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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: 9163898
Publication DOI: 10.1016/S0008-6215(97)00002-5
Journal NLM ID: 0043535
Publisher: Elsevier
Institutions: School of Pharmaceutical Sciences, Rhodes University, Grahamstown 6140, South Africa

The primary structure of the acidic capsular antigen of Escherichia coli O8:K41 :HI 1 was shown by monosaccharide analysis, methylation analysis, and by 1D and 2D 1H and 13C NMR spectroscopy to be composed of branched pentasaccharide repeating units with the structure:[formula: see in the text].

antigen, structural, capsular, analysis, acidic, Escherichia, Escherichia coli, structural analysis

Structure type: polymer chemical repeating unit
Location inside paper: abstract
Compound class: K-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_140628,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_423153,IEDB_983931,SB_192,SB_25,SB_7

Methods: methylation, NMR-2D, NMR, sugar analysis
Comments, role: suspicious NMR chemical shift of bDGalpNAc C5: 72.07

NCBI Taxonomy refs (TaxIDs): 562
Reference(s) to other database(s): GTC:G25814JB, GlycomeDB:25903
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,6,3	bDGlcpA	104.98	74.10	76.09	72.07	75.38	173.23
3,6	aDGalp	98.79	68.42	81.13	77.35	71.02	61.38
3,2	bDGlcp	102.88	74.69	76.80	70.64	76.93	61.86
3	bDGlcp	103.24	79.59	77.48	70.08	74.86	66.66
2	Ac
	bDGalpN	102.88	52.14	80.59	68.62	72.07	61.76


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,6,3	bDGlcpA	4.699	3.515	3.597	3.666	4.051	-
3,6	aDGalp	5.013	3.902	3.951	4.359	3.909	3.720-3.830
3,2	bDGlcp	4.849	3.276	3.511	3.400	3.391	3.731-3.912
3	bDGlcp	4.710	3.659	3.709	3.552	3.622	3.798-3.962
2	Ac
	bDGalpN	4.818	3.945	3.945	4.145	3.593	3.763-3.763


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,6,3	bDGlcpA	104.98/4.699	74.10/3.515	76.09/3.597	72.07/3.666	75.38/4.051	
3,6	aDGalp	98.79/5.013	68.42/3.902	81.13/3.951	77.35/4.359	71.02/3.909	61.38/3.720-3.830
3,2	bDGlcp	102.88/4.849	74.69/3.276	76.80/3.511	70.64/3.400	76.93/3.391	61.86/3.731-3.912
3	bDGlcp	103.24/4.710	79.59/3.659	77.48/3.709	70.08/3.552	74.86/3.622	66.66/3.798-3.962
2	Ac
	bDGalpN	102.88/4.818	52.14/3.945	80.59/3.945	68.62/4.145	72.07/3.593	61.76/3.763-3.763

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,6,3	bDGlcpA	4.699	3.515	3.597	3.666	4.051
3,6	aDGalp	5.013	3.902	3.951	4.359	3.909	3.720 3.830
3,2	bDGlcp	4.849	3.276	3.511	3.400	3.391	3.731 3.912
3	bDGlcp	4.710	3.659	3.709	3.552	3.622	3.798 3.962
2	Ac
	bDGalpN	4.818	3.945	3.945	4.145	3.593	3.763 3.763

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,6,3	bDGlcpA	104.98	74.10	76.09	72.07	75.38	173.23
3,6	aDGalp	98.79	68.42	81.13	77.35	71.02	61.38
3,2	bDGlcp	102.88	74.69	76.80	70.64	76.93	61.86
3	bDGlcp	103.24	79.59	77.48	70.08	74.86	66.66
2	Ac
	bDGalpN	102.88	52.14	80.59	68.62	72.07	61.76

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize