Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: nosocomial infections [ICD11:
XB25 
];
infection due to Enterobacter cloacae [ICD11:
XN3YM ]
The structure was elucidated in this paperNCBI PubMed ID: 25723621Publication DOI: 10.1016/j.carres.2015.01.015Journal 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
Mild acid degradation of the lipopolysaccharide of Enterobacter cloacae G3054 resulted in the cleavage of the O-polysaccharide at the linkage of residues of 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic acid (di-N-acetylpseudaminic acid, Pse5Ac7Ac) in the main chain. The resultant oligosaccharide and an alkali-treated lipopolysaccharide were studied by sugar analysis along with (1)H and (13)C NMR spectroscopy, and the following structure of the branched pentasaccharide O-unit of the O-polysaccharide was established: [structure: see text] The O-antigen gene cluster of E. cloacae G3054 between conserved genes galF and gnd was sequenced. Most genes necessary for the O-antigen synthesis were found in the cluster and their functions were tentatively assigned by comparison with sequences in the available databases.
O-antigen, pseudaminic acid, bacterial polysaccharide structure, O-antigen gene cluster, Enterobacter cloacae
Structure type: polymer chemical repeating unit
Location inside paper: p.62, chart 1, LPSOH
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,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, GLC, mild acid hydrolysis, NMR-1D, GPC, function analysis of gene clusters
Biosynthesis and genetic data: genetic data
Comments, role: O-deacylated LPS with aqueous ammonia.
Related record ID(s): 30836
NCBI Taxonomy refs (TaxIDs): 550Reference(s) to other database(s): GTC:G27149NC
Show glycosyltransferases
NMR conditions: in D2O at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
3,6,6,4 aDGalp 97.8 69.2 70.4 70.6 72.2 62.6
3,6,6,5 Ac 174.4-175.1 23.1-23.3
3,6,6,7 Ac 174.4-175.1 23.1-23.3
3,6,6 bXPsep 174.4 103.8 34.3 72.0 48.7 73.2 54.1 74.1 14.3
3,6 bDGalp 104.6 72.2 73.7 69.9 74.7 64.8
3 bDGalf 110.3 82.6 78.1 84.2 71.2 72.5
aDGalp 97.8 68.5 78.8 70.6 72.5 62.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
3,6,6,4 aDGalp 5.00 3.74 3.66 3.88 4.19 3.76-3.76
3,6,6,5 Ac - 1.91-1.96
3,6,6,7 Ac - 1.91-1.96
3,6,6 bXPsep - - 1.62-2.53 3.87 3.87 4.12 4.25 4.20 1.24
3,6 bDGalp 4.39 3.52 3.63 3.90 3.75 3.41-3.58
3 bDGalf 5.15 4.15 4.01 4.02 3.98 3.73-4.06
aDGalp 5.05 3.85 3.80 4.09 4.15 3.72-3.72
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
3,6,6,4 aDGalp 97.8/5.00 69.2/3.74 70.4/3.66 70.6/3.88 72.2/4.19 62.6/3.76-3.76
3,6,6,5 Ac 23.1-23.3/1.91-1.96
3,6,6,7 Ac 23.1-23.3/1.91-1.96
3,6,6 bXPsep 34.3/1.62-2.53 72.0/3.87 48.7/3.87 73.2/4.12 54.1/4.25 74.1/4.20 14.3/1.24
3,6 bDGalp 104.6/4.39 72.2/3.52 73.7/3.63 69.9/3.90 74.7/3.75 64.8/3.41-3.58
3 bDGalf 110.3/5.15 82.6/4.15 78.1/4.01 84.2/4.02 71.2/3.98 72.5/3.73-4.06
aDGalp 97.8/5.05 68.5/3.85 78.8/3.80 70.6/4.09 72.5/4.15 62.7/3.72-3.72
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 3,6,6,4 | aDGalp | 5.00 | 3.74 | 3.66 | 3.88 | 4.19 | 3.76
3.76 | |
| 3,6,6,5 | Ac |
| 1.91
1.96 | |
| 3,6,6,7 | Ac |
| 1.91
1.96 | |
| 3,6,6 | bXPsep |
|
| 1.62
2.53 | 3.87 | 3.87 | 4.12 | 4.25 | 4.20 | 1.24 |
| 3,6 | bDGalp | 4.39 | 3.52 | 3.63 | 3.90 | 3.75 | 3.41
3.58 | |
| 3 | bDGalf | 5.15 | 4.15 | 4.01 | 4.02 | 3.98 | 3.73
4.06 | |
| | aDGalp | 5.05 | 3.85 | 3.80 | 4.09 | 4.15 | 3.72
3.72 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 3,6,6,4 | aDGalp | 97.8 | 69.2 | 70.4 | 70.6 | 72.2 | 62.6 | |
| 3,6,6,5 | Ac | 174.4
175.1 | 23.1
23.3 | |
| 3,6,6,7 | Ac | 174.4
175.1 | 23.1
23.3 | |
| 3,6,6 | bXPsep | 174.4 | 103.8 | 34.3 | 72.0 | 48.7 | 73.2 | 54.1 | 74.1 | 14.3 |
| 3,6 | bDGalp | 104.6 | 72.2 | 73.7 | 69.9 | 74.7 | 64.8 | |
| 3 | bDGalf | 110.3 | 82.6 | 78.1 | 84.2 | 71.2 | 72.5 | |
| | aDGalp | 97.8 | 68.5 | 78.8 | 70.6 | 72.5 | 62.7 | |
|
There is only one chemically distinct structure:
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