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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Enterobacter cloacae [ICD11: XN3YM

]

The structure was elucidated in this paper
NCBI PubMed ID: 24837902
Publication DOI: 10.1016/j.carres.2014.01.012
Journal NLM ID: 0043535
Publisher: 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: oligomer
Location inside paper: p.22
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): 30053
NCBI Taxonomy refs (TaxIDs): 550
Reference(s) to other database(s): GTC:G71999YN
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
4,4,3	bDGalp	105.9	71.8	73.6	69.7	76.1	62.2
4,4,2	Ac	174.9-176.1	22.9-23.6
4,4	bDGalpN	103.7	52.7	80.8	69.2	75.7	62.2
4	aDGalp	96.0	69.4	70.6	77.8	71.6	61.4
5	Ac	174.9-176.1	22.9-23.6
7	Ac	174.9-176.1	22.9-23.6
	aXLegp	174.8	97.6	37.4	73.1	51.7	70.5	54.6	67.3	20.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
4,4,3	bDGalp	4.45	3.53	3.62	3.91	3.66	3.74-3.77
4,4,2	Ac	-	1.98-2.03
4,4	bDGalpN	4.68	4.01	3.89	4.14	3.67	3.74-3.77
4	aDGalp	5.00	3.64	3.78	4.14	3.75	3.70-3.82
5	Ac	-	1.98-2.03
7	Ac	-	1.98-2.03
	aXLegp	-	-	1.75-2.37	3.99	3.83	4.28	3.87	3.86	1.15


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
4,4,3	bDGalp	105.9/4.45	71.8/3.53	73.6/3.62	69.7/3.91	76.1/3.66	62.2/3.74-3.77
4,4,2	Ac		22.9-23.6/1.98-2.03
4,4	bDGalpN	103.7/4.68	52.7/4.01	80.8/3.89	69.2/4.14	75.7/3.67	62.2/3.74-3.77
4	aDGalp	96.0/5.00	69.4/3.64	70.6/3.78	77.8/4.14	71.6/3.75	61.4/3.70-3.82
5	Ac		22.9-23.6/1.98-2.03
7	Ac		22.9-23.6/1.98-2.03
	aXLegp			37.4/1.75-2.37	73.1/3.99	51.7/3.83	70.5/4.28	54.6/3.87	67.3/3.86	20.4/1.15

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
4,4,3	bDGalp	4.45	3.53	3.62	3.91	3.66	3.74 3.77
4,4,2	Ac		1.98 2.03
4,4	bDGalpN	4.68	4.01	3.89	4.14	3.67	3.74 3.77
4	aDGalp	5.00	3.64	3.78	4.14	3.75	3.70 3.82
5	Ac		1.98 2.03
7	Ac		1.98 2.03
	aXLegp			1.75 2.37	3.99	3.83	4.28	3.87	3.86	1.15

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
4,4,3	bDGalp	105.9	71.8	73.6	69.7	76.1	62.2
4,4,2	Ac	174.9 176.1	22.9 23.6
4,4	bDGalpN	103.7	52.7	80.8	69.2	75.7	62.2
4	aDGalp	96.0	69.4	70.6	77.8	71.6	61.4
5	Ac	174.9 176.1	22.9 23.6
7	Ac	174.9 176.1	22.9 23.6
	aXLegp	174.8	97.6	37.4	73.1	51.7	70.5	54.6	67.3	20.4

There is only one chemically distinct structure:

CC(=O)N[C@@H]1[C@@H](O[C@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O)[C@H]2O)C[C@](O)(C(=O)O)O[C@H]1[C@H](NC(C)=O)[C@@H](C)O

SVG MW SMILES 3D mol Ionize