Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 9652410Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: gw
admin.organ.su.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden
The structure of the O-antigenic polysaccharide from Escherichia coli O141 has been determined. NMR spectroscopy and sugar and methylation analyses were the principal methods used. The sequence of the sugar residues could be determined by NOESY and heteronuclear multiple-bond connectivity (HMBC-) NMR experiments. The polysaccharide is composed of pentasaccharide repeating units with 1 O-acetyl group/repeating unit. The following structure, where Rha is 6-deoxymannose is concluded: carbohydrate sequence [see text]
Lipopolysaccharide, NMR, structure, O-antigen, enterotoxigenic Escherichia coli
Structure type: suggested polymer biological repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983930,SB_197,SB_44,SB_67,SB_72
Methods: methylation, NMR-2D, NMR, sugar analysis, de-O-acetylation
Comments, role: chemical repeat frame is different in the paper
Related record ID(s): 20684
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G84496XY, GlycomeDB:
28125
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2 bDGlcpA 104.1 73.8 76.7 73.0 77.3 ?
3,3,3 aLRhap 98.0 71.8 71.6 73.7 70.3 17.4
3,3 aDManp 101.5 75.6 72.8 72.9 74.2 62.3
3,6 Ac ? 21.0
3 aDManp 102.8 71.4 80.1 67.0 72.6 64.8
2 Ac ? 23.1
bDGlcpN 102.2 56.2 82.1 72.6 77.6 62.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,2 bDGlcpA 4.52 3.38 3.51 3.62 3.86 -
3,3,3 aLRhap 4.94 3.98 3.95 3.47 4.25 1.31
3,3 aDManp 5.20 4.37 4.09 3.95 3.82 3.82
3,6 Ac - 2.16
3 aDManp 5.18 4.15 3.90 3.87 3.76 4.28-4.40
2 Ac - 2.04
bDGlcpN 5.45 3.79 3.69 3.49 3.44 3.75-3.94
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,2 bDGlcpA 104.1/4.52 73.8/3.38 76.7/3.51 73.0/3.62 77.3/3.86
3,3,3 aLRhap 98.0/4.94 71.8/3.98 71.6/3.95 73.7/3.47 70.3/4.25 17.4/1.31
3,3 aDManp 101.5/5.20 75.6/4.37 72.8/4.09 72.9/3.95 74.2/3.82 62.3/3.82
3,6 Ac 21.0/2.16
3 aDManp 102.8/5.18 71.4/4.15 80.1/3.90 67.0/3.87 72.6/3.76 64.8/4.28-4.40
2 Ac 23.1/2.04
bDGlcpN 102.2/5.45 56.2/3.79 82.1/3.69 72.6/3.49 77.6/3.44 62.9/3.75-3.94
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,2 | bDGlcpA | 4.52 | 3.38 | 3.51 | 3.62 | 3.86 |
|
| 3,3,3 | aLRhap | 4.94 | 3.98 | 3.95 | 3.47 | 4.25 | 1.31 |
| 3,3 | aDManp | 5.20 | 4.37 | 4.09 | 3.95 | 3.82 | 3.82 |
| 3,6 | Ac |
| 2.16 | |
| 3 | aDManp | 5.18 | 4.15 | 3.90 | 3.87 | 3.76 | 4.28
4.40 |
| 2 | Ac |
| 2.04 | |
| | bDGlcpN | 5.45 | 3.79 | 3.69 | 3.49 | 3.44 | 3.75
3.94 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2 | bDGlcpA | 104.1 | 73.8 | 76.7 | 73.0 | 77.3 | ? |
| 3,3,3 | aLRhap | 98.0 | 71.8 | 71.6 | 73.7 | 70.3 | 17.4 |
| 3,3 | aDManp | 101.5 | 75.6 | 72.8 | 72.9 | 74.2 | 62.3 |
| 3,6 | Ac | ? | 21.0 | |
| 3 | aDManp | 102.8 | 71.4 | 80.1 | 67.0 | 72.6 | 64.8 |
| 2 | Ac | ? | 23.1 | |
| | bDGlcpN | 102.2 | 56.2 | 82.1 | 72.6 | 77.6 | 62.9 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":104.1,"l":"1","c":[0,0,225]},{"s":73.8,"l":"2","c":[0,0,225]},{"s":76.7,"l":"3","c":[0,0,225]},{"s":73,"l":"4","c":[0,0,225]},{"s":77.3,"l":"5","c":[0,0,225]},{"s":98,"l":"1","c":[230,0,30]},{"s":71.8,"l":"2","c":[230,0,30]},{"s":71.6,"l":"3","c":[230,0,30]},{"s":73.7,"l":"4","c":[230,0,30]},{"s":70.3,"l":"5","c":[230,0,30]},{"s":17.4,"l":"6","c":[230,0,30]},{"s":101.5,"l":"1","c":[0,165,0]},{"s":75.6,"l":"2","c":[0,165,0]},{"s":72.8,"l":"3","c":[0,165,0]},{"s":72.9,"l":"4","c":[0,165,0]},{"s":74.2,"l":"5","c":[0,165,0]},{"s":62.3,"l":"6","c":[0,165,0]},{"s":21,"l":"2","c":[0,0,0]},{"s":102.8,"l":"1","c":[120,0,225]},{"s":71.4,"l":"2","c":[120,0,225]},{"s":80.1,"l":"3","c":[120,0,225]},{"s":67,"l":"4","c":[120,0,225]},{"s":72.6,"l":"5","c":[120,0,225]},{"s":64.8,"l":"6","c":[120,0,225]},{"s":23.1,"l":"2","c":[0,0,0]},{"s":102.2,"l":"1","c":[0,192,255]},{"s":56.2,"l":"2","c":[0,192,255]},{"s":82.1,"l":"3","c":[0,192,255]},{"s":72.6,"l":"4","c":[0,192,255]},{"s":77.6,"l":"5","c":[0,192,255]},{"s":62.9,"l":"6","c":[0,192,255]}])
The spectrum also has 3 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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