Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: lung infections [ICD11:
CA4Y 
, ICD11:
CA4Z ];
infection due to Burkholderia [ICD11:
XN01M ]
The structure was elucidated in this paperNCBI PubMed ID: 25665786Publication DOI: 10.1016/j.carres.2014Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: christian.vogel
uni-rostock.de
Institutions: University of Rostock, Institute of Chemistry, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany, Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29a, D-18059 Rostock, Germany, Department of Chemical Sciences, University of Naples 'Federico II', I-80126-Via Cinthia 4, Napoli, Italy
To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranoside (27) and hexasaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopyranoside (33) were synthesized. These oligosaccharides represent the repeating monomer and dimer of the O-antigen, respectively.
O-antigen, Oligosaccharides, L-rhamnose, glycosylation, D-galactose, Burkholderia anthina
Structure type: oligomer ; 991.3838 [M+Na]+
C
39H
68O
27Location inside paper: abstract, p.100, scheme 3, compound 33
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130669,IEDB_133754,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, UV, glycosylation, ESI-TOF-MS
Comments, role: repeating dimer of the O-antigen
Related record ID(s): 30644, 30819
NCBI Taxonomy refs (TaxIDs): 179879
Show glycosyltransferases
NMR conditions: in D2O at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
1,3,2,2,3,2 aLRhap 101.2 70.8 70.7 72.6 69.4 17.5
1,3,2,2,3 aDGalp 95.4-95.6 75.1 69.8 70.2 71.6 61.6
1,3,2,2 aLRhap 103.0 67.4 75.5 71.2 70.1 17.6
1,3,2 aLRhap 102.9 78.9 70.9 72.7 70.0 17.5
1,3 aDGalp 95.4-95.6 75.6 70.1 70.4 71.6 61.7
1 aLRhap 100.3 67.7 76.1 71.2 70.3 17.6
Pr
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,3,2,2,3,2 aLRhap 5.20 4.05-4.10 3.83-3.89 3.46 3.70-3.77 1.30
1,3,2,2,3 aDGalp 5.17 3.93 4.05-4.10 4.03 4.18-4.22 3.70-3.77
1,3,2,2 aLRhap 5.00 4.27 3.83-3.89 3.57-4.03 3.70-3.77 1.30
1,3,2 aLRhap 5.02 4.05-4.10 3.79 3.49 3.70-3.77 1.30
1,3 aDGalp 5.11 3.93 4.05-4.10 4.03 4.18-4.22 3.70-3.77
1 aLRhap 4.81 4.05-4.10 3.83-3.89 3.59 3.70-3.77 1.30
Pr
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1,3,2,2,3,2 aLRhap 101.2/5.20 70.8/4.05-4.10 70.7/3.83-3.89 72.6/3.46 69.4/3.70-3.77 17.5/1.30
1,3,2,2,3 aDGalp 95.4-95.6/5.17 75.1/3.93 69.8/4.05-4.10 70.2/4.03 71.6/4.18-4.22 61.6/3.70-3.77
1,3,2,2 aLRhap 103.0/5.00 67.4/4.27 75.5/3.83-3.89 71.2/3.57-4.03 70.1/3.70-3.77 17.6/1.30
1,3,2 aLRhap 102.9/5.02 78.9/4.05-4.10 70.9/3.79 72.7/3.49 70.0/3.70-3.77 17.5/1.30
1,3 aDGalp 95.4-95.6/5.11 75.6/3.93 70.1/4.05-4.10 70.4/4.03 71.6/4.18-4.22 61.7/3.70-3.77
1 aLRhap 100.3/4.81 67.7/4.05-4.10 76.1/3.83-3.89 71.2/3.59 70.3/3.70-3.77 17.6/1.30
Pr
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,3,2,2,3,2 | aLRhap | 5.20 | 4.05
4.10 | 3.83
3.89 | 3.46 | 3.70
3.77 | 1.30 |
| 1,3,2,2,3 | aDGalp | 5.17 | 3.93 | 4.05
4.10 | 4.03 | 4.18
4.22 | 3.70
3.77 |
| 1,3,2,2 | aLRhap | 5.00 | 4.27 | 3.83
3.89 | 3.57
4.03 | 3.70
3.77 | 1.30 |
| 1,3,2 | aLRhap | 5.02 | 4.05
4.10 | 3.79 | 3.49 | 3.70
3.77 | 1.30 |
| 1,3 | aDGalp | 5.11 | 3.93 | 4.05
4.10 | 4.03 | 4.18
4.22 | 3.70
3.77 |
| 1 | aLRhap | 4.81 | 4.05
4.10 | 3.83
3.89 | 3.59 | 3.70
3.77 | 1.30 |
| | Pr | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1,3,2,2,3,2 | aLRhap | 101.2 | 70.8 | 70.7 | 72.6 | 69.4 | 17.5 |
| 1,3,2,2,3 | aDGalp | 95.4
95.6 | 75.1 | 69.8 | 70.2 | 71.6 | 61.6 |
| 1,3,2,2 | aLRhap | 103.0 | 67.4 | 75.5 | 71.2 | 70.1 | 17.6 |
| 1,3,2 | aLRhap | 102.9 | 78.9 | 70.9 | 72.7 | 70.0 | 17.5 |
| 1,3 | aDGalp | 95.4
95.6 | 75.6 | 70.1 | 70.4 | 71.6 | 61.7 |
| 1 | aLRhap | 100.3 | 67.7 | 76.1 | 71.2 | 70.3 | 17.6 |
| | Pr | |
|
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
