Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 18457569Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: perepel
ioc.ac.ru; wangquan
mail.nankai.edu.cn
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, fax: (495) 1376148, TEDA School of Biological Sciences and Biotechnology and 3Tianjin Key Laboratory for Microbial Functional Genomics, TEDA College, Nankai University, 23 HongDa Street, TEDA, Tianjin 300457, P. R. China
An Opolysaccharide was isolated by mild acid degradation of the lipopolysaccharide of enteropathogenic Escherichia coli O49 and studied by sugar analysis along with one and twodimensional 1H and 13C NMR spectroscopy. The following structure of the linear tetrasaccharide repeating unit of the Opolysaccharide was established: →2)aDQuip4N(S3HOBut)(1→4)bDGalpNAc(1→4)aLRhap(1→3)bDGlcpNAc6Ac(1→, where DQui4N(S3HOBut) stands for 4,6dideoxy4[(S)3hydroxybutanoylamino]Dglucose and Oacetylation of GlcNAc is partial (~30%). To our knowledge, no N(3hydroxybutanoyl) derivative of Qui4N has been hitherto found in bacterial polysaccharides. Gene functions of the Oantigen gene cluster of E. coli O49 were assigned by bioinformatics analysis and found to correspond to the Opolysaccharide structure. Two new genes were revealed and suggested to be responsible for synthesis and transfer of the 3hydroxybutanoyl group.
Lipopolysaccharide, Escherichia coli, 6-dideoxy-d-glucose, bacterial polysaccharide structure, 4-amino-4, O-antigen gene cluster, 3-hydroxybutyrate
Structure type: polymer chemical repeating unit
Location inside paper: p.406, abstrsact, p.409
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, alkaline degradation, NMR-1D, genetic methods
Biosynthesis and genetic data: genetic data
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,4,4 lS3HOBut 175.9 46.7 66.6 23.6
3,4,4 aDQuip4N 102.0 82.6 70.9 58.4 69.3 18.3
3,4,2 Ac 175.8-176.6 ?
3,4 bDGalpN 103.8 54.7 72.4 80.2 76.6 62.4
3 aLRhap 102.7 72.7 72.0 82.3 68.9 18.6
2 Ac 175.8-176.6 ?
6 30%Ac
bDGlcpN 103.7 57.2 83.2 70.2 77.5 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,4,4 lS3HOBut - 2.47 4.19 1.23
3,4,4 aDQuip4N 5.14 3.73 3.92 3.65 4.15 1.12
3,4,2 Ac - 2.03-2.05
3,4 bDGalpN 4.75 3.92 3.76 4.02 3.71 3.88-3.92
3 aLRhap 4.85 3.73 3.83 3.60 4.01 1.30
2 Ac - 2.03-2.05
6 30%Ac
bDGlcpN 4.75 3.85 3.63 3.51 3.49 3.75-3.95
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,4,4 lS3HOBut 46.7/2.47 66.6/4.19 23.6/1.23
3,4,4 aDQuip4N 102.0/5.14 82.6/3.73 70.9/3.92 58.4/3.65 69.3/4.15 18.3/1.12
3,4,2 Ac ?/2.03-2.05
3,4 bDGalpN 103.8/4.75 54.7/3.92 72.4/3.76 80.2/4.02 76.6/3.71 62.4/3.88-3.92
3 aLRhap 102.7/4.85 72.7/3.73 72.0/3.83 82.3/3.60 68.9/4.01 18.6/1.30
2 Ac ?/2.03-2.05
6 30%Ac
bDGlcpN 103.7/4.75 57.2/3.85 83.2/3.63 70.2/3.51 77.5/3.49 62.3/3.75-3.95
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,4,4 | lS3HOBut |
| 2.47 | 4.19 | 1.23 | |
| 3,4,4 | aDQuip4N | 5.14 | 3.73 | 3.92 | 3.65 | 4.15 | 1.12 |
| 3,4,2 | Ac |
| 2.03
2.05 | |
| 3,4 | bDGalpN | 4.75 | 3.92 | 3.76 | 4.02 | 3.71 | 3.88
3.92 |
| 3 | aLRhap | 4.85 | 3.73 | 3.83 | 3.60 | 4.01 | 1.30 |
| 2 | Ac |
| 2.03
2.05 | |
| 6 | 30%Ac | |
| | bDGlcpN | 4.75 | 3.85 | 3.63 | 3.51 | 3.49 | 3.75
3.95 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,4,4 | lS3HOBut | 175.9 | 46.7 | 66.6 | 23.6 | |
| 3,4,4 | aDQuip4N | 102.0 | 82.6 | 70.9 | 58.4 | 69.3 | 18.3 |
| 3,4,2 | Ac | 175.8
176.6 | ? | |
| 3,4 | bDGalpN | 103.8 | 54.7 | 72.4 | 80.2 | 76.6 | 62.4 |
| 3 | aLRhap | 102.7 | 72.7 | 72.0 | 82.3 | 68.9 | 18.6 |
| 2 | Ac | 175.8
176.6 | ? | |
| 6 | 30%Ac | |
| | bDGlcpN | 103.7 | 57.2 | 83.2 | 70.2 | 77.5 | 62.3 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175.9,"l":"1","c":[0,0,225]},{"s":46.7,"l":"2","c":[0,0,225]},{"s":66.6,"l":"3","c":[0,0,225]},{"s":23.6,"l":"4","c":[0,0,225]},{"s":102,"l":"1","c":[230,0,30]},{"s":82.6,"l":"2","c":[230,0,30]},{"s":70.9,"l":"3","c":[230,0,30]},{"s":58.4,"l":"4","c":[230,0,30]},{"s":69.3,"l":"5","c":[230,0,30]},{"s":18.3,"l":"6","c":[230,0,30]},{"s":176.2,"l":"1","c":[0,0,0]},{"s":103.8,"l":"1","c":[0,165,0]},{"s":54.7,"l":"2","c":[0,165,0]},{"s":72.4,"l":"3","c":[0,165,0]},{"s":80.2,"l":"4","c":[0,165,0]},{"s":76.6,"l":"5","c":[0,165,0]},{"s":62.4,"l":"6","c":[0,165,0]},{"s":102.7,"l":"1","c":[120,0,225]},{"s":72.7,"l":"2","c":[120,0,225]},{"s":72,"l":"3","c":[120,0,225]},{"s":82.3,"l":"4","c":[120,0,225]},{"s":68.9,"l":"5","c":[120,0,225]},{"s":18.6,"l":"6","c":[120,0,225]},{"s":176.2,"l":"1","c":[0,0,0]},{"s":103.7,"l":"1","c":[220,0,180]},{"s":57.2,"l":"2","c":[220,0,180]},{"s":83.2,"l":"3","c":[220,0,180]},{"s":70.2,"l":"4","c":[220,0,180]},{"s":77.5,"l":"5","c":[220,0,180]},{"s":62.3,"l":"6","c":[220,0,180]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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