title: Identification and role of a 6-deoxy-4-keto-hexosamine in the lipopolysaccharide outer core of Yersinia enterocolitica serotype O:3.
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.
authors.affiliation: Infection Biology Research Program, Haartman Institute, Department of Bacteriology and Immunology, P.O.Box 21 (Haartmaninkatu 3), 00014 University of Helsinki, Finland.
authors.forename: Elise
authors.initials: E
authors.lastname: Pinta
authors.forename: Katarzyna A
authors.initials: KA
authors.lastname: Duda
authors.forename: Anna
authors.initials: A
authors.lastname: Hanuszkiewicz
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Kaczyński
authors.forename: Buko
authors.initials: B
authors.lastname: Lindner
authors.forename: Wayne L
authors.initials: WL
authors.lastname: Miller
authors.forename: Heidi
authors.initials: H
authors.lastname: Hyytiäinen
authors.forename: Christian
authors.initials: C
authors.lastname: Vogel
authors.forename: Sabine
authors.initials: S
authors.lastname: Borowski
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Kasperkiewicz
authors.forename: Joseph S
authors.initials: JS
authors.lastname: Lam
authors.forename: Joanna
authors.initials: J
authors.lastname: Radziejewska-Lebrecht
authors.forename: Mikael
authors.initials: M
authors.lastname: Skurnik
authors.forename: Otto
authors.initials: O
authors.lastname: Holst
mesh_terms: D001426:Bacterial Proteins / Q000378:metabolism; D019075:Electrophoresis, Capillary; D006595:Hexosamines / Q000096:biosynthesis / Q000737:chemistry / Q000502:physiology*; D008070:Lipopolysaccharides / Q000737:chemistry*; D012703:Serotyping; D015008:Yersinia enterocolitica / Q000737:chemistry*
chemical_list: D001426:Bacterial Proteins; D006595:Hexosamines; D008070:Lipopolysaccharides