Structure of the O-polysaccharide of Proteus mirabilis O38 containing 2-acetamidoethyl phosphate and N-linked D-aspartic acid |
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Authors: | Kondakova Anna N Senchenkova Sof'ya N Gremyakov Andrei I Shashkov Alexander S Knirel Yuriy A Fudala Rafal Kaca Wieslaw |
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Institution: | ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, Moscow 119991, Russia. |
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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: carbohydrate structure in text] 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 alpha-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. |
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Keywords: | Proteus mirabilis Lipopolysaccharide Aspartic acid O-polysaccharide structure Serogroup Classification |
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