Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 24745322Publication DOI: 10.1016/j.carres.2014.01.008Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Perepelov <perepel
ioc.ac.ru>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China
The acidic O-polysaccharide (O-antigen) of Escherichia coli O30 was isolated from the lipopolysaccharide and studied by sugar analysis and NMR spectroscopy. The following structure of the branched tetrasaccharide repeating unit was established, which is unique among known structures of bacterial polysaccharides: →4)-β-D-GlcpA-(1→4)[β-D-GlcpNAc-(1→2)]-β-D-GlcpA-(1→3)-α-D-GlcpNAc-(1→. The O-antigen gene cluster of E. coli O30 was sequenced. The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in full agreement with the O-polysaccharide structure.
Lipopolysaccharide, O-antigen, Escherichia coli, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.197
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_423153
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, GLC, mild acid hydrolysis, NMR-1D, GPC, analysis of gene
Biosynthesis and genetic data: genetic data
Comments, role: E. coli O30 type strain (laboratory stock number G1684)
NCBI Taxonomy refs (TaxIDs): 1095712Reference(s) to other database(s): GTC:G47891WR
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4 bDGlcpA 103.6 74.5 77.2 77.3 76.4 173.9
3,2,2 Ac 175.0-175.9 ?
3,2 bDGlcpN 102.9 56.9 75.0 71.1 77.0 62.2
3 bDGlcpA 101.0 80.6 76.4 81.5 75.0 174.9
2 Ac 175.0-175.9 ?
aDGlcpN 98.5 53.0 81.3 69.0 73.1 61.
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4 bDGlcpA 4.52 3.34 3.71 3.78 3.97 -
3,2,2 Ac - 2.04-2.05
3,2 bDGlcpN 4.78 3.71 3.53 3.41 3.38 3.70-3.89
3 bDGlcpA 4.68 3.56 3.68 3.75 3.98 -
2 Ac - 2.04-2.05
aDGlcpN 5.38 4.02 3.89 3.61 3.66 3.78-3.78
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4 bDGlcpA 103.6/4.52 74.5/3.34 77.2/3.71 77.3/3.78 76.4/3.97
3,2,2 Ac ?/2.04-2.05
3,2 bDGlcpN 102.9/4.78 56.9/3.71 75.0/3.53 71.1/3.41 77.0/3.38 62.2/3.70-3.89
3 bDGlcpA 101.0/4.68 80.6/3.56 76.4/3.68 81.5/3.75 75.0/3.98
2 Ac ?/2.04-2.05
aDGlcpN 98.5/5.38 53.0/4.02 81.3/3.89 69.0/3.61 73.1/3.66 61./3.78-3.78
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4 | bDGlcpA | 4.52 | 3.34 | 3.71 | 3.78 | 3.97 |
|
| 3,2,2 | Ac |
| 2.04
2.05 | |
| 3,2 | bDGlcpN | 4.78 | 3.71 | 3.53 | 3.41 | 3.38 | 3.70
3.89 |
| 3 | bDGlcpA | 4.68 | 3.56 | 3.68 | 3.75 | 3.98 |
|
| 2 | Ac |
| 2.04
2.05 | |
| | aDGlcpN | 5.38 | 4.02 | 3.89 | 3.61 | 3.66 | 3.78
3.78 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4 | bDGlcpA | 103.6 | 74.5 | 77.2 | 77.3 | 76.4 | 173.9 |
| 3,2,2 | Ac | 175.0
175.9 | ? | |
| 3,2 | bDGlcpN | 102.9 | 56.9 | 75.0 | 71.1 | 77.0 | 62.2 |
| 3 | bDGlcpA | 101.0 | 80.6 | 76.4 | 81.5 | 75.0 | 174.9 |
| 2 | Ac | 175.0
175.9 | ? | |
| | aDGlcpN | 98.5 | 53.0 | 81.3 | 69.0 | 73.1 | 61. |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":103.6,"l":"1","c":[0,0,225]},{"s":74.5,"l":"2","c":[0,0,225]},{"s":77.2,"l":"3","c":[0,0,225]},{"s":77.3,"l":"4","c":[0,0,225]},{"s":76.4,"l":"5","c":[0,0,225]},{"s":173.9,"l":"6","c":[0,0,225]},{"s":175.45,"l":"1","c":[0,0,0]},{"s":102.9,"l":"1","c":[230,0,30]},{"s":56.9,"l":"2","c":[230,0,30]},{"s":75,"l":"3","c":[230,0,30]},{"s":71.1,"l":"4","c":[230,0,30]},{"s":77,"l":"5","c":[230,0,30]},{"s":62.2,"l":"6","c":[230,0,30]},{"s":101,"l":"1","c":[0,165,0]},{"s":80.6,"l":"2","c":[0,165,0]},{"s":76.4,"l":"3","c":[0,165,0]},{"s":81.5,"l":"4","c":[0,165,0]},{"s":75,"l":"5","c":[0,165,0]},{"s":174.9,"l":"6","c":[0,165,0]},{"s":175.45,"l":"1","c":[0,0,0]},{"s":98.5,"l":"1","c":[120,0,225]},{"s":53,"l":"2","c":[120,0,225]},{"s":81.3,"l":"3","c":[120,0,225]},{"s":69,"l":"4","c":[120,0,225]},{"s":73.1,"l":"5","c":[120,0,225]},{"s":61,"l":"6","c":[120,0,225]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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