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: polymer biological repeating unit
Location inside paper: abstract, p.1373, PS
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_142345
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, GLC, composition analysis, NMR-1D, CE-MS, CE-MS/MS
Comments, role: OAc group at C4 presented at the terminal non-reducing end of PS chain.
Related record ID(s): 24257, 24258, 24259
NCBI Taxonomy refs (TaxIDs): 55601
Show glycosyltransferases
NMR conditions: in D2O at 318 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,4,2 %Ac
3,4,4,3,2 Fo 164.3
3,4,4,3 %xLAla? 175.4 49.1 17.6
3,4,4,6 NH2
3,4,4 bDGlcpN3NA 102.7 54.4 55.0 72.9 76.4 ?
3,4,2 Ac
3,4,3 Am 166.7 19.9
3,4 bDManpN3NA 100.7 51.0 55.7 71.9 79.0 ?
3,3 Ac
3 bDQuip3N 104.7 72.4 56.2 83.5 73.1 17.6
2 Ac
4 Ac
aDFucpN4N 97.8 48.7 76.6 53.9 67.5 16.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,4,2 %Ac
3,4,4,3,2 Fo 7.96
3,4,4,3 %xLAla? - 4.31 1.25
3,4,4,6 NH2
3,4,4 bDGlcpN3NA 4.64 3.73 4.25 3.95 4.04 -
3,4,2 Ac
3,4,3 Am ? 2.15
3,4 bDManpN3NA 4.83 4.52 4.00 3.77 3.79 -
3,3 Ac
3 bDQuip3N 4.43 3.22 3.79 3.32 3.50 1.25
2 Ac
4 Ac
aDFucpN4N 5.18 4.18 3.90 4.33 4.04 1.05
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,4,2 %Ac
3,4,4,3,2 Fo 164.3/7.96
3,4,4,3 %xLAla? 49.1/4.31 17.6/1.25
3,4,4,6 NH2
3,4,4 bDGlcpN3NA 102.7/4.64 54.4/3.73 55.0/4.25 72.9/3.95 76.4/4.04
3,4,2 Ac
3,4,3 Am 166.7/? 19.9/2.15
3,4 bDManpN3NA 100.7/4.83 51.0/4.52 55.7/4.00 71.9/3.77 79.0/3.79
3,3 Ac
3 bDQuip3N 104.7/4.43 72.4/3.22 56.2/3.79 83.5/3.32 73.1/3.50 17.6/1.25
2 Ac
4 Ac
aDFucpN4N 97.8/5.18 48.7/4.18 76.6/3.90 53.9/4.33 67.5/4.04 16.7/1.05
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,4,2 | %Ac | |
| 3,4,4,3,2 | Fo | 7.96 | |
| 3,4,4,3 | %xLAla? |
| 4.31 | 1.25 | |
| 3,4,4,6 | NH2 | |
| 3,4,4 | bDGlcpN3NA | 4.64 | 3.73 | 4.25 | 3.95 | 4.04 |
|
| 3,4,2 | Ac | |
| 3,4,3 | Am | ? | 2.15 | |
| 3,4 | bDManpN3NA | 4.83 | 4.52 | 4.00 | 3.77 | 3.79 |
|
| 3,3 | Ac | |
| 3 | bDQuip3N | 4.43 | 3.22 | 3.79 | 3.32 | 3.50 | 1.25 |
| 2 | Ac | |
| 4 | Ac | |
| | aDFucpN4N | 5.18 | 4.18 | 3.90 | 4.33 | 4.04 | 1.05 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,4,2 | %Ac | |
| 3,4,4,3,2 | Fo | 164.3 | |
| 3,4,4,3 | %xLAla? | 175.4 | 49.1 | 17.6 | |
| 3,4,4,6 | NH2 | |
| 3,4,4 | bDGlcpN3NA | 102.7 | 54.4 | 55.0 | 72.9 | 76.4 | ? |
| 3,4,2 | Ac | |
| 3,4,3 | Am | 166.7 | 19.9 | |
| 3,4 | bDManpN3NA | 100.7 | 51.0 | 55.7 | 71.9 | 79.0 | ? |
| 3,3 | Ac | |
| 3 | bDQuip3N | 104.7 | 72.4 | 56.2 | 83.5 | 73.1 | 17.6 |
| 2 | Ac | |
| 4 | Ac | |
| | aDFucpN4N | 97.8 | 48.7 | 76.6 | 53.9 | 67.5 | 16.7 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":164.3,"l":"1","c":[230,0,30]},{"s":175.4,"l":"1","c":[0,165,0]},{"s":49.1,"l":"2","c":[0,165,0]},{"s":17.6,"l":"3","c":[0,165,0]},{"s":102.7,"l":"1","c":[120,0,225]},{"s":54.4,"l":"2","c":[120,0,225]},{"s":55,"l":"3","c":[120,0,225]},{"s":72.9,"l":"4","c":[120,0,225]},{"s":76.4,"l":"5","c":[120,0,225]},{"s":166.7,"l":"1","c":[0,192,255]},{"s":19.9,"l":"2","c":[0,192,255]},{"s":100.7,"l":"1","c":[220,0,180]},{"s":51,"l":"2","c":[220,0,180]},{"s":55.7,"l":"3","c":[220,0,180]},{"s":71.9,"l":"4","c":[220,0,180]},{"s":79,"l":"5","c":[220,0,180]},{"s":104.7,"l":"1","c":[100,160,0]},{"s":72.4,"l":"2","c":[100,160,0]},{"s":56.2,"l":"3","c":[100,160,0]},{"s":83.5,"l":"4","c":[100,160,0]},{"s":73.1,"l":"5","c":[100,160,0]},{"s":17.6,"l":"6","c":[100,160,0]},{"s":97.8,"l":"1","c":[210,210,0]},{"s":48.7,"l":"2","c":[210,210,0]},{"s":76.6,"l":"3","c":[210,210,0]},{"s":53.9,"l":"4","c":[210,210,0]},{"s":67.5,"l":"5","c":[210,210,0]},{"s":16.7,"l":"6","c":[210,210,0]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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