Skip to main content
SpringerLink
Log in

D-Rhamnan and Pyruvate-Containing Teichuronic Acid from the Cell Wall of Rathayibacter sp. VKM Ac-2759

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

Abstract

Rathayibacter sp. VKM Ac-2759 (family Microbacteriaceae, class Actinobacteria) contains two glycopolymers in the cell wall. The main chain of rhamnan, glycopolymer 1, is built from the repeating tetrasaccharide units carrying terminal arabinofuranose residues at the non-reducing end, →3)-α-[α-D-Araf-(1→2)]-D-Rhap-(1→2)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→. Similar to other described Rathayibacter species, rhamnose in the neutral glycopolymer of the VKM Ac-2759 strain is present in the D-configuration. Acetalated with pyruvic acid teichuronic acid, glycopolymer 2, is composed of the repeating tetrasaccharide units, →4)-β-D-GlcpA-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→3)-β-[4,6-S-Pyr]-D-Manp-(1→. Glycopolymers 1 and 2 were identified in prokaryotic microorganisms for the first time and their structures were established by chemical analysis and NMR spectroscopy. The obtained data can be used in taxonomic research, as well as for elucidating the mechanisms of plant colonization and infection by bacteria of the Rathayibacter genus.

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

Fig. 1.
Fig. 2.
Table
Scheme
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

Abbreviations

δC and δH :

chemical shifts of 13C and 1H atoms, respectively

COSY:

correlation spectroscopy

HMBC:

heteronuclear multiple bond correlation between 1H and 13C

HSQC:

heteronuclear single quantum correlation

J :

coupling constant

ROESY:

rotating-frame nuclear Overhauser enhancement spectroscopy

TOCSY:

total correlation spectroscopy

References

  1. Zgurskaya, H. I., Evtushenko, L. I., Akimov, V. N., and Kalakoutskii, L. V. (1993) Rathayibacter gen, nov., including the species Rathayibacter rathayi comb. nov., Rathayibacter tritici comb. nov., Rathayibacter iranicus comb., nov., and six strains from annual grasses, Int. J. Sys. Bacteriol., 43, 143-149, https://doi.org/10.1099/00207713-43-1-143.

    Article  Google Scholar 

  2. Evtushenko, L. I., and Dorofeeva, L. V. (2012) Genus XXII. Rathayibacter Zgurskaya, Evtushenko, Akimov and Kalakoutskii 1993, 147VP in Bergey’s manual of systematic bacteriology (Goodfellow, M., Kämpfer, P., Busse, H.-J., Trujillo, M. E., Suzuki, K.-I., Ludwig, W., Whitman, W. B., eds.) 2nd Edn., Vol. 5, Springer, New York, Dordrecht, Heidelberg, London, pp. 953-964.

  3. Murray, T. D., Schroeder, B. K., Schneider, W. L., Luster, D. G., Sechler, A., et al. (2017) Rathayibacter toxicus, other Rathayibacter species inducing bacterial head blight of grasses, and the potential for livestock poisonings, Phytopathology, 107, 804-815, https://doi.org/10.1094/PHYTO-02-17-0047-RVW.

    Article  PubMed  Google Scholar 

  4. Murray, T. D., Barrantes-Infante, B., and Schroeder, B. K. (2020) First report of bacterial head blight of Pseudoroegneria spicata subsp. spicata caused by Rathayibacter agropyri in Idaho, Plant Disease, 104, 1534, https://doi.org/10.1094/PDIS-06-19-1233-PDN.

    Article  Google Scholar 

  5. Starodumova, I. P. (2018) Development of the classification system for actinobacteria of the genus Rathayibacter, candidate dissertation (in Russian), Moscow.

  6. Shashkov, A. S., Tul’skaya, E. M., Dmitrenok, A. S., Streshinskaya, G. M., Potekhina, N. V., et al. (2018) Rhamnose-containing cell wall glycopolymers from Rathayibacter toxicus VKM Ac-1600 and “Rathayibacter tanaceti” VKM Ac-2596, Biochemistry (Moscow), 83, 717-726, https://doi.org/10.1134/S0006297918060093.

    Article  CAS  Google Scholar 

  7. Dmitrenok, A. S., Shashkov, A. S., Streshinskaya, G. M., Tul’skaya, E. M., Potekhina, N. V., et al. (2019) New rhamnose-contaning glycopolymers from Rathayibacter iranicus VKM Ac-1602T cell wall, Carbohydr. Res., 482, 107728, https://doi.org/10.1016/j.carres.2019.06.007.

    Article  CAS  PubMed  Google Scholar 

  8. Shashkov, A. S., Tul’skaya, E. M., Streshinskaya, G. M., Dmitrenok, A. S., Potekhina, N. V., et al. (2020) Rhamnomannans and teichuronic acid from the cell wall of Rathayibacter tritici VKM Ac-1603T, Biochemistry (Moscow), 85, 369-377, https://doi.org/10.1134/S0006297920030128.

    Article  CAS  Google Scholar 

  9. Shashkov, A. S., Potekhina, N. V., Dmitrenok, A. S., Tul’skaya, E. M., Senchenkova, S. N., et al. (2021) D-Rhamnan and teichuronic acid from the cell wall of Rathayibacter caricis VKM Ac-1799T, Carbohydr. Res., 499, 108233.

    Article  CAS  Google Scholar 

  10. Tarlachkov, S. V., Starodumova, I. P., Dorofeeva, L. V., Prisyazhnaya, N. V., Leyn, S. A., et al. (2020) Complete and draft genome sequences of 12 plant-associated Rathayibacter strains of known and putative new species, Microbiol. Resour. Announc., 9, e00316-20, https://doi.org/10.1128/MRA.00316-20.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Potekhina, N. V., Streshinskaya, G. M., Tul’skaya, E. M., and Shashkov, A. S. (2011) Cell wall teichoic acids in the taxonomy and characterization of Gram-positive bacteria, in Methods in Microbiology (Rainey, F. A., and Oren, A., eds.) Vol. 38, Chap. 6, Academic Press, Elsevier, pp. 132-164, https://doi.org/10.1016/B978-0-12-387730-7.00020-6.

  12. Leontein, K., Lindberg, B., and Lönngren, J. (1978) Assignment of absolute configuration of sugars by GLC of their acetylated glycosides formed from chiral alcohols, Carbohyd. Res., 62, 359-362, https://doi.org/10.1016/S0008-6215(00)80882-4.

    Article  CAS  Google Scholar 

  13. Gerwig, G. J., Kamerling, I. P., and Vliegenthart, J. F. G. (1979) Determination of the absolute configuration of monosaccharides in complex carbohydrates by capillary GLC, Carbohydr. Res., 77, 1-7, https://doi.org/10.1016/s0008-6215(00)83788-x.

    Article  CAS  Google Scholar 

  14. Shashkov, A. S., Lipkind, G. M., Knirel, Y. A., and Kochetkov, N. K. (1988) Stereometrical factors determining the effects of glycosylation on the 13C chemical shifts in carbohydrates, Magn. Reson. Chem., 26, 735-747, https://doi.org/10.1002/mrc.1260260904.

    Article  CAS  Google Scholar 

  15. Garegg, P. J., Jansson, P.-E., Lindberg, B., Lindh, F., Lönngren, J. (1980) Configuration of the acetal carbon atom of pyruvic acid acetals in some bacterial polysaccharides, Carbohydr. Res., 79, 127-132, https://doi.org/10.1016/S0008-6215(00)83666-6.

    Article  Google Scholar 

  16. Mistou, M.-Y., Sutcliffe, I. C., and van Sorge, N. M. (2016) Bacterial glycobiology: rhamnose-containing cell wall polysaccharides in Gram-positive bacteria, FEMS Microbiol. Rev., 40, 464-479, https://doi.org/10.1093/femsre/fuw006.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Knirel, Y. A. (2010) O-Specific polysaccharides of Gram-negative bacteria, in Microbial Glycobiology (Holst, O., Brennan, P. J., von Itzstein, M., eds.) Vol. 4, Academic Press, pp. 57-73, https://doi.org/10.1016/B978-0-12-374546-0.X0001-6.

  18. Schaffer, C., Muller, N., Christian, R., Graninger, M., Wugeditsch, T., et al. (1999) Complete glycan structure of the S-layer glycoprotein of Aneurinibacillus thermoaerophilus GS4-97, Glycobiology, 9, 407-414, https://doi.org/10.1093/glycob/9.4.407.

    Article  CAS  PubMed  Google Scholar 

  19. Kaczynski, Z., Karapetyan, G., Evidente, A., Iacobellis, N. S., and Holst, O. (2006) The structure of a putative exopolysaccharide of Burkholderia gladioli pv. agaricicola, Carbohydr. Res., 341, 285-288, https://doi.org/10.1016/j.carres.2005.10.020.

    Article  CAS  PubMed  Google Scholar 

  20. Cimmino, A., Marchi, G., Hanuszkiewicz, A., Surico, G., Evidente, A., and Holst, O. (2008) The structure of the O-specific polysaccharide of the lipopolysaccharide from Pantoea agglomerans strain FL1, Carbohydr. Res., 343, 392-396, https://doi.org/10.1016/j.carres.2007.10.023.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Galina Matveevna Streshinskaya for help in our work and discussion of results.

Funding

This work was financially supported by the program CITIS: AAAA-A16-116021660068-1 of the Department of Microbiology of the Lomonosov Moscow State University for 2016-2022.

Author information

Authors and Affiliations

  1. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119334, Moscow, Russia

    Alexander S. Shashkov, Andrey S. Dmitrenok & Sofia N. Senchenkova

  2. Faculty of Biology, Lomonosov Moscow State University, 119234, Moscow, Russia

    Elena M. Tul’skaya, Natalia V. Potekhina & Vlad A. Zaychikov

  3. All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Pushchino Scientific Center for Biological Research, Russian Academy of Sciences, 142290, Pushchino, Moscow Region, Russia

    Lubov V. Dorofeeva & Lyudmila I. Evtushenko

Authors
  1. Alexander S. Shashkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elena M. Tul’skaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Natalia V. Potekhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Andrey S. Dmitrenok
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sofia N. Senchenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Vlad A. Zaychikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Lubov V. Dorofeeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Lyudmila I. Evtushenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Elena M. Tul’skaya.

Ethics declarations

The authors declare no conflict of interest in financial or any other sphere. This article does not contain any studies with human participants or animals performed by any of the authors.

Additional information

Published in Russian in Biokhimiya, 2021, Vol. 86, No. 4, pp. 595-606, https://doi.org/10.31857/S0320972521040114.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shashkov, A.S., Tul’skaya, E.M., Potekhina, N.V. et al. D-Rhamnan and Pyruvate-Containing Teichuronic Acid from the Cell Wall of Rathayibacter sp. VKM Ac-2759. Biochemistry Moscow 86, 506–516 (2021). https://doi.org/10.1134/S0006297921040118

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0006297921040118

Keywords

Search

Navigation