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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

The structure was elucidated in this paper
NCBI PubMed ID: 10091604
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: sml

fz-borstel.de
Institutions: Department of Chemistry, Carlsberg Laboratory, Valby, Denmark, Division of Biochemical and Medical Microbiology, Division of Biophysics, Research Center Borstel, Borstel, Germany.

The chemical structure of the phosphorylated lipopolysaccharide (LPS) of Escherichia coli J-5 was investigated because it is of biomedical interest in the context of septic shock, a syndrome often encountered in nosocomial infections with gram-negative pathogens. The successive de-O-acylation and de-N-acylation of J-5 LPS yielded phosphorylated oligosaccharides which represent the complete carbohydrate backbone. Five compounds were separated by high-performance anion-exchange chromatography and analysed by one-dimensional and two-dimensional homonuclear and heteronuclear 1H NMR, 13C NMR and 31P-NMR spectroscopy. The main product was a nonasaccharide of the structure α-D-Glcp-(1→3)-[α-D-GlcpN-(1→7)-α-L,D-Hepp-(1→7)]-α-L,D-Hepp-(1→3)-α -L,D-Hepp-4P-(1→5)-[α-Kdop-(2→4)]-α-Kdop-(2→6)-β-D-GlcpN-4P-(1→6)-α-D-GlcN-1P wherein all sugars are present as D-pyranoses. Hep and Kdo represent L-glycero-D-manno-heptose and 3-deoxy-D-manno-oct-2-ulosonic acid, respectively. In addition, two octasaccharides and two heptasaccharides were isolated that were partial structures of the nonasaccharide. In one octasaccharide the terminal α-D-GlcpN was missing and an additional phosphate group linked to O4 of the branched heptose was present, whereas in the other octasaccharide the side-chain Kdo was missing. In both heptasaccharides the side-chain α-D-GlcpN-(1→7)-L-α-D-Hepp-disaccharide was absent; they differed in their phosphate substitution. Whereas both heptasaccharides contained two phosphates in the lipid-A backbone (β-1,6-linked GlcpN-disaccharide at the reducing end) and one phosphate group at O4 of the first heptose, only one of them was additionally substituted with phosphate at O4 of the second heptose.

Lipopolysaccharide, biosynthesis, oligosaccharide, structural, analysis, Escherichia, Escherichia coli, antibodies, Oligosaccharides, structural analysis, phosphorylated, phosphorylated oligosaccharide, isolation, phosphorylation, MALDI-TOF MS, E-coli J-5, Escherichia coli J5, RcP(+)-chemotype

Structure type: oligomer
Location inside paper: Fig. 2, nonasaccharide I
Trivial name: core-lipid A backbone
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_130670,IEDB_135394,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192

Methods: NMR-2D, NMR, HPAEC, MALDI-TOF MS
3D data: molecular modeling, conformation data

Related record ID(s): 3801, 3802, 3803, 3804
NCBI Taxonomy refs (TaxIDs): 562
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There are 2 chemically distinct structures. Please, select:

N[C@H]1[C@@H](OP(=O)(O)O)O[C@H](CO[C@@H]2O[C@H](CO[C@]3(C(=O)O)C[C@@H](O[C@]4(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O4)[C@@H](O[C@H]4O[C@H]([C@@H](O)CO)[C@@H](OP(=O)(O)O)[C@H](O[C@H]5O[C@H]([C@@H](O)CO[C@H]6O[C@H]([C@@H](O)CO[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7N)[C@@H](O)[C@H](O)[C@@H]6O)[C@@H](O)[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H]5O)[C@@H]4O)[C@@H]([C@H](O)CO)O3)[C@@H](OP(=O)(O)O)[C@H](O)[C@H]2N)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize