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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

The structure was elucidated in this paper
NCBI PubMed ID: 21861990
Publication DOI: 10.1016/j.carres.2011.07.021
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

A structure of the O-polysaccharide (O-antigen) of Escherichia coli O158 has been reported (Datta, A. K.; Basu, S.; Roy, N. Carbohydr. Res.1999, 322, 219-227). In this work, we reinvestigated the O158 polysaccharide using sugar analyses, Smith degradation, and (1)H and (13)C NMR spectroscopy and established the following structure, which is at variance with the structure established earlier: [see formula in text]. This structure is in agreement with the predicted functions of genes found in the O-antigen gene cluster of E. coli O158.

O-antigen, Escherichia coli, O-antigen gene cluster, O-Polysaccharide structure

Structure type: oligomer
Location inside paper: p.2276, fig.2, 1
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_885813

Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, Smith degradation
Comments, role: OPS after Smith degradation

Related record ID(s): 26908, 26909
NCBI Taxonomy refs (TaxIDs): 2162918
Show glycosyltransferases

NMR conditions: in D2O at 303 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,2	Ac	176.0	23.6
3,4	bDGlcpN	102.4	57.2	74.8	71.2	77.3	62.0
3,2	Ac	177.1	23.6
3	bDManpN	100.1	54.3	72.5	78.7	76.6	62.0
	x?Thre-onic	179.9	73.2	81.7	63.3


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,2	Ac	-	2.08
3,4	bDGlcpN	4.53	3.73	3.57	3.46	3.47	3.75-3.93
3,2	Ac	-	2.08
3	bDManpN	4.85	4.52	3.89	3.57	3.40	3.68-3.82
	x?Thre-onic	-	4.00	4.16	3.72-3.72


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,2	Ac		23.6/2.08
3,4	bDGlcpN	102.4/4.53	57.2/3.73	74.8/3.57	71.2/3.46	77.3/3.47	62.0/3.75-3.93
3,2	Ac		23.6/2.08
3	bDManpN	100.1/4.85	54.3/4.52	72.5/3.89	78.7/3.57	76.6/3.40	62.0/3.68-3.82
	x?Thre-onic		73.2/4.00	81.7/4.16	63.3/3.72-3.72

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,2	Ac		2.08
3,4	bDGlcpN	4.53	3.73	3.57	3.46	3.47	3.75 3.93
3,2	Ac		2.08
3	bDManpN	4.85	4.52	3.89	3.57	3.40	3.68 3.82
	x?Thre-onic		4.00	4.16	3.72 3.72

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,2	Ac	176.0	23.6
3,4	bDGlcpN	102.4	57.2	74.8	71.2	77.3	62.0
3,2	Ac	177.1	23.6
3	bDManpN	100.1	54.3	72.5	78.7	76.6	62.0
	x?Thre-onic	179.9	73.2	81.7	63.3

There are 2 chemically distinct structures. Please, select:

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

SVG MW SMILES 3D mol Ionize