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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: 21074753
Publication DOI: 10.1016/j.carres.2010.10.012
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: E. Vinogradov <Evguenii.Vinogradov

nrc-cnrc.gc.ca>
Institutions: National Institute of Child Health and Human Development, National Institutes of Health, 9000 Rockville Pike, Bethesda, MD, USA

Recently it was demonstrated that Shigella dysenteriae type 1, a cause of severe dysentery epidemics, gained its O-specific polysaccharide (O-SP) from Escherichia coli O148. The O-SPs of these bacteria differ only by a galactose residue in the repeat unit of S. dysenteriae type 1 in place of a glucose residue in E. coli O148. Herein, we analyzed the core structure and its linkage to the O-SP in E. coli O148 LPS. Both were found to be identical to those of S. dysenteriae type 1 structures, further supporting the relatedness of these two bacteria. The following structure of the core with one repeat unit of the O-SP has been assigned (all have d-configuration except l-Rha): (formula: see text).

LPS, structure, core, O-specific polysaccharide, Escherichia coli O148

Structure type: oligomer
Location inside paper: abstract, fig.1
Compound class: core oligosaccharide with O-unit
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_131186,IEDB_133751,IEDB_135818,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, 31P NMR, ESI-MS, mild acid hydrolysis
Comments, role: Phosphorylation is minor, consists mainly of P or PPEtN on HepI(1-5) and PEtN on HepII(1-3).

Related record ID(s): 26257
NCBI Taxonomy refs (TaxIDs): 2162917
Show glycosyltransferases

NMR conditions: in D2O at 308 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
5,3,3,3,2,2	aDGalp	97.1	69.5	70.6	71.0	72.5	62.5
5,3,3,3,2	aDGalp	93.7	73.5	69.0	70.5	72.4	62.4
5,3,3,3,4,6,3,2,3,3	Subst
5,3,3,3,4,6,3,2,3	aLRhap	103.5	71.4	71.4	73.3	70.3	17.8
5,3,3,3,4,6,3,2	aLRhap	102.8	70.8	79.2	72.6	70.5	17.8
5,3,3,3,4,6,3	aDGlcp	98.7	77.9	73.6	70.3	73.5	61.4
5,3,3,3,4,6,2	Ac	?	23.4
5,3,3,3,4,6	aDGlcpN	102.5	55.4	79.2	72.5	77.0	61.7
5,3,3,3,4	bDGalp	104.3	72.1	73.6	69.3	74.0	68.5
5,3,3,3	aDGlcp	96.1	75.1	71.2	79.3	71.3	60.9
5,3,3	aDGlcp	102.6	71.4	77.8	71.5	73.6	61.0
5,3,4	P
5,3,7	aXLDmanHepp
5,3	aXLDmanHepp
5,4	P
5	aXLDmanHepp
	?XKdo?


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
5,3,3,3,2,2	aDGalp	5.27	3.86	3.97	4.02	4.17	3.76-3.76
5,3,3,3,2	aDGalp	5.58	4.02	4.12	4.07	4.10	3.77-3.77
5,3,3,3,4,6,3,2,3,3	Subst
5,3,3,3,4,6,3,2,3	aLRhap	5.08	4.07	3.85	3.47	3.85	1.32
5,3,3,3,4,6,3,2	aLRhap	5.09	4.17	3.88	3.56	3.88	1.32
5,3,3,3,4,6,3	aDGlcp	5.52	3.66	3.77	3.47	3.64	3.77-3.77
5,3,3,3,4,6,2	Ac	-	2.08
5,3,3,3,4,6	aDGlcpN	4.63	3.82	3.84	3.70	3.49	3.76-3.93
5,3,3,3,4	bDGalp	4.46	3.55	3.65	3.91	3.81	3.89-3.96
5,3,3,3	aDGlcp	5.76	3.78	4.03	3.73	4.18	3.88-4.01
5,3,3	aDGlcp	5.21	3.68	4.08	3.77	3.92	3.82-3.89
5,3,4	P
5,3,7	aXLDmanHepp
5,3	aXLDmanHepp
5,4	P
5	aXLDmanHepp
	?XKdo?


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
5,3,3,3,2,2	aDGalp	97.1/5.27	69.5/3.86	70.6/3.97	71.0/4.02	72.5/4.17	62.5/3.76-3.76
5,3,3,3,2	aDGalp	93.7/5.58	73.5/4.02	69.0/4.12	70.5/4.07	72.4/4.10	62.4/3.77-3.77
5,3,3,3,4,6,3,2,3,3	Subst
5,3,3,3,4,6,3,2,3	aLRhap	103.5/5.08	71.4/4.07	71.4/3.85	73.3/3.47	70.3/3.85	17.8/1.32
5,3,3,3,4,6,3,2	aLRhap	102.8/5.09	70.8/4.17	79.2/3.88	72.6/3.56	70.5/3.88	17.8/1.32
5,3,3,3,4,6,3	aDGlcp	98.7/5.52	77.9/3.66	73.6/3.77	70.3/3.47	73.5/3.64	61.4/3.77-3.77
5,3,3,3,4,6,2	Ac		23.4/2.08
5,3,3,3,4,6	aDGlcpN	102.5/4.63	55.4/3.82	79.2/3.84	72.5/3.70	77.0/3.49	61.7/3.76-3.93
5,3,3,3,4	bDGalp	104.3/4.46	72.1/3.55	73.6/3.65	69.3/3.91	74.0/3.81	68.5/3.89-3.96
5,3,3,3	aDGlcp	96.1/5.76	75.1/3.78	71.2/4.03	79.3/3.73	71.3/4.18	60.9/3.88-4.01
5,3,3	aDGlcp	102.6/5.21	71.4/3.68	77.8/4.08	71.5/3.77	73.6/3.92	61.0/3.82-3.89
5,3,4	P
5,3,7	aXLDmanHepp
5,3	aXLDmanHepp
5,4	P
5	aXLDmanHepp
	?XKdo?

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
5,3,3,3,2,2	aDGalp	5.27	3.86	3.97	4.02	4.17	3.76 3.76
5,3,3,3,2	aDGalp	5.58	4.02	4.12	4.07	4.10	3.77 3.77
5,3,3,3,4,6,3,2,3,3	Subst
5,3,3,3,4,6,3,2,3	aLRhap	5.08	4.07	3.85	3.47	3.85	1.32
5,3,3,3,4,6,3,2	aLRhap	5.09	4.17	3.88	3.56	3.88	1.32
5,3,3,3,4,6,3	aDGlcp	5.52	3.66	3.77	3.47	3.64	3.77 3.77
5,3,3,3,4,6,2	Ac		2.08
5,3,3,3,4,6	aDGlcpN	4.63	3.82	3.84	3.70	3.49	3.76 3.93
5,3,3,3,4	bDGalp	4.46	3.55	3.65	3.91	3.81	3.89 3.96
5,3,3,3	aDGlcp	5.76	3.78	4.03	3.73	4.18	3.88 4.01
5,3,3	aDGlcp	5.21	3.68	4.08	3.77	3.92	3.82 3.89
5,3,4	P
5,3,7	aXLDmanHepp
5,3	aXLDmanHepp
5,4	P
5	aXLDmanHepp
	?XKdo?

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
5,3,3,3,2,2	aDGalp	97.1	69.5	70.6	71.0	72.5	62.5
5,3,3,3,2	aDGalp	93.7	73.5	69.0	70.5	72.4	62.4
5,3,3,3,4,6,3,2,3,3	Subst
5,3,3,3,4,6,3,2,3	aLRhap	103.5	71.4	71.4	73.3	70.3	17.8
5,3,3,3,4,6,3,2	aLRhap	102.8	70.8	79.2	72.6	70.5	17.8
5,3,3,3,4,6,3	aDGlcp	98.7	77.9	73.6	70.3	73.5	61.4
5,3,3,3,4,6,2	Ac	?	23.4
5,3,3,3,4,6	aDGlcpN	102.5	55.4	79.2	72.5	77.0	61.7
5,3,3,3,4	bDGalp	104.3	72.1	73.6	69.3	74.0	68.5
5,3,3,3	aDGlcp	96.1	75.1	71.2	79.3	71.3	60.9
5,3,3	aDGlcp	102.6	71.4	77.8	71.5	73.6	61.0
5,3,4	P
5,3,7	aXLDmanHepp
5,3	aXLDmanHepp
5,4	P
5	aXLDmanHepp
	?XKdo?

The spectrum also has 1 signal at unknown position (not plotted).

There are 2 chemically distinct structures. Please, select:

[1*]O[C@@H]1[C@@H](O)[C@H](C)O[C@@H](O[C@@H]2[C@@H](O)[C@H](C)O[C@@H](O[C@H]3[C@@H](O[C@H]4[C@H](O)[C@@H](CO)O[C@H](OC[C@H]5O[C@@H](O[C@H]6[C@H](O)[C@@H](O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@@H](O[C@H]7[C@H](O)[C@@H](CO)O[C@H](O[C@@H]8[C@H](O)[C@@H](O[C@@H]9[C@H](O)[C@@H](O[C@@H]%10[C@H](O)CC(O)(C(=O)O)O[C@@H]%10[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]9OP(=O)(O)O)O[C@H]([C@@H](O)CO[C@H]9O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]9O)[C@H]8OP(=O)(O)O)[C@@H]7O)O[C@@H]6CO)[C@H](O)[C@@H](O)[C@H]5O)[C@@H]4NC(C)=O)O[C@H](CO)[C@@H](O)[C@@H]3O)[C@@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

R1 = O-antigen (ID 26257)