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

]

The structure was elucidated in this paper
NCBI PubMed ID: 17219455
Publication DOI: 10.1002/chem.200601406
Journal NLM ID: 9513783
Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: molinaro

unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli, Complesso Universitario Monte Sant'angelo, Via Cintia 4, 80126 Napoli, Italy, Fax: (+39) 081-674-393

Members of genus Burkholderia include opportunistic Gram-negative bacteria that are responsible for serious infections in immunocompromised and cystic fibrosis (CF) patients. The Burkholderia cepacia complex is a group of microorganisms composed of at least nine closely related genomovars. Among these, B. cenocepacia is widely recognized to cause epidemics associated with excessive mortality. Species that belong to this strain are problematic CF pathogens because of their high resistance to antibiotics, which makes respiratory infections difficult to treat and impossible to eradicate. Infection by these bacteria is associated with higher mortality in CF and poor outcomes following lung transplantation. One virulence factor contributing to this is the pro-inflammatory lipopolysaccharide (LPS) molecules. Thus, the knowledge of the lipopolysaccharide structure is an essential prerequisite to the understanding of the molecular mechanisms involved in the inflammatory process. Such data are instrumental in aiding the design of antimicrobial compounds and for developing therapeutic strategies against the inflammatory cascade. In particular, defining the structure of the LPS from B. cenocepacia ET-12 clone LMG 16656 (also known as J2315) is extremely important given the recent completion of the sequencing project at the Sanger Centre using this specific strain. In this paper we address this issue by defining the pro-inflammatory activity of the pure lipopolysaccharide, and by describing its full primary structure. The activity of the lipopolysaccharide was tested as a stimulant in human myelomonocytic U937 cells. The structural analysis was carried out by compositional analysis, mass spectrometry and 2D NMR spectroscopy on the intact lipooligosacchride (LOS) and its fragments, which were obtained by selective chemical degradations

lipopolysaccharides, NMR spectroscopy, mass spectrometry, cystic fibrosis, Burkholderia cenocepacia ET-12

Structure type: oligomer
Location inside paper: p.3508
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_136105,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_225177,IEDB_226811,IEDB_885823,IEDB_983931,SB_192,SB_7

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, chemical analysis, MALDI-MS, composition analysis, NMR-1D
Biological activity: biological activity data, pro-inflammatory activity (aTNF)

Related record ID(s): 21453
NCBI Taxonomy refs (TaxIDs): 95486
Reference(s) to other database(s): GlycomeDB:34713
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](OC(=O)C[C@H](O)CCCCCCCCCCC)[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]4OC[C@H](N)[C@H](O)[C@H]4O)[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]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]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@H]6NC(C)=O)[C@@H](O)[C@H](O)[C@@H]5O)[C@@H]4O)[C@@H]3O)[C@@H]([C@H](O)CO)O2)[C@@H](OP(=O)(O)O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC

SVG MW SMILES 3D mol Ionize