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Structure and characterization of the gene cluster of the O-antigen of Escherichia coli O49 containing 4,6-dideoxy-4-[(S-3-hydroxybutanoylamino]-D-glucose

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Abstract

An O-polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of enteropathogenic Escherichia coli O49 and studied by sugar analysis along with one- and two-dimensional 1H- and 13C-NMR spectroscopy. The following structure of the linear tetrasaccharide repeating unit of the O-polysaccharide was established:

$$ \to 2) - \alpha - D - Quip4N(S3HOBut) - (1 \to 4) - \beta - D - GalpNAc - (1 \to 4) - \alpha - L - Rhap - (1 \to 3) - \beta - D - GlcpNAc6Ac - (1 \to , $$

where d-Qui4N(S3HOBut) stands for 4,6-dideoxy-4-[(S)-3-hydroxybutanoylamino]-d-glucose and O-acetylation of GlcNAc is partial (∼30%). To our knowledge, no N-(3-hydroxybutanoyl) derivative of Qui4N has been hitherto found in bacterial polysaccharides. Gene functions of the O-antigen gene cluster of E. coli O49 were assigned by bioinformatics analysis and found to correspond to the O-polysaccharide structure. Two new genes were revealed and suggested to be responsible for synthesis and transfer of the 3-hydroxybutanoyl group.

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Abbreviations

DPS:

O-deacetylated polysaccharide

3HOBut:

3-hydroxybutyric acid

OPS:

O-polysaccharide

Qui4N:

4-amino-4,6-dideoxyglucose

Rha:

rhamnose

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Authors and Affiliations

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

    A. V. Perepelov, S. N. Senchenkova, S. D. Shevelev, A. S. Shashkov & Y. A. Knirel

  2. TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 HongDa Street, TEDA, Tianjin, 300457, P. R. China

    Quan Wang, Lu Feng & Lei Wang

  3. Tianjin Key Laboratory for Microbial Functional Genomics, TEDA College, Nankai University, 23 HongDa Street, TEDA, Tianjin, 300457, P. R. China

    Quan Wang, Lu Feng & Lei Wang

Authors
  1. A. V. Perepelov
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  2. Quan Wang
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  3. S. N. Senchenkova
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  4. S. D. Shevelev
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  5. A. S. Shashkov
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  6. Lu Feng
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  7. Y. A. Knirel
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  8. Lei Wang
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Corresponding author

Correspondence to A. V. Perepelov.

Additional information

Published in Russian in Biokhimiya, 2008, Vol. 73, No. 4, pp. 498–503.

Originally published in Biochemistry (Moscow) On-Line Papers in Press, as Manuscript BM07-237, November 11, 2007.

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Perepelov, A.V., Wang, Q., Senchenkova, S.N. et al. Structure and characterization of the gene cluster of the O-antigen of Escherichia coli O49 containing 4,6-dideoxy-4-[(S-3-hydroxybutanoylamino]-D-glucose. Biochemistry Moscow 73, 406–410 (2008). https://doi.org/10.1134/S0006297908040044

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  • DOI: https://doi.org/10.1134/S0006297908040044

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