Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: gastroenteritis [ICD11:
1A40.0 
];
infection due to Vibrio parahaemolyticus [ICD11:
XN1AA ]
The structure was elucidated in this paperNCBI PubMed ID: 7392309Publication DOI: 10.1016/j.carres.2016.06.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: goran.widmalm
su.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, International Centre for Diarrhoeal Disease Research, Dhaka, Bangladesh, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Microbiology, Karolinska University Hospital, Stockholm, Sweden
The structure of a polysaccharide from Vibrio parahaemolyticus strain AN-16000 has been investigated. The sugar and absolute configuration analysis revealed d-Glc, d-GalN, d-QuiN and l-FucN as major components. The PS was subjected to dephosphorylation with aqueous 40% HF to obtain an oligosaccharide that was analyzed by (1)H and (13)C NMR spectroscopy. The HR-MS spectrum of the oligosaccharide revealed a pentasaccharide composed of two Glc residues, one QuiNAc and one GalNAc, one FucNAc, as well as a glycerol moiety. The structure of the PS was determined using (1)H, (13)C, (15)N and (31)P NMR spectroscopy; inter-residue correlations were identified by (1)H,(13)C-heteronuclear multiple-bond correlation, (1)H,(1)H-NOESY and (1)H,(31)P-hetero-TOCSY experiments. The PS backbone has the following teichoic acid-like structure: →3)-d-Gro-(1-P-6)-β-d-Glcp-(1→4)-α-l-FucpNAc-(1→3)-β-d-QuipNAc-(1 → with a side-chain consisting of α-d-Glcp-(1→6)-α-d-GalpNAc-(1→ linked to the O3 position of the FucNAc residue.
NMR, Vibrio parahaemolyticus, dephosphorylation, Glycerol-1-phosphate
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.46, table 2, p.47, fig.6, fig.7
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_130695,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_241118,IEDB_885822,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, acid hydrolysis, GLC, NMR-1D, GPC, mild acid degradation
Related record ID(s): 11374, 11801, 11802, 11803, 11804, 11805
NCBI Taxonomy refs (TaxIDs): 670Reference(s) to other database(s): GTC:G79061JU
Show glycosyltransferases
NMR conditions: in D2O at 335 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,6,0 xRGro 67.19 70.30 71.79
3,4,6 P
3,4 bDGlcp 104.09 74.58 76.28 69.69 75.85 64.98
3,2 Ac 174.24 23.04
3,3,6 aDGlcp 97.98 72.04 74.52 70.53 72.60 61.62
3,3,2 Ac 174.68 23.17
3,3 aDGalpN 98.57 49.92 68.46 69.83 70.37 66.77
3 aLFucpN 98.57 49.87 70.74 78.61 68.52 16.19
2 Ac 174.72 22.98
bDQuipN 102.55 56.59 78.91 74.69 72.71 17.61
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,6,0 xRGro 3.84-3.90 3.96 3.61-3.92
3,4,6 P
3,4 bDGlcp 4.65 3.47 3.55 3.55 3.51 3.99-4.11
3,2 Ac - 1.95
3,3,6 aDGlcp 4.94 3.57 3.55 3.46 3.77 3.76-3.89
3,3,2 Ac - 2.02
3,3 aDGalpN 5.05 4.16 3.93 4.09 4.30 3.70-3.94
3 aLFucpN 4.97 4.39 4.05 4.18 4.51 1.32
2 Ac - 1.97
bDQuipN 4.46 3.85 3.66 3.39 3.50 1.33
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,6,0 xRGro 67.19/3.84-3.90 70.30/3.96 71.79/3.61-3.92
3,4,6 P
3,4 bDGlcp 104.09/4.65 74.58/3.47 76.28/3.55 69.69/3.55 75.85/3.51 64.98/3.99-4.11
3,2 Ac 23.04/1.95
3,3,6 aDGlcp 97.98/4.94 72.04/3.57 74.52/3.55 70.53/3.46 72.60/3.77 61.62/3.76-3.89
3,3,2 Ac 23.17/2.02
3,3 aDGalpN 98.57/5.05 49.92/4.16 68.46/3.93 69.83/4.09 70.37/4.30 66.77/3.70-3.94
3 aLFucpN 98.57/4.97 49.87/4.39 70.74/4.05 78.61/4.18 68.52/4.51 16.19/1.32
2 Ac 22.98/1.97
bDQuipN 102.55/4.46 56.59/3.85 78.91/3.66 74.69/3.39 72.71/3.50 17.61/1.33
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,6,0 | xRGro | 3.84
3.90 | 3.96 | 3.61
3.92 | |
| 3,4,6 | P | |
| 3,4 | bDGlcp | 4.65 | 3.47 | 3.55 | 3.55 | 3.51 | 3.99
4.11 |
| 3,2 | Ac |
| 1.95 | |
| 3,3,6 | aDGlcp | 4.94 | 3.57 | 3.55 | 3.46 | 3.77 | 3.76
3.89 |
| 3,3,2 | Ac |
| 2.02 | |
| 3,3 | aDGalpN | 5.05 | 4.16 | 3.93 | 4.09 | 4.30 | 3.70
3.94 |
| 3 | aLFucpN | 4.97 | 4.39 | 4.05 | 4.18 | 4.51 | 1.32 |
| 2 | Ac |
| 1.97 | |
| | bDQuipN | 4.46 | 3.85 | 3.66 | 3.39 | 3.50 | 1.33 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,6,0 | xRGro | 67.19 | 70.30 | 71.79 | |
| 3,4,6 | P | |
| 3,4 | bDGlcp | 104.09 | 74.58 | 76.28 | 69.69 | 75.85 | 64.98 |
| 3,2 | Ac | 174.24 | 23.04 | |
| 3,3,6 | aDGlcp | 97.98 | 72.04 | 74.52 | 70.53 | 72.60 | 61.62 |
| 3,3,2 | Ac | 174.68 | 23.17 | |
| 3,3 | aDGalpN | 98.57 | 49.92 | 68.46 | 69.83 | 70.37 | 66.77 |
| 3 | aLFucpN | 98.57 | 49.87 | 70.74 | 78.61 | 68.52 | 16.19 |
| 2 | Ac | 174.72 | 22.98 | |
| | bDQuipN | 102.55 | 56.59 | 78.91 | 74.69 | 72.71 | 17.61 |
|
There is only one chemically distinct structure:
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