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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: 1284112
Publication DOI: 10.1016/S0008-6215(92)84247-P
Journal NLM ID: 0043535
Publisher: Elsevier
Institutions: Institute of Biological Sciences, National Research Council of Canada, Ottawa, Ontario

The structure of the O-polysaccharide component of the lipopolysaccharide produced by Escherichia coli 0119 was determined by the use of methylation analysis, periodate oxidation, 1D and 2D nuclear magnetic resonance spectroscopy, and mass spectrometric methods. The O-polysaccharide was found to be a high molecular weight polymer of a repeating pentasaccharide unit composed of D-mannose, D-galactose, L-rhamnose, 2-acetamido-2-deoxy-D-glucose, and 2-acetamido-2,3-dideoxy-3-formamido-D-rhamnose residues (1:1:1:1:1) and had the structure: [formula: see text].

NMR, Escherichia coli, O-polysaccharide

Structure type: oligomer
Location inside paper: table IV, p.255, pentasaccharide O1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_141807,IEDB_144983,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_983930,SB_44,SB_7,SB_72

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, FAB-MS, Smith degradation
Comments, role: Smith degraded OPS; adhesive strain JCP88, NRCC 4326; nonadhesive strain 19392, NRCC 4325. Absolute configuration of RhapN3N was revised in [doi:10.1111/j.1574-695X.2010.00745.x].

Related record ID(s): 2729, 117023
NCBI Taxonomy refs (TaxIDs): 1450174, 562
Reference(s) to other database(s): GTC:G33620AI, GlycomeDB:3547
Show glycosyltransferases

NMR conditions: in D2O at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,2,2	Ac	174.25	22.72
2,3,2	aDGlcpN	97.29	54.30	72.01	70.46	71.74	61.22
2,3,3,2	Ac	175.70	22.72
2,3,3,3	Fo	165.14-168.20
2,3,3	bLRhapN3N	101.78	52.11	53.03	70.59	74.67	17.79
2,3	bDManp	102.44	74.29	83.34	66.98	77.33	61.38
2	aDGalp	99.29	68.80	79.84	69.74	72.01	61.75
	xL4dEry-ol	61.58	83.11	67.44	18.32


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,2,2	Ac	-	1.99
2,3,2	aDGlcpN	5.31	3.91	3.82	3.48	4.28	3.79-3.79
2,3,3,2	Ac	-	2.04
2,3,3,3	Fo	8.03
2,3,3	bLRhapN3N
2,3	bDManp	4.92	4.44	3.83	3.76	3.41	3.78-3.92
2	aDGalp	5.12	3.90	4.02	4.17	4.12	3.69-3.71
	xL4dEry-ol	3.76-3.76	3.64	4.04	1.23


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,3,2,2	Ac		22.72/1.99
2,3,2	aDGlcpN	97.29/5.31	54.30/3.91	72.01/3.82	70.46/3.48	71.74/4.28	61.22/3.79-3.79
2,3,3,2	Ac		22.72/2.04
2,3,3,3	Fo	165.14-168.20/8.03
2,3,3	bLRhapN3N	NMR TSV error 2: unequal length of 13C and 1H datasets
2,3	bDManp	102.44/4.92	74.29/4.44	83.34/3.83	66.98/3.76	77.33/3.41	61.38/3.78-3.92
2	aDGalp	99.29/5.12	68.80/3.90	79.84/4.02	69.74/4.17	72.01/4.12	61.75/3.69-3.71
	xL4dEry-ol	61.58/3.76-3.76	83.11/3.64	67.44/4.04	18.32/1.23

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,2,2	Ac		1.99
2,3,2	aDGlcpN	5.31	3.91	3.82	3.48	4.28	3.79 3.79
2,3,3,2	Ac		2.04
2,3,3,3	Fo	8.03
2,3,3	bLRhapN3N
2,3	bDManp	4.92	4.44	3.83	3.76	3.41	3.78 3.92
2	aDGalp	5.12	3.90	4.02	4.17	4.12	3.69 3.71
	xL4dEry-ol	3.76 3.76	3.64	4.04	1.23

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,2,2	Ac	174.25	22.72
2,3,2	aDGlcpN	97.29	54.30	72.01	70.46	71.74	61.22
2,3,3,2	Ac	175.70	22.72
2,3,3,3	Fo	165.14 168.20
2,3,3	bLRhapN3N	101.78	52.11	53.03	70.59	74.67	17.79
2,3	bDManp	102.44	74.29	83.34	66.98	77.33	61.38
2	aDGalp	99.29	68.80	79.84	69.74	72.01	61.75
	xL4dEry-ol	61.58	83.11	67.44	18.32

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize