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 ; 537.2167 [M+Na]+
C
21H
38O
14Location inside paper: abstract, p.100, scheme 3, compound 27
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130669,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 monomer of the O-antigen
Related record ID(s): 30644, 30820
NCBI Taxonomy refs (TaxIDs): 179879
Show glycosyltransferases
NMR conditions: in CD3OD at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
1,3,2 aLRhap 103.6 72.0 72.2 73.9 69.5-70.4 18.1
1,3 aDGalp 98.0 76.3 70.7 71.6 72.3 62.7
1 aLRhap 101.2 69.5 79.1 72.5 69.5-70.4 18.21
Pr
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,3,2 aLRhap 5.04 3.90-4.05 3.68-3.78 3.34-3.43 3.58-3.67 1.29
1,3 aDGalp 5.01 3.90-4.05 3.90-4.05 3.90-4.05 4.19 3.68-3.78
1 aLRhap 4.71 3.90-4.05 3.68-3.78 3.49 3.58-3.67 1.29
Pr
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1,3,2 aLRhap 103.6/5.04 72.0/3.90-4.05 72.2/3.68-3.78 73.9/3.34-3.43 69.5-70.4/3.58-3.67 18.1/1.29
1,3 aDGalp 98.0/5.01 76.3/3.90-4.05 70.7/3.90-4.05 71.6/3.90-4.05 72.3/4.19 62.7/3.68-3.78
1 aLRhap 101.2/4.71 69.5/3.90-4.05 79.1/3.68-3.78 72.5/3.49 69.5-70.4/3.58-3.67 18.21/1.29
Pr
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,3,2 | aLRhap | 5.04 | 3.90
4.05 | 3.68
3.78 | 3.34
3.43 | 3.58
3.67 | 1.29 |
| 1,3 | aDGalp | 5.01 | 3.90
4.05 | 3.90
4.05 | 3.90
4.05 | 4.19 | 3.68
3.78 |
| 1 | aLRhap | 4.71 | 3.90
4.05 | 3.68
3.78 | 3.49 | 3.58
3.67 | 1.29 |
| | Pr | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1,3,2 | aLRhap | 103.6 | 72.0 | 72.2 | 73.9 | 69.5
70.4 | 18.1 |
| 1,3 | aDGalp | 98.0 | 76.3 | 70.7 | 71.6 | 72.3 | 62.7 |
| 1 | aLRhap | 101.2 | 69.5 | 79.1 | 72.5 | 69.5
70.4 | 18.21 |
| | Pr | |
|
There is only one chemically distinct structure:
Found 
report error