Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
septicemia [ICD11:
MA15.Y ]
The structure was elucidated in this paperPublication DOI: 10.1002/ejoc.200801200Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: corsaro
unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy, Fax: +39-081-674393, Departamento Microbiología, Universidad de Barcelona, Diagonal 645, 08071 Barcelona, Spain
Plesiomonas shigelloides is a Gram-negative pathogenic bacterium belonging to the Enterobacteriaceae family. To date, only few lipopolysaccharide (LPS) structures from P. shigelloides strains are known. In particular, three core oligosaccharides have been found. Recently, we elucidated the structure of the O-antigen of P. shigelloides 302-73 (serotype O1) and in this paper we present the characterization of the core structure from the LPS of the same strain. The LPS was hydrolyzed under both alkaline and mildly acidic conditions. In both cases, a mixture of oligosaccharides was obtained, which was purified by gel filtration and HPAEC. The oligosaccharides were characterized by chemical analysis, 2D NMR spectroscopy and MALDI-TOF mass spectrometry. A new core structure was found for P. shigelloides. In particular, from the analysis of the acid hydrolysed product it was possible to reveal the presence of a of D-glycero-D-talo-2-octulopyranosonic acid (Ko) residue, which substitutes in part the terminal 3-doxy-D-manno-oct-2-ulosonic acid (Kdo) unit. The Ko residue is not frequently found in core structures.
Oligosaccharides, NMR spectroscopy, structure elucidation, sequence determination
Structure type: oligomer
Location inside paper: p.1370, scheme 2, OS3
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, de-O-acylation, SDS-PAGE, sugar analysis, acid hydrolysis, alkaline degradation, MALDI-TOF MS, NMR-1D, HPAEC-PAD
Related record ID(s): 23816, 24176, 24178
NCBI Taxonomy refs (TaxIDs): 1315976Reference(s) to other database(s): GTC:G33614CW, GlycomeDB:
37407
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
4 %aXKop
5,3,3,4 aDGlcpN 97.6 55.4 71.1 70.2 73.3 61.2
5,3,3 aDGalpA 99.5 69.9 69.6 80.5 72.9 176.1
5,3,7,7,4 aDGlcpN 95.2 55.5 70.9 70.4 73.3 61.2
5,3,7,7 aDGalpA 100.1 69.2 70.2 76.9 70.7 177.1
5,3,7 aXLDmanHepp 105.0 70.9 71.2 67.4 73.9 69.2 72.6
5,3 aXLDmanHepp 101.9 69.9 83.0 65.8 73.0 68.9 75.2
5,4 bDGalp 104.5 72.3 73.6 70.0 76.3 63.1
5 aXLDmanHepp 103.1 71.6 73.7 75.3 73.1 69.9 64.2
aXKdop ? ? 35.4 71.9 69.6 71.5 70.7 64.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
4 %aXKop
5,3,3,4 aDGlcpN 5.06 3.17 3.79 3.46 4.16 3.76
5,3,3 aDGalpA 5.21 3.76 4.19 4.32 4.46 -
5,3,7,7,4 aDGlcpN 5.19 3.10 3.86 3.42 4.01 3.74
5,3,7,7 aDGalpA 4.95 3.90 4.00 4.48 4.23 -
5,3,7 aXLDmanHepp 4.87 3.85 3.80 3.83 3.58 3.88 3.48-3.76
5,3 aXLDmanHepp 5.37 4.13 3.87 3.94 3.73 4.12 3.57-3.81
5,4 bDGalp 4.45 3.46 3.58 3.84 3.62 3.63
5 aXLDmanHepp 5.21 3.96 3.97 4.22 4.08 4.05 3.63-3.91
aXKdop - - 1.94 4.01 4.15 3.82 4.12 3.51-3.70
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
4 %aXKop
5,3,3,4 aDGlcpN 97.6/5.06 55.4/3.17 71.1/3.79 70.2/3.46 73.3/4.16 61.2/3.76
5,3,3 aDGalpA 99.5/5.21 69.9/3.76 69.6/4.19 80.5/4.32 72.9/4.46
5,3,7,7,4 aDGlcpN 95.2/5.19 55.5/3.10 70.9/3.86 70.4/3.42 73.3/4.01 61.2/3.74
5,3,7,7 aDGalpA 100.1/4.95 69.2/3.90 70.2/4.00 76.9/4.48 70.7/4.23
5,3,7 aXLDmanHepp 105.0/4.87 70.9/3.85 71.2/3.80 67.4/3.83 73.9/3.58 69.2/3.88 72.6/3.48-3.76
5,3 aXLDmanHepp 101.9/5.37 69.9/4.13 83.0/3.87 65.8/3.94 73.0/3.73 68.9/4.12 75.2/3.57-3.81
5,4 bDGalp 104.5/4.45 72.3/3.46 73.6/3.58 70.0/3.84 76.3/3.62 63.1/3.63
5 aXLDmanHepp 103.1/5.21 71.6/3.96 73.7/3.97 75.3/4.22 73.1/4.08 69.9/4.05 64.2/3.63-3.91
aXKdop 35.4/1.94 71.9/4.01 69.6/4.15 71.5/3.82 70.7/4.12 64.5/3.51-3.70
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 4 | %aXKop | |
| 5,3,3,4 | aDGlcpN | 5.06 | 3.17 | 3.79 | 3.46 | 4.16 | 3.76 | |
| 5,3,3 | aDGalpA | 5.21 | 3.76 | 4.19 | 4.32 | 4.46 |
| |
| 5,3,7,7,4 | aDGlcpN | 5.19 | 3.10 | 3.86 | 3.42 | 4.01 | 3.74 | |
| 5,3,7,7 | aDGalpA | 4.95 | 3.90 | 4.00 | 4.48 | 4.23 |
| |
| 5,3,7 | aXLDmanHepp | 4.87 | 3.85 | 3.80 | 3.83 | 3.58 | 3.88 | 3.48
3.76 | |
| 5,3 | aXLDmanHepp | 5.37 | 4.13 | 3.87 | 3.94 | 3.73 | 4.12 | 3.57
3.81 | |
| 5,4 | bDGalp | 4.45 | 3.46 | 3.58 | 3.84 | 3.62 | 3.63 | |
| 5 | aXLDmanHepp | 5.21 | 3.96 | 3.97 | 4.22 | 4.08 | 4.05 | 3.63
3.91 | |
| | aXKdop |
|
| 1.94 | 4.01 | 4.15 | 3.82 | 4.12 | 3.51
3.70 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 4 | %aXKop | |
| 5,3,3,4 | aDGlcpN | 97.6 | 55.4 | 71.1 | 70.2 | 73.3 | 61.2 | |
| 5,3,3 | aDGalpA | 99.5 | 69.9 | 69.6 | 80.5 | 72.9 | 176.1 | |
| 5,3,7,7,4 | aDGlcpN | 95.2 | 55.5 | 70.9 | 70.4 | 73.3 | 61.2 | |
| 5,3,7,7 | aDGalpA | 100.1 | 69.2 | 70.2 | 76.9 | 70.7 | 177.1 | |
| 5,3,7 | aXLDmanHepp | 105.0 | 70.9 | 71.2 | 67.4 | 73.9 | 69.2 | 72.6 | |
| 5,3 | aXLDmanHepp | 101.9 | 69.9 | 83.0 | 65.8 | 73.0 | 68.9 | 75.2 | |
| 5,4 | bDGalp | 104.5 | 72.3 | 73.6 | 70.0 | 76.3 | 63.1 | |
| 5 | aXLDmanHepp | 103.1 | 71.6 | 73.7 | 75.3 | 73.1 | 69.9 | 64.2 | |
| | aXKdop | ? | ? | 35.4 | 71.9 | 69.6 | 71.5 | 70.7 | 64.5 |
|
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The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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