Skip to main content

Antigenic polysaccharides of bacteria: 40. The structures of O-specific polysaccharides from Shigella dysenteriae types 3 and 9 and S. boydii type 4 revised by NMR spectroscopy

Abstract

The reported structures of O-specific polysaccharides from three type strains of Shigella bacteria were corrected by modern NMR techniques. The revisions concerned the configuration of the O-glycoside linkage (S. dysenteriae type 3, structure 1), the positions of monosaccharide residue glycosylation and acetalation by pyruvic acid (S. dysenteriae type 9, structure 2), and the attachment position of the side monosaccharide chain (S. boydii type 4, structure 3).

This is a preview of subscription content, access via your institution.

Abbreviations

D-GlcRLac:

glucolactic acid

HMBC:

Heteronuclear Multiple Bond Correlation

HSQC:

Heteronuclear Single Quantum Correlation

Lac:

lactic acid residue bonded via ether link

LPS:

lipopolysaccharide

NAc:

N-acetyl group

OPS:

O-specific polysaccharide chains

Pyr:

pyruvic acid acetal

ROESY:

nuclear Overhauser Effect Spectroscopy in the Rotating frame

Rha:

rhamnose

RLac:

D-glucose, ether linked to (R)-lactic acid

TOCSY:

Total Correlation Spectroscopy

References

  1. Paramonov, N.A., Shashkov, A.S., Knirel’, Yu.A., Soldatkina, M.A., and Zakharova, I.Ya., Bioorg. Khim., 1994, vol. 20, pp. 984–993.

    CAS  PubMed  Google Scholar 

  2. Duus, J.O., Gotfredsen, C.H., and Bock, K., Chem. Rev., 2000, vol. 100, pp. 4589–4614.

    CAS  Article  PubMed  Google Scholar 

  3. Dmitriev, B.A., L’vov, V.L., Gofman, I.L., and Kochetkov, N.K., Izv. Akad. Nauk SSSR, Ser. Khim., 1977, no. 10, pp. 1613–1619.

  4. Dmitriev, B.A., Backinowsky, L.V., Lvov, V.L., Kochetkov, N.K., and Hofman, I.L., Eur. J. Biochem., 1975, vol. 50, pp. 539–547.

    CAS  Article  PubMed  Google Scholar 

  5. Dmitriev, B.A., Knirel, Y.A., and Kochetkov, N.K., Carbohydr. Res., 1975, vol. 40, pp. 365–372.

    CAS  Article  PubMed  Google Scholar 

  6. Dmitriev, B.A., Lvov, V.L., and Kochetkov, N.K., Carbohydr. Res., 1977, vol. 56, pp. 207–209.

    CAS  Article  PubMed  Google Scholar 

  7. Linnerborg, M., Weintraub, A., and Widmalm, G., Eur. J. Biochem., 1999, vol. 266, pp. 460–466.

    CAS  Article  PubMed  Google Scholar 

  8. Senchenkova, S.N., Feng, L., Wang, Q., Perepelov, A.V., Qin, D., Shevelev, S.D., Wang, M., Shashkov, A.S., Knirel, Y.A., and Wang, L., Biochem. Biophys. Res. Commun., 2006, vol. 349, pp. 289–295.

    CAS  Article  PubMed  Google Scholar 

  9. Dmitriev, B.A., Lvov, V.L., Kochetkov, N.K., Jann, B., and Jann, K., Eur. J. Biochem., 1976, vol. 64, pp. 491–498.

    CAS  Article  PubMed  Google Scholar 

  10. Jonsson, K.H., Weintraub, A., and Widmalm, G., Carbohydr. Res., 2006, vol. 341, pp. 2986–2989.

    CAS  Article  PubMed  Google Scholar 

  11. Dmitriev, B.A., Knirel’, Yu.A., Vinogradov, E.V., Kochetkov, N.K., and Gofman, I.L., Bioorg. Khim., 1978, vol. 4, pp. 40–46.

    CAS  Google Scholar 

  12. Lipkind, G.M., Shashkov, A.S., Knirel, Y.A., Vinogradov, E.V., and Kochetkov, N.K., Carbohydr. Res., 1988, vol. 175, pp. 59–75.

    CAS  Article  PubMed  Google Scholar 

  13. Garegg, P.J., Jansson, P.-E., Lindberg, B., Lindh, F., Lönngren, J., Kvarnström, I., and Nimmich, W., Carbohydr. Res., 1980, vol. 78, pp. 127–132.

    CAS  Article  Google Scholar 

  14. Shashkov, A.S., Senchenkova, S.N., Vinogradov, E.V., Zatonsky, G.V., Knirel, Y.A., Literacka, E., and Kaca, W., Carbohydr. Res., 2000, vol. 329, pp. 453–457.

    CAS  Article  PubMed  Google Scholar 

  15. De Bruin, A.H., Parolis, H., and Parolis, L.A.S., Carbohydr. Res., 1992, vol. 233, pp. 195–204.

    Article  PubMed  Google Scholar 

  16. L’vov, V.L., Tokhtamysheva, N.V., Dmitriev, B.A., Kochetkov, N.K., and Gofman, I.L., Bioorg. Khim., 1980, vol. 6, pp. 1842–1850.

    Google Scholar 

  17. Robbins, P.W. and Uchida, T., Biochemistry, 1962, vol. 1, pp. 323–335.

    CAS  Article  PubMed  Google Scholar 

  18. Westphal, O. and Jann, K., Methods Carbohydr. Chem., 1965, vol. 5, pp. 83–91.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. V. Perepelov.

Additional information

Original Russian Text © A.V. Perepelov, S.N. Senchenkova, A.S. Shashkov, B. Lu, L. Feng, L. Wang, Yu.A. Knirel, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 1, pp. 121–128.

For communication 39, see [1].

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Perepelov, A.V., Senchenkova, S.N., Shashkov, A.S. et al. Antigenic polysaccharides of bacteria: 40. The structures of O-specific polysaccharides from Shigella dysenteriae types 3 and 9 and S. boydii type 4 revised by NMR spectroscopy. Russ J Bioorg Chem 34, 110–117 (2008). https://doi.org/10.1134/S1068162008010159

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162008010159

Key words

  • NMR spectroscopy
  • O-specific polysaccharide
  • Shigella dysenteriae
  • S. boydii
  • structure