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: 28651243Publication DOI: 10.1016/j.carres.2017.06.007Journal 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 12230: -6-α-d-Glc-4-β-d-GlcNHBu3NHBuA-3-β-d-QuiNAc4NABu- where ABu and HBu indicate (R)-3-aminobutanoyl and (R)-3-hydroxybutanoyl, respectively; all monosaccharides are in the pyranose form.
Lipopolysaccharide, NMR spectroscopy, polysaccharide structure, Fusobacterium nucleatum
Structure type: polymer chemical repeating unit
Location inside paper: abstract, table 1, p.117, fig.2
Compound class: O-polysaccharide, O-antigen, polysaccharide
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, periodate oxidation, NMR-2D, GC-MS, sugar analysis, ESI-MS, acid hydrolysis, GPC, reduction with NaBD4, acetylation
Comments, role: the NMR solution was not indicated.
Related record ID(s): 12260
NCBI Taxonomy refs (TaxIDs): 851
Show glycosyltransferases
NMR conditions: at 326 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4 aDGlcp 99.9 72.6 74.1 70.4 72.1 69.0
3,2 lR3HOBut 175.9 46.3 66.1 23.7
3,3 lR3HOBut 175.9 46.3 66.1 23.7
3 bDGlcpN3NA 103.1 55.0 55.5 76.1 79.8 175.9
2 Ac 175.2 24.0
4 Subst 173.7 39.9 46.6 19.0
bDQuipN4N 103.2 57.2 78.3 57.0 72.0 18.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4 aDGlcp 5.09 3.35 3.59 3.35 3.71 3.77-3.98
3,2 lR3HOBut - 2.32-2.38 4.11 1.21
3,3 lR3HOBut - 2.32-2.38 4.14 1.21
3 bDGlcpN3NA 4.59 3.80 4.13 3.98 3.81 -
2 Ac - 2.09
4 Subst - 2.66-2.77 3.74 1.43
bDQuipN4N 4.44 3.78 3.85 3.57 3.64 1.23
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4 aDGlcp 99.9/5.09 72.6/3.35 74.1/3.59 70.4/3.35 72.1/3.71 69.0/3.77-3.98
3,2 lR3HOBut 46.3/2.32-2.38 66.1/4.11 23.7/1.21
3,3 lR3HOBut 46.3/2.32-2.38 66.1/4.14 23.7/1.21
3 bDGlcpN3NA 103.1/4.59 55.0/3.80 55.5/4.13 76.1/3.98 79.8/3.81
2 Ac 24.0/2.09
4 Subst 39.9/2.66-2.77 46.6/3.74 19.0/1.43
bDQuipN4N 103.2/4.44 57.2/3.78 78.3/3.85 57.0/3.57 72.0/3.64 18.6/1.23
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4 | aDGlcp | 5.09 | 3.35 | 3.59 | 3.35 | 3.71 | 3.77
3.98 |
| 3,2 | lR3HOBut |
| 2.32
2.38 | 4.11 | 1.21 | |
| 3,3 | lR3HOBut |
| 2.32
2.38 | 4.14 | 1.21 | |
| 3 | bDGlcpN3NA | 4.59 | 3.80 | 4.13 | 3.98 | 3.81 |
|
| 2 | Ac |
| 2.09 | |
| 4 | Subst |
| 2.66
2.77 | 3.74 | 1.43 | |
| | bDQuipN4N | 4.44 | 3.78 | 3.85 | 3.57 | 3.64 | 1.23 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4 | aDGlcp | 99.9 | 72.6 | 74.1 | 70.4 | 72.1 | 69.0 |
| 3,2 | lR3HOBut | 175.9 | 46.3 | 66.1 | 23.7 | |
| 3,3 | lR3HOBut | 175.9 | 46.3 | 66.1 | 23.7 | |
| 3 | bDGlcpN3NA | 103.1 | 55.0 | 55.5 | 76.1 | 79.8 | 175.9 |
| 2 | Ac | 175.2 | 24.0 | |
| 4 | Subst | 173.7 | 39.9 | 46.6 | 19.0 | |
| | bDQuipN4N | 103.2 | 57.2 | 78.3 | 57.0 | 72.0 | 18.6 |
|
There is only one chemically distinct structure:
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