Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Bordetella bronchiseptica [ICD11:
XN173 
]
The structure was elucidated in this paperNCBI PubMed ID: 9171426Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Martine.Caroff
bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, URA 1116 du Centre National de la Recherche Scientifique, Université de Paris-Sud, Orsay, France
The structures of lipids A isolated from the lipopolysaccharides (LPSs; endotoxins) of three different pathogenic Bordetella bronchiseptica strains were investigated by chemical composition and methylation analysis, gas chromatography-mass spectrometry, nuclear magnetic resonance, and plasma desorption mass spectrometry (PDMS). The analyses revealed that the LPSs contain the classical lipid A bisphosphorylated β-(1→6)-linked D-glucosamine disaccharide with hydroxytetradecanoic acid in amide linkages. Their structures differ from that of the lipid A of Bordetella pertussis endotoxin by the replacement of hydroxydecanoic acid on the C-3 position with hydroxydodecanoic acid or dodecanoic acid and the presence of variable amounts of hexadecanoic acid. The dodecanoic acid is the first nonhydroxylated fatty acid to be found directly linked to a lipid A glucosamine. The lipids A were heterogeneous and composed of one to three major and several minor molecular species. The fatty acids in ester linkage were localized by PDMS of chemically modified lipids A. B. pertussis lipids A are usually hypoacylated with respect to those of enterobacterial lipids A. However, one of the three B. bronchiseptica strains had a major hexaacylated molecular species. C-4 and C-6' hydroxyl groups of the backbone disaccharide were unsubstituted, the latter being the proposed attachment site of the polysaccharide. The structural variability seen in these three lipids A was unusual for a single species and may have consequences for the pathogenicity of this Bordetella species.
lipid A, Bordetella bronchiseptica, MS, plasma desorption mass spectrometry, GLC-MS
Structure type: oligomer ; 1345
Location inside paper: p.3759, fig.3
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_141807,IEDB_151531,IEDB_176772,IEDB_534864
Methods: 1H NMR, GC-MS, TLC, 31P NMR, GLC, mild acid hydrolysis, composition analysis, PD-MS, mild alkali treatment, hydrazinolysis
Comments, role: major lipid A species
Related record ID(s): 5943, 31295, 31296, 31297
NCBI Taxonomy refs (TaxIDs): 518
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error