STRUCTURE OF THE O-POLYSACCHARIDE OF PROVIDENCIA ALCALIFACIENS O8 CONTAINING (2S,4R)-2,4-DIHYDROXYPENTANOIC ACID, A NEW NON-SUGAR COMPONENT OF BACTERIAL GLYCANS

Filip V. Toukacha, Nina A. Kocharovaa, Agnieszka Maszewskab, Alexander S. Shashkova, Yuriy A. Knirela and Antoni Rozalskib

aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
bDepartment of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Poland

KEYWORDS: Providencia alcalifaciens, Lipopolysaccharide, O-Antigen, Bacterial polysaccharide structure, 2,4-Dihydroxypentanoic acid

Carbohydrate Research, 2008, v. 343, pp. 2706-2711

DOI: 10.1016/j.carres.2008.08.011


A glycerol teichoic acid-like O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O8 and studied by chemical methods and NMR spectroscopy, including 2D ROESY, {1H,13C} HSQC, and HMQC-TOCSY experiments. It was found that the compound contains a new component of bacterial lipopolysaccharides: ether-linked (2S,4R)-2,4-dihydroxypentanoic acid (Dhpa), which was identified by NMR spectroscopy. The following structure of the repeating unit of the polysaccharide was established:

                           Dhpa(2
                                |
                                4
->3)-b-D-FucpNAc4N-(1->3)-b-D-GlcpNAc-(1->3)-b-D-Galp-(1->2)-D-Gro-3-P-(O->

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