Taxonomic group: bacteria / Fusobacteria
(Phylum: Fusobacteria)
Host organism: Homo sapiens
Associated disease: periodontitis [ICD11:
DA0C 
];
infection due to Fusobacterium nucleatum [ICD11:
XN4P8 ]
The structure was elucidated in this paperNCBI PubMed ID: 29753950Publication DOI: 10.1016/j.carres.2018.04.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Evguenii.Vinogradov
nrc-cnrc.gc.ca
Institutions: Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON, K1A 0R6, Canada
Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. It was also found in colorectal cancer tissues and is linked with pregnancy complications, including pre-term and still births. Cell surface structures of the bacterium could be implicated in pathogenesis. Here we report the following structure of the lipopolysaccharide O-chain of F. nucleatum strain MJR 7757B:where Lac is (R)-1-carboxyethyl (lactic acid residue); all monosaccharides are in the pyranose form. ManNAc4Lac, analogue of N-acetylmuramic acid, is found for the first time in natural sources.
Lipopolysaccharide, structure, polysaccharide, NMR spectroscopy, Fusobacterium nucleatum
Structure type: polymer chemical repeating unit ; n=15, 10000
Location inside paper: p.37, table 1
Compound class: O-antigen
Contained glycoepitopes: IEDB_142345,IEDB_142488,IEDB_146664,IEDB_885813,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, acid hydrolysis, GPC
NCBI Taxonomy refs (TaxIDs): 851
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2 Ac 175.6 23.2-23.7
3,4,4 lRLac 182.6 78.7 20.1
3,4 bDManpN 100.6 51.2 78.6 72.7 76.6 62.2
3,6 Ac 175.0 21.5
3 bDGlcp 105.5 73.6 74.9 79.6 73.4 63.9
2 Ac 175.6 23.2-23.7
bDFucpN4N 99.4 52.2 78.5 55.9 68.4 17.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 Ac - 2.01-2.04
3,4,4 lRLac - 4.57 1.33
3,4 bDManpN 4.74 4.62 4.14 3.62 3.44 3.91-3.94
3,6 Ac - 2.17
3 bDGlcp 4.53 3.35 3.63 3.67 3.69 4.33-4.42
2 Ac - 2.01-2.04
bDFucpN4N 4.66 3.95 4.21 3.81 4.06 1.40
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 Ac 23.2-23.7/2.01-2.04
3,4,4 lRLac 78.7/4.57 20.1/1.33
3,4 bDManpN 100.6/4.74 51.2/4.62 78.6/4.14 72.7/3.62 76.6/3.44 62.2/3.91-3.94
3,6 Ac 21.5/2.17
3 bDGlcp 105.5/4.53 73.6/3.35 74.9/3.63 79.6/3.67 73.4/3.69 63.9/4.33-4.42
2 Ac 23.2-23.7/2.01-2.04
bDFucpN4N 99.4/4.66 52.2/3.95 78.5/4.21 55.9/3.81 68.4/4.06 17.0/1.40
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | Ac |
| 2.01
2.04 | |
| 3,4,4 | lRLac |
| 4.57 | 1.33 | |
| 3,4 | bDManpN | 4.74 | 4.62 | 4.14 | 3.62 | 3.44 | 3.91
3.94 |
| 3,6 | Ac |
| 2.17 | |
| 3 | bDGlcp | 4.53 | 3.35 | 3.63 | 3.67 | 3.69 | 4.33
4.42 |
| 2 | Ac |
| 2.01
2.04 | |
| | bDFucpN4N | 4.66 | 3.95 | 4.21 | 3.81 | 4.06 | 1.40 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | Ac | 175.6 | 23.2
23.7 | |
| 3,4,4 | lRLac | 182.6 | 78.7 | 20.1 | |
| 3,4 | bDManpN | 100.6 | 51.2 | 78.6 | 72.7 | 76.6 | 62.2 |
| 3,6 | Ac | 175.0 | 21.5 | |
| 3 | bDGlcp | 105.5 | 73.6 | 74.9 | 79.6 | 73.4 | 63.9 |
| 2 | Ac | 175.6 | 23.2
23.7 | |
| | bDFucpN4N | 99.4 | 52.2 | 78.5 | 55.9 | 68.4 | 17.0 |
|
There is only one chemically distinct structure:
Found 
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