CSDB: Search results

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: 10629949
Publication DOI: 10.1016/S0008-6215(99)00212-8
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: malcolm.perry

nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ont., Canada K 1A 0R 6

The antigenic O-polysaccharide moiety of the lipopolysaccharide produced by Escherichia coli serotype O65 was investigated by composition, methylation, base hydrolysis, periodate oxidation, mass spectrometric methods, and by 1D and 2D NMR spectroscopy. The O-polysaccharide had [a]D108° (water) and is a high-molecular-weight unbranched linear polymer of repeating pentasaccharide units composed of 1:1:1:1:1 D-galacturonic acid (D-GalA), D-galacturonamide (D-GalANH2), 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), 2-acetamido-2-deoxy-D-galactose (DGalNAc),and 3-acetamido-3,6-dideoxy-D-glucose (D-Qui3NAc), and has the following structure: [see formula in text]

Lipopolysaccharide, Escherichia coli, NMR spectroscopy, polysaccharide structure

Structure type: suggested polymer biological repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822

Methods: methylation, periodate oxidation, NMR-2D, NMR, MS, composition analysis, base hydrolysis
Comments, role: chemical repeat frame is different in the paper; biological repeat frame was based on GNE gene presence

Related record ID(s): 4171, 10339, 20698
NCBI Taxonomy refs (TaxIDs): 2162912
Reference(s) to other database(s): GTC:G86652HR, GlycomeDB:28132
Show glycosyltransferases

NMR conditions: in D2O; pH 2.8 at 305 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4,4,3	Ac
3,4,4,4	bDQuip3N	103.76	73.73	56.44	73.72	73.73	17.55
3,4,4,6	NH2
3,4,4	aDGalpA	100.71	69.62	70.38	77.20	71.55	174.40
3,4,2	Ac
3,4	aDGalpN	99.24	50.55	67.28	77.67	71.88	60.27
3	bDGalpA	104.43	70.67	72.47	77.86	74.22	171.48
2	Ac
	aDGlcpN	95.52	52.43	83.21	69.14	73.22	61.42


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4,4,3	Ac
3,4,4,4	bDQuip3N	4.850	3.409	3.869	3.183	3.438	1.269
3,4,4,6	NH2
3,4,4	aDGalpA	5.083	3.767	4.081	4.508	4.802	-
3,4,2	Ac
3,4	aDGalpN	4.990	4.180	4.040	4.150	4.395	3.822-3.842
3	bDGalpA	4.431	3.579	3.825	4.410	4.460	-
2	Ac
	aDGlcpN	5.724	4.111	3.618	3.620	3.620	3.851-3.920


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,4,4,3	Ac
3,4,4,4	bDQuip3N	103.76/4.850	73.73/3.409	56.44/3.869	73.72/3.183	73.73/3.438	17.55/1.269
3,4,4,6	NH2
3,4,4	aDGalpA	100.71/5.083	69.62/3.767	70.38/4.081	77.20/4.508	71.55/4.802	
3,4,2	Ac
3,4	aDGalpN	99.24/4.990	50.55/4.180	67.28/4.040	77.67/4.150	71.88/4.395	60.27/3.822-3.842
3	bDGalpA	104.43/4.431	70.67/3.579	72.47/3.825	77.86/4.410	74.22/4.460	
2	Ac
	aDGlcpN	95.52/5.724	52.43/4.111	83.21/3.618	69.14/3.620	73.22/3.620	61.42/3.851-3.920

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4,4,3	Ac
3,4,4,4	bDQuip3N	4.850	3.409	3.869	3.183	3.438	1.269
3,4,4,6	NH2
3,4,4	aDGalpA	5.083	3.767	4.081	4.508	4.802
3,4,2	Ac
3,4	aDGalpN	4.990	4.180	4.040	4.150	4.395	3.822 3.842
3	bDGalpA	4.431	3.579	3.825	4.410	4.460
2	Ac
	aDGlcpN	5.724	4.111	3.618	3.620	3.620	3.851 3.920

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4,4,3	Ac
3,4,4,4	bDQuip3N	103.76	73.73	56.44	73.72	73.73	17.55
3,4,4,6	NH2
3,4,4	aDGalpA	100.71	69.62	70.38	77.20	71.55	174.40
3,4,2	Ac
3,4	aDGalpN	99.24	50.55	67.28	77.67	71.88	60.27
3	bDGalpA	104.43	70.67	72.47	77.86	74.22	171.48
2	Ac
	aDGlcpN	95.52	52.43	83.21	69.14	73.22	61.42

There is only one chemically distinct structure:

*O[C@H]1[C@H](O[C@H]2[C@@H](C(N)=O)O[C@H](O[C@H]3[C@@H](CO)O[C@H](O[C@H]4[C@@H](C(=O)O)O[C@@H](O[C@@H]5[C@@H](NC(C)=O)[C@@H](*)O[C@H](CO)[C@H]5O)[C@H](O)[C@H]4O)[C@H](NC(C)=O)[C@H]3O)[C@H](O)[C@H]2O)O[C@H](C)[C@@H](O)[C@@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize