Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: (Actinopterygii)
Associated disease: edwardsiellosis
The structure was elucidated in this paperNCBI PubMed ID: 34507179Publication DOI: 10.1016/j.carres.2021.108423Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: S. Gorska <sabina.gorska
hirszfeld.pl>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, R. Weigla 12, PL-53-114, Wroclaw, Poland
The chemical structure of the lipopolysaccharide O-polysaccharide repeating unit of Edwardsiella tarda strain PCM 1155 was studied for the first time. The complete structure of repeating unit was investigated by chemical methods, 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, and matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). The rarely occurring monosaccharide, 2,3-diacetamido-2,3,6-trideoxy-l-mannose (L-RhapNAc3NAc) was identified. The following structure was established.
Lipopolysaccharide, NMR spectroscopy, O-polysaccharide, 2, 3, MALDI-TOF mass spectrometry, 3-diacetamido-2, 6-trideoxy-L-mannose, Edwardsiella tarda
Structure type: polymer chemical repeating unit
Location inside paper: abstract, table 2, Fig. 3
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_153212,IEDB_423153,SB_74,SB_85
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, partial acid hydrolysis, sugar analysis, TLC, MALDI-TOF-MS
NCBI Taxonomy refs (TaxIDs): 636
Show glycosyltransferases
NMR conditions: in D2O at 278 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2 Ac 175.0 22.7
3,4,3,2 Ac 174.6-175.4 22.9-23.5
3,4,3,3 Ac 174.6-175.4 22.9-23.5
3,4,3 bLRhapN3N 99.7 52.0 54.5 70.6 74.4 18.0
3,4 bDGlcpN 101.6 54.7 77.9 75.4 74.9 60.7
3 bDGlcpA 103.4 73.0 74.3 80.7 75.0 174.4
2 Ac 174.0 23.4
bDGlcpN 101.2 55.8 83.0 69.5 76.7 61.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 Ac - 1.96
3,4,3,2 Ac - 2.05-2.07
3,4,3,3 Ac - 2.05-2.07
3,4,3 bLRhapN3N 5.09 4.60 3.94 3.30 3.52 1.37
3,4 bDGlcpN 4.55 3.69 3.86 3.89 3.45 3.89
3 bDGlcpA 4.57 3.40 3.64 3.79 3.90 -
2 Ac - 2.05
bDGlcpN 4.51 3.92 3.76 3.59 3.42 3.88
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 Ac 22.7/1.96
3,4,3,2 Ac 22.9-23.5/2.05-2.07
3,4,3,3 Ac 22.9-23.5/2.05-2.07
3,4,3 bLRhapN3N 99.7/5.09 52.0/4.60 54.5/3.94 70.6/3.30 74.4/3.52 18.0/1.37
3,4 bDGlcpN 101.6/4.55 54.7/3.69 77.9/3.86 75.4/3.89 74.9/3.45 60.7/3.89
3 bDGlcpA 103.4/4.57 73.0/3.40 74.3/3.64 80.7/3.79 75.0/3.90
2 Ac 23.4/2.05
bDGlcpN 101.2/4.51 55.8/3.92 83.0/3.76 69.5/3.59 76.7/3.42 61.6/3.88
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | Ac |
| 1.96 | |
| 3,4,3,2 | Ac |
| 2.05
2.07 | |
| 3,4,3,3 | Ac |
| 2.05
2.07 | |
| 3,4,3 | bLRhapN3N | 5.09 | 4.60 | 3.94 | 3.30 | 3.52 | 1.37 |
| 3,4 | bDGlcpN | 4.55 | 3.69 | 3.86 | 3.89 | 3.45 | 3.89 |
| 3 | bDGlcpA | 4.57 | 3.40 | 3.64 | 3.79 | 3.90 |
|
| 2 | Ac |
| 2.05 | |
| | bDGlcpN | 4.51 | 3.92 | 3.76 | 3.59 | 3.42 | 3.88 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | Ac | 175.0 | 22.7 | |
| 3,4,3,2 | Ac | 174.6
175.4 | 22.9
23.5 | |
| 3,4,3,3 | Ac | 174.6
175.4 | 22.9
23.5 | |
| 3,4,3 | bLRhapN3N | 99.7 | 52.0 | 54.5 | 70.6 | 74.4 | 18.0 |
| 3,4 | bDGlcpN | 101.6 | 54.7 | 77.9 | 75.4 | 74.9 | 60.7 |
| 3 | bDGlcpA | 103.4 | 73.0 | 74.3 | 80.7 | 75.0 | 174.4 |
| 2 | Ac | 174.0 | 23.4 | |
| | bDGlcpN | 101.2 | 55.8 | 83.0 | 69.5 | 76.7 | 61.6 |
|
There is only one chemically distinct structure:
Found 
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