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: 18684854Publication DOI: 10.1093/glycob/cwn074Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: molinaro
unita.it
Institutions: Istituto per la Chimica e la Tecnologia dei Materiali Polimerici - ICTMP - CNR, Catania, Italy, Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Napoli, Via Cintia, 4. I-80126 Italy, Centre for Veterinary Science, Department of Veterinary Medicine, University of Cambridge, Cambridge, UK, Department of Medical Microbiology and fCardiopulmonary Transplantation, Freeman Hospital, Newcastle, UK, Applied Immunobiology and Transplantation Group, Institute of Cellular Medicine, University of Newcastle, Newcastle, UK
The Burkholderia cepacia complex is a group of Gram negative bacteria that are opportunistic pathogens for humans especially in cystic fibrosis patients. Lipopolysaccharide molecules, are potent virulence factors of Gram negative bacteria organisms essential for bacterial survival. A complete analysis of the bacterial lipopolysaccharide structure to function relationship is required to understand the chemical basis of the inflammatory process. We have therefore investigated the structures of lipopolysaccharides from clonally identical Burkholderia multivorans strains (genomovar II) isolated pre- and post- lung transplantation through compositional analysis, mass spectrometry and 2D NMR spectroscopy. We tested the LPS' pro-inflammatory activity as a stimulant of human myelomonocytic U937 cell cytokine induction and assessed TLR4/MD2 signalling. Marked changes between the paired strains were found in the lipid A-inner core region. Such structural variations can contribute to the bacterial survival and persistence of infections despite the loss of a CF milieu following lung transplantation
Lipopolysaccharide, NMR spectroscopy, cystic fibrosis, virulence factor, Burkholderia cepacia complex, Burkholderia multivorans, lung transplantation
Structure type: oligomer
Location inside paper: p. 874, oligosaccharide X, suppl. table 2
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_136105,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_142488,IEDB_146664,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, SDS-PAGE, 31P NMR, MALDI-TOF MS, composition analysis, NMR-1D
Biological activity: biological activity data
Related record ID(s): 22979, 22980
NCBI Taxonomy refs (TaxIDs): 87883Reference(s) to other database(s): GTC:G83041FP, GlycomeDB:
36861
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
4 aXKop ? ? 70.8 68.8 70.2 72.3 70.4 63.7
5,3,2,3,2 Ac
5,3,2,3 bDQuipN 102.33 55.9 75.5 75.0 75.5 16.9
5,3,2 aLRhap 97.85 69.9 80.3 70.5 70.8 17.2
5,3,3 aLRhap 97.2 70.6 71.4 71.9 70.3 16.6
5,3,7 aXLDmanHepp 101.27 69.9 70.3 70.5 71.6 69.9 62.9
5,3 aXLDmanHepp 99.02 71.2 69.8 69.2 70.4 66.4 70.73
5,4,6 aXLDmanHepp 97.31 70.0 70.1 71.5 71.8 68.6 62.8
5,4 bDGlcp 102.3 73.5 75.6 70.5 72.0 65.3
5 aXLDmanHepp 98.72 70.6 70.5 70.2 72.8 68.8 61.7
aXKdo? ? ? 33.8 71.6 68.4 71.6 71.8 63.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
4 aXKop - - 3.74 3.87 3.95 3.54 3.92 3.59-3.83
5,3,2,3,2 Ac
5,3,2,3 bDQuipN 4.57 3.59 3.66 3.05 3.35 1.18
5,3,2 aLRhap 4.68 3.84 3.73 3.28 3.73 1.17
5,3,3 aLRhap 4.81 3.75 3.68 3.32 3.80 1.13
5,3,7 aXLDmanHepp 4.78 3.82 3.71 3.71 3.51 3.83 3.52-3.59
5,3 aXLDmanHepp 5.12 4.19 3.83 3.85 3.79 3.79 3.56-3.62
5,4,6 aXLDmanHepp 4.80 3.84 3.94 3.89 3.56 3.86 3.52-3.58
5,4 bDGlcp 4.39 3.15 3.34 3.28 3.56 3.82-3.89
5 aXLDmanHepp 5.15 3.93 3.91 3.94 3.62 3.85 3.57-3.66
aXKdo? - - 1.94-2.05 3.97 4.09 3.68 3.90 3.61-3.79
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
4 aXKop 70.8/3.74 68.8/3.87 70.2/3.95 72.3/3.54 70.4/3.92 63.7/3.59-3.83
5,3,2,3,2 Ac
5,3,2,3 bDQuipN 102.33/4.57 55.9/3.59 75.5/3.66 75.0/3.05 75.5/3.35 16.9/1.18
5,3,2 aLRhap 97.85/4.68 69.9/3.84 80.3/3.73 70.5/3.28 70.8/3.73 17.2/1.17
5,3,3 aLRhap 97.2/4.81 70.6/3.75 71.4/3.68 71.9/3.32 70.3/3.80 16.6/1.13
5,3,7 aXLDmanHepp 101.27/4.78 69.9/3.82 70.3/3.71 70.5/3.71 71.6/3.51 69.9/3.83 62.9/3.52-3.59
5,3 aXLDmanHepp 99.02/5.12 71.2/4.19 69.8/3.83 69.2/3.85 70.4/3.79 66.4/3.79 70.73/3.56-3.62
5,4,6 aXLDmanHepp 97.31/4.80 70.0/3.84 70.1/3.94 71.5/3.89 71.8/3.56 68.6/3.86 62.8/3.52-3.58
5,4 bDGlcp 102.3/4.39 73.5/3.15 75.6/3.34 70.5/3.28 72.0/3.56 65.3/3.82-3.89
5 aXLDmanHepp 98.72/5.15 70.6/3.93 70.5/3.91 70.2/3.94 72.8/3.62 68.8/3.85 61.7/3.57-3.66
aXKdo? 33.8/1.94-2.05 71.6/3.97 68.4/4.09 71.6/3.68 71.8/3.90 63.7/3.61-3.79
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 4 | aXKop |
|
| 3.74 | 3.87 | 3.95 | 3.54 | 3.92 | 3.59
3.83 |
| 5,3,2,3,2 | Ac | |
| 5,3,2,3 | bDQuipN | 4.57 | 3.59 | 3.66 | 3.05 | 3.35 | 1.18 | |
| 5,3,2 | aLRhap | 4.68 | 3.84 | 3.73 | 3.28 | 3.73 | 1.17 | |
| 5,3,3 | aLRhap | 4.81 | 3.75 | 3.68 | 3.32 | 3.80 | 1.13 | |
| 5,3,7 | aXLDmanHepp | 4.78 | 3.82 | 3.71 | 3.71 | 3.51 | 3.83 | 3.52
3.59 | |
| 5,3 | aXLDmanHepp | 5.12 | 4.19 | 3.83 | 3.85 | 3.79 | 3.79 | 3.56
3.62 | |
| 5,4,6 | aXLDmanHepp | 4.80 | 3.84 | 3.94 | 3.89 | 3.56 | 3.86 | 3.52
3.58 | |
| 5,4 | bDGlcp | 4.39 | 3.15 | 3.34 | 3.28 | 3.56 | 3.82
3.89 | |
| 5 | aXLDmanHepp | 5.15 | 3.93 | 3.91 | 3.94 | 3.62 | 3.85 | 3.57
3.66 | |
| | aXKdo? |
|
| 1.94
2.05 | 3.97 | 4.09 | 3.68 | 3.90 | 3.61
3.79 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 4 | aXKop | ? | ? | 70.8 | 68.8 | 70.2 | 72.3 | 70.4 | 63.7 |
| 5,3,2,3,2 | Ac | |
| 5,3,2,3 | bDQuipN | 102.33 | 55.9 | 75.5 | 75.0 | 75.5 | 16.9 | |
| 5,3,2 | aLRhap | 97.85 | 69.9 | 80.3 | 70.5 | 70.8 | 17.2 | |
| 5,3,3 | aLRhap | 97.2 | 70.6 | 71.4 | 71.9 | 70.3 | 16.6 | |
| 5,3,7 | aXLDmanHepp | 101.27 | 69.9 | 70.3 | 70.5 | 71.6 | 69.9 | 62.9 | |
| 5,3 | aXLDmanHepp | 99.02 | 71.2 | 69.8 | 69.2 | 70.4 | 66.4 | 70.73 | |
| 5,4,6 | aXLDmanHepp | 97.31 | 70.0 | 70.1 | 71.5 | 71.8 | 68.6 | 62.8 | |
| 5,4 | bDGlcp | 102.3 | 73.5 | 75.6 | 70.5 | 72.0 | 65.3 | |
| 5 | aXLDmanHepp | 98.72 | 70.6 | 70.5 | 70.2 | 72.8 | 68.8 | 61.7 | |
| | aXKdo? | ? | ? | 33.8 | 71.6 | 68.4 | 71.6 | 71.8 | 63.7 |
|
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The spectrum also has 4 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
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