Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperPublication DOI: 10.1166/asl.2009.1039Journal NLM ID: 101551253Publisher: American Scientific Publishers
Correspondence: knirel
ioc.ac.ru (Y.A. Knirel)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia,TEDA School of Biological Sciences and Biotechnology, and Tianjin Key Laboratory for Microbial Functional Genomics, TEDA College, Nankai University, 23 HongDa Street, TEDA, Tianjin 300457, P. R. China
5,7-Diacetamido-3,5,7,9-tetradeoxy-l-glycero-d-galacto-non-2-ulosonic (di-N-acetyl-8-epilegionaminic) acid was isolated, for the .first time, from the O-specific polysaccharide of Escherichia coli O108 by three sequential Smith degradations followed by mild acid hydrolysis of the resultant glycoside. The monosaccharide obtained was identifed by a comparison with the synthetic authentic sample using 1H and 13C NMR spectroscopy.
acid, identification, derivative, isolation
Structure type: oligomer
Location inside paper: p.385, fig. 1,1
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, Smith degradation
Comments, role: Product after one Smith degradation of O-polysaccharide.
Related record ID(s): 24055, 24056, 24057
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
1,4,3,2 Ac 175.0-175.8 23.1-23.8
1,4,3 aLFucpN 98.8 50.9 69.3 72.6 68.1 16.9
1,4,2 Ac 175.0-175.8 23.1-23.8
1,4 aDGlcpN 94.6 54.6 77.0 69.4 73.8 61.9
1,5 Ac 175.0-175.8 23.1-23.8
1,7 Ac 175.0-175.8 23.1-23.8
1 aX8eLegp 175.5 101.5 37.8 72.3 51.8 74.0 54.1 69.4 20.6
x?Gro 65.6 71.7 63.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
1,4,3,2 Ac - 1.93-2.05
1,4,3 aLFucpN 4.95 4.09 3.86 3.78 4.38 1.18
1,4,2 Ac - 1.93-2.05
1,4 aDGlcpN 4.88 4.03 3.64 3.54 3.55 3.80-3.84
1,5 Ac - 1.93-2.05
1,7 Ac - 1.93-2.05
1 aX8eLegp - - 1.52-2.47 4.01 3.79 4.02 3.99 4.09 1.19
x?Gro 3.36-3.52 3.88 3.60-3.66
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
1,4,3,2 Ac 23.1-23.8/1.93-2.05
1,4,3 aLFucpN 98.8/4.95 50.9/4.09 69.3/3.86 72.6/3.78 68.1/4.38 16.9/1.18
1,4,2 Ac 23.1-23.8/1.93-2.05
1,4 aDGlcpN 94.6/4.88 54.6/4.03 77.0/3.64 69.4/3.54 73.8/3.55 61.9/3.80-3.84
1,5 Ac 23.1-23.8/1.93-2.05
1,7 Ac 23.1-23.8/1.93-2.05
1 aX8eLegp 37.8/1.52-2.47 72.3/4.01 51.8/3.79 74.0/4.02 54.1/3.99 69.4/4.09 20.6/1.19
x?Gro 65.6/3.36-3.52 71.7/3.88 63.8/3.60-3.66
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 1,4,3,2 | Ac |
| 1.93
2.05 | |
| 1,4,3 | aLFucpN | 4.95 | 4.09 | 3.86 | 3.78 | 4.38 | 1.18 | |
| 1,4,2 | Ac |
| 1.93
2.05 | |
| 1,4 | aDGlcpN | 4.88 | 4.03 | 3.64 | 3.54 | 3.55 | 3.80
3.84 | |
| 1,5 | Ac |
| 1.93
2.05 | |
| 1,7 | Ac |
| 1.93
2.05 | |
| 1 | aX8eLegp |
|
| 1.52
2.47 | 4.01 | 3.79 | 4.02 | 3.99 | 4.09 | 1.19 |
| | x?Gro | 3.36
3.52 | 3.88 | 3.60
3.66 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 1,4,3,2 | Ac | 175.0
175.8 | 23.1
23.8 | |
| 1,4,3 | aLFucpN | 98.8 | 50.9 | 69.3 | 72.6 | 68.1 | 16.9 | |
| 1,4,2 | Ac | 175.0
175.8 | 23.1
23.8 | |
| 1,4 | aDGlcpN | 94.6 | 54.6 | 77.0 | 69.4 | 73.8 | 61.9 | |
| 1,5 | Ac | 175.0
175.8 | 23.1
23.8 | |
| 1,7 | Ac | 175.0
175.8 | 23.1
23.8 | |
| 1 | aX8eLegp | 175.5 | 101.5 | 37.8 | 72.3 | 51.8 | 74.0 | 54.1 | 69.4 | 20.6 |
| | x?Gro | 65.6 | 71.7 | 63.8 | |
|
There is only one chemically distinct structure:
Found 
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