Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
gastroenteritis [ICD11:
1A40.0 ]
The structure was elucidated in this paperNCBI PubMed ID: 21146157Publication DOI: 10.1016/j.carres.2010.11.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: olga.ovchinnikova
gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
An O-polysaccharide (O-antigen) was isolated by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O60 and studied by sugar and methylation analyses as well as (1)H and (13)C NMR spectroscopy, including 2D ROESY and (1)H,(13)C HMBC experiments in D(2)O and a ROESY experiment in a 9:1 H(2)O-D(2)O mixture to reveal correlations for NH protons. It was found that the polysaccharide is built up of linear pentasaccharide repeating units containing an amide of d-glucuronic acid with l-serine and has the following structure: The O-antigen studied is structurally and serologically closely related to the O-antigen of Proteus vulgaris O44.
Lipopolysaccharide, O-antigen, Providencia alcalifaciens, bacterial polysaccharide structure
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.379
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_144989,IEDB_146664,IEDB_150900,IEDB_151528,IEDB_153510,IEDB_190606,IEDB_423153,IEDB_983931,SB_192,SB_7
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, ESI-MS, mild acid hydrolysis, GC
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
3,4,4,3 bDGlcp 104.9 74.4 75.7 80.4 75.7 61.4
3,4,4 aDGalp 101.8 69.0 80.7 70.1 71.9 62.0
3,4,2 Ac 176.2 23.7
3,4 bDGalpN 101.9 54.0 72.1 78.5 76.9 61.9
3,6 xLSer 175.4 57.1 62.8
3 bDGlcpA 105.7 73.7 75.1 79.2 75.5 171.0
2 Ac 176.5 23.9
bDGalpN 102.9 52.8 81.7 69.2 76.4 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,4,3 bDGlcp 4.71 3.40 3.69 3.61 3.55 3.64-3.85
3,4,4 aDGalp 4.96 4.01 4.10 4.29 4.36 3.68-3.68
3,4,2 Ac - 2.03
3,4 bDGalpN 4.50 3.94 3.76 4.04 3.70 3.95-3.95
3,6 xLSer - 4.50 3.93-3.96
3 bDGlcpA 4.58 3.40 3.64 3.93 4.01 -
2 Ac - 2.04
bDGalpN 4.58 4.03 3.88 4.12 3.73 3.74-3.80
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,4,3 bDGlcp 104.9/4.71 74.4/3.40 75.7/3.69 80.4/3.61 75.7/3.55 61.4/3.64-3.85
3,4,4 aDGalp 101.8/4.96 69.0/4.01 80.7/4.10 70.1/4.29 71.9/4.36 62.0/3.68-3.68
3,4,2 Ac 23.7/2.03
3,4 bDGalpN 101.9/4.50 54.0/3.94 72.1/3.76 78.5/4.04 76.9/3.70 61.9/3.95-3.95
3,6 xLSer 57.1/4.50 62.8/3.93-3.96
3 bDGlcpA 105.7/4.58 73.7/3.40 75.1/3.64 79.2/3.93 75.5/4.01
2 Ac 23.9/2.04
bDGalpN 102.9/4.58 52.8/4.03 81.7/3.88 69.2/4.12 76.4/3.73 62.4/3.74-3.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,4,3 | bDGlcp | 4.71 | 3.40 | 3.69 | 3.61 | 3.55 | 3.64
3.85 |
| 3,4,4 | aDGalp | 4.96 | 4.01 | 4.10 | 4.29 | 4.36 | 3.68
3.68 |
| 3,4,2 | Ac |
| 2.03 | |
| 3,4 | bDGalpN | 4.50 | 3.94 | 3.76 | 4.04 | 3.70 | 3.95
3.95 |
| 3,6 | xLSer |
| 4.50 | 3.93
3.96 | |
| 3 | bDGlcpA | 4.58 | 3.40 | 3.64 | 3.93 | 4.01 |
|
| 2 | Ac |
| 2.04 | |
| | bDGalpN | 4.58 | 4.03 | 3.88 | 4.12 | 3.73 | 3.74
3.80 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,4,3 | bDGlcp | 104.9 | 74.4 | 75.7 | 80.4 | 75.7 | 61.4 |
| 3,4,4 | aDGalp | 101.8 | 69.0 | 80.7 | 70.1 | 71.9 | 62.0 |
| 3,4,2 | Ac | 176.2 | 23.7 | |
| 3,4 | bDGalpN | 101.9 | 54.0 | 72.1 | 78.5 | 76.9 | 61.9 |
| 3,6 | xLSer | 175.4 | 57.1 | 62.8 | |
| 3 | bDGlcpA | 105.7 | 73.7 | 75.1 | 79.2 | 75.5 | 171.0 |
| 2 | Ac | 176.5 | 23.9 | |
| | bDGalpN | 102.9 | 52.8 | 81.7 | 69.2 | 76.4 | 62.4 |
|
There is only one chemically distinct structure:
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