Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: infection due to Enterobacter cloacae [ICD11:
XN3YM 
]
The structure was elucidated in this paperPublication DOI: 10.1016/j.carres.2017.02.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru (A. V. Perepelov)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Key Laboratory of Molecular Microbiology and Technology of the Ministry of Education, College of Life Sciences, Nankai University, Tianjin, China, Tianjin Biochip Corporation, TEDA, Tianjin, China
On mild acid degradation of the lipopolysaccharide of Enterobacter cloacae C5529, the O-polysaccharide chain was cleaved at the linkages of 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-L-manno-non 2 ulosonic acid (di-N-acetylpseudaminic acid, Pse5Ac7Ac). The resultant oligosaccharide and an alkali-treated lipopolysaccharide were studied by sugar analysis along with 1H and 13C NMR spectroscopy, and the following structure of the tetrasaccharide repeating unit of the O-polysaccharide was established: [structure, see text].
O-antigen, pseudaminic acid, bacterial polysaccharide structure, O-antigen gene cluster, Enterobacter cloacae
Structure type: oligomer
Location inside paper: fig.1
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_838988,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, de-O-acylation, sugar analysis, DNA techniques, acid hydrolysis, GLC, mild acid hydrolysis, NMR-1D, GPC, function analysis of gene clusters
Biosynthesis and genetic data: genetic data
Comments, role: OS by degradation with dilute acetic acid of the LPS.
Related record ID(s): 30830, 30831
NCBI Taxonomy refs (TaxIDs): 550Reference(s) to other database(s): GTC:G32173QX
Show glycosyltransferases
NMR conditions: in D2O at 303 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
4,3,6 bDGalp 104.7 72.2 74.0 70.0 76.5 62.3
4,3 bDGalf 110.5 82.7 78.1 84.3 71.0 72.4
4 aDGalp 97.9 68.4 78.7 70.7 72.4 62.9
5 Ac 175.2 23.4-23.5
7 Ac 175.2 23.4-23.5
aXPsep 175.2 98.0 33.3 71.2 49.2 71.6 54.2 68.4 16.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
4,3,6 bDGalp 4.44 3.56 3.65 3.92 3.69 3.74-3.78
4,3 bDGalf 5.13 4.16 4.06 4.05 4.00 3.77-4.07
4 aDGalp 5.05 3.88 3.74 4.09 4.24 3.75-3.75
5 Ac - 1.97-2.02
7 Ac - 1.97-2.02
aXPsep - - 1.86-2.11 4.23 4.34 4.11 4.16 4.10 1.09
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
4,3,6 bDGalp 104.7/4.44 72.2/3.56 74.0/3.65 70.0/3.92 76.5/3.69 62.3/3.74-3.78
4,3 bDGalf 110.5/5.13 82.7/4.16 78.1/4.06 84.3/4.05 71.0/4.00 72.4/3.77-4.07
4 aDGalp 97.9/5.05 68.4/3.88 78.7/3.74 70.7/4.09 72.4/4.24 62.9/3.75-3.75
5 Ac 23.4-23.5/1.97-2.02
7 Ac 23.4-23.5/1.97-2.02
aXPsep 33.3/1.86-2.11 71.2/4.23 49.2/4.34 71.6/4.11 54.2/4.16 68.4/4.10 16.8/1.09
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 4,3,6 | bDGalp | 4.44 | 3.56 | 3.65 | 3.92 | 3.69 | 3.74
3.78 | |
| 4,3 | bDGalf | 5.13 | 4.16 | 4.06 | 4.05 | 4.00 | 3.77
4.07 | |
| 4 | aDGalp | 5.05 | 3.88 | 3.74 | 4.09 | 4.24 | 3.75
3.75 | |
| 5 | Ac |
| 1.97
2.02 | |
| 7 | Ac |
| 1.97
2.02 | |
| | aXPsep |
|
| 1.86
2.11 | 4.23 | 4.34 | 4.11 | 4.16 | 4.10 | 1.09 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 4,3,6 | bDGalp | 104.7 | 72.2 | 74.0 | 70.0 | 76.5 | 62.3 | |
| 4,3 | bDGalf | 110.5 | 82.7 | 78.1 | 84.3 | 71.0 | 72.4 | |
| 4 | aDGalp | 97.9 | 68.4 | 78.7 | 70.7 | 72.4 | 62.9 | |
| 5 | Ac | 175.2 | 23.4
23.5 | |
| 7 | Ac | 175.2 | 23.4
23.5 | |
| | aXPsep | 175.2 | 98.0 | 33.3 | 71.2 | 49.2 | 71.6 | 54.2 | 68.4 | 16.8 |
|
There is only one chemically distinct structure:
Found 
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