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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: (Actinopterygii); Homo sapiens
Associated disease: gastroenteritis [ICD11: 1A40.0

]; dysentery [ICD11: SA56

]; diarrhea [ICD11: ME05.1

, ICD11: SA55

]; meningitis [ICD11: 1D01

]

The structure was elucidated in this paper
NCBI PubMed ID: 20933222
Publication DOI: 10.1016/j.carres.2010.09.007
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: corsaro

unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy, Departamento Microbiología, Universidad de Barcelona, Diagonal 645, 08071 Barcelona, Spain, Division of Immunochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Parkallee 10, 23845 Borstel, Germany

Plesiomonas shigelloides is a Gram-negative opportunistic pathogen associated with gastrointestinal and extraintestinal infections, which especially invades immunocompromised patients and neonates. The lipopolysaccharides are one of the major virulence determinants in Gram-negative bacteria and are structurally composed of three different domains: the lipid A, the core oligosaccharide and the O-antigen polysaccharide. In the last few years we elucidated the structures of the O-chain and the core oligosaccharide from the P. shigelloides strain 302-73. In this paper we now report the characterization of the linkage between the core and the O-chain. The LPS obtained after PCP extraction contained a small number of O-chain repeating units. The product obtained by hydrazinolysis was analysed by FTICR-ESIMS and suggested the presence of an additional Kdo in the core oligosaccharide. Furthermore, the LPS was hydrolysed under mild acid conditions and a fraction that contained one O-chain repeating unit linked to a Kdo residue was isolated and characterized by FTICR-ESIMS and NMR spectroscopy. Moreover, after an alkaline reductive hydrolysis, a disaccharide α-Kdo-(2→6)-GlcNol was isolated and characterized. The data obtained proved the presence of an α-Kdo in the outer core and allowed the identification of the O-antigen biological repeating unit as well as its linkage with the core oligosaccharide.

NMR spectroscopy, structure elucidation, Plesiomonas, outer-core Kdo, reductive hydrolysis

Structure type: oligomer
Location inside paper: p.2527
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135607,IEDB_135609,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, de-O-acylation, sugar analysis, 31P NMR, mild acid hydrolysis, ESI-ICR-MS, MALDI-TOF MS, NMR-1D, hydrazinolysis, alkaline reductive hydrolysis
Comments, role: absolute configurations were assumed

Related record ID(s): 25397, 25809
NCBI Taxonomy refs (TaxIDs): 1315976
Show glycosyltransferases

There is only one chemically distinct structure:

[1*]O[C@@H]1[C@H](O)C[C@](OC[C@H]2O[C@H](O[C@H]3[C@@H](C(=O)O)O[C@H](O[2*]([2*]O[C@H]4O[C@H](C(=O)O)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5N)[C@H](O)[C@H]4O)(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[2*](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)O[C@@H]4[C@H](O[C@]5(C(=O)O)C[C@@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O5)C[C@](O)(C(=O)O)O[C@@H]4[C@H](O)CO)[C@H](O)[C@H]3O)[C@H](N)[C@@H](O)[C@@H]2O)(C(=O)O)O[C@@H]1[C@H](O)CO

SVG MW SMILES 3D mol Ionize

R1 = O-antigen (ID 25397)
R2 = a?Hepp