Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Gadus morhua
Associated disease: vibriosis [ICD11:
XN8RL 
]
The structure was elucidated in this paperNCBI PubMed ID: 19476924Publication DOI: 10.1016/j.carres.2009.04.027Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E. Altman <Eleonora.altman
nrc-cnrc.gc.ca>
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6
Vibrio anguillarum is a Gram-negative bacterium associated with vibriosis in Atlantic cod (Gadus morhua L.). Although farmed cod in Norway is routinely vaccinated against the infection, outbreaks of V. anguillarum-associated vibriosis still occur. Here, we describe the structural characterization of the LPS O-chain polysaccharide (O-PS) from atypical isolates of V. anguillarum strain 1282 and show that it is distinct from that previously established for V. anguillarum serotype O2. The structure of the purified O-PS was shown by 1D/2D NMR ((1)H, (13)C) spectroscopy and CE-MS studies to be a high-molecular mass linear polymer of tetrasaccharide repeating units, composed of 2-acetamido-3-(N-formyl-l-alanyl)amido-2,3-dideoxy-d-glucuronamide [GlcNAc3N(Fo-L-Ala)AN], 2-acetamido-3-acetamidino-2,3-dideoxy-d-mannuronic acid (ManNAc3NAmA), 3-acetamido-3-dideoxy-d-quinovose (Qui3NAc), and 2,4-diacetamido-2,4-dideoxy-d-fucose (FucNAc4NAc). NMR analysis of the partial hydrolysis-derived oligosaccharides confirmed the presence of an O-acetyl group at position O-4 of GlcNAc3N(Fo-l-Ala)AN and established that the above-mentioned structure represents the biological repeating unit of the O-PS. In addition, it was demonstrated that some of 2,3-diamino-2,3-dideoxy-glucuronamide in the O-PS was present in the form of 2,3-diamino-2,3-dideoxy-glucose.
structure, O-antigen, serotyping, Vibrio anguillarum, CE-MS, vibriosis
Structure type: oligomer
Location inside paper: p.1373, OS3
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, GLC, composition analysis, NMR-1D, CE-MS, CE-MS/MS
Related record ID(s): 23875, 24257, 24258
NCBI Taxonomy refs (TaxIDs): 55601Reference(s) to other database(s): GlycomeDB:
37437
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,4,3 xLAla? ? 51.4 17.7
4,4,2 Ac 176.2-177.7 22.8-23.5
4,4,4 Ac 176.2-177.7 22.8-23.5
4,4,6 NH2
4,4 bDGlcpN3N 102.9 53.7 53.2 71.2 74.9 ?
4,2 Ac 176.2-177.7 22.8-23.5
4,3 Am 167.6 20.0
4 bDManpN3NA 101.1 51.0 55.9 76.0 78.0 ?
3 Ac 176.2-177.7 22.8-23.5
xDQui3N-ol 63.9 71.9 52.2 84.4 68.3 17.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,4,3 xLAla? - 4.09 1.27
4,4,2 Ac
4,4,4 Ac
4,4,6 NH2
4,4 bDGlcpN3N 4.67 3.89 4.21 5.00 4.15 ?
4,2 Ac
4,3 Am ? 2.20
4 bDManpN3NA 5.05 4.67 4.07 4.04 3.96 -
3 Ac
xDQui3N-ol 3.54 3.83 4.04 3.88 3.97 1.15
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,4,3 xLAla? 51.4/4.09 17.7/1.27
4,4,2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
4,4,4 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
4,4,6 NH2
4,4 bDGlcpN3N 102.9/4.67 53.7/3.89 53.2/4.21 71.2/5.00 74.9/4.15 ?/?
4,2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
4,3 Am 167.6/? 20.0/2.20
4 bDManpN3NA 101.1/5.05 51.0/4.67 55.9/4.07 76.0/4.04 78.0/3.96
3 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
xDQui3N-ol 63.9/3.54 71.9/3.83 52.2/4.04 84.4/3.88 68.3/3.97 17.4/1.15
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,4,3 | xLAla? |
| 4.09 | 1.27 | |
| 4,4,2 | Ac | |
| 4,4,4 | Ac | |
| 4,4,6 | NH2 | |
| 4,4 | bDGlcpN3N | 4.67 | 3.89 | 4.21 | 5.00 | 4.15 | ? |
| 4,2 | Ac | |
| 4,3 | Am | ? | 2.20 | |
| 4 | bDManpN3NA | 5.05 | 4.67 | 4.07 | 4.04 | 3.96 |
|
| 3 | Ac | |
| | xDQui3N-ol | 3.54 | 3.83 | 4.04 | 3.88 | 3.97 | 1.15 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,4,3 | xLAla? | ? | 51.4 | 17.7 | |
| 4,4,2 | Ac | 176.2
177.7 | 22.8
23.5 | |
| 4,4,4 | Ac | 176.2
177.7 | 22.8
23.5 | |
| 4,4,6 | NH2 | |
| 4,4 | bDGlcpN3N | 102.9 | 53.7 | 53.2 | 71.2 | 74.9 | ? |
| 4,2 | Ac | 176.2
177.7 | 22.8
23.5 | |
| 4,3 | Am | 167.6 | 20.0 | |
| 4 | bDManpN3NA | 101.1 | 51.0 | 55.9 | 76.0 | 78.0 | ? |
| 3 | Ac | 176.2
177.7 | 22.8
23.5 | |
| | xDQui3N-ol | 63.9 | 71.9 | 52.2 | 84.4 | 68.3 | 17.4 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":51.4,"l":"2","c":[0,0,225]},{"s":17.7,"l":"3","c":[0,0,225]},{"s":176.95,"l":"1","c":[0,0,0]},{"s":23.15,"l":"2","c":[0,0,0]},{"s":176.95,"l":"1","c":[0,0,0]},{"s":23.15,"l":"2","c":[0,0,0]},{"s":102.9,"l":"1","c":[230,0,30]},{"s":53.7,"l":"2","c":[230,0,30]},{"s":53.2,"l":"3","c":[230,0,30]},{"s":71.2,"l":"4","c":[230,0,30]},{"s":74.9,"l":"5","c":[230,0,30]},{"s":176.95,"l":"1","c":[0,0,0]},{"s":23.15,"l":"2","c":[0,0,0]},{"s":167.6,"l":"1","c":[0,165,0]},{"s":20,"l":"2","c":[0,165,0]},{"s":101.1,"l":"1","c":[120,0,225]},{"s":51,"l":"2","c":[120,0,225]},{"s":55.9,"l":"3","c":[120,0,225]},{"s":76,"l":"4","c":[120,0,225]},{"s":78,"l":"5","c":[120,0,225]},{"s":176.95,"l":"1","c":[0,0,0]},{"s":23.15,"l":"2","c":[0,0,0]},{"s":63.9,"l":"1","c":[0,192,255]},{"s":71.9,"l":"2","c":[0,192,255]},{"s":52.2,"l":"3","c":[0,192,255]},{"s":84.4,"l":"4","c":[0,192,255]},{"s":68.3,"l":"5","c":[0,192,255]},{"s":17.4,"l":"6","c":[0,192,255]}])
The spectrum also has 3 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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