Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 10614068Publication DOI: 10.1016/S0008-6215(99)00187-1Journal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Pharmaceutical Sciences, Rhodes University, PO Box 94, Grahamstown 6140, South Africa
The primary structure of the O-antigen of Escherichia coli O116:K+:H10 was shown by monosaccharide analysis, a partial hydrolysis study and by 1D and 2D 1H and 13C NMR spectroscopy to be composed of linear pentasaccharide repeating units with the structure: →6)-a-D-GlcpNAc-(1→4)-a-D-GalpNAc-(1→4)-a-D-GalpA-(1→3)-b-D-GlcpNAc-(1→2)-b-D-Quip4NAc-(1→.
Lipopolysaccharide, structure, O-antigen, Escherichia coli, NMR spectroscopy, O116 antigen
Structure type: suggested polymer biological repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822
Methods: NMR-2D, partial acid hydrolysis, NMR, sugar analysis
Comments, role: chemical repeat frame is different in the paper; biological repeat frame was based on GT homology analysis
Related record ID(s): 3216, 20703
NCBI Taxonomy refs (TaxIDs): 2234129Reference(s) to other database(s): GTC:G34329UM, GlycomeDB:
28134
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,4,6,4 Ac 175.42 ?
3,4,4,6 bDQuip4N 102.69 80.31 75.63 57.84 71.53 17.47
3,4,4,2 Ac 175.04 ?
3,4,4 aDGlcpN 99.32 54.87 71.16 72.00 69.83 69.36
3,4,2 Ac 175.65 ?
3,4 aDGalpN 99.85 50.72 68.07 78.09 72.68 60.66
3 aDGalpA 101.12 69.22 69.83 80.67 72.16 175.14
2 Ac 175.04 ?
bDGlcpN 102.39 55.25 81.91 71.82 76.55 61.93
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,4,6,4 Ac
3,4,4,6 bDQuip4N 4.460 3.604 3.535 3.553 3.530 1.186
3,4,4,2 Ac
3,4,4 aDGlcpN 4.945 3.954 3.885 4.208 3.926 3.902-4.012
3,4,2 Ac
3,4 aDGalpN 5.009 4.278 4.004 4.067 4.346 3.678-3.678
3 aDGalpA 5.344 3.844 3.926 4.338 4.174 -
2 Ac
bDGlcpN 4.89 3.87 3.74 3.64 3.47 3.78-3.95
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,4,6,4 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
3,4,4,6 bDQuip4N 102.69/4.460 80.31/3.604 75.63/3.535 57.84/3.553 71.53/3.530 17.47/1.186
3,4,4,2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
3,4,4 aDGlcpN 99.32/4.945 54.87/3.954 71.16/3.885 72.00/4.208 69.83/3.926 69.36/3.902-4.012
3,4,2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
3,4 aDGalpN 99.85/5.009 50.72/4.278 68.07/4.004 78.09/4.067 72.68/4.346 60.66/3.678-3.678
3 aDGalpA 101.12/5.344 69.22/3.844 69.83/3.926 80.67/4.338 72.16/4.174
2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
bDGlcpN 102.39/4.89 55.25/3.87 81.91/3.74 71.82/3.64 76.55/3.47 61.93/3.78-3.95
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,4,6,4 | Ac | |
| 3,4,4,6 | bDQuip4N | 4.460 | 3.604 | 3.535 | 3.553 | 3.530 | 1.186 |
| 3,4,4,2 | Ac | |
| 3,4,4 | aDGlcpN | 4.945 | 3.954 | 3.885 | 4.208 | 3.926 | 3.902
4.012 |
| 3,4,2 | Ac | |
| 3,4 | aDGalpN | 5.009 | 4.278 | 4.004 | 4.067 | 4.346 | 3.678
3.678 |
| 3 | aDGalpA | 5.344 | 3.844 | 3.926 | 4.338 | 4.174 |
|
| 2 | Ac | |
| | bDGlcpN | 4.89 | 3.87 | 3.74 | 3.64 | 3.47 | 3.78
3.95 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,4,6,4 | Ac | 175.42 | ? | |
| 3,4,4,6 | bDQuip4N | 102.69 | 80.31 | 75.63 | 57.84 | 71.53 | 17.47 |
| 3,4,4,2 | Ac | 175.04 | ? | |
| 3,4,4 | aDGlcpN | 99.32 | 54.87 | 71.16 | 72.00 | 69.83 | 69.36 |
| 3,4,2 | Ac | 175.65 | ? | |
| 3,4 | aDGalpN | 99.85 | 50.72 | 68.07 | 78.09 | 72.68 | 60.66 |
| 3 | aDGalpA | 101.12 | 69.22 | 69.83 | 80.67 | 72.16 | 175.14 |
| 2 | Ac | 175.04 | ? | |
| | bDGlcpN | 102.39 | 55.25 | 81.91 | 71.82 | 76.55 | 61.93 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175.42,"l":"1","c":[0,0,0]},{"s":102.69,"l":"1","c":[0,0,225]},{"s":80.31,"l":"2","c":[0,0,225]},{"s":75.63,"l":"3","c":[0,0,225]},{"s":57.84,"l":"4","c":[0,0,225]},{"s":71.53,"l":"5","c":[0,0,225]},{"s":17.47,"l":"6","c":[0,0,225]},{"s":175.04,"l":"1","c":[0,0,0]},{"s":99.32,"l":"1","c":[230,0,30]},{"s":54.87,"l":"2","c":[230,0,30]},{"s":71.16,"l":"3","c":[230,0,30]},{"s":72,"l":"4","c":[230,0,30]},{"s":69.83,"l":"5","c":[230,0,30]},{"s":69.36,"l":"6","c":[230,0,30]},{"s":175.65,"l":"1","c":[0,0,0]},{"s":99.85,"l":"1","c":[0,165,0]},{"s":50.72,"l":"2","c":[0,165,0]},{"s":68.07,"l":"3","c":[0,165,0]},{"s":78.09,"l":"4","c":[0,165,0]},{"s":72.68,"l":"5","c":[0,165,0]},{"s":60.66,"l":"6","c":[0,165,0]},{"s":101.12,"l":"1","c":[120,0,225]},{"s":69.22,"l":"2","c":[120,0,225]},{"s":69.83,"l":"3","c":[120,0,225]},{"s":80.67,"l":"4","c":[120,0,225]},{"s":72.16,"l":"5","c":[120,0,225]},{"s":175.14,"l":"6","c":[120,0,225]},{"s":175.04,"l":"1","c":[0,0,0]},{"s":102.39,"l":"1","c":[0,192,255]},{"s":55.25,"l":"2","c":[0,192,255]},{"s":81.91,"l":"3","c":[0,192,255]},{"s":71.82,"l":"4","c":[0,192,255]},{"s":76.55,"l":"5","c":[0,192,255]},{"s":61.93,"l":"6","c":[0,192,255]}])
The spectrum also has 4 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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