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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

The structure was elucidated in this paper
NCBI PubMed ID: 12444988
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: sml

fz-borstel.de
Institutions: Borstel Research Center, Center for Medicine and Biosciences, Borstel, Germany.

Lipopolysaccharide (LPS) of Escherichia coli strain 2513 (R4 core-type) yielded after alkaline deacylation one major oligosaccharide by high- performance anion-exchange chromatography (HPAEC) which had a molecular mass of 2486.59 Da as determined by electrospray ionization mass spectrometry. This was in accordance with the calculated molecular mass of a tetraphosphorylated dodecasaccharide of the composition shown below. NMR-analyses identified the chemical structure as where L-α-D-Hep is L-glycero-α-D-manno-heptopyranose and Kdo is 3-deoxy-α-D-manno-oct-2-ulopyranosylonic acid and all hexoses are present as d- pyranoses. We have also isolated the complete core-oligosaccharides of E. coli F653 LPS for which only preliminary data were available and investigated the deacylated LPS by NMR and MS/ The proposal structure determined previously by methylation analysis was confirmed and is shown below. In additional we have quantified the side-chain heptose substitution of the inner core with GlcpN (~30%) and confirmed that this sugar is only present when the phosphate at the second LDHep residue is absent.

Lipopolysaccharide, LPS, oligosaccharide, structure, core, strain, structural, analysis, molecular, Escherichia, Escherichia coli, acid, Kdo, core oligosaccharide, high, electrospray, ionization mass spectrometry, spectrometry, structural analysis, chemical, chemical structure, mass spectrometry, hexose, Hexoses, alkaline, ionization, composition, molecular mass, deacylated, deacylation, chromatography, pyranose, anion-exchange, anion-exchange chromatography, Electrospray Ionization, electrospray-ionization, HPAEC, R3 core-type, R4 core-type

Structure type: oligomer ; 2486.59
Trivial name: core-lipid A carbohydrate backbone
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_130670,IEDB_131186,IEDB_133751,IEDB_135394,IEDB_135818,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150908,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

Methods: NMR, ESI-MS, HPAEC

Related record ID(s): 3805, 3900
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases

There are too many chemically distinct structures (~1024), so only one is shown:

aXKdop(2-4)[aDGalp(1-2)aDGalp(1-2)[bDGalp(1-4)]aDGlcp(1-3)aDGlcp(1-3)[aXLDmanHepp(1-7),P-4)]aXLDmanHepp(1-3)[P-4)]aXLDmanHepp(1-5)]aXKdop(2-6)[P-4)]bDGlcpN(1-6)aDGlcpN(1-P

N[C@H]1[C@@H](OP(=O)(O)O)O[C@H](CO[C@@H]2O[C@H](CO[C@]3(C(=O)O)C[C@@H](O[C@]4(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O4)[C@@H](O[C@H]4O[C@H]([C@@H](O)CO)[C@@H](OP(=O)(O)O)[C@H](O[C@H]5O[C@H]([C@@H](O)CO[C@H]6O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]6O)[C@@H](OP(=O)(O)O)[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@H](CO)[C@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@@H]5O)[C@@H]4O)[C@@H]([C@H](O)CO)O3)[C@@H](OP(=O)(O)O)[C@H](O)[C@H]2N)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize