Identification and Role of a 6‐Deoxy‐4‐Keto‐Hexosamine in the Lipopolysaccharide Outer Core of Yersinia enterocolitica Serotype O:3 |
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| Authors: | Elise Pinta Katarzyna A Duda Dr Anna Hanuszkiewicz Dr Zbigniew Kaczyński Dr Buko Lindner Dr Wayne L Miller Dr Heidi Hyytiäinen Dr Christian Vogel Dr Sabine Borowski Katarzyna Kasperkiewicz Dr Joseph S Lam Dr Joanna Radziejewska‐Lebrecht Dr Mikael Skurnik Dr Otto Holst Dr |
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| Institution: | 1. Infection Biology Research Program, Haartman Institute, Department of Bacteriology and Immunology, P.O.Box 21 (Haartmaninkatu 3), 00014 University of Helsinki (Finland), Fax: (+358)?9‐191 26382;2. Department of Medical Biochemistry and Genetics, University of Turku, 20520 Turku (Finland);3. Division of Structural Biochemistry, Research Center Borstel, Leibniz‐Center for Medicine and Biosciences, 23845 Borstel (Germany);4. Department of Microbiology, University of Silesia, 40‐032 Katowice (Poland);5. Department of Chemistry, University of Gdańsk, 80‐952 Gdańsk (Poland);6. Division of Immunochemistry, Research Center Borstel, Leibniz‐Center for Medicine and Biosciences, 23845 Borstel (Germany);7. Department of Molecular and Cellular Biology, University of Guelph, Ontario N1G 2W1 (Canada);8. Institute of Chemistry, University of Rostock, 18059 Rostock (Germany);9. Helsinki University Central Hospital Laboratory Diagnostics, 00029 Helsinki (Finland) |
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| Abstract: | The outer core (OC) region of Yersinia enterocolitica serotype O:3 lipopolysaccharide is a hexasaccharide essential for the integrity of the outer membrane. It is involved in resistance against cationic antimicrobial peptides and plays a role in virulence during early phases of infection. We show here that the proximal residue of the OC hexasaccharide is a rarely encountered 4‐keto‐hexosamine, 2‐acetamido‐2,6‐dideoxy‐D ‐xylo‐hex‐4‐ulopyranose (Sugp) and that WbcP is a UDP‐GlcNAc‐4,6‐dehydratase enzyme responsible for the biosynthesis of the nucleotide‐activated form of this rare sugar converting UDP‐2‐acetamido‐2‐deoxy‐D ‐glucopyranose (UDP‐D ‐GlcpNAc) to UDP‐2‐acetamido‐2,6‐dideoxy‐D ‐xylo‐hex‐4‐ulopyranose (UDP‐ Sugp). In an aqueous environment, the 4‐keto group of this sugar was present in the 4‐dihydroxy form, due to hydration. Furthermore, evidence is provided that the axial 4‐hydroxy group of this dihydroxy function was crucial for the biological role of the OC, that is, in the bacteriophage and enterocoliticin receptor structure and in the epitope of a monoclonal antibody. |
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| Keywords: | biosynthesis hexosamines lipopolysaccharides receptors structural biology |
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