Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 29738687Publication DOI: 10.1134/S0006297918050061Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: Y. A. Knirel <yknirel
gmail.com>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, 300457, China, Winogradsky Institute of Microbiology, Research Center of Biotechnology, Russian Academy of Sciences, Moscow, Russia, Federal Research and Clinical Centre of Physico-Chemical Medicine, Moscow, Russia
Glycerophosphate-containing O-specific polysaccharides (OPSs) were obtained by mild acidic degradation of lipopolysaccharides isolated from Escherichia coli type strain O81 and E. coli strain HS3-104 from horse feces. The structures of both OPSs and of the oligosaccharide derived from the strain O81 OPS by treatment with 48% HF were studied by monosaccharide analysis and one- and two-dimensional 1H- and 13C-NMR spectroscopy. Both OPSs had similar structures and differed only in the presence of a side-chain glucose residue in the strain HS3-104 OPS. The genes and the organization of the O-antigen biosynthesis gene cluster in both strains are almost identical with the exception of the gtr gene cluster responsible for glucosylations in the strain HS3-104, which is located elsewhere in the genome.
Escherichia coli, O-specific polysaccharide, bacterial polysaccharide structure, ipopolysaccharide, O-antigen gene cluster, glucosylation
Structure type: polymer chemical repeating unit
Location inside paper: p.537, fig.2, E. coli O81 OPS, table 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130695,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_7
Methods: 13C NMR, 1H NMR, gel filtration, NMR-2D, DNA sequencing, sugar analysis, 31P NMR, GC, HF treatment, mild acid degradation, function analysis of gene clusters
Enzymes that release or process the structure: Wzy, Orf9 (WbdN), Orf8 (WffI), Orf7, Orf4, Orf5
Comments, role: E. coli O81 (laboratory stock number G1217);
Related record ID(s): 12454, 12456, 12461
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G95157DB
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,4,2 Ac 175.2-176.4 23.7-23.9
3,4,4 bDGalpN 103.8 53.6 72.8 69.1 74.3 69.3
3,4,2 Ac 175.2-176.4 23.7-23.9
3,4,3,0 xDGro 67.8 72.2 63.7
3,4,3 P
3,4 bDGalpN 102.9 53.2 75.9 75.7 75.6 62.3
3,6 aDGalp 100.3 69.7 70.8 70.7 72.7 62.6
3 bDGlcp 105.1 73.8 75.7 80.9 74.8 67.8
2 Ac 175.2-176.4 23.7-23.9
bDGalpN 102.6 52.5 81.7 69.4 76.1 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,4,2 Ac - 2.03-2.08
3,4,4 bDGalpN 4.66 3.97 3.68 3.90 3.75 3.84-3.99
3,4,2 Ac - 2.03-2.08
3,4,3,0 xDGro 3.86-3.89 3.89 3.60-3.65
3,4,3 P
3,4 bDGalpN 4.52 3.94 4.23 4.20 3.71 3.71-3.80
3,6 aDGalp 4.97 3.83 3.81 3.99 3.87 3.76
3 bDGlcp 4.50 3.32 3.63 3.56 3.68 3.74-3.77
2 Ac - 2.03-2.08
bDGalpN 4.56 3.99 3.88 4.09 3.67 3.80
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,4,2 Ac 23.7-23.9/2.03-2.08
3,4,4 bDGalpN 103.8/4.66 53.6/3.97 72.8/3.68 69.1/3.90 74.3/3.75 69.3/3.84-3.99
3,4,2 Ac 23.7-23.9/2.03-2.08
3,4,3,0 xDGro 67.8/3.86-3.89 72.2/3.89 63.7/3.60-3.65
3,4,3 P
3,4 bDGalpN 102.9/4.52 53.2/3.94 75.9/4.23 75.7/4.20 75.6/3.71 62.3/3.71-3.80
3,6 aDGalp 100.3/4.97 69.7/3.83 70.8/3.81 70.7/3.99 72.7/3.87 62.6/3.76
3 bDGlcp 105.1/4.50 73.8/3.32 75.7/3.63 80.9/3.56 74.8/3.68 67.8/3.74-3.77
2 Ac 23.7-23.9/2.03-2.08
bDGalpN 102.6/4.56 52.5/3.99 81.7/3.88 69.4/4.09 76.1/3.67 62.4/3.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,4,2 | Ac |
| 2.03
2.08 | |
| 3,4,4 | bDGalpN | 4.66 | 3.97 | 3.68 | 3.90 | 3.75 | 3.84
3.99 |
| 3,4,2 | Ac |
| 2.03
2.08 | |
| 3,4,3,0 | xDGro | 3.86
3.89 | 3.89 | 3.60
3.65 | |
| 3,4,3 | P | |
| 3,4 | bDGalpN | 4.52 | 3.94 | 4.23 | 4.20 | 3.71 | 3.71
3.80 |
| 3,6 | aDGalp | 4.97 | 3.83 | 3.81 | 3.99 | 3.87 | 3.76 |
| 3 | bDGlcp | 4.50 | 3.32 | 3.63 | 3.56 | 3.68 | 3.74
3.77 |
| 2 | Ac |
| 2.03
2.08 | |
| | bDGalpN | 4.56 | 3.99 | 3.88 | 4.09 | 3.67 | 3.80 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,4,2 | Ac | 175.2
176.4 | 23.7
23.9 | |
| 3,4,4 | bDGalpN | 103.8 | 53.6 | 72.8 | 69.1 | 74.3 | 69.3 |
| 3,4,2 | Ac | 175.2
176.4 | 23.7
23.9 | |
| 3,4,3,0 | xDGro | 67.8 | 72.2 | 63.7 | |
| 3,4,3 | P | |
| 3,4 | bDGalpN | 102.9 | 53.2 | 75.9 | 75.7 | 75.6 | 62.3 |
| 3,6 | aDGalp | 100.3 | 69.7 | 70.8 | 70.7 | 72.7 | 62.6 |
| 3 | bDGlcp | 105.1 | 73.8 | 75.7 | 80.9 | 74.8 | 67.8 |
| 2 | Ac | 175.2
176.4 | 23.7
23.9 | |
| | bDGalpN | 102.6 | 52.5 | 81.7 | 69.4 | 76.1 | 62.4 |
|
There is only one chemically distinct structure:
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