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  • Title: Lipopolysaccharides possessing two L-glycero-D-manno-heptopyranosyl-alpha -(1-->5)-3-deoxy-D-manno-oct-2-ulopyranosonic acid moieties in the core region. The structure of the core region of the lipopolysaccharides from Burkholderia caryophylli.
    Author: Molinaro A, De Castro C, Lanzetta R, Evidente A, Parrilli M, Holst O.
    Journal: J Biol Chem; 2002 Mar 22; 277(12):10058-63. PubMed ID: 11790781.
    Abstract:
    The carbohydrate backbone of the core-lipid A region was characterized from the lipopolysaccharides (LPSs) of the plant-pathogenic bacterium Burkholderia caryophylli. For the first time, the presence of two moieties of l-glycero-d-manno-heptopyranosyl-alpha-(1-->5)-3-deoxy-d-manno-oct-2-ulopyranosonic acid was identified in a core region, which is of particular interest with regard to the biosynthesis of this and of LPSs in general. The LPSs of B. caryophylli were degraded by mild hydrazinolysis (de-O-acylation), treatment with 48% aqueous HF at 4 degrees C (cleavage of phosphate groups and destruction of the O-specific polysaccharides), reduction with NaBH4, and de-N-acylation utilizing hot KOH. The major oligosaccharide representing the carbohydrate backbone of the core region and lipid A was isolated by high-performance anion-exchange chromatography. Its analysis employing compositional and methylation analyses, matrix-assisted laser desorption/ionization mass spectrometry, and (1)H and (13)C NMR spectroscopy applying various one-dimensional and two-dimensional experiments identified the following structure. Structure I All sugars are pyranoses and alpha-linked, if not stated otherwise. Hep is l-glycero-d-manno-heptose, Kdo is 3-deoxy-d-manno-oct-2-ulosonic acid.
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