Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ]
The structure was elucidated in this paperPublication DOI: 10.1002/ejoc.201200318Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: olga.ovchinnikova
gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
O-Polysaccharides (O-antigens) are highly diverse glycopolymers present on the cell surface of Gram-negative bacteria, including the human opportunistic pathogen Providencia alcalifaciens. They define serospecificity of strains and are used for the serotyping of bacteria. In this work, a phosphorylated O-polysaccharide was isolated from P. alcalifaciens O22 and analyzed by chemical methods, ESI-MS, and 1H, 13C, and 31P NMR spectroscopy. It was found to contain two unusual components, 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose (D-FucNAc4N) and D-glyceramide 2-phosphate (D-GroAN-2-P), the latter being identified for the first time in bacterial polysaccharides. The structure of the trisaccharide repeating unit of the O-polysaccharide was established to be →4)-(D-GroAN-2→P→3)-D-GalNAc-(1→4)-D-Gal-(1→3)-D-FucNAc4N-(1→.
carbohydrates, lipopolysaccharides, antigens, structure elucidation
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.3504, fig.4
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142345,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_25,SB_7,SB_88
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, acid hydrolysis, GLC
Related record ID(s): 28552
NCBI Taxonomy refs (TaxIDs): 126385
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2 Ac 175.7-176.6 23.6-23.8
3,4,3,0,1 NH2
3,4,3,0 lDGroA 175.6 77.4 63.9
3,4,3 P
3,4 bDGalpN 104.3 52.8 76.2 75.8 75.2 62.0
3 bDGalp 106.4 71.8 73.4 78.2 75.5 62.4
2 Ac 175.7-176.6 23.6-23.8
bDFucpN4N 103.3 52.0 77.9 56.1 68.5 16.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 Ac - 2.05-2.07
3,4,3,0,1 NH2
3,4,3,0 lDGroA - 4.59 3.91-3.96
3,4,3 P
3,4 bDGalpN 4.66 3.98 4.30 4.26 3.70 3.73-3.78
3 bDGalp 4.49 3.41 3.73 4.08 3.70 3.80-3.80
2 Ac - 2.05-2.07
bDFucpN4N 4.78 4.02 4.18 3.84 4.02 1.35
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 Ac 23.6-23.8/2.05-2.07
3,4,3,0,1 NH2
3,4,3,0 lDGroA 77.4/4.59 63.9/3.91-3.96
3,4,3 P
3,4 bDGalpN 104.3/4.66 52.8/3.98 76.2/4.30 75.8/4.26 75.2/3.70 62.0/3.73-3.78
3 bDGalp 106.4/4.49 71.8/3.41 73.4/3.73 78.2/4.08 75.5/3.70 62.4/3.80-3.80
2 Ac 23.6-23.8/2.05-2.07
bDFucpN4N 103.3/4.78 52.0/4.02 77.9/4.18 56.1/3.84 68.5/4.02 16.8/1.35
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | Ac |
| 2.05
2.07 | |
| 3,4,3,0,1 | NH2 | |
| 3,4,3,0 | lDGroA |
| 4.59 | 3.91
3.96 | |
| 3,4,3 | P | |
| 3,4 | bDGalpN | 4.66 | 3.98 | 4.30 | 4.26 | 3.70 | 3.73
3.78 |
| 3 | bDGalp | 4.49 | 3.41 | 3.73 | 4.08 | 3.70 | 3.80
3.80 |
| 2 | Ac |
| 2.05
2.07 | |
| | bDFucpN4N | 4.78 | 4.02 | 4.18 | 3.84 | 4.02 | 1.35 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | Ac | 175.7
176.6 | 23.6
23.8 | |
| 3,4,3,0,1 | NH2 | |
| 3,4,3,0 | lDGroA | 175.6 | 77.4 | 63.9 | |
| 3,4,3 | P | |
| 3,4 | bDGalpN | 104.3 | 52.8 | 76.2 | 75.8 | 75.2 | 62.0 |
| 3 | bDGalp | 106.4 | 71.8 | 73.4 | 78.2 | 75.5 | 62.4 |
| 2 | Ac | 175.7
176.6 | 23.6
23.8 | |
| | bDFucpN4N | 103.3 | 52.0 | 77.9 | 56.1 | 68.5 | 16.8 |
|
There is only one chemically distinct structure:
Found 
report error