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: p.15, table 1, DPS
Compound class: O-polysaccharide
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
Comments, role: de-O-acetylated OPS
Related record ID(s): 29313
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G01658YP
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,4 bDGlcpA 104.6 74.4 75.3 81.0 77.7 175.5
3,4,2 Ac 175.6 23.2
3,4 bDGalpN 103.5 54.5 72.8 77.6 75.6 62.3
3,2 Ac 175.8 23.5
3 aDGalpN 95.1 51.8 69.0 76.6 71.9 61.6
2 Ac 176.3 23.7
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 4.65 3.50 3.62 3.82 3.70 -
3,4,2 Ac - 2.03
3,4 bDGalpN 4.73 3.99 3.85 4.14 3.67 3.82-3.82
3,2 Ac - 2.04
3 aDGalpN 5.00 4.15 3.90 4.20 3.81 3.72-3.81
2 Ac - 2.06
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 104.6/4.65 74.4/3.50 75.3/3.62 81.0/3.82 77.7/3.70
3,4,2 Ac 23.2/2.03
3,4 bDGalpN 103.5/4.73 54.5/3.99 72.8/3.85 77.6/4.14 75.6/3.67 62.3/3.82-3.82
3,2 Ac 23.5/2.04
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 23.7/2.06
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 | 4.65 | 3.50 | 3.62 | 3.82 | 3.70 |
|
| 3,4,2 | Ac |
| 2.03 | |
| 3,4 | bDGalpN | 4.73 | 3.99 | 3.85 | 4.14 | 3.67 | 3.82
3.82 |
| 3,2 | Ac |
| 2.04 | |
| 3 | aDGalpN | 5.00 | 4.15 | 3.90 | 4.20 | 3.81 | 3.72
3.81 |
| 2 | Ac |
| 2.06 | |
| | 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 | 104.6 | 74.4 | 75.3 | 81.0 | 77.7 | 175.5 |
| 3,4,2 | Ac | 175.6 | 23.2 | |
| 3,4 | bDGalpN | 103.5 | 54.5 | 72.8 | 77.6 | 75.6 | 62.3 |
| 3,2 | Ac | 175.8 | 23.5 | |
| 3 | aDGalpN | 95.1 | 51.8 | 69.0 | 76.6 | 71.9 | 61.6 |
| 2 | Ac | 176.3 | 23.7 | |
| | bDGalpN | 102.3 | 51.9 | 75.5 | 64.6 | 76.3 | 62.2 |
|
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
