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: polymer chemical repeating unit
Location inside paper: abstract, p.432
Compound class: O-polysaccharide, O-antigen
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
Related record ID(s): 26311, 26911
NCBI Taxonomy refs (TaxIDs): 666
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,3,4,2 Ac 174.6-175.6 23.1-23.7
3,4,3,4 xLaThr 175.8 60.7 68.3 20.0
3,4,3 bDQuip4N 105.0 73.5 78.1 57.8 72.1 18.0
3,4,2 Ac 174.6-175.6 23.1-23.7
3,4 aDGalpNA 99.4 49.6 78.1 69.9 72.2 172.9
3,2 Ac 174.6-175.6 23.1-23.7
3 aDGalpN 98.3 50.9 68.1 77.4 72.8 61.0
2 Ac 174.6-175.6 23.1-23.7
aDQuipN 97.4 53.1 77.2 77.7 69.2 17.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,3,4,2 Ac - 2.00-2.07
3,4,3,4 xLaThr - 4.23 4.02 1.20
3,4,3 bDQuip4N 4.59 3.45 3.78 3.83 3.58 1.21
3,4,2 Ac - 2.00-2.07
3,4 aDGalpNA 5.07 4.43 4.16 4.54 4.90 -
3,2 Ac - 2.00-2.07
3 aDGalpN 5.52 4.24 3.83 4.09 3.84 3.70-3.74
2 Ac - 2.00-2.07
aDQuipN 5.02 3.94 3.81 3.40 4.17 1.23
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,3,4,2 Ac 23.1-23.7/2.00-2.07
3,4,3,4 xLaThr 60.7/4.23 68.3/4.02 20.0/1.20
3,4,3 bDQuip4N 105.0/4.59 73.5/3.45 78.1/3.78 57.8/3.83 72.1/3.58 18.0/1.21
3,4,2 Ac 23.1-23.7/2.00-2.07
3,4 aDGalpNA 99.4/5.07 49.6/4.43 78.1/4.16 69.9/4.54 72.2/4.90
3,2 Ac 23.1-23.7/2.00-2.07
3 aDGalpN 98.3/5.52 50.9/4.24 68.1/3.83 77.4/4.09 72.8/3.84 61.0/3.70-3.74
2 Ac 23.1-23.7/2.00-2.07
aDQuipN 97.4/5.02 53.1/3.94 77.2/3.81 77.7/3.40 69.2/4.17 17.4/1.23
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,3,4,2 | Ac |
| 2.00
2.07 | |
| 3,4,3,4 | xLaThr |
| 4.23 | 4.02 | 1.20 | |
| 3,4,3 | bDQuip4N | 4.59 | 3.45 | 3.78 | 3.83 | 3.58 | 1.21 |
| 3,4,2 | Ac |
| 2.00
2.07 | |
| 3,4 | aDGalpNA | 5.07 | 4.43 | 4.16 | 4.54 | 4.90 |
|
| 3,2 | Ac |
| 2.00
2.07 | |
| 3 | aDGalpN | 5.52 | 4.24 | 3.83 | 4.09 | 3.84 | 3.70
3.74 |
| 2 | Ac |
| 2.00
2.07 | |
| | aDQuipN | 5.02 | 3.94 | 3.81 | 3.40 | 4.17 | 1.23 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,3,4,2 | Ac | 174.6
175.6 | 23.1
23.7 | |
| 3,4,3,4 | xLaThr | 175.8 | 60.7 | 68.3 | 20.0 | |
| 3,4,3 | bDQuip4N | 105.0 | 73.5 | 78.1 | 57.8 | 72.1 | 18.0 |
| 3,4,2 | Ac | 174.6
175.6 | 23.1
23.7 | |
| 3,4 | aDGalpNA | 99.4 | 49.6 | 78.1 | 69.9 | 72.2 | 172.9 |
| 3,2 | Ac | 174.6
175.6 | 23.1
23.7 | |
| 3 | aDGalpN | 98.3 | 50.9 | 68.1 | 77.4 | 72.8 | 61.0 |
| 2 | Ac | 174.6
175.6 | 23.1
23.7 | |
| | aDQuipN | 97.4 | 53.1 | 77.2 | 77.7 | 69.2 | 17.4 |
|
There is only one chemically distinct structure:
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