Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 16313893Publication DOI: 10.1016/j.carres.2005.11.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Peng G. Wang <wang.892
osu.edu>
Institutions: Department of Biochemistry, The Ohio State University, Columbus, OH 43210, USA, Department of Chemistry, University of Maryland, Baltimore County, MD 21250, USA
The structure of a new O-polysaccharide from Escherichia coli O86:K62:B7 was determined using NMR and methylation analysis. The structure is as follows: [carbohydrate: see text]. Comparison with the previously published structure from E. coli O86:K2:H2 revealed that the O-polysaccharides from these two E. coli O86 serotypes share the same branched pentasaccharide repeating unit. However, they differ in the anomeric configuration of the linkage, the linkage position, and the identity of the residue through which polymerization occurs. The immunochemical activity of these two forms of LPS toward anti-B antibody was studied and compared. The results showed that LPS from E. coli O86:K2:H2 strain possesses higher blood group B reactivity. The immunoreactivity difference was explained by modeling of the O-repeating unit tetrasaccharide fragments. This finding provides a good system for the further study of O-polysaccharide biosynthesis especially the repeating unit polymerization mechanism.
Lipopolysaccharide, O-polysaccharide, molecular modeling, blood group antigens, polymerization, O-Repeating unit, Blood group antigens; Lipopolysaccharide; Molecular modeling; O-Polysaccharide; O-Repeating unit; Polymerization
Structure type: polymer biological repeating unit
Location inside paper: p.103, fig. 2, Table 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391963,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141814,IEDB_142489,IEDB_143260,IEDB_144562,IEDB_144990,IEDB_150766,IEDB_150948,IEDB_151528,IEDB_152213,IEDB_152214,IEDB_152215,IEDB_152218,IEDB_153205,IEDB_153222,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_241096,IEDB_461710,IEDB_461714,IEDB_461719,IEDB_885822,SB_149,SB_154,SB_165,SB_166,SB_187,SB_195,SB_23,SB_24,SB_7,SB_8,SB_86,SB_88
Methods: methylation, GC-MS, NMR, ELISA, composition analysis
Biological activity: serological data, biological activities data
Enzymes that release or process the structure: polymerase wzy
3D data: molecular modeling
Related record ID(s): 20226, 20507, 20508
NCBI Taxonomy refs (TaxIDs): 2162909Reference(s) to other database(s): GTC:G47141RI, GlycomeDB:
28087
Show glycosyltransferases
NMR conditions: in D2O at 323 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,3,2 aLFucp 99.8 69.0 71.1 73.0 67.7 16.4
3,2,3 bDGalp 103.5 74.0 76.5 63.9 75.8 61.9
3,2,2 Ac ? 23.1
3,2 aDGalpN 94.0 49.8 75.6 69.9 71.9 62.1
3 aDGalp 90.1 72.3 69.3 70.3 71.9 62.3
2 Ac ? 23.7
aDGalpN 94.8 48.7 73.0 65.6 71.9 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,3,2 aLFucp 5.308 3.76 3.605 3.66 4.27 1.15
3,2,3 bDGalp 4.693 3.86 3.925 4.27 3.65 3.76
3,2,2 Ac - 2.04
3,2 aDGalpN 5.066 4.215 3.94 4.22 3.91 3.76
3 aDGalp 5.447 3.99 4.04 4.01 4.19 3.76
2 Ac - 2.12
aDGalpN 5.232 4.43 4.03 4.13 4.02 3.76
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,3,2 aLFucp 99.8/5.308 69.0/3.76 71.1/3.605 73.0/3.66 67.7/4.27 16.4/1.15
3,2,3 bDGalp 103.5/4.693 74.0/3.86 76.5/3.925 63.9/4.27 75.8/3.65 61.9/3.76
3,2,2 Ac 23.1/2.04
3,2 aDGalpN 94.0/5.066 49.8/4.215 75.6/3.94 69.9/4.22 71.9/3.91 62.1/3.76
3 aDGalp 90.1/5.447 72.3/3.99 69.3/4.04 70.3/4.01 71.9/4.19 62.3/3.76
2 Ac 23.7/2.12
aDGalpN 94.8/5.232 48.7/4.43 73.0/4.03 65.6/4.13 71.9/4.02 62.3/3.76
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,3,2 | aLFucp | 5.308 | 3.76 | 3.605 | 3.66 | 4.27 | 1.15 |
| 3,2,3 | bDGalp | 4.693 | 3.86 | 3.925 | 4.27 | 3.65 | 3.76 |
| 3,2,2 | Ac |
| 2.04 | |
| 3,2 | aDGalpN | 5.066 | 4.215 | 3.94 | 4.22 | 3.91 | 3.76 |
| 3 | aDGalp | 5.447 | 3.99 | 4.04 | 4.01 | 4.19 | 3.76 |
| 2 | Ac |
| 2.12 | |
| | aDGalpN | 5.232 | 4.43 | 4.03 | 4.13 | 4.02 | 3.76 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,3,2 | aLFucp | 99.8 | 69.0 | 71.1 | 73.0 | 67.7 | 16.4 |
| 3,2,3 | bDGalp | 103.5 | 74.0 | 76.5 | 63.9 | 75.8 | 61.9 |
| 3,2,2 | Ac | ? | 23.1 | |
| 3,2 | aDGalpN | 94.0 | 49.8 | 75.6 | 69.9 | 71.9 | 62.1 |
| 3 | aDGalp | 90.1 | 72.3 | 69.3 | 70.3 | 71.9 | 62.3 |
| 2 | Ac | ? | 23.7 | |
| | aDGalpN | 94.8 | 48.7 | 73.0 | 65.6 | 71.9 | 62.3 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":99.8,"l":"1","c":[0,0,225]},{"s":69,"l":"2","c":[0,0,225]},{"s":71.1,"l":"3","c":[0,0,225]},{"s":73,"l":"4","c":[0,0,225]},{"s":67.7,"l":"5","c":[0,0,225]},{"s":16.4,"l":"6","c":[0,0,225]},{"s":103.5,"l":"1","c":[230,0,30]},{"s":74,"l":"2","c":[230,0,30]},{"s":76.5,"l":"3","c":[230,0,30]},{"s":63.9,"l":"4","c":[230,0,30]},{"s":75.8,"l":"5","c":[230,0,30]},{"s":61.9,"l":"6","c":[230,0,30]},{"s":23.1,"l":"2","c":[0,0,0]},{"s":94,"l":"1","c":[0,165,0]},{"s":49.8,"l":"2","c":[0,165,0]},{"s":75.6,"l":"3","c":[0,165,0]},{"s":69.9,"l":"4","c":[0,165,0]},{"s":71.9,"l":"5","c":[0,165,0]},{"s":62.1,"l":"6","c":[0,165,0]},{"s":90.1,"l":"1","c":[120,0,225]},{"s":72.3,"l":"2","c":[120,0,225]},{"s":69.3,"l":"3","c":[120,0,225]},{"s":70.3,"l":"4","c":[120,0,225]},{"s":71.9,"l":"5","c":[120,0,225]},{"s":62.3,"l":"6","c":[120,0,225]},{"s":23.7,"l":"2","c":[0,0,0]},{"s":94.8,"l":"1","c":[0,192,255]},{"s":48.7,"l":"2","c":[0,192,255]},{"s":73,"l":"3","c":[0,192,255]},{"s":65.6,"l":"4","c":[0,192,255]},{"s":71.9,"l":"5","c":[0,192,255]},{"s":62.3,"l":"6","c":[0,192,255]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
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