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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

NCBI PubMed ID: 1284111
Publication DOI: 10.1016/S0008-6215(92)84229-L
Journal NLM ID: 0043535
Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow

A computer-assisted approach to the analysis of the structure of branched polysaccharides that contain 2,3-di-O-glycosylated α-rhamnopyranose and α-mannopyranose residues is based on evaluation of the 13C NMR spectra, using glycosylation effects and their deviations from additivity (delta delta values) at the branch points. This approach, in combination with monosaccharide and methylation analysis data, has been verified on a series of bacterial polysaccharides of known structure

Structure type: suggested polymer biological repeating unit
Location inside paper: p.13, table II, structure 5
Compound class: O-polysaccharide, core oligosaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144983,IEDB_150899,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_44,SB_67,SB_7,SB_72,SB_88

Methods: 13C NMR
Comments, role: polymerization frame corrected

Related record ID(s): 2162, 10463, 11786, 20641, 23054, 23640, 29648, 30268, 108701, 114155, 116990, 116991, 116992, 116993, 116994, 116995, 116996
NCBI Taxonomy refs (TaxIDs): 2162916
Reference(s) to other database(s): GTC:G47971KQ, GlycomeDB:27141
Show glycosyltransferases

[as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,2,4	Ac
3,4,2	bDQuip4N	103.9	74.3	79.4	57.3	72.2	17.8
3,4,3	aLRhap	97.3	71.2	71.7	73.3	69.9	17.8
3,4	aDManp	100.6	74.3	75.2	65.9	73.3	61.5
3	bDGalp	104.7	72.0	73.3	78.0	76.2	61.4
2	Ac
	aDGlcpN	98.9	53.5	81.9	69.4	72.5	61.7


1H NMR data:
missing...

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,2,4	Ac
3,4,2	bDQuip4N	103.9	74.3	79.4	57.3	72.2	17.8
3,4,3	aLRhap	97.3	71.2	71.7	73.3	69.9	17.8
3,4	aDManp	100.6	74.3	75.2	65.9	73.3	61.5
3	bDGalp	104.7	72.0	73.3	78.0	76.2	61.4
2	Ac
	aDGlcpN	98.9	53.5	81.9	69.4	72.5	61.7

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize