google Scholar 

  22. J. B. Epp, T. S. Widlanski, J. Org. Chem., 1999, 64,293.

    Article  CAS  Google Scholar 

  23. H. Tanaka, T. Kawai, Y. Adachi, S. Hanashima, Y. Yamaguchi, N. Ohno, T. Takahashi, Bioorg. Med. Chem., 2012, 20, 3898.

    Article  CAS  Google Scholar 

  24. F. M. Ibatullin, K. A. Shabalin, J. V. Jänis, A. G. Shavva, Tetrahedron Lett., 2003, 44, 7961.

    Article  CAS  Google Scholar 

  25. V. Jadhav, C. M. Pedersen, M. Bols, Org. Biomol. Chem., 2011, 9, 7525.

    Article  CAS  Google Scholar 

  26. G. W. J. Twaddle, D. V. Yashunsky, A. V. Nikolaev, Org. Biomol. Chem., 2003, 1,623.

    Article  CAS  Google Scholar 

  27. K. Takeo, T. Fukatsu, T. Yasato, Carbohydr. Res., 1982, 107,71.

    Article  CAS  Google Scholar 

  28. M. Alonso-Lopez, J. Barbat, E. Fanton, A. Fernandez-Mayoralas, J. Gelas, D. Horton, M. Martin-Lomas, S. Penades, Tetrahedron, 1987, 43, 1169.

    Article  CAS  Google Scholar 

  29. E. A. Kurbatova, E. A. Akhmatov, N. K. Akhmatova, N. B. Egorova, N. E. Yastrebova, E. E. Romanenko, A. Y. Leonova, A. V. Poddubikov, Y. E. Tsvetkov, E. V. Sukhova, M. L. Gening, D. V. Yashunsky, N. E. Nifantiev, Russ. Chem. Bull. (Int. Ed.), 2016, 65, 1608 [Izv. Acad. Nauk, Ser. Khim. 2016, 1608].

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. E. Nifantiev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0111—0122, January, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tsvetkov, Y.E., Yashunsky, D.V., Sukhova, E.V. et al. Synthesis of oligosaccharides structurally related to fragments of Streptococcus pneumoniae type 3 capsular polysaccharide. Russ Chem Bull 66, 111–122 (2017). https://doi.org/10.1007/s11172-017-1708-9

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-1708-9

Keywords

Navigation