Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Canis lupus familiaris; Ovis aries
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 26382081Publication DOI: 10.1016/j.carres.2015.08.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru (A.V. Perepelov)
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, 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, Department of Laboratory Medicine, Division of Clinical Microbiology, Karolinska Institute, Karolinska University Hospital, Stockholm, Sweden
Enterotoxigenic Escherichia coli are causative agents of diarrhea in humans as well as animals, and E.coli O170 belongs to this virotype. Upon mild acid degradation of the lipopolysaccharide of E.coli O170, the branched O-polysaccharide chain was partially cleaved at ?-d-glactofuranosidic linkages to give multiple products, including a linear tetrasaccharide and oligomers thereof. Studies of the acid degradation products and O-deacylated lipopolysaccharide by 1D and 2D 1H and 13C NMR spectroscopy enabled elucidation of the following O-polysaccharide structure: Functions of genes in the O-antigen biosynthesis gene cluster were tentatively assigned and found to be in agreement with the O-polysaccharide structure.
Lipopolysaccharide, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.14, chart 1, OPS 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_153212,IEDB_190606,IEDB_423153,SB_74,SB_85
Methods: 13C NMR, 1H NMR, NMR-2D, de-O-acylation, sugar analysis, acid hydrolysis, GLC, mild acid hydrolysis, NMR-1D, GPC
Related record ID(s): 30862, 30863, 30864
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G62660VU
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 175.5-175.6 23.4-23.7
3,3,4,3 bDGalf 108.9 82.4 78.7 85.1 72.3 64.2-64.3
3,3,4 bDGlcpN 101.7 56.4-56.6 77.4 75.2 76.7 61.3
3,3 bDGlcpA 103.5 73.8 75.0 81.2 76.6 174.8
3 bDGalf 109.6 81.2 85.8 83.4 71.5 64.2-64.3
2 Ac 175.5-175.6 23.4-23.7
bDGlcpN 101.2 56.4-56.6 82.1 69.2 77.1 62.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,4,2 Ac - 2.02-2.03
3,3,4,3 bDGalf 5.16 4.01 4.01 4.21 3.81 3.67-3.74
3,3,4 bDGlcpN 4.58 3.82 3.81 3.82 3.51 3.72-3.90
3,3 bDGlcpA 4.60 3.36 3.61 3.75 3.83 -
3 bDGalf 5.05 4.18 4.20 4.18 3.87 3.60-3.63
2 Ac - 2.02-2.03
bDGlcpN 4.58 3.82 3.69 3.45 3.42 3.74-3.90
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,4,2 Ac 23.4-23.7/2.02-2.03
3,3,4,3 bDGalf 108.9/5.16 82.4/4.01 78.7/4.01 85.1/4.21 72.3/3.81 64.2-64.3/3.67-3.74
3,3,4 bDGlcpN 101.7/4.58 56.4-56.6/3.82 77.4/3.81 75.2/3.82 76.7/3.51 61.3/3.72-3.90
3,3 bDGlcpA 103.5/4.60 73.8/3.36 75.0/3.61 81.2/3.75 76.6/3.83
3 bDGalf 109.6/5.05 81.2/4.18 85.8/4.20 83.4/4.18 71.5/3.87 64.2-64.3/3.60-3.63
2 Ac 23.4-23.7/2.02-2.03
bDGlcpN 101.2/4.58 56.4-56.6/3.82 82.1/3.69 69.2/3.45 77.1/3.42 62.1/3.74-3.90
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,4,2 | Ac |
| 2.02
2.03 | |
| 3,3,4,3 | bDGalf | 5.16 | 4.01 | 4.01 | 4.21 | 3.81 | 3.67
3.74 |
| 3,3,4 | bDGlcpN | 4.58 | 3.82 | 3.81 | 3.82 | 3.51 | 3.72
3.90 |
| 3,3 | bDGlcpA | 4.60 | 3.36 | 3.61 | 3.75 | 3.83 |
|
| 3 | bDGalf | 5.05 | 4.18 | 4.20 | 4.18 | 3.87 | 3.60
3.63 |
| 2 | Ac |
| 2.02
2.03 | |
| | bDGlcpN | 4.58 | 3.82 | 3.69 | 3.45 | 3.42 | 3.74
3.90 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,4,2 | Ac | 175.5
175.6 | 23.4
23.7 | |
| 3,3,4,3 | bDGalf | 108.9 | 82.4 | 78.7 | 85.1 | 72.3 | 64.2
64.3 |
| 3,3,4 | bDGlcpN | 101.7 | 56.4
56.6 | 77.4 | 75.2 | 76.7 | 61.3 |
| 3,3 | bDGlcpA | 103.5 | 73.8 | 75.0 | 81.2 | 76.6 | 174.8 |
| 3 | bDGalf | 109.6 | 81.2 | 85.8 | 83.4 | 71.5 | 64.2
64.3 |
| 2 | Ac | 175.5
175.6 | 23.4
23.7 | |
| | bDGlcpN | 101.2 | 56.4
56.6 | 82.1 | 69.2 | 77.1 | 62.1 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
