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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacteremia [ICD11: MA15.0

]; septicemia [ICD11: MA15.Y

]; respiratory diseases [ICD11: 12

]

The structure was elucidated in this paper
NCBI PubMed ID: 19011031
Publication DOI: 10.1128/JB.00891-08
Journal NLM ID: 2985120R
Publisher: American Society for Microbiology
Correspondence: czaja

iitd.pan.wroc.pl
Institutions: Department of Immunochemistry, L. Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland

Hafnia alvei, a gram-negative bacterium, is an opportunistic pathogen associated with mixed hospital infections, bacteremia, septicemia, and respiratory diseases. Various 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo)-containing fragments different from known structures of core oligosaccharides were previously found among fractions obtained by mild acid hydrolysis of some H. alvei lipopolysaccharides (LPSs). However, the positions of these segments in the LPS structure were not known. Analysis of de-N,O-acylated LPS by nuclear magnetic resonance spectroscopy and mass spectrometry allowed the determination of the location of a Kdo-containing trisaccharide in the structure of H. alvei PCM 32 LPS. It was established that the trisaccharide {L-α-D-Hepp-(1→4)-[α-D-Galp6OAc-(1→7)]-α-Kdop-(2→} is an integral part of the outer-core oligosaccharide of H. alvei 32 LPS. The very labile ketosidic linkage between →4,7)-α-Kdop and →2)-Glcp in the core oligosaccharide was identified. Screening for this Kdo-containing trisaccharide was performed on the group of 37 O serotypes of H. alvei LPSs using monospecific antibodies recognizing the structure. It was established that this trisaccharide is a characteristic component of the outer-core oligosaccharides of H. alvei 2, 32, 600, 1192, 1206, and 1211 LPSs. The weaker cross-reactions with LPSs of strains 974, 1188, 1198, 1204, and 1214 suggest the presence of similar structures in these LPSs, as well. Thus, we have identified new examples of endotoxins among those elucidated so far. This type of core oligosaccharide deviates from the classical scheme by the presence of the structural Kdo-containing motif in the outer-core region.

Lipopolysaccharide, 3-deoxy-D-manno-oct-2-ulosonic acid, core oligosaccharide, Hafnia alvei, serotyping, Enterobacteriaceae infections

Structure type: oligomer
Location inside paper: p.539, fig.4
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_136906,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192,SB_7

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, de-O-acylation, SDS-PAGE, sugar analysis, ELISA, 31P NMR, ESI-MS, mild acid hydrolysis, MALDI-TOF MS, NMR-1D, serological methods, immunoblotting, de-N-acylation
Comments, role: minor OS form of OS32 isolated from de-N,O-acylated LPS. Phosphate group substituted HepI or HepII.

Related record ID(s): 23778, 24089
NCBI Taxonomy refs (TaxIDs): 569
Reference(s) to other database(s): GlycomeDB:37375
Show glycosyltransferases

There is only one chemically distinct structure:

N[C@H]1[C@H](OC[C@H]2O[C@H](OP(=O)(O)O)[C@H](N)[C@@H](O)[C@@H]2O)O[C@H](CO[C@]2(C(=O)O)C[C@@H](O)[C@@H](O[C@H]3O[C@H]([C@@H](O)CO)[C@@H](OP(=O)(O)O)[C@H](O[C@H]4O[C@H]([C@@H](O)CO[C@H]5O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]5O)[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]6O[C@]6(C(=O)O)C[C@@H](O[C@H]7O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]7O)[C@@H](O)[C@@H]([C@@H](CO)O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)O6)[C@H]5O)[C@@H]4O)[C@@H]3O)[C@@H]([C@H](O)CO)O2)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize