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Structure of the O-Polysaccharide of Providencia alcalifaciens O22 Containing D-Glyceramide 2-Phosphate

  1. Olga G. Ovchinnikova1,
  2. Nina A. Kocharova1,
  3. Magdalena Bialczak-Kokot2,
  4. Alexander S. Shashkov1,
  5. Antoni Rozalski2,
  6. Yuriy A. Knirel1

Article first published online: 9 MAY 2012

DOI: 10.1002/ejoc.201200318

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2012, Issue 18, pages 3500–3506, June 2012

Additional Information

How to Cite

Ovchinnikova, O. G., Kocharova, N. A., Bialczak-Kokot, M., Shashkov, A. S., Rozalski, A. and Knirel, Y. A. (2012), Structure of the O-Polysaccharide of Providencia alcalifaciens O22 Containing D-Glyceramide 2-Phosphate. Eur. J. Org. Chem., 2012: 3500–3506. doi: 10.1002/ejoc.201200318

Author Information

  1. 1

    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, Russian Federation, Fax: +7-499-1355328

  2. 2

    Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland

Publication History

  1. Issue published online: 11 JUN 2012
  2. Article first published online: 9 MAY 2012
  3. Manuscript Received: 10 MAR 2012

Funded by

  • Russian Foundation for Basic Research. Grant Number: 08-04-92221
  • Federal Targeted Program for Research and Development in Priority Areas of Russia's Science and Technology Complex. Grant Numbers: 16.552.11.7050, Ministry of Science and Higher Education, Poland, 803

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Keywords:

  • Carbohydrates;
  • Structure elucidation;
  • Lipopolysaccharides;
  • Antigens

Abstract

O-Polysaccharides (O-antigens) are highly diverse glycopolymers present on the cell surface of Gram-negative bacteria, including the human opportunistic pathogen Providencia alcalifaciens. They define serospecificity of strains and are used for the serotyping of bacteria. In this work, a phosphorylated O-polysaccharide was isolated from P. alcalifaciens O22 and analyzed by chemical methods, ESI-MS, and 1H, 13C, and 31P NMR spectroscopy. It was found to contain two unusual components, 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose (D-FucNAc4N) and D-glyceramide 2-phosphate (D-GroAN-2-P), the latter being identified for the first time in bacterial polysaccharides. The structure of the trisaccharide repeating unit of the O-polysaccharide was established to be 4)-(D-GroAN-2-P-3-)--D-GalNAc-(14)--D-Gal-(13)--D-FucNAc4N-(1.

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