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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Bordetella pertussis [ICD11: XN23B

]

Publication DOI: 10.4052/tigg.14.87
Journal NLM ID: 9425898
Correspondence: oholst

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

Lipopolysaccharides (LPS) are the endotoxins of Gram-negative bacteria and very well known for their immunological, pharmacological and pathophysiological effects displayed in eucaryotic cells and organisms. To date, much emphasis has been put on the elucidation of the chemical structures of LPS and on their relation, or that of substructures, to the various biological effects. The lipid part of LPS, the lipid A, was proven to represent the toxic principle of endotoxin. However, lipid A toxicity depends strongly on its structure, and is influenced by a second region of LPS, the core region, that is covalently linked to lipid A. Also, the core region possesses immunogenic properties. Therefore, complete structural analyses of the core region and the comparison of its structures with biological features of LPS are of high importance for a better understanding of LPS action, and one prerequesite for strategies aimed at the treatment of endotoxicosis. In the past, quite a number of structures of the core regions from various Gram-negative bacteria were published and summarized in several overviews. The present review adds to this knowledge those structures that were published between October 1998 and December 2001.

lipopolysaccharides, heptose, Kdo, chemical structure, core region, tructure

Structure type: oligomer
Location inside paper: p.100, table VI, B. pertussis
The structure in this paper was incorrect:

Original structure from CSDB record 31812

← originally published structure

Show legend

Aglycon: lipid A
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_115136,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_137340,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_2275071,IEDB_2275073,IEDB_2275074,IEDB_983931,SB_192

Comments, role: review; structure from ref. [60], Caroff M., et al., FEBS Letters 2000, 477(1-2), 8-14, DOI:10.1016/s0014-5793(00)01720-8.

NCBI Taxonomy refs (TaxIDs): 520
Reference(s) to other database(s): GTC:G45716UO
Show glycosyltransferases

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize