Elsevier

Carbohydrate Research

Volume 343, Issue 5, 7 April 2008, Pages 977-981
Carbohydrate Research

Note
The O-polysaccharide of Escherichia coli O112ac has the same structure as that of Shigella dysenteriae type 2 but is devoid of O-acetylation: a revision of the S. dysenteriae type 2 O-polysaccharide structure

https://doi.org/10.1016/j.carres.2008.02.002Get rights and content

Abstract

The O-antigen structure of Shigella dysenteriae type 2 was reinvestigated using chemical modifications along with high-resolution 2D 1H and 13C NMR spectroscopy. The O-antigen was found to contain a pyruvic acid acetal, which was overlooked in an early study, and the following revised structure of the pentasaccharide repeating unit was established:

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where ∼70% GlcNAc residues bear an O-acetyl group at position 3. The O-antigen of Escherichia coli O112ac was found to have the same carbohydrate structure but to lack O-acetylation.

Section snippets

Bacterial strains and isolation of lipopolysaccharides

S. dysenteriae type 2 (G1252) was from the Institute of Medical and Veterinary Science, Adelaide, Australia, and E. coli O112ac:K66:H (CCUG 11414) was from the Culture Collection, University of Gothenburg, Sweden. Bacteria were grown to late log phase using a fermentor under constant aeration at 37 °C and pH 7.0 as described for S. dysenteriae type 4;6 bacterial cells were washed and dried. Lipopolysaccharides were isolated from dried bacterial cells by the phenol–water method14 in a yield of

Acknowledgments

This work was supported by the Russian Foundation for Basic Research (Project 05-04-48992), the Russian Science Support Foundation, the Council on Grants at the President of the Russian Federation for Support of Young Russian Scientists (MK-157.2007.4), the Swedish Research Council, the Swedish Agency for Research Cooperation with Developing Countries, Tianjin Municipal Special Fund for Science and Technology Innovation Grant 05FZZDSH00800, the NSFC Key Programs Grants 30530010 and 20536040,

References (16)

  • K.H.M. Jonsson et al.

    Carbohydr. Res.

    (2006)
  • G. Zhao et al.

    Carbohydr. Res.

    (2007)
  • A.V. Perepelov et al.

    Carbohydr. Res.

    (2007)
  • P.-E. Jansson et al.

    Carbohydr. Res.

    (1989)
  • P.J. Garegg et al.

    Carbohydr. Res.

    (1980)
  • A.V. Perepelov et al.

    Carbohydr. Res.

    (2008)
  • E.A. Larsson et al.

    Carbohydr. Res.

    (2004)
  • G.J. Gerwig et al.

    Carbohydr. Res.

    (1979)
There are more references available in the full text version of this article.

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