Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cystic fibrosis (CF) [ICD11:
CA25 
]
The structure was elucidated in this paperPublication DOI: 10.1002/ejoc.200901200Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: molinaro
unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli 'Federico II', Via Cintia 4, 80126 Napoli, Italy, CNR-ICTP Catania, Via Gaifami 18, 95126 Catania, Italy, Newcastle University, Institute of Cellular Medicine, The Medical School, Newcastle, NE2 4HH, UK, Department of Medical Microbiology, The Freeman Hospital, Newcastle upon Tyne Hospitals Trust, Newcastle, NE7 7DN, UK
In this work, we carried out the elucidation of a novel lipooligosaccharide (LOS) from a clinical strain of the most virulent strain of the Burkholderia cepacia complex, which was of B. cenocepacia ET‐12 epidemic strain lineage. The strain was isolated from a cystic fibrosis patient who had successfully undergone lung transplantation. This molecule presents some specific chemical differences when compared to the LOS reported so far from other B. cenocepacia ET‐12 clones. The new endotoxin was also tested as a cytokine enhancer on human myelomonocytic U937 cells. Lipopolysaccharides are the main virulence factors of Gram‐negative bacteria, and since they are exposed to the extracellular space, they are deeply involved in bacterial adaptation to the host environment. The characterisation of structural motifs present in these molecules is essential to the comprehension of the persistence/survival mechanisms and inflammatory potential of these bacteria.
Oligosaccharides, immunology, inflammation, innate immunity, Burkholderia cenocepacia, lung transplantation
Structure type: oligomer
Location inside paper: p.1302, scheme 1, p.1301, table 1
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_136906,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_192,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, GLC-MS, MALDI-TOF MS, composition analysis, methanolysis, acetylation, pulsed-field gel electrophoresis
NCBI Taxonomy refs (TaxIDs): 95486Reference(s) to other database(s): GTC:G84208RC
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
5,3,3,6 aDGlcp 97.8 71.6 73.2 69.7 70.6 60.4
5,3,3 aDGlcp 100.1 71.7 73.1 71.6 71.8 65.2
5,3,7 aXLDmanHepp 100.7 70.5 70.6 71.3 70.7 69.0 63.7
5,3 aXLDmanHepp 100.3 69.4 79.8 69.6 73.4 70.0 69.9
5,4,6 aDGalp 97.8 68.5 69.4 68.9 69.9 61.1
5,4 bDGlcp 102.1 73.5 75.8 69.7 74.5 62.9
5 aXLDmanHepp 99.2 70.4 72.0 72.1 71.8 69.8 63.6
aXKdop ? ? 34.0 71.2 69.3 70.9 71.1 62.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
5,3,3,6 aDGlcp 5.00 3.59 3.78 3.45 3.87 3.79-3.86
5,3,3 aDGlcp 5.30 3.60 3.82 3.71 3.61 3.71-4.10
5,3,7 aXLDmanHepp 4.94 4.01 3.88 3.66 3.89 4.04 3.71-3.76
5,3 aXLDmanHepp 5.14 4.24 4.02 3.90 3.78 4.00 3.77
5,4,6 aDGalp 5.07 3.84 3.90 4.03 4.00 3.77-3.87
5,4 bDGlcp 4.62 3.35 3.53 3.47 3.68 3.89-3.99
5 aXLDmanHepp 5.30 4.08 4.11 4.13 3.63 4.11 3.70-3.77
aXKdop - - 2.05-2.20 4.16 4.28 4.13 4.00 3.77-3.88
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
5,3,3,6 aDGlcp 97.8/5.00 71.6/3.59 73.2/3.78 69.7/3.45 70.6/3.87 60.4/3.79-3.86
5,3,3 aDGlcp 100.1/5.30 71.7/3.60 73.1/3.82 71.6/3.71 71.8/3.61 65.2/3.71-4.10
5,3,7 aXLDmanHepp 100.7/4.94 70.5/4.01 70.6/3.88 71.3/3.66 70.7/3.89 69.0/4.04 63.7/3.71-3.76
5,3 aXLDmanHepp 100.3/5.14 69.4/4.24 79.8/4.02 69.6/3.90 73.4/3.78 70.0/4.00 69.9/3.77
5,4,6 aDGalp 97.8/5.07 68.5/3.84 69.4/3.90 68.9/4.03 69.9/4.00 61.1/3.77-3.87
5,4 bDGlcp 102.1/4.62 73.5/3.35 75.8/3.53 69.7/3.47 74.5/3.68 62.9/3.89-3.99
5 aXLDmanHepp 99.2/5.30 70.4/4.08 72.0/4.11 72.1/4.13 71.8/3.63 69.8/4.11 63.6/3.70-3.77
aXKdop 34.0/2.05-2.20 71.2/4.16 69.3/4.28 70.9/4.13 71.1/4.00 62.7/3.77-3.88
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 5,3,3,6 | aDGlcp | 5.00 | 3.59 | 3.78 | 3.45 | 3.87 | 3.79
3.86 | |
| 5,3,3 | aDGlcp | 5.30 | 3.60 | 3.82 | 3.71 | 3.61 | 3.71
4.10 | |
| 5,3,7 | aXLDmanHepp | 4.94 | 4.01 | 3.88 | 3.66 | 3.89 | 4.04 | 3.71
3.76 | |
| 5,3 | aXLDmanHepp | 5.14 | 4.24 | 4.02 | 3.90 | 3.78 | 4.00 | 3.77 | |
| 5,4,6 | aDGalp | 5.07 | 3.84 | 3.90 | 4.03 | 4.00 | 3.77
3.87 | |
| 5,4 | bDGlcp | 4.62 | 3.35 | 3.53 | 3.47 | 3.68 | 3.89
3.99 | |
| 5 | aXLDmanHepp | 5.30 | 4.08 | 4.11 | 4.13 | 3.63 | 4.11 | 3.70
3.77 | |
| | aXKdop |
|
| 2.05
2.20 | 4.16 | 4.28 | 4.13 | 4.00 | 3.77
3.88 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 5,3,3,6 | aDGlcp | 97.8 | 71.6 | 73.2 | 69.7 | 70.6 | 60.4 | |
| 5,3,3 | aDGlcp | 100.1 | 71.7 | 73.1 | 71.6 | 71.8 | 65.2 | |
| 5,3,7 | aXLDmanHepp | 100.7 | 70.5 | 70.6 | 71.3 | 70.7 | 69.0 | 63.7 | |
| 5,3 | aXLDmanHepp | 100.3 | 69.4 | 79.8 | 69.6 | 73.4 | 70.0 | 69.9 | |
| 5,4,6 | aDGalp | 97.8 | 68.5 | 69.4 | 68.9 | 69.9 | 61.1 | |
| 5,4 | bDGlcp | 102.1 | 73.5 | 75.8 | 69.7 | 74.5 | 62.9 | |
| 5 | aXLDmanHepp | 99.2 | 70.4 | 72.0 | 72.1 | 71.8 | 69.8 | 63.6 | |
| | aXKdop | ? | ? | 34.0 | 71.2 | 69.3 | 70.9 | 71.1 | 62.7 |
|
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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