Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: corneal ulcer [ICD11:
9A76 
];
infection due to Burkholderia [ICD11:
XN01M ]
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.70, table 2
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, GC, composition analysis, NMR-1D
Comments, role: type A backbone in B. oklahomensis E0147
Related record ID(s): 30137, 30473
NCBI Taxonomy refs (TaxIDs): 441163Reference(s) to other database(s): GTC:G00784ZG, GlycomeDB:
3464
Show glycosyltransferases
NMR conditions: in D2O at 330 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3 bDGlcp 104.5 76.1 84.6 70.5 78.5 63.5
2 Ac
aL6dTalp 101.2 72.9 75.7 71.2 69.8 18.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3 bDGlcp 4.61 3.46 3.61 3.48 3.44 3.72-3.85
2 Ac - 2.16
aL6dTalp 5.23 5.23 4.24 3.94 4.36 1.25
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3 bDGlcp 104.5/4.61 76.1/3.46 84.6/3.61 70.5/3.48 78.5/3.44 63.5/3.72-3.85
2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
aL6dTalp 101.2/5.23 72.9/5.23 75.7/4.24 71.2/3.94 69.8/4.36 18.0/1.25
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3 | bDGlcp | 4.61 | 3.46 | 3.61 | 3.48 | 3.44 | 3.72
3.85 |
| 2 | Ac |
| 2.16 | |
| | aL6dTalp | 5.23 | 5.23 | 4.24 | 3.94 | 4.36 | 1.25 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3 | bDGlcp | 104.5 | 76.1 | 84.6 | 70.5 | 78.5 | 63.5 |
| 2 | Ac | |
| | aL6dTalp | 101.2 | 72.9 | 75.7 | 71.2 | 69.8 | 18.0 |
|
There is only one chemically distinct structure:
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: corneal ulcer [ICD11:
9A76 ];
infection due to Burkholderia [ICD11:
XN01M ]
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: fragment of a bigger structure
Location inside paper: p.70, table 2
Aglycon: (->3) O-antigen
Compound class: O-antigen
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, GC, composition analysis, NMR-1D
Comments, role: terminal part of OPS, part of structure of the B. oklahomensis E0147 (see ID: 30472); NMR data for aL6dTalp2Ac3Me4Ac residue; NMR data for aL6dTalp2Ac3Me residue 1H: #2_Ac // #3_Me 3.41// #_aL6dTalp 5.26 5.24 3.77 3.94 ? ?//, 13C: #2_Ac // #3_Me 58.3// #_aL6dTalp 101.2 70.7 76.4 70.5 ? ?//.
Related record ID(s): 30137, 30472
NCBI Taxonomy refs (TaxIDs): 441163Reference(s) to other database(s): GTC:G07963ZS
Show glycosyltransferases
NMR conditions: in D2O at 330 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2 Ac
3 Me 59.5
4 %Ac
aL6dTalp 101.2 70.3 75.7 72.4 68.4 17.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2 Ac
3 Me 3.40
4 %Ac
aL6dTalp 5.26 5.26 3.95 5.33 4.51 1.14
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2 Ac
3 Me 59.5/3.40
4 %Ac
aL6dTalp 101.2/5.26 70.3/5.26 75.7/3.95 72.4/5.33 68.4/4.51 17.8/1.14
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2 | Ac | |
| 3 | Me | 3.40 | |
| 4 | %Ac | |
| | aL6dTalp | 5.26 | 5.26 | 3.95 | 5.33 | 4.51 | 1.14 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2 | Ac | |
| 3 | Me | 59.5 | |
| 4 | %Ac | |
| | aL6dTalp | 101.2 | 70.3 | 75.7 | 72.4 | 68.4 | 17.8 |
|
There is only one chemically distinct structure:
Found 
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