Skip to main content
SpringerLink
Log in

Teichuronic and teichulosonic acids of actinomycetes

  • Review
  • Published:
Biochemistry (Moscow) Aims and scope Submit manuscript

Abstract

The subject of the present review is the structural diversity and abundance of cell wall teichuronic and teichulosonic acids of representatives of the order Actinomycetales. Recently found teichulosonic acids are a new class of natural glycopolymers with ald-2-ulosonic acid residues: Kdn (3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid) or di-N-acyl derivatives of Pse (5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic or pseudaminic acid) as the obligatory component. The structures of teichuronic and teichulosonic acids are presented. Data are summarized on the occurrence of the glycopolymers of different nature in the cell wall of the studied actinomycetes. The biological role of the glycopolymers and their possible taxonomic implication are discussed. The comprehensive tables given in the Supplement show 13C NMR spectroscopic data of teichuronic and teichulosonic acids obtained by the authors.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

Gal2,3OMe:

2,3-di-O-methylgalactose

Gal3OMe:

3-O-methylgalactose (madurose)

GlcNAc3NAc:

2,3-diacetami-do-2,3-dideoxyglucose

GlcNAc3NAcA:

2,3-diacetamido-2,3-dideoxyglucuronic acid

Glu:

glutamic acid

Kdn:

3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid

ManNAcA:

2-acetami-do-2-deoxymannuronic acid

ManNAc3NAcA:

2,3-diacetamido-2,3-dideoxymannuronic acid

NP:

neutral polysaccharide

PGP:

poly(glycosyl 1-phosphate)

Pse:

5,7-diamino-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic (pseudaminic) acid

Pyr:

pyruvic acid

Rha:

rhamnose

TA:

teichoic acid

TUA:

teichuronic acid

TULA:

teichulosonic acid

References

  1. Naumova, I. B., and Shashkov, A. S. (1997) Biochemistry (Moscow), 62, 809–840.

    CAS  Google Scholar 

  2. Diaz-Maurino, T., and Perkins, H. R. (1974) J. Gen. Microbiol., 80, 533–539.

    PubMed  CAS  Google Scholar 

  3. Petersen, B. O., Sara, M., Madler, C., Mayer, H. F., Sleytr, U. B., Pabst, M., Puchberger, M., Krause, E., Hofinger, A., Duus, J. Ø., and Kosma, P. (2008) Carbohydr. Res., 343, 1346–1358.

    Article  PubMed  CAS  Google Scholar 

  4. Iwasaki, H., Araki, Y., Kaya, S., and Ito, E. (1989) Eur. J. Biochem., 178, 643–648.

    Article  PubMed  CAS  Google Scholar 

  5. Tul’skaya, E. M., Shashkov, A. S., Senchenkova, S. N., Akimov, V. N., Bueva, O. V., Stupar’, O. S., and Evtushenko, L. I. (2007) Russ. J. Bioorg. Chem., 33, 251–257.

    Article  Google Scholar 

  6. Yoneyama, T., Araki, Y., and Ito, E. (1984) Eur. J. Biochem., 141, 83–89.

    Article  PubMed  CAS  Google Scholar 

  7. Ward, J. B. (1981) Microbiol. Rev., 45, 211–243.

    PubMed  CAS  Google Scholar 

  8. Janczura, E., Perkins, H. E., and Rogers, H. J. (1961) Biochem. J., 80, 82–93.

    PubMed  CAS  Google Scholar 

  9. Shashkov, A. S., Kochanowski, H., Kozlova, Yu. I., Streshinskaya, G. M., Terekhova, L. P., and Galatenko, O. A. (1994) Biochim. Biophys. Acta, 1201, 333–338.

    Article  PubMed  Google Scholar 

  10. Kosmachevskaya, L. N., Streshinskaya, G. M., Evtushenko, L. I., Bueva, O. V., Denisenko, V. A., Naumova, I. B., and Stackebrandt, E. (2002) Eur. J. Biochem., 269, 6020–6025.

    Article  PubMed  Google Scholar 

  11. Shashkov, A. S., Kozlova, Yu. I., Streshinskaya, G. M., Kosmachevskaya, L. N., Bueva, O. V., Evtushenko, L. I., and Naumova, I. B. (2001) Microbiology, 70, 413–421.

    Article  CAS  Google Scholar 

  12. Tul’skaya, E. M., Shashkov, A. S., Evtushenko, L. I., Stomakhin, A. A., Denisenko, V. A., Ivanyuk, V. G., and Naumova, I. B. (2003) in Proc. Int. Commemorative Research and Practice Conf. Dedicated to 75th Anniversary of the Institute of Potato Growing of the National Academy of Sciences of Belarus [in Russian], Pt. II, Belarusskaya Nauka, Minsk, pp. 200–210.

    Google Scholar 

  13. Tul’skaya, E. M., Streshinskaya, G. M., Shashkov, A. S., Bueva, O. V., Baryshnikova, L. M., and Evtushenko, L. I. (2010) in State of the Art and Prospects for the Development of Microbiology and Biotechnology, Proc. VII Int. Conf. [in Russian], Minsk, May 31–June 4, 2010, Belarusskaya Nauka, Minsk, pp. 469–471.

    Google Scholar 

  14. Shashkov, A. S., Tul’skaya, E. M., Streshinskaya, G. M., Senchenkova, S. N., Avtukh, A. N., and Evtushenko, L. I. (2009) Carbohydr. Res., 344, 2255–2262.

    Article  PubMed  CAS  Google Scholar 

  15. Ellwood, D. C., and Tempest, D. W. (1969) Biochem. J., 111, 1–5.

    PubMed  CAS  Google Scholar 

  16. White, P. (1977) J. Gen. Microbiol., 102, 435–439.

    PubMed  CAS  Google Scholar 

  17. Lifley, M. R., Tarelli, E., and Baddiley, J. (1980) Biochem. J., 191, 305–318.

    Google Scholar 

  18. Hughes, R. S., Pavlik, J. G., Rogers, H. J., and Tanner, P. J. (1968) Nature (London), 219, 642–644.

    Article  CAS  Google Scholar 

  19. Seltmann, G., and Holst, O. (2002) The Bacterial Cell Wall, Springer-Verlag, Berlin, pp. 133–144.

    Google Scholar 

  20. Tul’skaya, E. M., Streshinskaya, G. M., Shashkov, A. S., Senchenkova, S. N., Avtukh, A. N., Baryshnikova, L. M., and Evtushenko, L. I. (2011) Carbohydr. Res., 346, doi: 10.1016/j.carres.2011.06.003.

  21. Wright, J., and Heckels, J. E. (1975) Biochem. J., 147, 187–189.

    PubMed  CAS  Google Scholar 

  22. Hase, S., and Matsushima, Y. (1972) J. Biochem. (Tokyo), 72, 1117–1128.

    CAS  Google Scholar 

  23. Din, N. U., and Jeanloz, R. W. (1976) Carbohydr. Res., 47, 245–260.

    Article  PubMed  CAS  Google Scholar 

  24. Johnson, S. D., Lacher, K. P., and Anderson, J. S. (1981) Biochemistry, 20, 4781–4785.

    Article  PubMed  CAS  Google Scholar 

  25. Wu, T. C., and Park, J. T. (1971) J. Bacteriol., 108, 874–884.

    PubMed  CAS  Google Scholar 

  26. Nagaoka, M., Kamisango K., Fujii, H., Uchikawa, K., Sekikawa, I., and Azuma, I. (1985) J. Biochem. (Tokyo), 97, 1669–1678.

    CAS  Google Scholar 

  27. Knirel, Y. A. (2009) in Progress in the Synthesis of Complex Carbohydrate Chains of Plant and Microbial Polysaccharides (Nifantiev, N. E., ed.) Transworld Research Network, Kerala, India, pp. 181–198.

    Google Scholar 

  28. Shashkov, A. S., Streshinskaya, G. M., Kosmachevskaya, L. N., Evtushenko, L. I., and Naumova, I. B. (2000) Mendeleev Commun., 5, 167–168.

    Article  Google Scholar 

  29. Shashkov, A. S., Tul’skaya, E. M., Evtushenko, L. I., Denisenko, V. A., Ivanyuk, V. G., Stomakhin, A. A., Naumova, I. B., and Stackebrandt, E. (2002) Carbohydr. Res., 337, 2255–2261.

    Article  PubMed  CAS  Google Scholar 

  30. Tul’skaya, E. M., Shashkov, A. S., Bueva, O. V., and Evtushenko, L. I. (2007) Microbiology, 72, 39–44.

    Article  Google Scholar 

  31. Potekhina, N. V., Shashkov, A. S., Senchenkova, S. N., Kozlova, Yu. I., Streshinskaya, G. M., Dorofeeva, L. V., Yastrebova, O. V., and Evtushenko, L. I. (2010) State of the Art and Prospects for the Development of Microbiology and Biotechnology, Proc. VII Int. Conf. [in Russian], Minsk, May 31–June 4, 2010, Belarusskaya Nauka, Minsk, pp. 148–150.

  32. Potekhina, N. V., Evtushenko, L. I., Senchenkova, S. N., and Shashkov, A. S. (2007) Russ. J. Bioorg. Chem., 33, 66–72.

    Article  CAS  Google Scholar 

  33. Naumova, I. B., Belozersky, A. N., and Shafikova, F. A. (1962) Dokl. Akad. Nauk SSSR, 143, 730–734.

    CAS  Google Scholar 

  34. Bhavsar, A. P., Erdman, L. K., Schertzer, J. W., and Brown, E. D. (2004) J. Bacteriol., 186, 7865–7873.

    Article  PubMed  CAS  Google Scholar 

  35. Knirel, Yu. A., Shashkov, A. S., Tsvetkov, Yu. E., Jansson, P-.E., and Zahringer, U. (2003) Adv. Carbohydr. Chem. Biochem., 58, 371–417.

    Article  PubMed  CAS  Google Scholar 

  36. Reuhs, B. L., Kim, J. S., and Matthysse, A. G. (1997) J. Bacteriol., 179, 5372–5379.

    PubMed  CAS  Google Scholar 

  37. Inoue, S., and Kitajima, K. (2006) Glycoconj. J., 23, 277–290.

    Article  PubMed  CAS  Google Scholar 

  38. Lewis, A. L., Desa, N., Hansen, E. E., Knirel, Yu. A., Gordon, J. I., Gagneux, P., Nizet, V., and Varki, A. (2009) Proc. Natl. Acad. Sci. USA, 106, 13552–13557.

    Article  PubMed  CAS  Google Scholar 

  39. Tul’skaya, E. M., Shashkov, A. S., Streshinskaya, G. M., Potekhina, N. V., Kozlova, Yu. I., Senchenkova, S. N., and Evtushenko, L. I. (2009) in State-of-the Art Problems of Ecology and Biotechnology of Microorganisms, Proc. All-Russian Symp. [in Russian], MAKS Press, Moscow, p. 182.

    Google Scholar 

  40. Stackebrandt, E. (2006) in The Prokaryotes: A Handbook on the Biology of Bacteria, Vol. 1 (Falkow, S., Rosenberg, E., Schleifer, K.-H., Stackebrandt, E., and Dworkin, M., eds.) 3rd Edn., Springer, Berlin, pp. 29–57.

    Google Scholar 

  41. Kampfer, P. (2010) Int. J. Syst. Evol. Microbiol., 60, 7.

    Article  PubMed  Google Scholar 

  42. Tindall, B. J., Rossello-Mora, R., Busse, H.-J., Ludwig, W., and Kampfer, P. (2010) Int. J. Syst. Evol. Microbiol., 60, 249–266.

    Article  PubMed  CAS  Google Scholar 

  43. Streshinskaya, G. M., Shashkov, A. S., and Naumova, I. B. (1995) Biochemistry (Moscow), 60, 963–970.

    Google Scholar 

  44. Streshinskaya, G. M., Kozlova, Yu. I., Shashkov, A. S., Evtushenko, L. I., and Naumova, I. B. (2003) Microbiology, 72, 455–460.

    Article  CAS  Google Scholar 

  45. Naumova, I. B., Shashkov, A. S., Tul’skaya, E. M., Streshinskaya, G. M., Kozlova, Y. I., Potekhina, N. V., Evtushenko, L. I., and Stackebrandt, E. (2001) FEMS Microbiol. Rev., 25, 269–284.

    Article  PubMed  CAS  Google Scholar 

  46. Potekhina, N. V., Tul’skaya, E. M., Naumova, I. B., Shashkov, A. S., and Evtushenko, L. I. (1993) Eur. J. Biochem., 218, 371–375.

    Article  PubMed  CAS  Google Scholar 

  47. Tul’skaya, E. M., Potekhina, N. V., Naumova, I. B., Shashkov, A. S., and Evtushenko, L. I. (1993) Microbiology, 62, 557–559.

    Google Scholar 

  48. Shashkov, A. S., Tul’skaya, E. M., Evtushenko, L. I., and Naumova, I. B. (1999) Biochemistry (Moscow), 64, 1305–1309.

    CAS  Google Scholar 

  49. Shashkov, A. S., Tul’skaya, E. M., Evtushenko, L. I., Grachev, A. A., and Naumova, I. B. (2000) Biochemistry (Moscow), 65, 509–514.

    CAS  Google Scholar 

  50. Tul’skaya, E. M., Krausova, V. I., Gavrish, E. Yu., Shashkov, A. S., Evtushenko, L. I., and Naumova, I. B. (2003) in Abst. Book of the 1st FEMS Congr. European Microbiologists, Ljubljana, Slovenia, June 29–July 3, p. 357.

  51. Tul’skaya, E. M., Vylegzhanina, E. S., Streshinskaya, G. M., Shashkov, A. S., and Naumova, I. B. (1991) Biochim. Biophys. Acta, 1074, 237–242.

    Article  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biological Faculty, Lomonosov Moscow State University, 119991, Moscow, Russia

    E. M. Tul’skaya, G. M. Streshinskaya, N. V. Potekhina & Yu. I. Kozlova

  2. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991, Moscow, Russia

    A. S. Shashkov & S. N. Senchenkova

  3. All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, pr. Nauki 5, 142290, Pushchino, Moscow Region, Russia

    L. I. Evtushenko

Authors
  1. E. M. Tul’skaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Shashkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. M. Streshinskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. N. Senchenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. V. Potekhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yu. I. Kozlova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. L. I. Evtushenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. M. Tul’skaya.

Additional information

Original Russian Text © E. M. Tul’skaya, A. S. Shashkov, G. M. Streshinskaya, S. N. Senchenkova, N. V. Potekhina, Yu. I. Kozlova, L. I. Evtushenko, 2011, published in Biokhimiya, 2011, Vol. 76, No. 7, pp. 904–913.

This review is based on a presentation made at the 4th Baltic Conference on Microbial Carbohydrates, Hyytiälä Forestry Field Station, Finland, September 19–22, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tul’skaya, E.M., Shashkov, A.S., Streshinskaya, G.M. et al. Teichuronic and teichulosonic acids of actinomycetes. Biochemistry Moscow 76, 736–744 (2011). https://doi.org/10.1134/S0006297911070030

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0006297911070030

Key words

Search

Navigation