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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter coli [ICD11: XN0BA

]

The structure was elucidated in this paper
NCBI PubMed ID: 8454598
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Chemistry, York University, Toronto, Ontario, M3J lP3, Canada, Carbohydrate Research Center, Department of Molecular Biology and Medical Genetics, Department of Microbiology, University of Toronto, Toronto, Ontario M58 IA8, Canada

Lipopolysaccharide from phenol-water extraction of cells of Campylobacter coli serotype O:30 was separated as a water-insoluble gel of low M(r) from a water-soluble antigenic polysaccharide of high M(r). Acetic acid hydrolysis of the ketosidic linkages to lipid A in the lipopolysaccharide furnished a core oligosaccharide. Structural investigations were performed using 1H and 13C NMR, fast atom bombardment-mass spectrometry of permethylated derivatives, and methylation linkage analysis on the core oligosaccharide and the products of two successive Smith degradations. It is concluded that the highly branched 3-deoxy-D-manno-octulosonic acid-terminated oligosaccharide chains carried at the nonreducing end disaccharide units of β-D-Qui3NAc-(1→2)-β-D-Qui3NAc (where Qui3NAc represents 3-acylamino-3,6-dideoxy-D-glucose), in which N-acyl residues were either both (R)-3-hydroxybutanoyl or both 3-hydroxy-2,3-dimethyl-5-oxoprolyl. The demonstration of these unusual features provides further evidence for a wide variety of structures within the core oligosaccharide region of lipopolysaccharides from Campylobacter sp.Lipopolysaccharide from phenol-water extraction of cells of Campylobacter coli serotype O:30 was separated as a water-insoluble gel of low M(r) from a water-soluble antigenic polysaccharide of high M(r). Acetic acid hydrolysis of the ketosidic linkages to lipid A in the lipopolysaccharide furnished a core oligosaccharide. Structural investigations were performed using 1H and 13C NMR, fast atom bombardment-mass spectrometry of permethylated derivatives, and methylation linkage analysis on the core oligosaccharide and the products of two successive Smith degradations. It is concluded that the highly branched 3-deoxy-D-manno-octulosonic acid-terminated oligosaccharide chains carried at the nonreducing end disaccharide units of β-D-Qui3NAc-(1→2)-β-D-Qui3NAc (where Qui3NAc represents 3-acylamino-3,6-dideoxy-D-glucose), in which N-acyl residues were either both (R)-3-hydroxybutanoyl or both 3-hydroxy-2,3-dimethyl-5-oxoprolyl. The demonstration of these unusual features provides further evidence for a wide variety of structures within the core oligosaccharide region of lipopolysaccharides from Campylobacter sp.

Lipopolysaccharide, structure, Campylobacter coli

Structure type: oligomer
Location inside paper: p.6266, fig.2
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_131186,IEDB_135813,IEDB_135818,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_167072,IEDB_190606,IEDB_2189047,IEDB_742245,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_7,SB_88

NCBI Taxonomy refs (TaxIDs): 195
Reference(s) to other database(s): GTC:G48581HJ, GlycomeDB:28578
Show glycosyltransferases

There are 4 chemically distinct structures. Please, select:

CC(=O)N[C@H]1[C@H](O)[C@@H](C)O[C@@H](O[C@H]2[C@H](O[C@H]3[C@H](O)[C@@H](CO)O[C@@H](O[C@H]4[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]5[C@H](O[C@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@@H](O[C@@H]6[C@H](O)[C@@H](O[C@@H]7[C@H](O)C[C@](O)(C(=O)O)O[C@@H]7[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@H]7O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]7O)[C@H]6O)O[C@H]([C@@H](O)CO)[C@H]5O)[C@@H]4O[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@@H]3NC(C)=O)O[C@H](C)[C@@H](O)[C@@H]2NC(C)=O)[C@@H]1O

SVG MW SMILES 3D mol Ionize