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: oligomer ; 804.2532 [M-H]-
C
29H
46N
3O
23Location inside paper: p.13, chart 1, Tetrasaccharide (TS)
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_140630,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_423153,IEDB_885822
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: Partial acid hydrolysis of the O-deacetylated polysaccharide (PS-2).
Related record ID(s): 30646, 30821, 30822, 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 100.7 72.7 73.9 73.1 74.3 177.6
3,4 bDGlcpN 103.1 56.4 75.2 78.0 75.9 61.8
3 bDGlcpA 105.4-105.6 73.6-73.7 75.4 83.6 77.5 176.2
2 Ac 176.0-176.1 23.3-23.5
aDGalpN 92.5 50.1 78.7 69.8 71.6 62.5
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 5.42 3.60 3.68 3.49 3.97 -
3,4 bDGlcpN 4.53-4.54 3.81 3.81 3.71 3.67 3.79-3.93
3 bDGlcpA 4.50-4.56 3.36 3.62 3.65 3.70 -
2 Ac - 2.01
aDGalpN 5.20 4.27 3.98 4.17 4.10 3.72
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 100.7/5.42 72.7/3.60 73.9/3.68 73.1/3.49 74.3/3.97
3,4 bDGlcpN 103.1/4.53-4.54 56.4/3.81 75.2/3.81 78.0/3.71 75.9/3.67 61.8/3.79-3.93
3 bDGlcpA 105.4-105.6/4.50-4.56 73.6-73.7/3.36 75.4/3.62 83.6/3.65 77.5/3.70
2 Ac 23.3-23.5/2.01
aDGalpN 92.5/5.20 50.1/4.27 78.7/3.98 69.8/4.17 71.6/4.10 62.5/3.72
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 | 5.42 | 3.60 | 3.68 | 3.49 | 3.97 |
|
| 3,4 | bDGlcpN | 4.53
4.54 | 3.81 | 3.81 | 3.71 | 3.67 | 3.79
3.93 |
| 3 | bDGlcpA | 4.50
4.56 | 3.36 | 3.62 | 3.65 | 3.70 |
|
| 2 | Ac |
| 2.01 | |
| | aDGalpN | 5.20 | 4.27 | 3.98 | 4.17 | 4.10 | 3.72 |
|
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 | 100.7 | 72.7 | 73.9 | 73.1 | 74.3 | 177.6 |
| 3,4 | bDGlcpN | 103.1 | 56.4 | 75.2 | 78.0 | 75.9 | 61.8 |
| 3 | bDGlcpA | 105.4
105.6 | 73.6
73.7 | 75.4 | 83.6 | 77.5 | 176.2 |
| 2 | Ac | 176.0
176.1 | 23.3
23.5 | |
| | aDGalpN | 92.5 | 50.1 | 78.7 | 69.8 | 71.6 | 62.5 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
