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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cystic fibrosis (CF) [ICD11: CA25

]

The structure was elucidated in this paper
NCBI PubMed ID: 22278934
Publication DOI: 10.1177/1753425911435954
Journal NLM ID: 101469670
Publisher: Sage Publications
Correspondence: pcescutti

units.it
Institutions: Dipartimento di Scienze della Vita, Universita di Trieste, Trieste, Italy, Istituto di Chimica e Tecnologia dei Polimeri, Catania, Italy

Reactive oxygen species (ROS) are part of the weapons used by the immune system to kill and degrade infecting microorganisms. Bacteria can produce macromolecules, such as polysaccharides, that are able to scavenge ROS. Species belonging to the Burkholderia cepacia complex are involved in serious lung infection in cystic fibrosis patients and produce a characteristic polysaccharide, cepacian. The interaction between ROS and bacterial polysaccharides was first investigated by killing experiments, where bacteria cells were incubated with sodium hypochlorite (NaClO) with and without prior incubation with cepacian. The results showed that the polysaccharide had a protective effect towards bacterial cells. Cepacian was then treated with different concentrations of NaClO and the course of reactions was followed by means of capillary viscometry. The degradation products were characterised by size-exclusion chromatography, NMR and mass spectrometry. The results showed that hypochlorite depolymerised cepacian, removed side chains and O-acetyl groups, but did not cleave the glycosidic bond between glucuronic acid and rhamnose. The structure of some oligomers produced by NaClO oxidation is reported.

Burkholderia cepacia complex, cepacian polysaccharide, reactive oxygen species

Structure type: oligomer
Location inside paper: p.669, fig.7B
Trivial name: cepacian
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88

Methods: 13C NMR, 1H NMR, MALDI-MS, de-O-acetylation, viscosity measurement, dialysis
Comments, role: de-acetylated cepacian repeating unit degraded with 60mM NaClO, fraction named Cep-deAc-60 is composed of a mixture of oligosaccharides.

Related record ID(s): 29460, 29462, 29953
NCBI Taxonomy refs (TaxIDs): 60550
Reference(s) to other database(s): GTC:G05337EU
Show glycosyltransferases

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize