Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 16997291Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: 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, 23 HongDa Street, TEDA, Tianjin, China,Tianjin Key Laboratory for Microbial Functional Genomics, TEDA College, Nankai University, 23 HongDa Street, TEDA,Tianjin, China
An acidic O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Escherichia coli O150 and studied by sugar and methylation analyses, tri?ic acid solvolysis, Smith degradation, 1H and 13C NMR spectroscopy, including 2D ROESY, 1H,13C HSQC, HMQC-TOCSY, and HMBC experiments. The polysaccharide was found to contain a regioisomer of N-acetylisomuramic acid, 2-acetamido-4-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose [D-GlcNAc4(Slac)]. The structure of its hexasaccharide repeating unit was established.
O-antigen, Escherichia coli, teichoic acid, O-Polysaccharide structure, 2-Acetamido-4-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose, Trific acid solvolysis
Structure type: oligomer ; 714.27
Location inside paper: p.650, chart 1, compound 1
Contained glycoepitopes: IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, chemical analysis, ESI-MS, GLC, mild acid hydrolysis, Smith degradation, NMR-1D, triflic acid solvolysis
Comments, role: O-polysaccharide was subjected to Smith degradation
Related record ID(s): 21743, 21744
NCBI Taxonomy refs (TaxIDs): 2067427
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,3,3 aLRhap 102.3 72.1 71.3 73.5 70.2 17.9
2,3,2 Ac 175.2 24.0-24.1
2,3 bDGlcpN 101.5 57.9 82.2 70.0 77.3 62.5
2,2 Ac 175.2 24.0-24.1
2,4 lSLac ? 78.8 18.8
2 bDGlcpN 102.5 56.7 80.3 74.0 76.2 ?
x?Gro-al 90.0 83.9 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2,3,3 aLRhap 4.86 3.81 3.75 3.42 3.97 1.24
2,3,2 Ac - 2.01-2.06
2,3 bDGlcpN 4.63 3.62 3.72 3.48 3.32 3.72-3.87
2,2 Ac - 2.01-2.06
2,4 lSLac - 4.45 1.29
2 bDGlcpN 4.59 3.84 4.01 3.52 3.53 3.77-3.95
x?Gro-al 5.05 3.73 3.63-3.87
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2,3,3 aLRhap 102.3/4.86 72.1/3.81 71.3/3.75 73.5/3.42 70.2/3.97 17.9/1.24
2,3,2 Ac 24.0-24.1/2.01-2.06
2,3 bDGlcpN 101.5/4.63 57.9/3.62 82.2/3.72 70.0/3.48 77.3/3.32 62.5/3.72-3.87
2,2 Ac 24.0-24.1/2.01-2.06
2,4 lSLac 78.8/4.45 18.8/1.29
2 bDGlcpN 102.5/4.59 56.7/3.84 80.3/4.01 74.0/3.52 76.2/3.53 ?/3.77-3.95
x?Gro-al 90.0/5.05 83.9/3.73 62.0/3.63-3.87
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2,3,3 | aLRhap | 4.86 | 3.81 | 3.75 | 3.42 | 3.97 | 1.24 |
| 2,3,2 | Ac |
| 2.01
2.06 | |
| 2,3 | bDGlcpN | 4.63 | 3.62 | 3.72 | 3.48 | 3.32 | 3.72
3.87 |
| 2,2 | Ac |
| 2.01
2.06 | |
| 2,4 | lSLac |
| 4.45 | 1.29 | |
| 2 | bDGlcpN | 4.59 | 3.84 | 4.01 | 3.52 | 3.53 | 3.77
3.95 |
| | x?Gro-al | 5.05 | 3.73 | 3.63
3.87 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,3,3 | aLRhap | 102.3 | 72.1 | 71.3 | 73.5 | 70.2 | 17.9 |
| 2,3,2 | Ac | 175.2 | 24.0
24.1 | |
| 2,3 | bDGlcpN | 101.5 | 57.9 | 82.2 | 70.0 | 77.3 | 62.5 |
| 2,2 | Ac | 175.2 | 24.0
24.1 | |
| 2,4 | lSLac | ? | 78.8 | 18.8 | |
| 2 | bDGlcpN | 102.5 | 56.7 | 80.3 | 74.0 | 76.2 | ? |
| | x?Gro-al | 90.0 | 83.9 | 62.0 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":102.3,"l":"1","c":[0,0,225]},{"s":72.1,"l":"2","c":[0,0,225]},{"s":71.3,"l":"3","c":[0,0,225]},{"s":73.5,"l":"4","c":[0,0,225]},{"s":70.2,"l":"5","c":[0,0,225]},{"s":17.9,"l":"6","c":[0,0,225]},{"s":175.2,"l":"1","c":[0,0,0]},{"s":24.05,"l":"2","c":[0,0,0]},{"s":101.5,"l":"1","c":[230,0,30]},{"s":57.9,"l":"2","c":[230,0,30]},{"s":82.2,"l":"3","c":[230,0,30]},{"s":70,"l":"4","c":[230,0,30]},{"s":77.3,"l":"5","c":[230,0,30]},{"s":62.5,"l":"6","c":[230,0,30]},{"s":175.2,"l":"1","c":[0,0,0]},{"s":24.05,"l":"2","c":[0,0,0]},{"s":78.8,"l":"2","c":[0,165,0]},{"s":18.8,"l":"3","c":[0,165,0]},{"s":102.5,"l":"1","c":[120,0,225]},{"s":56.7,"l":"2","c":[120,0,225]},{"s":80.3,"l":"3","c":[120,0,225]},{"s":74,"l":"4","c":[120,0,225]},{"s":76.2,"l":"5","c":[120,0,225]},{"s":90,"l":"1","c":[0,192,255]},{"s":83.9,"l":"2","c":[0,192,255]},{"s":62,"l":"3","c":[0,192,255]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Found 
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