Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: septicemia [ICD11:
MA15.Y 
];
meningitis [ICD11:
1D01 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 9851702Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: G. Widmalm <gw
organ.su.se>
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Karolinska Institute, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical and Oral Bacteriology, Huddinge University Hospital, Huddinge, Sweden
The structure of the O-antigenic polysaccharide from Escherichia coli O35 has been investigated with the aid of NMR spectroscopy, sugar and methylation analyses. The sequence of the sugar residues could be determined by NOESY and heteronuclear-multiple-bond-connectivity NMR experiments. The polysaccharide is composed of hexasaccharide repeating units with the following structure, where Rha and GalNAcAN represent rhamnose and 2-acetamido-2-deoxy-galacturonamide, respectively: carbohydrate sequence [see text]. The O-antigen of Escherichia coli O35 is similar to the O-specific polysaccharide from Salmonella arizonae O62, which instead has a terminal 2-acetamido-2-deoxy-α-D-galacturonic acid residue. Immunochemical analyses using a rabbit antiserum specific for the Salmonella arizonae O62 O-antigen showed an identical reactivity with both lipopolysaccharides
Lipopolysaccharide, NMR, LPS, structure, structural, polysaccharide, O-antigen, Escherichia, Escherichia coli, determination, O-antigenic, O-antigenic polysaccharide, structural determination, Salmonella, cross-reactivity, crossreactivity, Salmonella arizonae
Structure type: suggested polymer biological repeating unit
Location inside paper: p.139, p.142
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_143254,IEDB_151531,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, EIA
Biosynthesis and genetic data: serological data
Comments, role: chemical repeat frame is different in the paper
Related record ID(s): 20697, 30390
NCBI Taxonomy refs (TaxIDs): 2072460Reference(s) to other database(s): GTC:G30649ZY, GlycomeDB:
28131
Show glycosyltransferases
NMR conditions: in D2O at 323 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,3,2,2,2 Ac 175.4 22.8
3,2,3,2,2,6 NH2
3,2,3,2,2 aDGalpNA 95.6 50.0 67.8 69.5 72.0 174.6
3,2,3,2 aLRhap 99.5 75.3 79.2 72.2 70.3 17.5
3,2,3 aLRhap 101.7 78.4 70.6 72.9 69.7 17.5
3,2 aLRhap 103.1 70.6 78.4 72.1 69.7 17.5
3 aLRhap 100.6 80.6 70.6 73.1 69.7 17.5
2 Ac 175.1 23.4
bDGlcpN 103.4 56.7 82.3 70.0 76.4 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,3,2,2,2 Ac - 2.03
3,2,3,2,2,6 NH2 7.80
3,2,3,2,2 aDGalpNA 5.12 4.16 4.00 4.35 4.82 -
3,2,3,2 aLRhap 4.95 4.35 3.91 3.54 3.71 1.27
3,2,3 aLRhap 5.15 4.05 3.94 3.44 3.81 1.29
3,2 aLRhap 4.86 4.11 3.82 3.54 3.76 1.27
3 aLRhap 5.01 3.78 3.87 3.45 3.99 1.24
2 Ac - 2.06
bDGlcpN 4.69 3.71 3.59 3.32 3.41 3.66-3.90
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,3,2,2,2 Ac 22.8/2.03
3,2,3,2,2,6 NH2 NMR TSV error 2: unequal length of 13C and 1H datasets
3,2,3,2,2 aDGalpNA 95.6/5.12 50.0/4.16 67.8/4.00 69.5/4.35 72.0/4.82
3,2,3,2 aLRhap 99.5/4.95 75.3/4.35 79.2/3.91 72.2/3.54 70.3/3.71 17.5/1.27
3,2,3 aLRhap 101.7/5.15 78.4/4.05 70.6/3.94 72.9/3.44 69.7/3.81 17.5/1.29
3,2 aLRhap 103.1/4.86 70.6/4.11 78.4/3.82 72.1/3.54 69.7/3.76 17.5/1.27
3 aLRhap 100.6/5.01 80.6/3.78 70.6/3.87 73.1/3.45 69.7/3.99 17.5/1.24
2 Ac 23.4/2.06
bDGlcpN 103.4/4.69 56.7/3.71 82.3/3.59 70.0/3.32 76.4/3.41 62.0/3.66-3.90
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,3,2,2,2 | Ac |
| 2.03 | |
| 3,2,3,2,2,6 | NH2 | 7.80 | |
| 3,2,3,2,2 | aDGalpNA | 5.12 | 4.16 | 4.00 | 4.35 | 4.82 |
|
| 3,2,3,2 | aLRhap | 4.95 | 4.35 | 3.91 | 3.54 | 3.71 | 1.27 |
| 3,2,3 | aLRhap | 5.15 | 4.05 | 3.94 | 3.44 | 3.81 | 1.29 |
| 3,2 | aLRhap | 4.86 | 4.11 | 3.82 | 3.54 | 3.76 | 1.27 |
| 3 | aLRhap | 5.01 | 3.78 | 3.87 | 3.45 | 3.99 | 1.24 |
| 2 | Ac |
| 2.06 | |
| | bDGlcpN | 4.69 | 3.71 | 3.59 | 3.32 | 3.41 | 3.66
3.90 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,3,2,2,2 | Ac | 175.4 | 22.8 | |
| 3,2,3,2,2,6 | NH2 | |
| 3,2,3,2,2 | aDGalpNA | 95.6 | 50.0 | 67.8 | 69.5 | 72.0 | 174.6 |
| 3,2,3,2 | aLRhap | 99.5 | 75.3 | 79.2 | 72.2 | 70.3 | 17.5 |
| 3,2,3 | aLRhap | 101.7 | 78.4 | 70.6 | 72.9 | 69.7 | 17.5 |
| 3,2 | aLRhap | 103.1 | 70.6 | 78.4 | 72.1 | 69.7 | 17.5 |
| 3 | aLRhap | 100.6 | 80.6 | 70.6 | 73.1 | 69.7 | 17.5 |
| 2 | Ac | 175.1 | 23.4 | |
| | bDGlcpN | 103.4 | 56.7 | 82.3 | 70.0 | 76.4 | 62.0 |
|
There is only one chemically distinct structure:
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