Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: melioidosis [ICD11:
1C42 
, ICD11:
XN3LD ];
infection due to Burkholderia pseudomallei [ICD11:
XN3LD ]
The structure was elucidated in this paperNCBI PubMed ID: 24491843Publication DOI: 10.1016/j.carres.2013.08.011Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A. Tuanyok <Apichai.Tuanyok
gmail.com>
Institutions: Complex Carbohydrate Research Center, The University of Georgia, Athens, GA 30602, USA, Department of Biological Sciences, Northern Arizona University, 1298 S. Knoles Dr. Building #56, Flagstaff, AZ 86011, USA, Department of Chemistry, Northern Arizona University, Flagstaff, AZ 86011, USA
Burkholderia oklahomensis E0147 is a US isolated bacterium believed to express a similar O-antigen to type A structure of the highly pathogenic species, Burkholderia pseudomallei. Both species are genetically closely related. Lipopolysaccharide was collected from E0147 and structurally characterized to test this hypothesis. Glycosyl composition and linkage analyses in conjunction with 1D and 2D 1H and 13C NMR spectroscopy showed that the O-antigen was a repeating disaccharide with the following structure: [3)-β-D-Glcp-(1→3)-2OAc-α-L-6dTalp-(1→]n NMR spectroscopy also revealed the presence of a co-extracted exopolysaccharide previously described in B. pseudomallei, with the structure: [3)-2OAc-β-D-Galp-(1→4)-α-D-Galp-(1→3)-β-D-Galp-(1→5)-β-D-Kdop -(2→]n.
Lipopolysaccharide, NMR, structure, O-antigen, exopolysaccharide, Burkholderia oklahomensis
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.71, table 2
Trivial name: K-antigen, galactan-Kdo, Kdo-EPS
Compound class: CPS, EPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_36,SB_7,SB_87,SB_88,SB_9
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, GC, composition analysis, NMR-1D
Related record ID(s): 30472, 30473
NCBI Taxonomy refs (TaxIDs): 441163,
28450,
292Reference(s) to other database(s): GTC:G77110LE, GlycomeDB:
25312
Show glycosyltransferases
NMR conditions: in D2O at 330 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
5,3,4,2 Ac
5,3,4 bDGalp 104.7 73.6 77.8 71.4 77.6 63.5
5,3 aDGalp 98.2 71.2 71.7 80.1 72.9 63.3
5 bDGalp 107.1 72.4 80.0 67.9 77.4 63.3
bXKdop 175.3 104.6 38.7 70.5 77.8 76.1 71.8 66.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
5,3,4,2 Ac
5,3,4 bDGalp 4.83 4.89 4.16 4.10 3.75 3.71-3.85
5,3 aDGalp 5.08 3.68 4.02 4.16 4.18 3.68-3.79
5 bDGalp 4.65 3.75 3.74 4.12 3.70 3.70-3.79
bXKdop - - 1.83-2.50 3.82 4.15 3.5 4.05 3.73-3.78
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
5,3,4,2 Ac
5,3,4 bDGalp 104.7/4.83 73.6/4.89 77.8/4.16 71.4/4.10 77.6/3.75 63.5/3.71-3.85
5,3 aDGalp 98.2/5.08 71.2/3.68 71.7/4.02 80.1/4.16 72.9/4.18 63.3/3.68-3.79
5 bDGalp 107.1/4.65 72.4/3.75 80.0/3.74 67.9/4.12 77.4/3.70 63.3/3.70-3.79
bXKdop 38.7/1.83-2.50 70.5/3.82 77.8/4.15 76.1/3.5 71.8/4.05 66.6/3.73-3.78
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 5,3,4,2 | Ac | |
| 5,3,4 | bDGalp | 4.83 | 4.89 | 4.16 | 4.10 | 3.75 | 3.71
3.85 | |
| 5,3 | aDGalp | 5.08 | 3.68 | 4.02 | 4.16 | 4.18 | 3.68
3.79 | |
| 5 | bDGalp | 4.65 | 3.75 | 3.74 | 4.12 | 3.70 | 3.70
3.79 | |
| | bXKdop |
|
| 1.83
2.50 | 3.82 | 4.15 | 3.5 | 4.05 | 3.73
3.78 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 5,3,4,2 | Ac | |
| 5,3,4 | bDGalp | 104.7 | 73.6 | 77.8 | 71.4 | 77.6 | 63.5 | |
| 5,3 | aDGalp | 98.2 | 71.2 | 71.7 | 80.1 | 72.9 | 63.3 | |
| 5 | bDGalp | 107.1 | 72.4 | 80.0 | 67.9 | 77.4 | 63.3 | |
| | bXKdop | 175.3 | 104.6 | 38.7 | 70.5 | 77.8 | 76.1 | 71.8 | 66.6 |
|
There is only one chemically distinct structure:
Found 
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