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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
Publication DOI: 10.1007/s11172-018-2253-x
Journal NLM ID: 100912060
Publisher: New York: Consultants Bureau
Correspondence: yknirel

gmail.com
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, Higher Chemical College of the Russian Academy of Sciences, D.I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia

O-Polysaccharides (O-antigens) of a number of genetically related Escherichia coli O-serogroups (O17, O44, O73, O77, and O106) and Salmonella enterica O:6,14 possess an identical main chain composed of d-GlcNAc and d-Man residues and differ from each other by the absence or presence of glucose side chains at various positions. Using two-dimensional NMR spectroscopy, we established the structure of the O-polysaccharide of E. coli O106 having two glucose side chains in a hexasaccharide repeating unit.

O-antigen, Escherichia coli, NMR spectroscopy, O-polysaccharide, bacterial polysaccharide structure, glucosylation

Structure type: polymer biological repeating unit
Location inside paper: p.1539, table 1, p.1540, table 3, E. coli O106
The structure in this paper was incorrect:

Original structure from CSDB record 12978

← originally published structure

Show legend

Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, GPC, mild acid degradation
Comments, role: error structure (table 3, in the English version of the article)

Related record ID(s): 12788, 12789, 12790, 12791, 12792
NCBI Taxonomy refs (TaxIDs): 2234096
Reference(s) to other database(s): GTC:G05460OB
Show glycosyltransferases

NMR conditions: in D2O at 328 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,2	aDManp	103.8	71.3	72.1	67.3	72.9	66.5
3,2	aDManp	100.6	79.0	71.5	68.1	73.2	62.2
3,4	aDGlcp	101.4	73.2	74.3	70.9	74.1	62.1
3	bDManp	101.2	76.6	75.7	77.0	76.6	62.3
2	Ac	175.0	23.4
6	aDGlcp	99.1	72.9	74.5	71.0	73.2	62.0
	aDGlcpN	98.6	54.2	81.9	69.7	71.7	67.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,2,2	aDManp	5.07	4.11	3.85	3.97	3.78	3.53-4.13
3,2	aDManp	5.33	4.09	4.02	3.76	3.96	3.80-3.95
3,4	aDGlcp	5.29	3.55	3.67	3.40	3.72	3.75-3.85
3	bDManp	4.78	3.98	3.98	3.83	3.54	3.74-3.85
2	Ac	-	2.05
6	aDGlcp	4.97	3.56	3.73	3.43	3.71	3.77-3.85
	aDGlcpN	4.85	4.11	3.93	3.65	3.92	3.78-4.00


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,2,2	aDManp	103.8/5.07	71.3/4.11	72.1/3.85	67.3/3.97	72.9/3.78	66.5/3.53-4.13
3,2	aDManp	100.6/5.33	79.0/4.09	71.5/4.02	68.1/3.76	73.2/3.96	62.2/3.80-3.95
3,4	aDGlcp	101.4/5.29	73.2/3.55	74.3/3.67	70.9/3.40	74.1/3.72	62.1/3.75-3.85
3	bDManp	101.2/4.78	76.6/3.98	75.7/3.98	77.0/3.83	76.6/3.54	62.3/3.74-3.85
2	Ac		23.4/2.05
6	aDGlcp	99.1/4.97	72.9/3.56	74.5/3.73	71.0/3.43	73.2/3.71	62.0/3.77-3.85
	aDGlcpN	98.6/4.85	54.2/4.11	81.9/3.93	69.7/3.65	71.7/3.92	67.0/3.78-4.00

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,2,2	aDManp	5.07	4.11	3.85	3.97	3.78	3.53 4.13
3,2	aDManp	5.33	4.09	4.02	3.76	3.96	3.80 3.95
3,4	aDGlcp	5.29	3.55	3.67	3.40	3.72	3.75 3.85
3	bDManp	4.78	3.98	3.98	3.83	3.54	3.74 3.85
2	Ac		2.05
6	aDGlcp	4.97	3.56	3.73	3.43	3.71	3.77 3.85
	aDGlcpN	4.85	4.11	3.93	3.65	3.92	3.78 4.00

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,2	aDManp	103.8	71.3	72.1	67.3	72.9	66.5
3,2	aDManp	100.6	79.0	71.5	68.1	73.2	62.2
3,4	aDGlcp	101.4	73.2	74.3	70.9	74.1	62.1
3	bDManp	101.2	76.6	75.7	77.0	76.6	62.3
2	Ac	175.0	23.4
6	aDGlcp	99.1	72.9	74.5	71.0	73.2	62.0
	aDGlcpN	98.6	54.2	81.9	69.7	71.7	67.0

There is only one chemically distinct structure:

*OC[C@H]1O[C@H](O[C@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]2O[C@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](CO)O[C@H]2O[C@@H]2[C@@H](NC(C)=O)[C@@H](*)O[C@H](CO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize