Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: (Actinopterygii); Homo sapiens
Associated disease: vibriosis [ICD11:
XN8RL 
];
infection due to Vibrio vulnificus [ICD11:
XN44G ]
The structure was elucidated in this paperNCBI PubMed ID: 19128797Publication DOI: 10.1016/j.carres.2008.12.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Departamento de Microbiología y Ecología, Universidad de València, E-46100 Burjassot, Valencia, Spain, Departamento Microbiología, Facultad Biología, Universidad de Barcelona, E-08071 Barcelona, Spain
A polysaccharide was isolated by GPC after mild acid treatment of the lipopolysaccharide of Vibrio vulnificus CECT4602 and found to contain L-Rha, D-GlcpNAc and 2-acetamido-2,3,6-trideoxy-3-(3-hydroxybutanoylamino)-L-mannose (L-RhaNAc3NHb). GLC analysis of the trifluoroacetylated (S)-2-octyl esters derived by full acid hydrolysis of the polysaccharide showed that approximately 80% of the 3-hydroxybutanoic acid has the S configuration and approximately 20% the R configuration. The following structure of the polysaccharide was established by (1)H and (13)C NMR spectroscopies, including 2D ROESY and (1)H/(13)C HMBC experiments: [carbohydrate sequence see in text].
Lipopolysaccharide, bacterial polysaccharide structure, 2, 3, 3-diamino-2, 6-trideoxy-L-mannose, 3-hydroxybutanoyl group; Vibrio vulnificus
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.482,chart 1
Compound class: O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823,SB_74,SB_85
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis
NCBI Taxonomy refs (TaxIDs): 672
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2 Ac 175.4 23.6
3,3,3,2 Ac 175.7-176.2 23.5
3,3,3 bLRhapN3N 100.5 52.8 55.0 71.4 75.0 18.5
3,3 aDGlcpN 95.3 53.3 77.5 76.5 72.2 60.9
3 aLRhap 102.4 68.8 76.5 71.5 70.4 18.0
2 Ac 175.7-176.2 23.5
bDGlcpN 101.5 57.5 83.0 70.4 77.8 62.4
3,3,3,3 20%lR3HOBut 175.4 46.2 66.4 23.3
3,3,3,3 80%lS3HOBut 175.4 46.2 66.4 23.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2 Ac - 2.04
3,3,3,2 Ac - 2.02
3,3,3 bLRhapN3N 5.06 4.58 4.00 3.29 3.52 1.35
3,3 aDGlcpN 4.98 3.93 4.02 3.91 3.97 3.68-3.81
3 aLRhap 4.87 3.88 3.79 3.49 4.02 1.25
2 Ac - 2.02
bDGlcpN 4.52 3.84 3.69 3.56 3.4 3.84-3.89
3,3,3,3 20%lR3HOBut - 2.36 4.17 1.14
3,3,3,3 80%lS3HOBut - 2.36 4.17 1.14
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2 Ac 23.6/2.04
3,3,3,2 Ac 23.5/2.02
3,3,3 bLRhapN3N 100.5/5.06 52.8/4.58 55.0/4.00 71.4/3.29 75.0/3.52 18.5/1.35
3,3 aDGlcpN 95.3/4.98 53.3/3.93 77.5/4.02 76.5/3.91 72.2/3.97 60.9/3.68-3.81
3 aLRhap 102.4/4.87 68.8/3.88 76.5/3.79 71.5/3.49 70.4/4.02 18.0/1.25
2 Ac 23.5/2.02
bDGlcpN 101.5/4.52 57.5/3.84 83.0/3.69 70.4/3.56 77.8/3.4 62.4/3.84-3.89
3,3,3,3 20%lR3HOBut 46.2/2.36 66.4/4.17 23.3/1.14
3,3,3,3 80%lS3HOBut 46.2/2.36 66.4/4.17 23.3/1.14
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2 | Ac |
| 2.04 | |
| 3,3,3,2 | Ac |
| 2.02 | |
| 3,3,3 | bLRhapN3N | 5.06 | 4.58 | 4.00 | 3.29 | 3.52 | 1.35 |
| 3,3 | aDGlcpN | 4.98 | 3.93 | 4.02 | 3.91 | 3.97 | 3.68
3.81 |
| 3 | aLRhap | 4.87 | 3.88 | 3.79 | 3.49 | 4.02 | 1.25 |
| 2 | Ac |
| 2.02 | |
| | bDGlcpN | 4.52 | 3.84 | 3.69 | 3.56 | 3.4 | 3.84
3.89 |
| 3,3,3,3 | 20%lR3HOBut |
| 2.36 | 4.17 | 1.14 | |
| 3,3,3,3 | 80%lS3HOBut |
| 2.36 | 4.17 | 1.14 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2 | Ac | 175.4 | 23.6 | |
| 3,3,3,2 | Ac | 175.7
176.2 | 23.5 | |
| 3,3,3 | bLRhapN3N | 100.5 | 52.8 | 55.0 | 71.4 | 75.0 | 18.5 |
| 3,3 | aDGlcpN | 95.3 | 53.3 | 77.5 | 76.5 | 72.2 | 60.9 |
| 3 | aLRhap | 102.4 | 68.8 | 76.5 | 71.5 | 70.4 | 18.0 |
| 2 | Ac | 175.7
176.2 | 23.5 | |
| | bDGlcpN | 101.5 | 57.5 | 83.0 | 70.4 | 77.8 | 62.4 |
| 3,3,3,3 | 20%lR3HOBut | 175.4 | 46.2 | 66.4 | 23.3 | |
| 3,3,3,3 | 80%lS3HOBut | 175.4 | 46.2 | 66.4 | 23.3 | |
|
There is only one chemically distinct structure:
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Found 1 record.
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