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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Bordetella bronchiseptica [ICD11: XN173

]

The structure was elucidated in this paper
NCBI PubMed ID: 10880983
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov

nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada

The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.

lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure

Structure type: oligomer
Location inside paper: p.4579, scheme 1, table 1, 6c
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142345,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192

Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
Comments, role: Kdo linkage is erroneuosly reported as (1-6) in the paper

Related record ID(s): 5501, 5604, 15601, 15602, 15603, 15604, 15605
NCBI Taxonomy refs (TaxIDs): 518
Show glycosyltransferases

There is only one chemically distinct structure:

CN[C@@H]1[C@H](OC2O[C@H](C(=O)O)C=C(N)[C@H]2N)[C@@H](NC(C)=O)[C@H](O[C@@H](CO)[C@H]2O[C@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO[C@H]5O[C@H](C(=O)O)[C@H](O)[C@H](O)[C@H]5N)O[C@@H](O[C@@H]5[C@@H]([C@@H](O)CO)O[C@H](O[C@@H]6[C@H](OP(=O)(O)O)C[C@](OC[C@H]7O[C@@H](OC[C@H]8O[C@H](OP(=O)(O)O)[C@H](N)[C@@H](O)[C@@H]8O)[C@H](N)[C@@H](O)[C@@H]7OP(=O)(O)O)(C(=O)O)O[C@@H]6[C@H](O)CO)[C@@H](O)[C@H]5O[C@H]5O[C@H]([C@@H](O)CO[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6N)[C@@H](OP(=O)(O)O)[C@H](O)[C@@H]5O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](N)[C@H]3O)[C@@H](O)[C@@H](O)[C@@H]2O)O[C@@H]1C

SVG MW SMILES 3D mol Ionize