Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 29864581Publication DOI: 10.1016/j.carres.2018.05.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: andreivperepelov
gmail.com
Institutions: Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky Prosp., Moscow, Russian Federation, Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
Mild acid hydrolysis of the lipopolysaccharide of Escherichia coli O57 afforded an O-polysaccharide, which was isolated by gel permeation chromatography (GPC) and studied by sugar analysis, Smith degradation and solvolysis with trifluoroacetic acid, along with 2D 1H and 13C NMR spectroscopy. The O-polysaccharide was found to contain d-Glc, d-Gal, d-GalA, d-GlcNAc, and l-FucNAc, as well as O-acetyl groups. Smith degradation of the O-deacetylated polysaccharide destroyed side-branch β-Glсp and α-GalpA to give a modified linear polysaccharide. Solvolysis cleaved selectively the linkage of α-l-FucpNAc to give a pentasaccharide corresponding to the O-polysaccharide repeat. A comparison of the NMR spectra of the initial and O-deacetylated polysaccharides showed that α-GalpA is non-stoichiometrically O-acetylated at position either 2 (~30%) or 3 (~40%). The following structure of the O-polysaccharide was established, which is unique among known bacterial polysaccharide structures.
O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, CF3CO2H solvolysis
Structure type: oligomer
Location inside paper: abstract, table 1, p.3, chart 1, structure OS2
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_983931,SB_192,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, Smith degradation, de-O-acetylation, GPC, delipidation, solvolysis with trifluoroacetic acid
Comments, role: OS2 was obtained by deacetylation of OS1.
Related record ID(s): 12731, 12732, 12733, 12735, 12951
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G63648WU
Show glycosyltransferases
NMR conditions: in D2O at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2 aDGalpA 95.4 69.0 70.9 71.5 72.8 ?
3,3,2 Ac 175.0-175.7 23.1-24.1
3,3 aDGlcpN 93.0 54.7 72.7 71.0 73.1 62.6
3 aDGalp 96.7 69.0 71.4 65.6 72.6 62.0
2 Ac 175.0-175.7 23.1-24.1
4 bDGlcp 103.8 75.0 77.0 71.4 78.1 63.0
aLFucpN 92.0 51.3 71.8 78.0 68.4 17.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2 aDGalpA 5.07 3.81 3.87 4.33 4.48 -
3,3,2 Ac - 1.96-2.09
3,3 aDGlcpN 5.14 3.96 3.65 3.58 3.83 3.85-3.94
3 aDGalp 5.52 4.17 4.11 4.24 4.22 3.70-3.75
2 Ac - 1.96-2.09
4 bDGlcp 4.62 3.42 3.49 3.33 3.43 3.73-3.94
aLFucpN 5.16 4.34 4.30 4.25 4.28 1.32
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2 aDGalpA 95.4/5.07 69.0/3.81 70.9/3.87 71.5/4.33 72.8/4.48
3,3,2 Ac 23.1-24.1/1.96-2.09
3,3 aDGlcpN 93.0/5.14 54.7/3.96 72.7/3.65 71.0/3.58 73.1/3.83 62.6/3.85-3.94
3 aDGalp 96.7/5.52 69.0/4.17 71.4/4.11 65.6/4.24 72.6/4.22 62.0/3.70-3.75
2 Ac 23.1-24.1/1.96-2.09
4 bDGlcp 103.8/4.62 75.0/3.42 77.0/3.49 71.4/3.33 78.1/3.43 63.0/3.73-3.94
aLFucpN 92.0/5.16 51.3/4.34 71.8/4.30 78.0/4.25 68.4/4.28 17.5/1.32
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2 | aDGalpA | 5.07 | 3.81 | 3.87 | 4.33 | 4.48 |
|
| 3,3,2 | Ac |
| 1.96
2.09 | |
| 3,3 | aDGlcpN | 5.14 | 3.96 | 3.65 | 3.58 | 3.83 | 3.85
3.94 |
| 3 | aDGalp | 5.52 | 4.17 | 4.11 | 4.24 | 4.22 | 3.70
3.75 |
| 2 | Ac |
| 1.96
2.09 | |
| 4 | bDGlcp | 4.62 | 3.42 | 3.49 | 3.33 | 3.43 | 3.73
3.94 |
| | aLFucpN | 5.16 | 4.34 | 4.30 | 4.25 | 4.28 | 1.32 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2 | aDGalpA | 95.4 | 69.0 | 70.9 | 71.5 | 72.8 | ? |
| 3,3,2 | Ac | 175.0
175.7 | 23.1
24.1 | |
| 3,3 | aDGlcpN | 93.0 | 54.7 | 72.7 | 71.0 | 73.1 | 62.6 |
| 3 | aDGalp | 96.7 | 69.0 | 71.4 | 65.6 | 72.6 | 62.0 |
| 2 | Ac | 175.0
175.7 | 23.1
24.1 | |
| 4 | bDGlcp | 103.8 | 75.0 | 77.0 | 71.4 | 78.1 | 63.0 |
| | aLFucpN | 92.0 | 51.3 | 71.8 | 78.0 | 68.4 | 17.5 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":95.4,"l":"1","c":[0,0,225]},{"s":69,"l":"2","c":[0,0,225]},{"s":70.9,"l":"3","c":[0,0,225]},{"s":71.5,"l":"4","c":[0,0,225]},{"s":72.8,"l":"5","c":[0,0,225]},{"s":175.35,"l":"1","c":[0,0,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":93,"l":"1","c":[230,0,30]},{"s":54.7,"l":"2","c":[230,0,30]},{"s":72.7,"l":"3","c":[230,0,30]},{"s":71,"l":"4","c":[230,0,30]},{"s":73.1,"l":"5","c":[230,0,30]},{"s":62.6,"l":"6","c":[230,0,30]},{"s":96.7,"l":"1","c":[0,165,0]},{"s":69,"l":"2","c":[0,165,0]},{"s":71.4,"l":"3","c":[0,165,0]},{"s":65.6,"l":"4","c":[0,165,0]},{"s":72.6,"l":"5","c":[0,165,0]},{"s":62,"l":"6","c":[0,165,0]},{"s":175.35,"l":"1","c":[0,0,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":103.8,"l":"1","c":[120,0,225]},{"s":75,"l":"2","c":[120,0,225]},{"s":77,"l":"3","c":[120,0,225]},{"s":71.4,"l":"4","c":[120,0,225]},{"s":78.1,"l":"5","c":[120,0,225]},{"s":63,"l":"6","c":[120,0,225]},{"s":92,"l":"1","c":[0,192,255]},{"s":51.3,"l":"2","c":[0,192,255]},{"s":71.8,"l":"3","c":[0,192,255]},{"s":78,"l":"4","c":[0,192,255]},{"s":68.4,"l":"5","c":[0,192,255]},{"s":17.5,"l":"6","c":[0,192,255]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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