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, Asc-lacking polysaccharide (PS-3)
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: Asc-lacking polysaccharide (PS-3) was a O-deacetylated polysaccharide (PS-2) partial loss of ascarylose during mild acid degradation of the LPS.
Related record ID(s): 30646, 30821, 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 aDGlcpA 102.3 73.0 74.2 73.1 74.7 177.4
3,4 bDGlcpN 103.2 56.2 74.9 80.1 74.3 69.0
3 bDGlcpA 105.6 73.8 75.3 83.4 77.5 176.1
2 Ac 176.0 23.7-23.8
bDGalpN 103.0 52.3 82.0 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 aDGlcpA 5.17 3.64 3.68 3.50 3.99 -
3,4 bDGlcpN 4.50 3.75 3.77 3.63 3.72 3.74-4.22
3 bDGlcpA 4.55 3.33 3.60 3.61 3.72 -
2 Ac - 2.04-2.05
bDGalpN 4.40 4.06 3.79 4.10 3.65 3.73-3.78
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 aDGlcpA 102.3/5.17 73.0/3.64 74.2/3.68 73.1/3.50 74.7/3.99
3,4 bDGlcpN 103.2/4.50 56.2/3.75 74.9/3.77 80.1/3.63 74.3/3.72 69.0/3.74-4.22
3 bDGlcpA 105.6/4.55 73.8/3.33 75.3/3.60 83.4/3.61 77.5/3.72
2 Ac 23.7-23.8/2.04-2.05
bDGalpN 103.0/4.40 52.3/4.06 82.0/3.79 69.2/4.10 76.1/3.65 62.3/3.73-3.78
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 | aDGlcpA | 5.17 | 3.64 | 3.68 | 3.50 | 3.99 |
|
| 3,4 | bDGlcpN | 4.50 | 3.75 | 3.77 | 3.63 | 3.72 | 3.74
4.22 |
| 3 | bDGlcpA | 4.55 | 3.33 | 3.60 | 3.61 | 3.72 |
|
| 2 | Ac |
| 2.04
2.05 | |
| | bDGalpN | 4.40 | 4.06 | 3.79 | 4.10 | 3.65 | 3.73
3.78 |
|
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 | aDGlcpA | 102.3 | 73.0 | 74.2 | 73.1 | 74.7 | 177.4 |
| 3,4 | bDGlcpN | 103.2 | 56.2 | 74.9 | 80.1 | 74.3 | 69.0 |
| 3 | bDGlcpA | 105.6 | 73.8 | 75.3 | 83.4 | 77.5 | 176.1 |
| 2 | Ac | 176.0 | 23.7
23.8 | |
| | bDGalpN | 103.0 | 52.3 | 82.0 | 69.2 | 76.1 | 62.3 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
