Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperPublication DOI: 10.1080/07328300903296394Journal NLM ID: 8218151Publisher: Marcel Dekker
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
On mild acid degradation of the lipopolysaccharide of Escherichia coli O61, the O-polysaccharide chain was cleaved at a linkage of 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-D-galacto-non-2-ulosonic acid (di-N-acetyl-8-epilegionaminic acid, 8eLeg5Ac7Ac). The resultant trisaccharide, an O-deacylated lipopolysaccharide and an O-deacetylated trisaccharide derived from the latter were studied by sugar analyses along with 1H and 13C NMR spectroscopy, and the following structure of the O-polysaccharide was established: [formula, see text].
Lipopolysaccharide, O-antigen, Escherichia coli, nonulosonic acid, bacterial polysaccharide structure, 8-epilegionaminic acid
Structure type: polymer chemical repeating unit
Location inside paper: p.464, p.470
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_885822,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, alkaline degradation, mild acid degradation
Comments, role: The signals for NAc are 1.95-2.03; 23.3-23.7(Me) and 175.0-175.9(CO); 1.98-2.02, 23.3-23.7 (Me) and 175.1-176.0 (CO); 1.99 (Me); 23.0-23.6 (Me) and 175.1-176.0 (CO).
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G67059IO
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
3,4,5 Ac
3,4,7 Ac
3,4,8 70%Ac ? 21.9
3,4 aX8eLegp ? 101.9 37.6 72.4 51.7 75.2 55.0 69.5 20.2
3 bDGlcp 105.8 74.3 76.2 73.2 76.2 61.3
2 Ac
aDGalpN 94.6 49.4 79.2 70.0 73.2 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
3,4,5 Ac
3,4,7 Ac
3,4,8 70%Ac - 2.00
3,4 aX8eLegp - - 1.63-2.78 3.72 3.72 3.86 3.91 3.98 1.22
3 bDGlcp 4.45 3.27 3.51 3.98 3.41 3.76-3.84
2 Ac
aDGalpN 5.01 3.34 3.70 4.17 3.72 3.69-3.71
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
3,4,5 Ac
3,4,7 Ac
3,4,8 70%Ac 21.9/2.00
3,4 aX8eLegp 37.6/1.63-2.78 72.4/3.72 51.7/3.72 75.2/3.86 55.0/3.91 69.5/3.98 20.2/1.22
3 bDGlcp 105.8/4.45 74.3/3.27 76.2/3.51 73.2/3.98 76.2/3.41 61.3/3.76-3.84
2 Ac
aDGalpN 94.6/5.01 49.4/3.34 79.2/3.70 70.0/4.17 73.2/3.72 62.2/3.69-3.71
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 3,4,5 | Ac | |
| 3,4,7 | Ac | |
| 3,4,8 | 70%Ac |
| 2.00 | |
| 3,4 | aX8eLegp |
|
| 1.63
2.78 | 3.72 | 3.72 | 3.86 | 3.91 | 3.98 | 1.22 |
| 3 | bDGlcp | 4.45 | 3.27 | 3.51 | 3.98 | 3.41 | 3.76
3.84 | |
| 2 | Ac | |
| | aDGalpN | 5.01 | 3.34 | 3.70 | 4.17 | 3.72 | 3.69
3.71 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 3,4,5 | Ac | |
| 3,4,7 | Ac | |
| 3,4,8 | 70%Ac | ? | 21.9 | |
| 3,4 | aX8eLegp | ? | 101.9 | 37.6 | 72.4 | 51.7 | 75.2 | 55.0 | 69.5 | 20.2 |
| 3 | bDGlcp | 105.8 | 74.3 | 76.2 | 73.2 | 76.2 | 61.3 | |
| 2 | Ac | |
| | aDGalpN | 94.6 | 49.4 | 79.2 | 70.0 | 73.2 | 62.2 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":21.9,"l":"2","c":[0,0,225]},{"s":101.9,"l":"2","c":[230,0,30]},{"s":37.6,"l":"3","c":[230,0,30]},{"s":72.4,"l":"4","c":[230,0,30]},{"s":51.7,"l":"5","c":[230,0,30]},{"s":75.2,"l":"6","c":[230,0,30]},{"s":55,"l":"7","c":[230,0,30]},{"s":69.5,"l":"8","c":[230,0,30]},{"s":20.2,"l":"9","c":[230,0,30]},{"s":105.8,"l":"1","c":[0,165,0]},{"s":74.3,"l":"2","c":[0,165,0]},{"s":76.2,"l":"3","c":[0,165,0]},{"s":73.2,"l":"4","c":[0,165,0]},{"s":76.2,"l":"5","c":[0,165,0]},{"s":61.3,"l":"6","c":[0,165,0]},{"s":94.6,"l":"1","c":[120,0,225]},{"s":49.4,"l":"2","c":[120,0,225]},{"s":79.2,"l":"3","c":[120,0,225]},{"s":70,"l":"4","c":[120,0,225]},{"s":73.2,"l":"5","c":[120,0,225]},{"s":62.2,"l":"6","c":[120,0,225]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Found 
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