Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 8706764Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
The structure of the polysaccharide part of the lipopolysaccharide obtained from the enteropathogenic Escherichia coli O125 has been investigated. Methylation analysis, 1H NMR spectroscopy and 13C NMR spectroscopy revealed that the polysaccharide is composed of repeating hexasaccharide units. Smith degradation of the native O-polysaccharide resulted in a polysaccharide with four sugar residues in the repeating unit. Information on the sequence of the native O-polysaccharide and the Smith-degraded product was obtained by two-dimensional techniques, namely heteronuclear-multiple-bond-connectivity and NOESY experiments. The structure of the repeating unit of the O-polysaccharide of E. coli strain O125, which has two adjacent branch-point residues, is [sequence: see text].
Lipopolysaccharide, NMR, antigen, LPS, structural, polysaccharide, analysis, Escherichia, Escherichia coli, O-antigenic, O-antigenic polysaccharide, O-polysaccharide, structural analysis, enteropathogenic
Structure type: suggested polymer biological repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_134627,IEDB_136044,IEDB_136045,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_147450,IEDB_152206,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_885822,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_23,SB_24,SB_44,SB_67,SB_7,SB_72,SB_8,SB_86,SB_88
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, SDS-PAGE, sugar analysis, GC, Smith degradation, GPC
Comments, role: biological repeat frame was based on GT homology analysis; chemical repeat frame is different in the paper
Related record ID(s): 1286, 20678
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G41918HP, GlycomeDB:
25322
Show glycosyltransferases
NMR conditions: in D2O at 348 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2,2 Ac 175.5-175.6 23.3-23.5
3,3,2,3 bDGalp 106.0 71.5 73.5 69.6 75.9 ?
3,3,2 bDGalpN 101.8 52.6 79.0 74.8 76.3 ?
3,3,3 aDGlcp 101.3 72.7 74.2 70.9 72.9 ?
3,3 aDManp 100.2 78.8 77.0 67.7 74.9 ?
3 aLFucp 101.8 68.4 78.3 72.4 67.8 16.0
2 Ac 175.5-175.6 23.3-23.5
aDGalpN 98.5 49.8 76.4 69.3 71.0 ?
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2,2 Ac - 2.05-2.11
3,3,2,3 bDGalp 4.45 3.54 3.63 3.92 3.66 ?
3,3,2 bDGalpN 4.60 4.17 3.95 4.29 3.74 ?
3,3,3 aDGlcp 5.26 3.57 3.74 3.40 3.91 ?
3,3 aDManp 5.11 4.22 4.11 3.82 3.75 ?
3 aLFucp 5.10 3.88 4.00 3.96 4.17 1.22
2 Ac - 2.05-2.11
aDGalpN 5.06 4.48 4.10 4.14 4.51 3.79
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2,2 Ac 23.3-23.5/2.05-2.11
3,3,2,3 bDGalp 106.0/4.45 71.5/3.54 73.5/3.63 69.6/3.92 75.9/3.66 ?/?
3,3,2 bDGalpN 101.8/4.60 52.6/4.17 79.0/3.95 74.8/4.29 76.3/3.74 ?/?
3,3,3 aDGlcp 101.3/5.26 72.7/3.57 74.2/3.74 70.9/3.40 72.9/3.91 ?/?
3,3 aDManp 100.2/5.11 78.8/4.22 77.0/4.11 67.7/3.82 74.9/3.75 ?/?
3 aLFucp 101.8/5.10 68.4/3.88 78.3/4.00 72.4/3.96 67.8/4.17 16.0/1.22
2 Ac 23.3-23.5/2.05-2.11
aDGalpN 98.5/5.06 49.8/4.48 76.4/4.10 69.3/4.14 71.0/4.51 ?/3.79
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2,2 | Ac |
| 2.05
2.11 | |
| 3,3,2,3 | bDGalp | 4.45 | 3.54 | 3.63 | 3.92 | 3.66 | ? |
| 3,3,2 | bDGalpN | 4.60 | 4.17 | 3.95 | 4.29 | 3.74 | ? |
| 3,3,3 | aDGlcp | 5.26 | 3.57 | 3.74 | 3.40 | 3.91 | ? |
| 3,3 | aDManp | 5.11 | 4.22 | 4.11 | 3.82 | 3.75 | ? |
| 3 | aLFucp | 5.10 | 3.88 | 4.00 | 3.96 | 4.17 | 1.22 |
| 2 | Ac |
| 2.05
2.11 | |
| | aDGalpN | 5.06 | 4.48 | 4.10 | 4.14 | 4.51 | 3.79 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2,2 | Ac | 175.5
175.6 | 23.3
23.5 | |
| 3,3,2,3 | bDGalp | 106.0 | 71.5 | 73.5 | 69.6 | 75.9 | ? |
| 3,3,2 | bDGalpN | 101.8 | 52.6 | 79.0 | 74.8 | 76.3 | ? |
| 3,3,3 | aDGlcp | 101.3 | 72.7 | 74.2 | 70.9 | 72.9 | ? |
| 3,3 | aDManp | 100.2 | 78.8 | 77.0 | 67.7 | 74.9 | ? |
| 3 | aLFucp | 101.8 | 68.4 | 78.3 | 72.4 | 67.8 | 16.0 |
| 2 | Ac | 175.5
175.6 | 23.3
23.5 | |
| | aDGalpN | 98.5 | 49.8 | 76.4 | 69.3 | 71.0 | ? |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175.55,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":106,"l":"1","c":[0,0,225]},{"s":71.5,"l":"2","c":[0,0,225]},{"s":73.5,"l":"3","c":[0,0,225]},{"s":69.6,"l":"4","c":[0,0,225]},{"s":75.9,"l":"5","c":[0,0,225]},{"s":101.8,"l":"1","c":[230,0,30]},{"s":52.6,"l":"2","c":[230,0,30]},{"s":79,"l":"3","c":[230,0,30]},{"s":74.8,"l":"4","c":[230,0,30]},{"s":76.3,"l":"5","c":[230,0,30]},{"s":101.3,"l":"1","c":[0,165,0]},{"s":72.7,"l":"2","c":[0,165,0]},{"s":74.2,"l":"3","c":[0,165,0]},{"s":70.9,"l":"4","c":[0,165,0]},{"s":72.9,"l":"5","c":[0,165,0]},{"s":100.2,"l":"1","c":[120,0,225]},{"s":78.8,"l":"2","c":[120,0,225]},{"s":77,"l":"3","c":[120,0,225]},{"s":67.7,"l":"4","c":[120,0,225]},{"s":74.9,"l":"5","c":[120,0,225]},{"s":101.8,"l":"1","c":[0,192,255]},{"s":68.4,"l":"2","c":[0,192,255]},{"s":78.3,"l":"3","c":[0,192,255]},{"s":72.4,"l":"4","c":[0,192,255]},{"s":67.8,"l":"5","c":[0,192,255]},{"s":16,"l":"6","c":[0,192,255]},{"s":175.55,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":98.5,"l":"1","c":[220,0,180]},{"s":49.8,"l":"2","c":[220,0,180]},{"s":76.4,"l":"3","c":[220,0,180]},{"s":69.3,"l":"4","c":[220,0,180]},{"s":71,"l":"5","c":[220,0,180]}])
The spectrum also has 5 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
