Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Enterobacter cloacae [ICD11:
XN3YM 
]
The structure was elucidated in this paperNCBI PubMed ID: 24837902Publication DOI: 10.1016/j.carres.2014.01.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: perepel
ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
On mild acid degradation of the lipopolysaccharide of Enterobacter cloacae C6285, the O-polysaccharide was cleaved at residues of 5,7-diacetamido-3,5,7,9-tetradeoxy-d-glycero-d-galacto-non-2-ulosonic acid (di-N-acetyllegionaminic acid, Leg5Ac7Ac) 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 tetrasaccharide repeating unit of the linear O-polysaccharide was established: →4)-α-d-Galp-(1→4)-α-Legp5Ac7Ac-(2→3)-β-d-Galp-(1→3)-β-d-GalpNAc-(1→ The O-antigen gene cluster of E. cloacae C6285 was sequenced, the gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in agreement with the O-polysaccharide structure.
O-antigen, bacterial polysaccharide structure, legionaminic acid, O-antigen gene cluster, Enterobacter cloacae
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.23
Compound class: O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_147450,IEDB_151528,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, HF solvolysis, sugar analysis, DNA techniques, 31P NMR, GLC, mild acid hydrolysis, alkaline degradation, genetic methods
Related record ID(s): 30234
NCBI Taxonomy refs (TaxIDs): 550Reference(s) to other database(s): GTC:G70504FT
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
3,3,4 aDGalp 96.3 69.5 70.7 77.8 71.7 61.5
3,3,5 Ac 174.5-174.9 23.2-23.7
3,3,7 Ac 174.5-174.9 23.2-23.7
3,3 aXLegp ? ? 38.4 72.7 51.1 74.3 55.2 68.3 19.5
3 bDGalp 105.7 70.2 77.0 68.5 76.1 62.3
2 Ac 174.5-174.9 23.2-23.7
bDGalpN 103.5 52.8 80.6 69.3 75.8 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
3,3,4 aDGalp 5.04 3.68 3.79 4.14 3.74 3.68-3.79
3,3,5 Ac - 1.95-2.04
3,3,7 Ac - 1.95-2.04
3,3 aXLegp - - 1.66-2.95 3.92 3.84 3.65 3.88 3.93 1.16
3 bDGalp 4.49 3.57 4.06 3.96 3.60 3.73-3.78
2 Ac - 1.95-2.04
bDGalpN 4.71 4.03 3.91 4.12 3.69 3.73-3.78
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
3,3,4 aDGalp 96.3/5.04 69.5/3.68 70.7/3.79 77.8/4.14 71.7/3.74 61.5/3.68-3.79
3,3,5 Ac 23.2-23.7/1.95-2.04
3,3,7 Ac 23.2-23.7/1.95-2.04
3,3 aXLegp 38.4/1.66-2.95 72.7/3.92 51.1/3.84 74.3/3.65 55.2/3.88 68.3/3.93 19.5/1.16
3 bDGalp 105.7/4.49 70.2/3.57 77.0/4.06 68.5/3.96 76.1/3.60 62.3/3.73-3.78
2 Ac 23.2-23.7/1.95-2.04
bDGalpN 103.5/4.71 52.8/4.03 80.6/3.91 69.3/4.12 75.8/3.69 62.3/3.73-3.78
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 3,3,4 | aDGalp | 5.04 | 3.68 | 3.79 | 4.14 | 3.74 | 3.68
3.79 | |
| 3,3,5 | Ac |
| 1.95
2.04 | |
| 3,3,7 | Ac |
| 1.95
2.04 | |
| 3,3 | aXLegp |
|
| 1.66
2.95 | 3.92 | 3.84 | 3.65 | 3.88 | 3.93 | 1.16 |
| 3 | bDGalp | 4.49 | 3.57 | 4.06 | 3.96 | 3.60 | 3.73
3.78 | |
| 2 | Ac |
| 1.95
2.04 | |
| | bDGalpN | 4.71 | 4.03 | 3.91 | 4.12 | 3.69 | 3.73
3.78 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 3,3,4 | aDGalp | 96.3 | 69.5 | 70.7 | 77.8 | 71.7 | 61.5 | |
| 3,3,5 | Ac | 174.5
174.9 | 23.2
23.7 | |
| 3,3,7 | Ac | 174.5
174.9 | 23.2
23.7 | |
| 3,3 | aXLegp | ? | ? | 38.4 | 72.7 | 51.1 | 74.3 | 55.2 | 68.3 | 19.5 |
| 3 | bDGalp | 105.7 | 70.2 | 77.0 | 68.5 | 76.1 | 62.3 | |
| 2 | Ac | 174.5
174.9 | 23.2
23.7 | |
| | bDGalpN | 103.5 | 52.8 | 80.6 | 69.3 | 75.8 | 62.3 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":96.3,"l":"1","c":[0,0,225]},{"s":69.5,"l":"2","c":[0,0,225]},{"s":70.7,"l":"3","c":[0,0,225]},{"s":77.8,"l":"4","c":[0,0,225]},{"s":71.7,"l":"5","c":[0,0,225]},{"s":61.5,"l":"6","c":[0,0,225]},{"s":174.7,"l":"1","c":[0,0,0]},{"s":23.45,"l":"2","c":[0,0,0]},{"s":174.7,"l":"1","c":[0,0,0]},{"s":23.45,"l":"2","c":[0,0,0]},{"s":38.4,"l":"3","c":[230,0,30]},{"s":72.7,"l":"4","c":[230,0,30]},{"s":51.1,"l":"5","c":[230,0,30]},{"s":74.3,"l":"6","c":[230,0,30]},{"s":55.2,"l":"7","c":[230,0,30]},{"s":68.3,"l":"8","c":[230,0,30]},{"s":19.5,"l":"9","c":[230,0,30]},{"s":105.7,"l":"1","c":[0,165,0]},{"s":70.2,"l":"2","c":[0,165,0]},{"s":77,"l":"3","c":[0,165,0]},{"s":68.5,"l":"4","c":[0,165,0]},{"s":76.1,"l":"5","c":[0,165,0]},{"s":62.3,"l":"6","c":[0,165,0]},{"s":174.7,"l":"1","c":[0,0,0]},{"s":23.45,"l":"2","c":[0,0,0]},{"s":103.5,"l":"1","c":[120,0,225]},{"s":52.8,"l":"2","c":[120,0,225]},{"s":80.6,"l":"3","c":[120,0,225]},{"s":69.3,"l":"4","c":[120,0,225]},{"s":75.8,"l":"5","c":[120,0,225]},{"s":62.3,"l":"6","c":[120,0,225]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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