Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 17880932Publication DOI: 10.1016/j.carres.2007.08.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
The O-polysaccharide was isolated from the lipopolysaccharide of Escherichia coli O168 and studied by chemical analyses and Smith degradation along with (1)H and (13)C NMR spectroscopies. The following structure of the branched pentasaccharide repeating unit of the O-polysaccharide was established: [carbohydrate structure: see text] where 6-O-acetylation of GlcNAc is partial. Reinvestigation of the O-polysaccharide of Shigella dysenteriae type 4 established earlier showed it to have the same structure except for that the lateral Fuc residue is nonstoichiometrically O-acetylated at each position.
O-antigen, Escherichia coli, bacterial polysaccharide structure, Shigella dysenteriae, methodology
Structure type: polymer chemical repeating unit
Location inside paper: p.2677
Trivial name: DPS
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136045,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151531,IEDB_152214,IEDB_174333,SB_74,SB_85,SB_86
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, chemical analysis, mild acid hydrolysis, Smith degradation, NMR-1D, alkaline hydrolysis
Comments, role: treatment OPS with aqueous ammonia.
Related record ID(s): 21738, 21739, 21740, 21741, 23210, 26212
NCBI Taxonomy refs (TaxIDs): 2603287Reference(s) to other database(s): GTC:G69278UM, GlycomeDB:
34667
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,4,2 Ac 175.7-176.2 23.5-23.7
3,3,4,3 aLFucp 99.7 69.2 70.7 73.3 68.0 16.9
3,3,4 aDGlcpN 99.6 55.3 73.3 79.3 73.3 60.8
3,3 aDGlcpA 102.0 73.3 74.6 79.3 73.7 175.7
3 aLFucp 101.6 68.7 74.6 73.7 68.4 16.5
2 Ac 175.7-176.2 23.5-23.7
bDGlcpN 101.5 57.0 81.9 ? 77.6 63.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,4,2 Ac - 2.02-2.04
3,3,4,3 aLFucp 5.11 3.68 3.95 3.79 4.72 1.25
3,3,4 aDGlcpN 5.17 4.13 3.91 3.87 3.72 3.71-3.83
3,3 aDGlcpA 5.17 3.57 3.73 3.73 4.18 -
3 aLFucp 4.97 3.88 3.89 3.91 4.31 1.14
2 Ac - 2.02-2.04
bDGlcpN 4.55 3.80 3.63 3.31 3.44 3.59-3.96
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,4,2 Ac 23.5-23.7/2.02-2.04
3,3,4,3 aLFucp 99.7/5.11 69.2/3.68 70.7/3.95 73.3/3.79 68.0/4.72 16.9/1.25
3,3,4 aDGlcpN 99.6/5.17 55.3/4.13 73.3/3.91 79.3/3.87 73.3/3.72 60.8/3.71-3.83
3,3 aDGlcpA 102.0/5.17 73.3/3.57 74.6/3.73 79.3/3.73 73.7/4.18
3 aLFucp 101.6/4.97 68.7/3.88 74.6/3.89 73.7/3.91 68.4/4.31 16.5/1.14
2 Ac 23.5-23.7/2.02-2.04
bDGlcpN 101.5/4.55 57.0/3.80 81.9/3.63 ?/3.31 77.6/3.44 63.2/3.59-3.96
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,4,2 | Ac |
| 2.02
2.04 | |
| 3,3,4,3 | aLFucp | 5.11 | 3.68 | 3.95 | 3.79 | 4.72 | 1.25 |
| 3,3,4 | aDGlcpN | 5.17 | 4.13 | 3.91 | 3.87 | 3.72 | 3.71
3.83 |
| 3,3 | aDGlcpA | 5.17 | 3.57 | 3.73 | 3.73 | 4.18 |
|
| 3 | aLFucp | 4.97 | 3.88 | 3.89 | 3.91 | 4.31 | 1.14 |
| 2 | Ac |
| 2.02
2.04 | |
| | bDGlcpN | 4.55 | 3.80 | 3.63 | 3.31 | 3.44 | 3.59
3.96 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,4,2 | Ac | 175.7
176.2 | 23.5
23.7 | |
| 3,3,4,3 | aLFucp | 99.7 | 69.2 | 70.7 | 73.3 | 68.0 | 16.9 |
| 3,3,4 | aDGlcpN | 99.6 | 55.3 | 73.3 | 79.3 | 73.3 | 60.8 |
| 3,3 | aDGlcpA | 102.0 | 73.3 | 74.6 | 79.3 | 73.7 | 175.7 |
| 3 | aLFucp | 101.6 | 68.7 | 74.6 | 73.7 | 68.4 | 16.5 |
| 2 | Ac | 175.7
176.2 | 23.5
23.7 | |
| | bDGlcpN | 101.5 | 57.0 | 81.9 | ? | 77.6 | 63.2 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175.95,"l":"1","c":[0,0,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":99.7,"l":"1","c":[0,0,225]},{"s":69.2,"l":"2","c":[0,0,225]},{"s":70.7,"l":"3","c":[0,0,225]},{"s":73.3,"l":"4","c":[0,0,225]},{"s":68,"l":"5","c":[0,0,225]},{"s":16.9,"l":"6","c":[0,0,225]},{"s":99.6,"l":"1","c":[230,0,30]},{"s":55.3,"l":"2","c":[230,0,30]},{"s":73.3,"l":"3","c":[230,0,30]},{"s":79.3,"l":"4","c":[230,0,30]},{"s":73.3,"l":"5","c":[230,0,30]},{"s":60.8,"l":"6","c":[230,0,30]},{"s":102,"l":"1","c":[0,165,0]},{"s":73.3,"l":"2","c":[0,165,0]},{"s":74.6,"l":"3","c":[0,165,0]},{"s":79.3,"l":"4","c":[0,165,0]},{"s":73.7,"l":"5","c":[0,165,0]},{"s":175.7,"l":"6","c":[0,165,0]},{"s":101.6,"l":"1","c":[120,0,225]},{"s":68.7,"l":"2","c":[120,0,225]},{"s":74.6,"l":"3","c":[120,0,225]},{"s":73.7,"l":"4","c":[120,0,225]},{"s":68.4,"l":"5","c":[120,0,225]},{"s":16.5,"l":"6","c":[120,0,225]},{"s":175.95,"l":"1","c":[0,0,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":101.5,"l":"1","c":[0,192,255]},{"s":57,"l":"2","c":[0,192,255]},{"s":81.9,"l":"3","c":[0,192,255]},{"s":77.6,"l":"5","c":[0,192,255]},{"s":63.2,"l":"6","c":[0,192,255]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
