Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella dysenteriae [ICD11:
XN285 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 17081507Publication DOI: 10.1016/j.carres.2006.10.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm <gw
organ.su.se>
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institutet, Department of Laboratory Medicine, Division of Clinical Bacteriology, Karolinska University, Hospital, Huddinge, Stockholm, Sweden
The structures of the O-antigenic part of the lipopolysaccharides from Shigella dysenteriae type 3 and Escherichia coli O124 have been reinvestigated. (1)H and (13)C NMR spectroscopy in combination with selected 2D NMR techniques were used to determine the O-antigen pentasaccharide repeating units with the following structure: From biosynthetic considerations this should also be the biological repeating unit. The structures of the repeating units also explain the previously observed cross-reactivity between the strains and to E. coli O164, which only differs in the terminal sugar residue that is lacking the (R)-1-carboxyethyl group.
Lipopolysaccharide, NMR, cross-reactivity, Escherichia coli O164, Lactyl
Structure type: polymer biological repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_21,SB_7,SB_88
Methods: NMR
Biological activity: serological data
Comments, role: revision of previously elucidated structure ID 122423
Related record ID(s): 11568, 20016, 20677, 22714, 23064, 108646, 122423
NCBI Taxonomy refs (TaxIDs): 984896,
562
Show glycosyltransferases
NMR conditions: in D2O at 318 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,6,4,6,4 lRLac 182.2 78.7 19.7
3,6,4,6 bDGlcp 103.5 74.0 76.7 77.7 75.7 61.9
3,6,4 aDGlcp 100.0 72.8 73.5 69.7 71.3 68.8
3,6 bDGalp 104.3 71.7 81.5 76.2 76.2 60.8
3 bDGalf 110.0 82.1 78.0 84.2 70.9 72.1
2 Ac 175.4 23.2
bDGalpN 104.2 52.3 79.3 68.8 75.7 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,6,4,6,4 lRLac - 4.34 1.36
3,6,4,6 bDGlcp 4.47 3.35 3.62 3.39 3.48 3.84-3.91
3,6,4 aDGlcp 4.92 3.51 3.73 3.65 4.32 4.05-4.31
3,6 bDGalp 4.50 3.67 3.83 4.25 3.77 3.82-3.87
3 bDGalf 5.09 4.10 4.03 4.05 4.01 3.74-4.08
2 Ac - 2.04
bDGalpN 4.71 3.94 3.81 4.05 3.67 3.79-3.86
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,6,4,6,4 lRLac 78.7/4.34 19.7/1.36
3,6,4,6 bDGlcp 103.5/4.47 74.0/3.35 76.7/3.62 77.7/3.39 75.7/3.48 61.9/3.84-3.91
3,6,4 aDGlcp 100.0/4.92 72.8/3.51 73.5/3.73 69.7/3.65 71.3/4.32 68.8/4.05-4.31
3,6 bDGalp 104.3/4.50 71.7/3.67 81.5/3.83 76.2/4.25 76.2/3.77 60.8/3.82-3.87
3 bDGalf 110.0/5.09 82.1/4.10 78.0/4.03 84.2/4.05 70.9/4.01 72.1/3.74-4.08
2 Ac 23.2/2.04
bDGalpN 104.2/4.71 52.3/3.94 79.3/3.81 68.8/4.05 75.7/3.67 62.0/3.79-3.86
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,6,4,6,4 | lRLac |
| 4.34 | 1.36 | |
| 3,6,4,6 | bDGlcp | 4.47 | 3.35 | 3.62 | 3.39 | 3.48 | 3.84
3.91 |
| 3,6,4 | aDGlcp | 4.92 | 3.51 | 3.73 | 3.65 | 4.32 | 4.05
4.31 |
| 3,6 | bDGalp | 4.50 | 3.67 | 3.83 | 4.25 | 3.77 | 3.82
3.87 |
| 3 | bDGalf | 5.09 | 4.10 | 4.03 | 4.05 | 4.01 | 3.74
4.08 |
| 2 | Ac |
| 2.04 | |
| | bDGalpN | 4.71 | 3.94 | 3.81 | 4.05 | 3.67 | 3.79
3.86 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,6,4,6,4 | lRLac | 182.2 | 78.7 | 19.7 | |
| 3,6,4,6 | bDGlcp | 103.5 | 74.0 | 76.7 | 77.7 | 75.7 | 61.9 |
| 3,6,4 | aDGlcp | 100.0 | 72.8 | 73.5 | 69.7 | 71.3 | 68.8 |
| 3,6 | bDGalp | 104.3 | 71.7 | 81.5 | 76.2 | 76.2 | 60.8 |
| 3 | bDGalf | 110.0 | 82.1 | 78.0 | 84.2 | 70.9 | 72.1 |
| 2 | Ac | 175.4 | 23.2 | |
| | bDGalpN | 104.2 | 52.3 | 79.3 | 68.8 | 75.7 | 62.0 |
|
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
