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, 2b fraction I
Compound class: CPS
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. Structure (1b) has Ac instead of 3HOBut.
Related record ID(s): 27270, 28542, 28543, 28544, 28545, 28547, 28548, 28549, 28550, 28551, 31084
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
3,2 Ac 174.7-175.9 23.3-23.9
3 aDGalpNA 100.1 50.8 68.3 71.2 73.4 ?
2 Ac 174.7-175.9 23.3-23.9
4 lS3HOBut ? 45.9 66.2 23.5
xDQuiN4N-ol 61.9 55.1 77.1 57.0 67.1 20.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2 Ac - 1.90-2.13
3 aDGalpNA 5.19 4.23 3.98 4.32 4.26 -
2 Ac - 1.90-2.13
4 lS3HOBut - 2.51 4.21 1.24
xDQuiN4N-ol 3.49-3.63 4.00 4.28 3.89 3.69 1.18
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2 Ac 23.3-23.9/1.90-2.13
3 aDGalpNA 100.1/5.19 50.8/4.23 68.3/3.98 71.2/4.32 73.4/4.26
2 Ac 23.3-23.9/1.90-2.13
4 lS3HOBut 45.9/2.51 66.2/4.21 23.5/1.24
xDQuiN4N-ol 61.9/3.49-3.63 55.1/4.00 77.1/4.28 57.0/3.89 67.1/3.69 20.6/1.18
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2 | Ac |
| 1.90
2.13 | |
| 3 | aDGalpNA | 5.19 | 4.23 | 3.98 | 4.32 | 4.26 |
|
| 2 | Ac |
| 1.90
2.13 | |
| 4 | lS3HOBut |
| 2.51 | 4.21 | 1.24 | |
| | xDQuiN4N-ol | 3.49
3.63 | 4.00 | 4.28 | 3.89 | 3.69 | 1.18 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2 | Ac | 174.7
175.9 | 23.3
23.9 | |
| 3 | aDGalpNA | 100.1 | 50.8 | 68.3 | 71.2 | 73.4 | ? |
| 2 | Ac | 174.7
175.9 | 23.3
23.9 | |
| 4 | lS3HOBut | ? | 45.9 | 66.2 | 23.5 | |
| | xDQuiN4N-ol | 61.9 | 55.1 | 77.1 | 57.0 | 67.1 | 20.6 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175.3,"l":"1","c":[0,0,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":100.1,"l":"1","c":[0,0,225]},{"s":50.8,"l":"2","c":[0,0,225]},{"s":68.3,"l":"3","c":[0,0,225]},{"s":71.2,"l":"4","c":[0,0,225]},{"s":73.4,"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":45.9,"l":"2","c":[230,0,30]},{"s":66.2,"l":"3","c":[230,0,30]},{"s":23.5,"l":"4","c":[230,0,30]},{"s":61.9,"l":"1","c":[0,165,0]},{"s":55.1,"l":"2","c":[0,165,0]},{"s":77.1,"l":"3","c":[0,165,0]},{"s":57,"l":"4","c":[0,165,0]},{"s":67.1,"l":"5","c":[0,165,0]},{"s":20.6,"l":"6","c":[0,165,0]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Found 
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