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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: 7544238
Publication DOI: 10.1016/0008-6215(95)00041-Q
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: torgov

ioc.ac.ru
Institutions: Max-Planck-Institut für Immunbiologie, Freiburg, Germany

Structures for the N-acetylneuraminic acid (Neu5Ac)-containing O56 and O24 polysaccharides of Escherichia coli have been reported previously. During these studies unusual chemical shifts had been observed for the NMR signals for H-3eq and C-3 of the Neu5Ac residues of both polysaccharides. In further pursuing this phenomenon, we have reinvestigated the O56 and O24 polysaccharides as well as derived oligosaccharides by one- and two-dimensional NMR spectroscopy. The results showed that structures of both polysaccharides (PSs) had to be modified and formulated as [formula: see text] 2D ROESY spectra revealed a strong NOE between H-3eq of Neu5Ac and the protons of the side-chain sugar (H-3 and H-5 of α-D-Galp in the O56 PS and H-3 of α-D-Glcp in the O24 PS) and also between H-3ax of Neu5Ac and H-3 of β-D-Glcp in the main chain. This indicated a close spatial association of the seven-linked α-Neu5Ac and the side-chain residues α-D-Galp (O56 PS) and α-D-Glcp (O25 PS), respectively. The strong long-range spatial contacts caused the unusual chemical shifts of H-3eq and C-3 of Neu5Ac.

Escherichia coli, NMR spectroscopy, polysaccharide structure, 024 and 056 antigens

Structure type: oligomer
Location inside paper: p.81, octasaccharide IV, table 7
Contained glycoepitopes: IEDB_135813,IEDB_136794,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_423085,IEDB_983931,SB_170,SB_171,SB_172,SB_192,SB_7,SB_84

Methods: NMR-2D, NMR, sugar analysis, Smith degradation
Comments, role: NMR temperature was not specified

Related record ID(s): 326, 328, 8382, 8411, 8412, 8413, 8414
NCBI Taxonomy refs (TaxIDs): 562
Reference(s) to other database(s): GTC:G01415HK
Show glycosyltransferases

NMR conditions: in D2O; pH 6 [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
7,3,2	aDGalp	97.0	69.8	70.7	70.5	72.1	62.3-62.7
7,3,3,7,3,2	aDGalp	98.6	69.9	70.7	70.5	72.1	62.3-62.7
7,3,3,7,3	bDGlcp	103.1	77.8	76.0	69.9	77.3	62.3-62.7
7,3,3,7,2	Ac
7,3,3,7	bDGlcpN	102.9	57.1	80.7	70.5	76.7	62.3-62.7
7,3,3,5	Ac
7,3,3	aXNeup	176.0	101.6	37.4	68.8	54.2	73.1	79.5	73.0	63.7-63.8
7,3	bDGlcp	103.2	73.1	80.7	69.6	76.0	62.0
7,2	Ac
7	bDGlcpN	102.6	57.0	80.8	70.9	76.7	62.3-62.7
5	Ac
	bXNeup	176.0	96.8	40.1	66.9	55.5	70.5	79.5	72.6	63.7-63.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
7,3,2	aDGalp	5.55	3.82	3.91	3.99	4.13	3.68
7,3,3,7,3,2	aDGalp	5.38	3.86	3.92	4.03	4.23	3.82-3.82
7,3,3,7,3	bDGlcp	4.64	3.51	3.58	3.50	3.45	3.73-3.92
7,3,3,7,2	Ac
7,3,3,7	bDGlcpN	4.77	3.67	4.07	3.56	3.56	3.81-4.02
7,3,3,5	Ac
7,3,3	aXNeup	-	-	2.00-2.51	4.02	3.99	3.84	3.70	3.83	3.60-3.76
7,3	bDGlcp	4.71	3.66	4.18	3.51	3.45	3.81-3.98
7,2	Ac
7	bDGlcpN	4.87	3.66	4.14	3.56	3.48	3.86-4.01
5	Ac
	bXNeup	-	-	1.87-2.17	4.25	3.81	4.41	3.88	3.84	3.51-3.77


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
7,3,2	aDGalp	97.0/5.55	69.8/3.82	70.7/3.91	70.5/3.99	72.1/4.13	62.3-62.7/3.68
7,3,3,7,3,2	aDGalp	98.6/5.38	69.9/3.86	70.7/3.92	70.5/4.03	72.1/4.23	62.3-62.7/3.82-3.82
7,3,3,7,3	bDGlcp	103.1/4.64	77.8/3.51	76.0/3.58	69.9/3.50	77.3/3.45	62.3-62.7/3.73-3.92
7,3,3,7,2	Ac
7,3,3,7	bDGlcpN	102.9/4.77	57.1/3.67	80.7/4.07	70.5/3.56	76.7/3.56	62.3-62.7/3.81-4.02
7,3,3,5	Ac
7,3,3	aXNeup			37.4/2.00-2.51	68.8/4.02	54.2/3.99	73.1/3.84	79.5/3.70	73.0/3.83	63.7-63.8/3.60-3.76
7,3	bDGlcp	103.2/4.71	73.1/3.66	80.7/4.18	69.6/3.51	76.0/3.45	62.0/3.81-3.98
7,2	Ac
7	bDGlcpN	102.6/4.87	57.0/3.66	80.8/4.14	70.9/3.56	76.7/3.48	62.3-62.7/3.86-4.01
5	Ac
	bXNeup			40.1/1.87-2.17	66.9/4.25	55.5/3.81	70.5/4.41	79.5/3.88	72.6/3.84	63.7-63.8/3.51-3.77

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
7,3,2	aDGalp	5.55	3.82	3.91	3.99	4.13	3.68
7,3,3,7,3,2	aDGalp	5.38	3.86	3.92	4.03	4.23	3.82 3.82
7,3,3,7,3	bDGlcp	4.64	3.51	3.58	3.50	3.45	3.73 3.92
7,3,3,7,2	Ac
7,3,3,7	bDGlcpN	4.77	3.67	4.07	3.56	3.56	3.81 4.02
7,3,3,5	Ac
7,3,3	aXNeup			2.00 2.51	4.02	3.99	3.84	3.70	3.83	3.60 3.76
7,3	bDGlcp	4.71	3.66	4.18	3.51	3.45	3.81 3.98
7,2	Ac
7	bDGlcpN	4.87	3.66	4.14	3.56	3.48	3.86 4.01
5	Ac
	bXNeup			1.87 2.17	4.25	3.81	4.41	3.88	3.84	3.51 3.77

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
7,3,2	aDGalp	97.0	69.8	70.7	70.5	72.1	62.3 62.7
7,3,3,7,3,2	aDGalp	98.6	69.9	70.7	70.5	72.1	62.3 62.7
7,3,3,7,3	bDGlcp	103.1	77.8	76.0	69.9	77.3	62.3 62.7
7,3,3,7,2	Ac
7,3,3,7	bDGlcpN	102.9	57.1	80.7	70.5	76.7	62.3 62.7
7,3,3,5	Ac
7,3,3	aXNeup	176.0	101.6	37.4	68.8	54.2	73.1	79.5	73.0	63.7 63.8
7,3	bDGlcp	103.2	73.1	80.7	69.6	76.0	62.0
7,2	Ac
7	bDGlcpN	102.6	57.0	80.8	70.9	76.7	62.3 62.7
5	Ac
	bXNeup	176.0	96.8	40.1	66.9	55.5	70.5	79.5	72.6	63.7 63.8

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize