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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: 17182015
Journal NLM ID: 0043535
Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Department of Laboratory Medicine, Division of Clinical Bacteriology, Karolinska Institutet, Karolinska University Hospital, Huddinge, Stockholm, Sweden

The structure of the O-antigenic part of the lipopolysaccharide (LPS) obtained from the verotoxin-producing Escherichia coli O171 has been determined. (1)H and (13)C NMR spectroscopy techniques in combination with component analysis were used to elucidate the O-antigen structure of O-deacylated LPS. Subsequent NMR analysis of the native LPS revealed acetylation at O-7/O-9 of the sialic acid residue. The sequence of sugars was determined by inter-residue correlations in (1)H,(1)H-NOESY and (1)H,(13)C-heteronuclear multiple-bond correlation spectra. The O-antigen is composed of pentasaccharide repeating units with one equivalent of O-acetyl groups distributed over two positions: Based on biosynthetic considerations, this should also be the biological repeating unit

Lipopolysaccharide, NMR, LPS, structure, biosynthetic, chemistry, clinical, correlation, structural, polysaccharide, O-antigen, repeating unit, analysis, O antigen, group, Escherichia, Escherichia coli, determination, O-antigenic, O-antigenic polysaccharide, structural determination, acid, NMR spectroscopy, biological, sugar, position, medicine, spectroscopy, sialic acid, sequence, pentasaccharide, sugars, component, O-deacylated, NMR analysis, acetylation, PDF, organic, bacteriology, native, O-acetyl, biological repeating unit, verotoxin-producing Escherichia coli

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.1881
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_149174,IEDB_158551,IEDB_190606,IEDB_983931,SB_126,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_23,SB_24,SB_7,SB_8,SB_84,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, GLC, composition analysis
Comments, role: O-acetylation at C7 or C9 is equal probability. 1H and 13C NMR data from O-antigen part of 0-deacylated LPS from Escherichia coli O171

NCBI Taxonomy refs (TaxIDs): 2100484
Reference(s) to other database(s): GTC:G92084YQ, GlycomeDB:27881
Show glycosyltransferases

NMR conditions: in D2O at 293 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
3,3,6,6,5	Ac	175.0	23.0
3,3,6,6,7	Ac
3,3,6,6	aXNeup	174.2	101.2	40.8	78.4	50.8	73.5	69.0	72.6	63.5
3,3,6	bDGalp	104.5	71.6	73.5	69.4	74.3	64.1
3,3	bDGlcp	104.7	74.1	76.3	70.2	75.6	69.7
3	bDGalp	105.4	70.6	83.0	69.1	75.5	61.8
2	Ac	175.2	23.2
	bDGalpN	102.9	52.2	81.1	68.7	75.5	61.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
3,3,6,6,5	Ac	-	2.03
3,3,6,6,7	Ac
3,3,6,6	aXNeup	-	-	1.76-2.95	3.73	3.92	3.72	3.54	3.86	3.62-3.86
3,3,6	bDGalp	4.40	3.51	3.62	3.93	3.75	3.61-3.90
3,3	bDGlcp	4.65	3.36	3.50	3.50	3.59	3.81-4.21
3	bDGalp	4.48	3.65	3.77	4.17	3.66	3.74
2	Ac	-	2.0
	bDGalpN	4.57	3.95	3.86	4.18	3.69	3.74-3.82


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
3,3,6,6,5	Ac		23.0/2.03
3,3,6,6,7	Ac
3,3,6,6	aXNeup			40.8/1.76-2.95	78.4/3.73	50.8/3.92	73.5/3.72	69.0/3.54	72.6/3.86	63.5/3.62-3.86
3,3,6	bDGalp	104.5/4.40	71.6/3.51	73.5/3.62	69.4/3.93	74.3/3.75	64.1/3.61-3.90
3,3	bDGlcp	104.7/4.65	74.1/3.36	76.3/3.50	70.2/3.50	75.6/3.59	69.7/3.81-4.21
3	bDGalp	105.4/4.48	70.6/3.65	83.0/3.77	69.1/4.17	75.5/3.66	61.8/3.74
2	Ac		23.2/2.0
	bDGalpN	102.9/4.57	52.2/3.95	81.1/3.86	68.7/4.18	75.5/3.69	61.8/3.74-3.82

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
3,3,6,6,5	Ac		2.03
3,3,6,6,7	Ac
3,3,6,6	aXNeup			1.76 2.95	3.73	3.92	3.72	3.54	3.86	3.62 3.86
3,3,6	bDGalp	4.40	3.51	3.62	3.93	3.75	3.61 3.90
3,3	bDGlcp	4.65	3.36	3.50	3.50	3.59	3.81 4.21
3	bDGalp	4.48	3.65	3.77	4.17	3.66	3.74
2	Ac		2.0
	bDGalpN	4.57	3.95	3.86	4.18	3.69	3.74 3.82

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
3,3,6,6,5	Ac	175.0	23.0
3,3,6,6,7	Ac
3,3,6,6	aXNeup	174.2	101.2	40.8	78.4	50.8	73.5	69.0	72.6	63.5
3,3,6	bDGalp	104.5	71.6	73.5	69.4	74.3	64.1
3,3	bDGlcp	104.7	74.1	76.3	70.2	75.6	69.7
3	bDGalp	105.4	70.6	83.0	69.1	75.5	61.8
2	Ac	175.2	23.2
	bDGalpN	102.9	52.2	81.1	68.7	75.5	61.8

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize