Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 23770694Publication DOI: 10.1016/j.carres.2013.04.027Journal 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 (O-antigen) of Escherichia coli O76 was studied by sugar analysis along with 1D and 2D (1)H,(13)C NMR spectroscopies. The following structure of the linear tetrasaccharide repeating unit was established: →4)-β-D-GlcpA-(1→4)-β-D-GalpNAc3Ac-(1→4)-α-D-GalpNAc-(1→3)-β-D-GalpNAc-(1→. The degree of O-acetylation of 4-substituted β-GalNAc residue is ~70%. The O-antigen gene cluster of E. coli O76 was sequenced. The functions of genes in the O-antigen gene cluster were tentatively assigned by comparison with sequences in the available databases and found to be in full agreement with the E. coli O76 O-antigen structure.
Lipopolysaccharide, O-antigen, Escherichia coli, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.15, table 1, OPS
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_136021,IEDB_137473,IEDB_1391961,IEDB_140630,IEDB_141582,IEDB_141584,IEDB_153207,IEDB_423153,IEDB_885822
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, GLC, mild acid hydrolysis, de-O-acetylation, NMR-1D
Biosynthesis and genetic data: genetic data
Related record ID(s): 29716
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G84996FP
Show glycosyltransferases
NMR conditions: in D2O at 323 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,4 bDGlcpA 104.7 73.6 75.1 81.2 76.3 172.9
3,4,2 Ac 175.5-176.2 23.1-23.5
3,4,3 70%Ac 174.2 21.3
3,4 bDGalpN 103.0 52.3 73.7 75.2 75.0 62.2
3,2 Ac 175.5-176.2 23.1-23.5
3 aDGalpN 95.1 51.8 69.0 76.6 71.9 61.6
2 Ac 175.5-176.2 23.1-23.5
bDGalpN 102.3 51.9 75.5 64.6 76.3 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,4 bDGlcpA 4.50 3.51 3.64 3.90 3.85 -
3,4,2 Ac - 1.97
3,4,3 70%Ac - 2.10
3,4 bDGalpN 4.85 4.17 5.08 4.24 3.90 3.81-3.81
3,2 Ac - 2.01
3 aDGalpN 5.00 4.15 3.90 4.20 3.81 3.72-3.81
2 Ac - 2.03
bDGalpN 4.58 4.02 3.77 4.07 3.66 3.75-3.75
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,4 bDGlcpA 104.7/4.50 73.6/3.51 75.1/3.64 81.2/3.90 76.3/3.85
3,4,2 Ac 23.1-23.5/1.97
3,4,3 70%Ac 21.3/2.10
3,4 bDGalpN 103.0/4.85 52.3/4.17 73.7/5.08 75.2/4.24 75.0/3.90 62.2/3.81-3.81
3,2 Ac 23.1-23.5/2.01
3 aDGalpN 95.1/5.00 51.8/4.15 69.0/3.90 76.6/4.20 71.9/3.81 61.6/3.72-3.81
2 Ac 23.1-23.5/2.03
bDGalpN 102.3/4.58 51.9/4.02 75.5/3.77 64.6/4.07 76.3/3.66 62.2/3.75-3.75
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,4 | bDGlcpA | 4.50 | 3.51 | 3.64 | 3.90 | 3.85 |
|
| 3,4,2 | Ac |
| 1.97 | |
| 3,4,3 | 70%Ac |
| 2.10 | |
| 3,4 | bDGalpN | 4.85 | 4.17 | 5.08 | 4.24 | 3.90 | 3.81
3.81 |
| 3,2 | Ac |
| 2.01 | |
| 3 | aDGalpN | 5.00 | 4.15 | 3.90 | 4.20 | 3.81 | 3.72
3.81 |
| 2 | Ac |
| 2.03 | |
| | bDGalpN | 4.58 | 4.02 | 3.77 | 4.07 | 3.66 | 3.75
3.75 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,4 | bDGlcpA | 104.7 | 73.6 | 75.1 | 81.2 | 76.3 | 172.9 |
| 3,4,2 | Ac | 175.5
176.2 | 23.1
23.5 | |
| 3,4,3 | 70%Ac | 174.2 | 21.3 | |
| 3,4 | bDGalpN | 103.0 | 52.3 | 73.7 | 75.2 | 75.0 | 62.2 |
| 3,2 | Ac | 175.5
176.2 | 23.1
23.5 | |
| 3 | aDGalpN | 95.1 | 51.8 | 69.0 | 76.6 | 71.9 | 61.6 |
| 2 | Ac | 175.5
176.2 | 23.1
23.5 | |
| | bDGalpN | 102.3 | 51.9 | 75.5 | 64.6 | 76.3 | 62.2 |
|
There is only one chemically distinct structure:
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