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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11: ME05.1

, ICD11: SA55

]; dysentery [ICD11: SA56

]; infection due to Escherichia coli [ICD11: XN6P4

]

The structure was elucidated in this paper
NCBI PubMed ID: 8864227
Journal NLM ID: 0043535
Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm Unit ersit3, Stockholm, Sweden, Karolinska Institute, Department of Immunology Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology Huddinge University Hospital, S-141 86 Huddinge, Sweden

The structure of the O-specific side-chain of the lipopolysaccharide from Escherichia coli O28 has been investigated. NMR spectroscopy has been the main method used, complemented with sugar and methylation analyses. The polysaccharide contains one equivalent of O-acetyl groups per repeating unit. Selective cleavage of the O-deacetylated polymer was performed by treatment with aqueous hydrofluoric acid, and resulted in a trisaccharide-glycerol. The polysaccharide thus is of the teichoic acid type and composed of repeating units in which the trisaccharide-glycerol residues are joined by phosphodiester linkages. The O-antigen polysaccharide has the following structure. [sequence: see text] The absolute configuration of the glycerol moiety as R, (i.e., D-glycerol 1-phosphate) was determined by a new method based on TEMPO oxidation of the polysaccharide, followed by GLC analysis of the (+)-2-butyl ester of the resulting glyceric acid

Lipopolysaccharide, Escherichia coli, phosphodiester, Teichoic acid type, Enteroinvasive

Structure type: polymer chemical repeating unit
Location inside paper: Table 2
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130695,IEDB_135813,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_151531,IEDB_190606

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, FAB-MS, sugar analysis, 31P NMR
Comments, role: O-deacetylated polysaccharide

Related record ID(s): 4385, 4478
NCBI Taxonomy refs (TaxIDs): 562
Reference(s) to other database(s): GTC:G57961YA
Show glycosyltransferases

NMR conditions: in D2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,3,3,2	Ac	175.3	23.1
0,2,3,3	bDGlcpN	101.3	56.2	73.7	75.0	75.9	61.3
0,2,3	bDGalf	109.0	80.7	85.1	82.5	71.2	63.8
0,2,2	Ac	175.0	23.0
0,2	aDGlcpN	97.7	53.8	78.6	69.2	73.0	61.4
0	xDGro	65.3	78.1	62.1
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,3,3,2	Ac	-	2.10
0,2,3,3	bDGlcpN	4.68	3.73	3.76	3.97	3.56	3.77-3.92
0,2,3	bDGalf	5.07	4.04	4.21	4.18	3.91	3.65-3.69
0,2,2	Ac	-	2.09
0,2	aDGlcpN	5.05	4.08	3.86	3.48	3.89	3.77-3.82
0	xDGro	4.04-4.08	3.79	3.75-3.75
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,2,3,3,2	Ac		23.1/2.10
0,2,3,3	bDGlcpN	101.3/4.68	56.2/3.73	73.7/3.76	75.0/3.97	75.9/3.56	61.3/3.77-3.92
0,2,3	bDGalf	109.0/5.07	80.7/4.04	85.1/4.21	82.5/4.18	71.2/3.91	63.8/3.65-3.69
0,2,2	Ac		23.0/2.09
0,2	aDGlcpN	97.7/5.05	53.8/4.08	78.6/3.86	69.2/3.48	73.0/3.89	61.4/3.77-3.82
0	xDGro	65.3/4.04-4.08	78.1/3.79	62.1/3.75-3.75
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,3,3,2	Ac		2.10
0,2,3,3	bDGlcpN	4.68	3.73	3.76	3.97	3.56	3.77 3.92
0,2,3	bDGalf	5.07	4.04	4.21	4.18	3.91	3.65 3.69
0,2,2	Ac		2.09
0,2	aDGlcpN	5.05	4.08	3.86	3.48	3.89	3.77 3.82
0	xDGro	4.04 4.08	3.79	3.75 3.75
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,3,3,2	Ac	175.3	23.1
0,2,3,3	bDGlcpN	101.3	56.2	73.7	75.0	75.9	61.3
0,2,3	bDGalf	109.0	80.7	85.1	82.5	71.2	63.8
0,2,2	Ac	175.0	23.0
0,2	aDGlcpN	97.7	53.8	78.6	69.2	73.0	61.4
0	xDGro	65.3	78.1	62.1
	P

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize