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Biochemistry (Moscow)

, 73:406 | Cite as

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

  • A. V. PerepelovEmail author
  • Quan Wang
  • S. N. Senchenkova
  • S. D. Shevelev
  • A. S. Shashkov
  • Lu Feng
  • Y. A. Knirel
  • Lei Wang
Article

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.

Key words

Escherichia coli lipopolysaccharide bacterial polysaccharide structure 3-hydroxybutyrate 4-amino-4,6-dideoxy-d-glucose O-antigen gene cluster 

Abbreviations

DPS

O-deacetylated polysaccharide

3HOBut

3-hydroxybutyric acid

OPS

O-polysaccharide

Qui4N

4-amino-4,6-dideoxyglucose

Rha

rhamnose

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Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • A. V. Perepelov
    • 1
    Email author
  • Quan Wang
    • 2
    • 3
  • S. N. Senchenkova
    • 1
  • S. D. Shevelev
    • 1
  • A. S. Shashkov
    • 1
  • Lu Feng
    • 2
    • 3
  • Y. A. Knirel
    • 1
  • Lei Wang
    • 2
    • 3
  1. 1.Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia
  2. 2.TEDA School of Biological Sciences and BiotechnologyNankai UniversityTianjinP. R. China
  3. 3.Tianjin Key Laboratory for Microbial Functional Genomics, TEDA CollegeNankai UniversityTianjinP. R. China

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