Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cystic fibrosis (CF) [ICD11:
CA25 
]
The structure was elucidated in this paperNCBI PubMed ID: 23544536Publication DOI: 10.1016/j.carbpol.2013.01.047Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: P. Cescutti <pcescutti
units.it>
Institutions: Dipartimento di Scienze della Vita, Universita degli Studi di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy
Burkholderia vietnamiensis belongs to the Burkholderia cepacia complex and is an opportunistic pathogen for cystic fibrosis patients. As many other Burkholderia species, it has a mucoide phenotype, producing abundant exopolysaccharide. In general, polysaccharides contribute to bacterial survival in a hostile environment, are recognised as virulence factors and as important components in biofilm formation. The primary structure of the exopolysaccharide produced by B. vietnamiensis LMG 10929 was determined mainly by use of 1D and 2D NMR spectroscopy and ESI mass spectrometry. The polymer consists of the trisaccharidic backbone 3)-β-D-Glcp-(1→4)-α-D-Glcp-(1→3)-α-L-Fucp-(1→ with the side chain α-D-Glcp-(1→4)-α-D-GlcAp-(1→3)-α-L-Fucp-(1→ linked to C-3 of the α-D-Glcp residue. The polysaccharide also bears acetyl substituents on about 20% of its repeating units and on at least two different positions. The presence of fucose residues is a novel structural feature among the exopolysaccharides produced by species of the B. cepacia complex.
polysaccharide, NMR spectroscopy, fucose, cystic fibrosis, Burkholderia vietnamiensis, ESI mass spectrometry
Structure type: oligomer
Location inside paper: p.259, scheme 1, BV-RU (β-anomer)
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_140629,IEDB_140630,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_983931,SB_192,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, de-O-acylation, sugar analysis, ESI-MS, acid hydrolysis, carboxyl reduction, GC, Smith degradation, NMR-1D, methanolysis, HPSEC
Comments, role: EPS repeating unit after partial acid hydrolysis of the EPS.
Related record ID(s): 29443, 29444, 29933
NCBI Taxonomy refs (TaxIDs): 1449978Reference(s) to other database(s): GTC:G58011SQ
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,3,4 bDGlcp 99.44 72.57 72.57 70.08 73.67 60.84
3,3,3 aDGlcpA 101.45 72.50 74.40 77.86 73.88 ?
3,3 aLFucp 99.56 68.14 78.13 72.85 67.12 16.05
3,4 aDGlcp 102.09 74.62 76.43 71.46 77.35 62.97
3 aDGlcp 101.54 73.84 75.98 73.55 72.66 60.37
bLFucp 96.89 71.63 82.41 72.24 71.62 16.24
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,3,4 bDGlcp 5.46 3.52 3.72 3.40 3.69 3.78
3,3,3 aDGlcpA 5.20 3.65 4.03 3.80 4.12 -
3,3 aLFucp 5.39 3.99 3.91 3.87 4.78 1.20
3,4 aDGlcp 4.47 3.19 3.46 3.09 3.41 3.62-3.88
3 aDGlcp 5.17 3.80 4.04 3.88 3.97 3.88
bLFucp 4.60 3.64 3.71 3.91 3.81 1.23
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,3,4 bDGlcp 99.44/5.46 72.57/3.52 72.57/3.72 70.08/3.40 73.67/3.69 60.84/3.78
3,3,3 aDGlcpA 101.45/5.20 72.50/3.65 74.40/4.03 77.86/3.80 73.88/4.12
3,3 aLFucp 99.56/5.39 68.14/3.99 78.13/3.91 72.85/3.87 67.12/4.78 16.05/1.20
3,4 aDGlcp 102.09/4.47 74.62/3.19 76.43/3.46 71.46/3.09 77.35/3.41 62.97/3.62-3.88
3 aDGlcp 101.54/5.17 73.84/3.80 75.98/4.04 73.55/3.88 72.66/3.97 60.37/3.88
bLFucp 96.89/4.60 71.63/3.64 82.41/3.71 72.24/3.91 71.62/3.81 16.24/1.23
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,3,4 | bDGlcp | 5.46 | 3.52 | 3.72 | 3.40 | 3.69 | 3.78 |
| 3,3,3 | aDGlcpA | 5.20 | 3.65 | 4.03 | 3.80 | 4.12 |
|
| 3,3 | aLFucp | 5.39 | 3.99 | 3.91 | 3.87 | 4.78 | 1.20 |
| 3,4 | aDGlcp | 4.47 | 3.19 | 3.46 | 3.09 | 3.41 | 3.62
3.88 |
| 3 | aDGlcp | 5.17 | 3.80 | 4.04 | 3.88 | 3.97 | 3.88 |
| | bLFucp | 4.60 | 3.64 | 3.71 | 3.91 | 3.81 | 1.23 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,3,4 | bDGlcp | 99.44 | 72.57 | 72.57 | 70.08 | 73.67 | 60.84 |
| 3,3,3 | aDGlcpA | 101.45 | 72.50 | 74.40 | 77.86 | 73.88 | ? |
| 3,3 | aLFucp | 99.56 | 68.14 | 78.13 | 72.85 | 67.12 | 16.05 |
| 3,4 | aDGlcp | 102.09 | 74.62 | 76.43 | 71.46 | 77.35 | 62.97 |
| 3 | aDGlcp | 101.54 | 73.84 | 75.98 | 73.55 | 72.66 | 60.37 |
| | bLFucp | 96.89 | 71.63 | 82.41 | 72.24 | 71.62 | 16.24 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":99.44,"l":"1","c":[0,0,225]},{"s":72.57,"l":"2","c":[0,0,225]},{"s":72.57,"l":"3","c":[0,0,225]},{"s":70.08,"l":"4","c":[0,0,225]},{"s":73.67,"l":"5","c":[0,0,225]},{"s":60.84,"l":"6","c":[0,0,225]},{"s":101.45,"l":"1","c":[230,0,30]},{"s":72.5,"l":"2","c":[230,0,30]},{"s":74.4,"l":"3","c":[230,0,30]},{"s":77.86,"l":"4","c":[230,0,30]},{"s":73.88,"l":"5","c":[230,0,30]},{"s":99.56,"l":"1","c":[0,165,0]},{"s":68.14,"l":"2","c":[0,165,0]},{"s":78.13,"l":"3","c":[0,165,0]},{"s":72.85,"l":"4","c":[0,165,0]},{"s":67.12,"l":"5","c":[0,165,0]},{"s":16.05,"l":"6","c":[0,165,0]},{"s":102.09,"l":"1","c":[120,0,225]},{"s":74.62,"l":"2","c":[120,0,225]},{"s":76.43,"l":"3","c":[120,0,225]},{"s":71.46,"l":"4","c":[120,0,225]},{"s":77.35,"l":"5","c":[120,0,225]},{"s":62.97,"l":"6","c":[120,0,225]},{"s":101.54,"l":"1","c":[0,192,255]},{"s":73.84,"l":"2","c":[0,192,255]},{"s":75.98,"l":"3","c":[0,192,255]},{"s":73.55,"l":"4","c":[0,192,255]},{"s":72.66,"l":"5","c":[0,192,255]},{"s":60.37,"l":"6","c":[0,192,255]},{"s":96.89,"l":"1","c":[220,0,180]},{"s":71.63,"l":"2","c":[220,0,180]},{"s":82.41,"l":"3","c":[220,0,180]},{"s":72.24,"l":"4","c":[220,0,180]},{"s":71.62,"l":"5","c":[220,0,180]},{"s":16.24,"l":"6","c":[220,0,180]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
