Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ]
The structure was elucidated in this paperNCBI PubMed ID: 21232736Publication DOI: 10.1016/j.carres.2010.12.009Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
The O-polysaccharide of Vibrio cholerae O43 was studied using chemical analyses, triflic acid solvolysis and 2D NMR spectroscopy, including (1)H/(1)H COSY, TOCSY, NOESY and (1)H/(13)C gradient-selected HSQC experiments. The following structure of the tetrasaccharide repeating unit of the polysaccharide was established: →3)-β-D-Quip4NAcyl-(1→3)-α-D-GalpNAcA-(1→4)-α-D-GalpNAc-(1→3)-α-D-QuipNAc-(1→ where D-QuiNAc stands for 2-acetamido-2,6-dideoxy-D-glucose, D-Qui4NAcyl for 4-(N-acetyl-L-allothreonyl)amino-4,6-dideoxy-D-glucose and D-GalNAcA for 2-acetamido-2-deoxy-D-galacturonic acid.
Lipopolysaccharide, bacterial polysaccharide structure, Vibrio cholerae, 4-amino-4, O-antigen gene cluster, L-allothreonine, 6-D-dideoxy-D-glucose
Structure type: oligomer
Location inside paper: p.431, 1
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_885822
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, GLC, triflic acid solvolysis, delipidation, function analysis of gene clusters
Biosynthesis and genetic data: genetic data
Comments, role: Solvolysis of the OPS with triflic acid.
Related record ID(s): 26911, 26912
NCBI Taxonomy refs (TaxIDs): 666Reference(s) to other database(s): GTC:G39763JM
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2 Ac 174.6-175.6 23.1-23.7
3,4 aDGalpNA 99.3 50.8 68.1 69.9 72.5 ?
3,2 Ac 174.6-175.6 23.1-23.7
3 aDGalpN 100.2 50.9 67.9 77.4 73.2 61.1
2 Ac 174.6-175.6 23.1-23.7
xDQuiN-ol 61.5 54.8 77.2 75.3 67.8 19.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 Ac - 2.00-2.07
3,4 aDGalpNA 5.08 4.24 4.11 4.32 4.89 -
3,2 Ac - 2.00-2.07
3 aDGalpN 5.19 4.28 4.05 4.13 4.06 3.71-3.77
2 Ac - 2.00-2.07
xDQuiN-ol 3.75-3.85 4.23 4.07 3.47 3.69 1.20
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 Ac 23.1-23.7/2.00-2.07
3,4 aDGalpNA 99.3/5.08 50.8/4.24 68.1/4.11 69.9/4.32 72.5/4.89
3,2 Ac 23.1-23.7/2.00-2.07
3 aDGalpN 100.2/5.19 50.9/4.28 67.9/4.05 77.4/4.13 73.2/4.06 61.1/3.71-3.77
2 Ac 23.1-23.7/2.00-2.07
xDQuiN-ol 61.5/3.75-3.85 54.8/4.23 77.2/4.07 75.3/3.47 67.8/3.69 19.9/1.20
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | Ac |
| 2.00
2.07 | |
| 3,4 | aDGalpNA | 5.08 | 4.24 | 4.11 | 4.32 | 4.89 |
|
| 3,2 | Ac |
| 2.00
2.07 | |
| 3 | aDGalpN | 5.19 | 4.28 | 4.05 | 4.13 | 4.06 | 3.71
3.77 |
| 2 | Ac |
| 2.00
2.07 | |
| | xDQuiN-ol | 3.75
3.85 | 4.23 | 4.07 | 3.47 | 3.69 | 1.20 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | Ac | 174.6
175.6 | 23.1
23.7 | |
| 3,4 | aDGalpNA | 99.3 | 50.8 | 68.1 | 69.9 | 72.5 | ? |
| 3,2 | Ac | 174.6
175.6 | 23.1
23.7 | |
| 3 | aDGalpN | 100.2 | 50.9 | 67.9 | 77.4 | 73.2 | 61.1 |
| 2 | Ac | 174.6
175.6 | 23.1
23.7 | |
| | xDQuiN-ol | 61.5 | 54.8 | 77.2 | 75.3 | 67.8 | 19.9 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175.1,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":99.3,"l":"1","c":[0,0,225]},{"s":50.8,"l":"2","c":[0,0,225]},{"s":68.1,"l":"3","c":[0,0,225]},{"s":69.9,"l":"4","c":[0,0,225]},{"s":72.5,"l":"5","c":[0,0,225]},{"s":175.1,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":100.2,"l":"1","c":[230,0,30]},{"s":50.9,"l":"2","c":[230,0,30]},{"s":67.9,"l":"3","c":[230,0,30]},{"s":77.4,"l":"4","c":[230,0,30]},{"s":73.2,"l":"5","c":[230,0,30]},{"s":61.1,"l":"6","c":[230,0,30]},{"s":175.1,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":61.5,"l":"1","c":[0,165,0]},{"s":54.8,"l":"2","c":[0,165,0]},{"s":77.2,"l":"3","c":[0,165,0]},{"s":75.3,"l":"4","c":[0,165,0]},{"s":67.8,"l":"5","c":[0,165,0]},{"s":19.9,"l":"6","c":[0,165,0]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Found 
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