Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ]
The structure was elucidated in this paperNCBI PubMed ID: 22230711Publication DOI: 10.1016/j.carres.2011.12.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: olga.ovchinnikova
gmail.com
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 Lodz, PL 90-237 Lodz, Poland
An acidic polysaccharide was isolated from Providencia rustigianii O11 by the phenol-water extraction. The polysaccharide was cleaved by solvolysis with triflic acid to yield disaccharides with uronic acid derivatives at the non-reducing end. The polysaccharide and the disaccharides were studied by chemical analyses, high-resolution ESI MS, and 2D (1)H and (13)C NMR spectroscopy, and the following structure of the tetrasaccharide repeating unit of the polysaccharide was established: where GalNAcA stands for 2-acetamido-2-deoxygalacturonic acid, GalNAcA6GluAla for N-(2-acetamido-2-deoxygalacturonoyl)-l-glutam-1-yl-l-alanine, QuiNAc4NAcyl for 2-acetamido-4-[(S)-3-hydroxybutanoylamino]-2,4,6-trideoxyglucose (~75%) or 2,4-diacetamido-2,4,6-trideoxyglucose (~25%); the d configuration of GalNA and QuiN4N was ascribed tentatively. To the best of our knowledge, this is for the first time that an amide of uronic acid with a dipeptide is found in bacterial polysaccharides.
Lipopolysaccharide, bacterial polysaccharide structure, Providencia rustigianii, 2-acetamido-2-deoxygalacturonamide, dipeptide
Structure type: oligomer
Location inside paper: p.98, table 1, 3b fraction II
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, de-O-acylation, ESI-MS, acid hydrolysis, composition analysis, methanolysis, GPC, triflic acid solvolysis
Comments, role: Disaccharide obtained by triflic acid solvolysis of the acid-treated polysaccharide.
Related record ID(s): 27270, 28542, 28543, 28544, 28545, 28546, 28547, 28548, 28549, 28550, 28551
NCBI Taxonomy refs (TaxIDs): 158850
Show glycosyltransferases
NMR conditions: in 90%H2O / 10%D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,6 xLGlu ? 54.7 28.2 31.8 179.2
4,2 Ac 174.7-175.9 23.3-23.9
4 aDGalpNA 99.7 51.0 68.4 70.0 72.8 171.3
2 Ac 174.7-175.9 23.3-23.9
xDGalN-ol 62.5 53.0 71.3 80.2 72.8 63.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,6 xLGlu - 4.36 1.96-2.19 2.45 -
4,2 Ac - 1.90-2.13
4 aDGalpNA 5.20 4.21 3.96 4.33 4.57 -
2 Ac - 1.90-2.13
xDGalN-ol 3.55-3.60 4.13 3.99 3.82 4.00 3.67
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,6 xLGlu 54.7/4.36 28.2/1.96-2.19 31.8/2.45
4,2 Ac 23.3-23.9/1.90-2.13
4 aDGalpNA 99.7/5.20 51.0/4.21 68.4/3.96 70.0/4.33 72.8/4.57
2 Ac 23.3-23.9/1.90-2.13
xDGalN-ol 62.5/3.55-3.60 53.0/4.13 71.3/3.99 80.2/3.82 72.8/4.00 63.6/3.67
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,6 | xLGlu |
| 4.36 | 1.96
2.19 | 2.45 |
| |
| 4,2 | Ac |
| 1.90
2.13 | |
| 4 | aDGalpNA | 5.20 | 4.21 | 3.96 | 4.33 | 4.57 |
|
| 2 | Ac |
| 1.90
2.13 | |
| | xDGalN-ol | 3.55
3.60 | 4.13 | 3.99 | 3.82 | 4.00 | 3.67 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,6 | xLGlu | ? | 54.7 | 28.2 | 31.8 | 179.2 | |
| 4,2 | Ac | 174.7
175.9 | 23.3
23.9 | |
| 4 | aDGalpNA | 99.7 | 51.0 | 68.4 | 70.0 | 72.8 | 171.3 |
| 2 | Ac | 174.7
175.9 | 23.3
23.9 | |
| | xDGalN-ol | 62.5 | 53.0 | 71.3 | 80.2 | 72.8 | 63.6 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":54.7,"l":"2","c":[0,0,225]},{"s":28.2,"l":"3","c":[0,0,225]},{"s":31.8,"l":"4","c":[0,0,225]},{"s":179.2,"l":"5","c":[0,0,225]},{"s":175.3,"l":"1","c":[0,0,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":99.7,"l":"1","c":[230,0,30]},{"s":51,"l":"2","c":[230,0,30]},{"s":68.4,"l":"3","c":[230,0,30]},{"s":70,"l":"4","c":[230,0,30]},{"s":72.8,"l":"5","c":[230,0,30]},{"s":171.3,"l":"6","c":[230,0,30]},{"s":175.3,"l":"1","c":[0,0,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":62.5,"l":"1","c":[0,165,0]},{"s":53,"l":"2","c":[0,165,0]},{"s":71.3,"l":"3","c":[0,165,0]},{"s":80.2,"l":"4","c":[0,165,0]},{"s":72.8,"l":"5","c":[0,165,0]},{"s":63.6,"l":"6","c":[0,165,0]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Found 
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