Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: urinary tract infections (UTI) [ICD11:
GC08 
];
infectious gastroenteritis [ICD11:
1A40.Z ]
The structure was elucidated in this paperNCBI PubMed ID: 25464076Publication DOI: 10.1016/j.carres.2014.10.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yknirel
gmail.com (Y.A. Knirel)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, PL 90-237 Łódź, Poland
The O-polysaccharide was obtained by degradation of the lipopolysaccharide of Providencia alcalifaciens O2 under mild acidic conditions followed by GPC. The polysaccharide was found to contain two unusual components: 3,6-dideoxy-L-arabino-hexose (ascarylose, Asc) and 2-(L-alanyl)amino-2-deoxy-D-glucose (GlcNAla). Ascarylose was partially split off during lipopolysaccharide degradation and could be eliminated completely by selective acid hydrolysis, which also partially cleaved the β-GAlNAc-(1→6) linkage. The following structure of the branched pentasaccharide repeating unit was established by (1)H and (13)C NMR spectroscopy of the O-polysaccharide and O-deacetylated polysaccharide, as well as products of partial acid hydrolysis: α-Ascp-(1→4)-α-D-GlcpA-(1→4)→6)-β-D-GlcpNAla-(1→4)-β-D-GlpA-(1→3)-β-D-GalpNAc-(1→ ~60% OAc--3).
Lipopolysaccharide, O-antigen, Providencia alcalifaciens, bacterial polysaccharide structure, Ascarylose
Structure type: polymer chemical repeating unit
Location inside paper: p.13, chart 1, PS-2
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_137473,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_153510,IEDB_423153
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, ESI-MS, GLC, de-O-acetylation, composition analysis, methanolysis, GPC, mild acid degradation
Comments, role: O-deacetylated polysaccharide.
Related record ID(s): 30646, 30822, 30823, 30824
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 xLAla? 172.6-172.7 50.9 17.7-18.0
3,4,4,4 %aXAscp 100.9 68.9 34.6 68.1 71.5 18.0
3,4,4 aDGlcpA 102.4 73.1 73.0 80.1 73.6 175.7
3,4 bDGlcpN 103.1 56.2 74.3 80.4 74.8 68.9
3 bDGlcpA 105.6 73.7 75.3 83.1 76.8 175.0
2 Ac 176.0 23.7-23.8
bDGalpN 102.9 52.4 81.8 69.2 76.1 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 xLAla? - 4.04-4.05 1.52-1.53
3,4,4,4 %aXAscp 4.57 3.94 1.89-2.02 3.58 3.99 1.21
3,4,4 aDGlcpA 5.18 3.67 3.73 3.62 4.12 -
3,4 bDGlcpN 4.52 3.76 3.74 3.63 3.78 3.75-4.21
3 bDGlcpA 4.56 3.34 3.62 3.65 3.82 -
2 Ac - 2.04-2.05
bDGalpN 4.41 4.05 3.80 4.09 3.63 3.72-3.79
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 xLAla? 50.9/4.04-4.05 17.7-18.0/1.52-1.53
3,4,4,4 %aXAscp 100.9/4.57 68.9/3.94 34.6/1.89-2.02 68.1/3.58 71.5/3.99 18.0/1.21
3,4,4 aDGlcpA 102.4/5.18 73.1/3.67 73.0/3.73 80.1/3.62 73.6/4.12
3,4 bDGlcpN 103.1/4.52 56.2/3.76 74.3/3.74 80.4/3.63 74.8/3.78 68.9/3.75-4.21
3 bDGlcpA 105.6/4.56 73.7/3.34 75.3/3.62 83.1/3.65 76.8/3.82
2 Ac 23.7-23.8/2.04-2.05
bDGalpN 102.9/4.41 52.4/4.05 81.8/3.80 69.2/4.09 76.1/3.63 62.3/3.72-3.79
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | xLAla? |
| 4.04
4.05 | 1.52
1.53 | |
| 3,4,4,4 | %aXAscp | 4.57 | 3.94 | 1.89
2.02 | 3.58 | 3.99 | 1.21 |
| 3,4,4 | aDGlcpA | 5.18 | 3.67 | 3.73 | 3.62 | 4.12 |
|
| 3,4 | bDGlcpN | 4.52 | 3.76 | 3.74 | 3.63 | 3.78 | 3.75
4.21 |
| 3 | bDGlcpA | 4.56 | 3.34 | 3.62 | 3.65 | 3.82 |
|
| 2 | Ac |
| 2.04
2.05 | |
| | bDGalpN | 4.41 | 4.05 | 3.80 | 4.09 | 3.63 | 3.72
3.79 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | xLAla? | 172.6
172.7 | 50.9 | 17.7
18.0 | |
| 3,4,4,4 | %aXAscp | 100.9 | 68.9 | 34.6 | 68.1 | 71.5 | 18.0 |
| 3,4,4 | aDGlcpA | 102.4 | 73.1 | 73.0 | 80.1 | 73.6 | 175.7 |
| 3,4 | bDGlcpN | 103.1 | 56.2 | 74.3 | 80.4 | 74.8 | 68.9 |
| 3 | bDGlcpA | 105.6 | 73.7 | 75.3 | 83.1 | 76.8 | 175.0 |
| 2 | Ac | 176.0 | 23.7
23.8 | |
| | bDGalpN | 102.9 | 52.4 | 81.8 | 69.2 | 76.1 | 62.3 |
|
There is only one chemically distinct structure:
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