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

]

NCBI PubMed ID: 20593263
Publication DOI: 10.1007/978-90-481-9078-2_4
Publisher: Springer Science+Business Media B.V.
Editors: Wang X, Quinn PJ
Correspondence: molinaro

unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Complesso Universitario Monte Santangelo, Via Cintia 4, Napoli, I-80126, Italy

Bacterial lipopolysaccharides (LPSs) are the major component of the outer membrane of Gram-negative bacteria. They have a structural role since they contribute to the cellular rigidity by increasing the strength of cell wall and mediating contacts with the external environment that can induce structural changes to allow life in different conditions. Furthermore, the low permeability of the outer membrane acts as a barrier to protect bacteria from host-derived antimicrobial compounds. Lipopolysaccharides are amphiphilic macromolecules generally comprising three defined regions distinguished by their genetics, structures and function: the lipid A, the core oligosaccharide and a polysaccharide portion, the O-chain. In some Gram-negative bacteria LPS can terminate with the core portion to form rough type LPS (R-LPS, LOS). The core oligosaccharide is an often branched and phosphorylated heterooligosaccharide with less than fifteen sugars, more conserved in the inner region, proximal to the lipid A, and often carrying non-stoichiometric substitutions leading to variation and micro-heterogeneity. The core oligosaccharide contributes to the bacterial viability and stability of the outer membrane, can assure the serological specificity and possesses antigenic properties.

core oligosaccharide, endotoxin, Gram-negative bacteria, innate immunity, glyco-conjugates

Structure type: oligomer
Location inside paper: p.76, fig.4.1
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130659,IEDB_130670,IEDB_133751,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150901,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_232584,IEDB_983931,SB_192,SB_7

NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases

There is only one chemically distinct structure:

CC(=O)N[C@H]1[C@@H](OC[C@H](O)[C@H]2O[C@H](OC[C@H](O)[C@H]3O[C@H](O[C@@H]4[C@H](O)[C@@H](O[C@@H]5[C@H](O[C@]6(C(=O)O)C[C@@H](O[C@]7(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O7)[C@@H](O)[C@@H]([C@@H](CO)OP(=O)(O)OCCN)O6)C[C@](O)(C(=O)O)O[C@@H]5[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]4OP(=O)(O)OP(=O)(O)OCCN)[C@@H](O)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@H]5O[C@H](CO)[C@H](O)[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6NC(C)=O)[C@H]5O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O)[C@@H]3OP(=O)(O)O)[C@@H](O)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize