Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
hemorrhagic colitis (HC) [ICD11:
1A40.0 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 22572125Publication DOI: 10.1016/j.carres.2012.02.020Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm <gw
organ.su.se>
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
The structure of the repeating unit of the O-antigenic polysaccharide (PS) from Escherichia coli O174 has been determined. Component analysis together with (1)H and (13)C NMR spectroscopy experiments were employed to elucidate the structure. Inter-residue correlations were determined by (1)H,(13)C-heteronuclear multiple-bond correlation and (1)H,(1)H-NOESY experiments. The PS is composed of tetrasaccharide repeating units with the following structure: Cross-peaks of low intensity were present in the NMR spectra consistent with a β-D-GlcpNAc-(1→2)-β-D-GlcpA(1→ structural element at the terminal part of the polysaccharide, which on average is composed of approximately 15 repeating units. Consequently the biological repeating unit has a 3-substituted N-acetyl-d-galactosamine residue at its reducing end.
Lipopolysaccharide, NMR, Escherichia coli, biological repeating unit
Structure type: polymer biological repeating unit ; n=15
Location inside paper: abstract, p.103
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_134627,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_147450,IEDB_151531,IEDB_190606,IEDB_423153,SB_165,SB_166,SB_187,SB_195,SB_23,SB_24,SB_7,SB_8,SB_88
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, sugar analysis, GLC, NMR-1D
Related record ID(s): 28337, 28338, 28862, 29965, 30040
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G25286AF
Show glycosyltransferases
NMR conditions: in D2O at 331 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,2 Ac 175.54 23.11
3,3,2 bDGlcpN 102.76 56.86 74.54 71.13 77.01 61.96
3,3 bDGlcpA 103.19 81.60 75.30 80.26 77.06 175.15
3 bDGalp 104.71 70.38 84.96 68.52 75.53 61.85
2 Ac 175.42 23.50
bDGalpN 101.54 51.72 81.10 68.70 75.64 61.94
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,2 Ac - 2.04
3,3,2 bDGlcpN 4.81 3.67 3.56 3.37 3.47 3.71-3.93
3,3 bDGlcpA 4.68 3.61 3.65 3.78 3.69 -
3 bDGalp 4.51 3.68 3.68 4.10 3.64 3.72
2 Ac - 2.02
bDGalpN 4.53 4.01 3.83 4.17 3.70 3.77-3.80
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,2 Ac 23.11/2.04
3,3,2 bDGlcpN 102.76/4.81 56.86/3.67 74.54/3.56 71.13/3.37 77.01/3.47 61.96/3.71-3.93
3,3 bDGlcpA 103.19/4.68 81.60/3.61 75.30/3.65 80.26/3.78 77.06/3.69
3 bDGalp 104.71/4.51 70.38/3.68 84.96/3.68 68.52/4.10 75.53/3.64 61.85/3.72
2 Ac 23.50/2.02
bDGalpN 101.54/4.53 51.72/4.01 81.10/3.83 68.70/4.17 75.64/3.70 61.94/3.77-3.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,2 | Ac |
| 2.04 | |
| 3,3,2 | bDGlcpN | 4.81 | 3.67 | 3.56 | 3.37 | 3.47 | 3.71
3.93 |
| 3,3 | bDGlcpA | 4.68 | 3.61 | 3.65 | 3.78 | 3.69 |
|
| 3 | bDGalp | 4.51 | 3.68 | 3.68 | 4.10 | 3.64 | 3.72 |
| 2 | Ac |
| 2.02 | |
| | bDGalpN | 4.53 | 4.01 | 3.83 | 4.17 | 3.70 | 3.77
3.80 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,2 | Ac | 175.54 | 23.11 | |
| 3,3,2 | bDGlcpN | 102.76 | 56.86 | 74.54 | 71.13 | 77.01 | 61.96 |
| 3,3 | bDGlcpA | 103.19 | 81.60 | 75.30 | 80.26 | 77.06 | 175.15 |
| 3 | bDGalp | 104.71 | 70.38 | 84.96 | 68.52 | 75.53 | 61.85 |
| 2 | Ac | 175.42 | 23.50 | |
| | bDGalpN | 101.54 | 51.72 | 81.10 | 68.70 | 75.64 | 61.94 |
|
There is only one chemically distinct structure:
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