title: Investigation of the chemical structure and biological activity of oligosaccharides isolated from rough-type Xanthomonas campestris pv. campestris B100 lipopolysaccharide.
abstract: The rough-type lipopolysaccharide (LPS) of the phytopathogenic bacterium Xanthomonas campestris pv. campestris B 100 was isolated utilizing the hot phenol-water method and successively de-acylated by treatment with hydrazine and hot potassium hydroxide. Four compounds were separated by preparative high-performance anion-exchange chromatography and studied by sugar analysis and by 1D and 2D homonuclear and heteronuclear (1)H-, (13)C- and (31)P-NMR spectroscopy as well as ESI FT-MS. The two main products were a heptasaccharide and a pentasaccharide of the structures alpha-D-Manp-(1-->3)-alpha-D-Man p-(1-->4)-beta-D-Glcp-(1-->4)-alpha-D-Manp-3P -(1-->5)-alpha-Kdo-(2-->6)-beta-D-GlcpN-4P-(1-->6)-alpha-D-Glc pN-1P (1) and beta-D-Glcp-(1-->4)-alpha-D-Man p-3P-(1-->5)-alpha-Kdo-(2-->6)-beta-D-GlcpN-4 P-(1-->6)-alpha-D-GlcpN-1P (2), respectively. The products in smaller amounts were a heptasaccharide and pentasaccharide possessing the above structures plus a phosphate group at C-4 of the Kdo residue (compounds 3 and 4). Both, heptasaccharide 1 and pentasaccharide 2 were able to induce an oxidative burst in cell cultures of the non-host plant tobacco.
authors.affiliation: Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Kaczyński
authors.forename: Sebastian
authors.initials: S
authors.lastname: Braun
authors.forename: Buko
authors.initials: B
authors.lastname: Lindner
authors.forename: Karsten
authors.initials: K
authors.lastname: Niehaus
authors.forename: Otto
authors.initials: O
authors.lastname: Holst
mesh_terms: D002240:Carbohydrate Sequence; D002460:Cell Line; D002852:Chromatography, Ion Exchange; D008070:Lipopolysaccharides / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry* / Q000378:metabolism*; D016897:Respiratory Burst; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014026:Nicotiana / Q000378:metabolism / Q000382:microbiology; D016959:Xanthomonas campestris / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D008070:Lipopolysaccharides; D009844:Oligosaccharides