Structure of the O-polysaccharide of Proteus mirabilis O38 containing 2-acetamidoethyl phosphate and N-linked D-aspartic acid

Anna N. Kondakova, Sof'ya N. Senchenkova, Andrei I. Gremyakov, Alexander S. Shashkov, Yuriy A. Knirel, Rafal Fudala, Wieslaw Kaca

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Abstract

The O-antigen of Proteus mirabilis O38 was found to be unique among bacterial polysaccharides and to have the following structure: AcEtnP|6 → 3)-α-D-GlcpNAc-(1 → 3)-β-D-Quip4N(Ac-D-Asp)-(1 → 6)-α-D-Glcp-(1 → 4)-α-D-GalpA-(1 → where D-Qui4N(Ac-D-Asp) is 4-(N-acetyl-D-aspart-4-ylamino)-4,6-dideoxy-D-glucose and AcEtnP is 2-acetamidoethyl phosphate. Neither of these entities have been hitherto found in natural polysaccharides. Structural studies were performed using 1D and 2D NMR spectroscopy, including experiments run in an H2O/D2O mixture to reveal correlations for NH protons. In addition, dephosphorylation, carboxyl reduction and selective cleavages were applied. Solvolysis of the polysaccharide with anhydrous HF gave an α-D-GlcNAc-(1 → 3)-D-Qui4N(Ac-D-Asp) disaccharide. Solvolysis with trifluoromethanesulfonic (triflic) acid afforded D-GlcNAc6(AcEtnP), thus showing the suitability of this reagent for the preparation of phosphorylated sugar derivatives.

Original languageEnglish
Pages (from-to)2387-2392
Number of pages6
JournalCarbohydrate Research
Volume338
Issue number22
DOIs
StatePublished - 31 Oct 2003

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Keywords

  • Aspartic acid, O-polysaccharide structure
  • Classification
  • Lipopolysaccharide
  • Proteus mirabilis
  • Serogroup

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