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. Toukach^a, Nina A. Kocharova^a, Agnieszka Maszewska^b, Alexander S. Shashkov^a, Yuriy A. Knirel^a and Antoni Rozalski^b

^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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