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

]; pneumonia [ICD11: CA40

]

The structure was elucidated in this paper
NCBI PubMed ID: 23733445
Publication DOI: 10.1002/cbic.201300062
Journal NLM ID: 100937360
Publisher: Weinheim, Germany: Wiley Interscience
Correspondence: molinaro

unina.it
Institutions: Dipartimento di Scienze Chimiche, Universita di Napoli Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli (Italy)

This is the first report of the chemical and biological properties of the lipooligosaccharide (LOS) endotoxin isolated from Burkholderia dolosa IST4208, an isolate recovered from a cystic fibrosis (CF) patient in a Portuguese CF center. B. dolosa is a member of the Burkholderia cepacia complex, a group of closely related species that are highly problematic and opportunistic pathogens in CF. B. dolosa infection leads to accelerated loss of lung function and decreased survival. The structural determination of its endotoxin was achieved using a combination of chemistry and spectroscopy, and has revealed a novel endotoxin structure. The purified LOS was tested for its immunostimulatory activity on human HEK 293 cells expressing TLR-4, MD-2, and CD-14. In these assays, the LOS showed strong proinflammatory activity.

structure, Lipooligosaccharide, NMR spectroscopy, endotoxin, mass spectrometry, survival, CD14, Burkholderia dolosa

Structure type: oligomer
Location inside paper: p.1112, scheme 1
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_176772,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, SDS-PAGE, sugar analysis, ELISA, mild acid hydrolysis, MALDI-TOF MS, NMR-1D, methanolysis, statistical analysis
Biological activity: proinflammatory activity of the LOS
Comments, role: Ara4N residues were assumed to be in β-L form (as usually in lipid A), although they were depicted as α-D in the figure (anomericity was not discussed in the text; absolute configuration was reported as L)

Related record ID(s): 29261
NCBI Taxonomy refs (TaxIDs): 152500
Show glycosyltransferases

There is only one chemically distinct structure:

CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCCCC)CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@H](OP(=O)(O)O[C@H]3OC[C@H](N)[C@H](O)[C@H]3O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCCCC)[C@@H](O)[C@@H]2O)O[C@H](CO[C@]2(C(=O)O)C[C@@H](O[C@@]3(C(=O)O)O[C@H]([C@H](O)CO)[C@H](O)[C@H](O)[C@@H]3O)[C@@H](O[C@H]3O[C@H]([C@@H](O)CO)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O[C@H]4O[C@H]([C@@H](O)CO[C@H]5O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]5O)[C@@H](O)[C@H](O[C@H]5O[C@H](CO[C@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@H](O)[C@H](O)[C@H]5O[C@H]5O[C@H]([C@@H](O)CO[C@@H]6O[C@H](C)[C@@H](O)[C@H](O)[C@H]6NC(C)=O)[C@@H](O)[C@H](O[C@H]6O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]6O)[C@@H]5O)[C@@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]3O)[C@@H]([C@H](O)CO)O2)[C@@H](OP(=O)(O)O[C@H]2OC[C@H](N)[C@H](O)[C@H]2O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC

SVG MW SMILES 3D mol Ionize