Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: functional gastrointestinal disorders [ICD11:
DD9Y 
]
The structure was elucidated in this paperNCBI PubMed ID: 19117553Publication DOI: 10.1016/j.carres.2008.12.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.N. Kondakova <annakond
gmail.com>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
The O-specific polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Yersinia pseudotuberculosis O:4a and studied by NMR spectroscopy, including 2D ROESY and (1)H, (13)C HMBC experiments. The following structure of the pentasaccharide repeating unit of the polysaccharide was established, which differs from the structure reported earlier [Gorshkova, R. P. et al., Bioorg. Khim. 1983, 9, 1401-1407] in the linkage modes between the monosaccharides: [carbohydrate sequence see in text] where Tyv stands for 3,6-dideoxy-D-arabino-hexose (tyvelose). The structure of the Y. pseudotuberculosis O:4a antigen resembles that of Y. pseudotuberculosis O:2c, which differs in the presence of abequose (3,6-dideoxy-D-xylo-hexose) in place of tyvelose only.
O-antigen, Yersinia pseudotuberculosis, bacterial polysaccharide structure, tyvelose
Structure type: polymer chemical repeating unit
Location inside paper: p.533
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130660,IEDB_130701,IEDB_136104,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_139421,IEDB_140116,IEDB_141584,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_885822,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D
NCBI Taxonomy refs (TaxIDs): 633Reference(s) to other database(s): GTC:G32052FV, GlycomeDB:
37278
Show glycosyltransferases
NMR conditions: in D2O at 323 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,2,3 aXTyvp 102.4 68.9 34.8 68.3 71.6 18.1
3,2,2 aDManp 103.8 71.1 79.7 66.6 73.3 66.3
3,2 aDManp 100.7 79.7 71.5 68.0 73.8 62.0
3 bDManp 102.7 76.9 75.3 68.3 78.1 62.4
2 Ac 175.3 23.5
aDGalpN 98.6 50.4 78.3 70.0 72.3 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,2,3 aXTyvp 4.90 4.06 1.90-2.07 3.64 3.84 1.28
3,2,2 aDManp 5.04 4.21 3.93 4.06 3.85 3.58-4.12
3,2 aDManp 5.34 4.08 4.04 3.81 4.01 3.81-3.81
3 bDManp 4.82 4.00 3.72 3.64 3.40 3.74-3.93
2 Ac - 2.05
aDGalpN 4.93 4.33 4.05 4.19 3.99 3.76-3.76
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,2,3 aXTyvp 102.4/4.90 68.9/4.06 34.8/1.90-2.07 68.3/3.64 71.6/3.84 18.1/1.28
3,2,2 aDManp 103.8/5.04 71.1/4.21 79.7/3.93 66.6/4.06 73.3/3.85 66.3/3.58-4.12
3,2 aDManp 100.7/5.34 79.7/4.08 71.5/4.04 68.0/3.81 73.8/4.01 62.0/3.81-3.81
3 bDManp 102.7/4.82 76.9/4.00 75.3/3.72 68.3/3.64 78.1/3.40 62.4/3.74-3.93
2 Ac 23.5/2.05
aDGalpN 98.6/4.93 50.4/4.33 78.3/4.05 70.0/4.19 72.3/3.99 62.4/3.76-3.76
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,2,3 | aXTyvp | 4.90 | 4.06 | 1.90
2.07 | 3.64 | 3.84 | 1.28 |
| 3,2,2 | aDManp | 5.04 | 4.21 | 3.93 | 4.06 | 3.85 | 3.58
4.12 |
| 3,2 | aDManp | 5.34 | 4.08 | 4.04 | 3.81 | 4.01 | 3.81
3.81 |
| 3 | bDManp | 4.82 | 4.00 | 3.72 | 3.64 | 3.40 | 3.74
3.93 |
| 2 | Ac |
| 2.05 | |
| | aDGalpN | 4.93 | 4.33 | 4.05 | 4.19 | 3.99 | 3.76
3.76 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,2,3 | aXTyvp | 102.4 | 68.9 | 34.8 | 68.3 | 71.6 | 18.1 |
| 3,2,2 | aDManp | 103.8 | 71.1 | 79.7 | 66.6 | 73.3 | 66.3 |
| 3,2 | aDManp | 100.7 | 79.7 | 71.5 | 68.0 | 73.8 | 62.0 |
| 3 | bDManp | 102.7 | 76.9 | 75.3 | 68.3 | 78.1 | 62.4 |
| 2 | Ac | 175.3 | 23.5 | |
| | aDGalpN | 98.6 | 50.4 | 78.3 | 70.0 | 72.3 | 62.4 |
|
There is only one chemically distinct structure:
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