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 paperNCBI PubMed ID: 20933222Publication DOI: 10.1016/j.carres.2010.09.007Journal NLM ID: 0043535Publisher: 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 ; 401.155
Location inside paper: p.2526, OS3
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650
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
Related record ID(s): 5628, 25397, 25810
NCBI Taxonomy refs (TaxIDs): 1315976Reference(s) to other database(s): GTC:G56119AB, GlycomeDB:
26718
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
6 aXKdop 176.9 100.8 34.7 66.9 66.6 71.9 69.9 63.6
xDGlcN-ol 59.5 56.0 66.6 ? ? 65.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
6 aXKdop - - 1.84-2.10 4.15 4.06 3.71 3.98 3.71-3.94
xDGlcN-ol 3.80-3.90 3.55 4.14 ? ? 3.57-3.69
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
6 aXKdop 34.7/1.84-2.10 66.9/4.15 66.6/4.06 71.9/3.71 69.9/3.98 63.6/3.71-3.94
xDGlcN-ol 59.5/3.80-3.90 56.0/3.55 66.6/4.14 ?/? ?/? 65.3/3.57-3.69
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 6 | aXKdop |
|
| 1.84
2.10 | 4.15 | 4.06 | 3.71 | 3.98 | 3.71
3.94 |
| | xDGlcN-ol | 3.80
3.90 | 3.55 | 4.14 | ? | ? | 3.57
3.69 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 6 | aXKdop | 176.9 | 100.8 | 34.7 | 66.9 | 66.6 | 71.9 | 69.9 | 63.6 |
| | xDGlcN-ol | 59.5 | 56.0 | 66.6 | ? | ? | 65.3 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":176.9,"l":"1","c":[0,0,225]},{"s":100.8,"l":"2","c":[0,0,225]},{"s":34.7,"l":"3","c":[0,0,225]},{"s":66.9,"l":"4","c":[0,0,225]},{"s":66.6,"l":"5","c":[0,0,225]},{"s":71.9,"l":"6","c":[0,0,225]},{"s":69.9,"l":"7","c":[0,0,225]},{"s":63.6,"l":"8","c":[0,0,225]},{"s":59.5,"l":"1","c":[230,0,30]},{"s":56,"l":"2","c":[230,0,30]},{"s":66.6,"l":"3","c":[230,0,30]},{"s":65.3,"l":"6","c":[230,0,30]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Found 
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