Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 27203746Publication DOI: 10.1016/j.carres.2016.04.028Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, State Key Laboratory for Infectious Disease Prevention and Control, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, National Institute for Communicable Disease Control and Prevention, Chin
The O-specific polysaccharide (O-antigen) of Escherichia coli O133 was obtained by mild acid hydrolysis of the lipopolysaccharide of E. coli O133. The structure of the hexasaccharide repeating unit of the polysaccharide was elucidated by (1)H and (13)C NMR spectroscopy, including a two-dimensional (1)H-(1)H ROESY experiment: Functions of genes in the O-antigen gene cluster were putatively identified by comparison with sequences in the available databases and, particularly, an encoded predicted multifunctional glycosyltransferase was assigned to three a-l-rhamnosidic linkages.
Escherichia coli, O-Specific polysaccharide structure, Glycosyltransferase trifunctional, O-antigen biosynthesis gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.83
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_141807,IEDB_142488,IEDB_144825,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, GPC, mild acid degradation, function analysis of gene clusters
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G14694RX
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2,2 aLRhap 103.4 68.0 76.5 71.6 70.5 17.9
3,4,2 aLRhap 101.1 80.0 71.0 73.4 70.4 17.9
3,4 aLRhap 98.9 76.9 72.0 73.4 70.4 17.8
3,3 aDGlcp 97.9 72.5 74.2 70.7 73.2 61.8
3 aDGalpA 102.1 68.6 77.7 72.3 72.9 175.0
2 Ac 175.7 23.3
aDGlcpN 95.6 53.4 80.9 71.6 72.9 61.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2,2 aLRhap 4.97 4.22 3.83 3.53 3.76 1.29
3,4,2 aLRhap 5.30 4.07 3.88 3.44 3.79 1.31
3,4 aLRhap 5.62 4.05 3.86 3.41 3.72 1.25
3,3 aDGlcp 5.15 3.59 3.64 3.44 3.96 3.76-3.83
3 aDGalpA 5.37 4.10 4.07 4.61 4.22 -
2 Ac - 1.99
aDGlcpN 5.03 4.06 3.99 3.77 4.04 3.79-3.81
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2,2 aLRhap 103.4/4.97 68.0/4.22 76.5/3.83 71.6/3.53 70.5/3.76 17.9/1.29
3,4,2 aLRhap 101.1/5.30 80.0/4.07 71.0/3.88 73.4/3.44 70.4/3.79 17.9/1.31
3,4 aLRhap 98.9/5.62 76.9/4.05 72.0/3.86 73.4/3.41 70.4/3.72 17.8/1.25
3,3 aDGlcp 97.9/5.15 72.5/3.59 74.2/3.64 70.7/3.44 73.2/3.96 61.8/3.76-3.83
3 aDGalpA 102.1/5.37 68.6/4.10 77.7/4.07 72.3/4.61 72.9/4.22
2 Ac 23.3/1.99
aDGlcpN 95.6/5.03 53.4/4.06 80.9/3.99 71.6/3.77 72.9/4.04 61.4/3.79-3.81
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2,2 | aLRhap | 4.97 | 4.22 | 3.83 | 3.53 | 3.76 | 1.29 |
| 3,4,2 | aLRhap | 5.30 | 4.07 | 3.88 | 3.44 | 3.79 | 1.31 |
| 3,4 | aLRhap | 5.62 | 4.05 | 3.86 | 3.41 | 3.72 | 1.25 |
| 3,3 | aDGlcp | 5.15 | 3.59 | 3.64 | 3.44 | 3.96 | 3.76
3.83 |
| 3 | aDGalpA | 5.37 | 4.10 | 4.07 | 4.61 | 4.22 |
|
| 2 | Ac |
| 1.99 | |
| | aDGlcpN | 5.03 | 4.06 | 3.99 | 3.77 | 4.04 | 3.79
3.81 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2,2 | aLRhap | 103.4 | 68.0 | 76.5 | 71.6 | 70.5 | 17.9 |
| 3,4,2 | aLRhap | 101.1 | 80.0 | 71.0 | 73.4 | 70.4 | 17.9 |
| 3,4 | aLRhap | 98.9 | 76.9 | 72.0 | 73.4 | 70.4 | 17.8 |
| 3,3 | aDGlcp | 97.9 | 72.5 | 74.2 | 70.7 | 73.2 | 61.8 |
| 3 | aDGalpA | 102.1 | 68.6 | 77.7 | 72.3 | 72.9 | 175.0 |
| 2 | Ac | 175.7 | 23.3 | |
| | aDGlcpN | 95.6 | 53.4 | 80.9 | 71.6 | 72.9 | 61.4 |
|
There is only one chemically distinct structure:
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