Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 26232763Publication DOI: 10.1016/j.carres.2015.05.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru (A. V. Perepelov)
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Laboratory Medicine, Division of Clinical Microbiology, Karolinska Institute, Karolinska University Hospital, Stockholm, Sweden
The O-polysaccharide (O-antigen) of Escherichia coli O169 was studied by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the branched hexasaccharide repeating unit was established: [Formula: see text] The O-polysaccharide of E. coli O169 differs from that of Shigella boydii type 6 only in the presence of a side-chain glucose residue. A comparison of the O-antigen biosynthesis gene clusters between the galF to gnd genes in the genomes of the two bacteria revealed their close relationship. The glycosyltransferase gene responsible for the formation of the β-D-Glcp-(1→6)-α-D-Galp linkage in the O-antigen was identified in the gene cluster.
O-antigen, Escherichia coli, bacterial polysaccharide structure, Shigella boydii, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.49, chart 1, E. coli O169
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_130701,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_423153,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_21,SB_44,SB_67,SB_7,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, Smith degradation, NMR-1D, GPC, function analysis of gene clusters
Biosynthesis and genetic data: genetic data
Related record ID(s): 30837, 30838
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G37981QG
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,6,4 bDGlcpA 103.9 75.6 77.7 73.9 77.6 176.6
3,2,6,6 bDGlcp 104.7 75.3 77.8 71.8 78.0 62.
3,2,6 aDGalp 100.4 69.7 81.3 78.3 72.1 71.8
3,2 aDManp 104.3 72.2 73.5 68.1 72.7 67.4
3 aDManp 96.7 80.7 72.5 68.4 75.6 63.0
2 Ac 176.6 24.6
bDGalpN 105.3 53.2 77.6 65.7 76.8 63.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,6,4 bDGlcpA 4.94 3.30 3.55 3.53 3.76 -
3,2,6,6 bDGlcp 4.46 3.27 3.48 3.38 3.42 3.79-3.90
3,2,6 aDGalp 4.97 4.04 4.07 4.47 4.15 3.86-4.06
3,2 aDManp 5.06 4.08 3.87 3.95 3.83 3.54-4.17
3 aDManp 5.13 4.01 3.84 3.72 3.55 3.75-3.84
2 Ac - 2.02
bDGalpN 4.72 4.04 3.83 4.13 3.64 3.79-3.79
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,6,4 bDGlcpA 103.9/4.94 75.6/3.30 77.7/3.55 73.9/3.53 77.6/3.76
3,2,6,6 bDGlcp 104.7/4.46 75.3/3.27 77.8/3.48 71.8/3.38 78.0/3.42 62./3.79-3.90
3,2,6 aDGalp 100.4/4.97 69.7/4.04 81.3/4.07 78.3/4.47 72.1/4.15 71.8/3.86-4.06
3,2 aDManp 104.3/5.06 72.2/4.08 73.5/3.87 68.1/3.95 72.7/3.83 67.4/3.54-4.17
3 aDManp 96.7/5.13 80.7/4.01 72.5/3.84 68.4/3.72 75.6/3.55 63.0/3.75-3.84
2 Ac 24.6/2.02
bDGalpN 105.3/4.72 53.2/4.04 77.6/3.83 65.7/4.13 76.8/3.64 63.2/3.79-3.79
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,6,4 | bDGlcpA | 4.94 | 3.30 | 3.55 | 3.53 | 3.76 |
|
| 3,2,6,6 | bDGlcp | 4.46 | 3.27 | 3.48 | 3.38 | 3.42 | 3.79
3.90 |
| 3,2,6 | aDGalp | 4.97 | 4.04 | 4.07 | 4.47 | 4.15 | 3.86
4.06 |
| 3,2 | aDManp | 5.06 | 4.08 | 3.87 | 3.95 | 3.83 | 3.54
4.17 |
| 3 | aDManp | 5.13 | 4.01 | 3.84 | 3.72 | 3.55 | 3.75
3.84 |
| 2 | Ac |
| 2.02 | |
| | bDGalpN | 4.72 | 4.04 | 3.83 | 4.13 | 3.64 | 3.79
3.79 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,6,4 | bDGlcpA | 103.9 | 75.6 | 77.7 | 73.9 | 77.6 | 176.6 |
| 3,2,6,6 | bDGlcp | 104.7 | 75.3 | 77.8 | 71.8 | 78.0 | 62. |
| 3,2,6 | aDGalp | 100.4 | 69.7 | 81.3 | 78.3 | 72.1 | 71.8 |
| 3,2 | aDManp | 104.3 | 72.2 | 73.5 | 68.1 | 72.7 | 67.4 |
| 3 | aDManp | 96.7 | 80.7 | 72.5 | 68.4 | 75.6 | 63.0 |
| 2 | Ac | 176.6 | 24.6 | |
| | bDGalpN | 105.3 | 53.2 | 77.6 | 65.7 | 76.8 | 63.2 |
|
There is only one chemically distinct structure:
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