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Structure of the O-antigen and characterization of the O-antigen gene cluster of Escherichia coli O108 containing 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-d-galacto-non-2-ulosonic (8-epilegionaminic) acid

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Abstract

On mild acid degradation of the lipopolysaccharide of Escherichia coli O108, the O-polysaccharide was isolated and studied by sugar analysis and one- and two-dimensional 1H- and 13C-NMR spectroscopy. The polysaccharide was found to contain an unusual higher sugar, 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-d-galacto-non-2-ulosonic acid (di-N-acetyl-8-epilegionaminic acid, 8eLeg5Ac7Ac). The following structure of the tetrasaccharide repeating unit of the polysac-charide was established: →4)-α-8eLegp5Ac7Ac-(2→6)-α-D-Galp-(1→3)-α-L-FucpNAc-(1→3)-α-D-GlcpNAc-(1→. Functions of the E. coli O108 antigen biosynthetic genes, including seven putative genes for synthesis of 8eLeg5Ac7Ac, were assigned by sequencing the O-antigen gene cluster along with comparison with gene databases and known biosynthetic pathways for related nonulosonic acids.

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Abbreviations

COSY:

correlation spectroscopy

HSQC:

heteronuclear single-quantum coherence

OPS:

O-polysaccharide (O-antigen)

ROESY:

rotating-frame nuclear Overhauser effect spectroscopy

TOCSY:

total correlation spectroscopy

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Authors and Affiliations

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

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

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

    Bin Liu, 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

    Bin Liu, Lu Feng & Lei Wang

Authors
  1. A. V. Perepelov
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  2. Bin Liu
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  3. S. N. Senchenkova
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  4. A. S. Shashkov
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  5. S. D. Shevelev
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  6. Lu Feng
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  7. Lei Wang
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  8. Y. A. Knirel
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Correspondence to A. V. Perepelov.

Additional information

Published in Russian in Biokhimiya, 2010, Vol. 75, No. 1, pp. 27–33.

Originally published in Biochemistry (Moscow) On-Line Papers in Press, as Manuscript BM09-096, December 13, 2009.

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Perepelov, A.V., Liu, B., Senchenkova, S.N. et al. Structure of the O-antigen and characterization of the O-antigen gene cluster of Escherichia coli O108 containing 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-d-galacto-non-2-ulosonic (8-epilegionaminic) acid. Biochemistry Moscow 75, 19–24 (2010). https://doi.org/10.1134/S0006297910010037

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  • DOI: https://doi.org/10.1134/S0006297910010037

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