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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: 27293097
Publication DOI: 10.1134/S0006297916040106
Journal NLM ID: 0376536
Publisher: Nauka/Interperiodica
Correspondence: yknirel

gmail.com
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Nankai University, TEDA Institute of Biological Sciences and Biotechnology,300457 Tianjin, P. R. China

Two polysaccharides were isolated from Escherichia coli O12, the major being identified as the O12-antigen and the minor as the K5-antigen. The polysaccharides were studied by sugar analysis, Smith degradation, and one- and two-dimensional (1)H and (13)C NMR spectroscopy. As a result, the following structure of the O12-polysaccharide was elucidated, which, to our knowledge, has not been hitherto found in bacterial carbohydrates: →2)-β-d-Glcp-(1→6)-α-d-GlcpNAc-(1→3)-α-l-FucpNAc-(1→3)-β-d-GlcpNAc-(1→. The →4)-β-d-GlcpA-(1→4)-α-d-GlcpNAc-(1→ structure established for the K5-polysaccharide (heparosan) is previously known. Functions of genes in the O-antigen biosynthesis gene cluster of E. coli O12 were assigned by comparison with sequences in the available databases and found to be consistent with the O12-polysaccharide structure.

Escherichia coli, glycosyltransferase, O-antigen gene cluster, O-Polysaccharide structure

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.403, table 1, p.404, fig.2
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, Smith degradation, NMR-1D, GPC, mild acid degradation, function analysis of gene clusters
Comments, role: The major polysaccharide from E. coli O12.

Related record ID(s): 11247, 11553, 11554
NCBI Taxonomy refs (TaxIDs): 562
Reference(s) to other database(s): GTC:G38226FL
Show glycosyltransferases

NMR conditions: in D2O at 313 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,6	bDGlcp	103.0	80.8	77.9	71.0	76.9	61.9
3,3,2	Ac	174.9-175.2	23.2-23.6
3,3	aDGlcpN	99.9	54.7	72.1	72.0	72.8	70.0
3,2	Ac	174.9-175.2	23.2-23.6
3	aLFucpN	98.7	49.7	75.0	72.1	67.8	16.5
2	Ac	174.9-175.2	23.2-23.6
	bDGlcpN	102.6	57.1	79.3	69.9	77.1	62.3


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,6	bDGlcp	4.51	3.49	3.49	3.38	3.40	3.71-3.89
3,3,2	Ac	-	1.97-2.04
3,3	aDGlcpN	5.01	3.96	3.76	3.77	3.84	3.97-4.08
3,2	Ac	-	1.97-2.04
3	aLFucpN	4.99	4.28	3.97	3.88	4.41	1.16
2	Ac	-	1.97-2.04
	bDGlcpN	4.79	3.88	3.69	3.50	3.44	3.80-3.94


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,6	bDGlcp	103.0/4.51	80.8/3.49	77.9/3.49	71.0/3.38	76.9/3.40	61.9/3.71-3.89
3,3,2	Ac		23.2-23.6/1.97-2.04
3,3	aDGlcpN	99.9/5.01	54.7/3.96	72.1/3.76	72.0/3.77	72.8/3.84	70.0/3.97-4.08
3,2	Ac		23.2-23.6/1.97-2.04
3	aLFucpN	98.7/4.99	49.7/4.28	75.0/3.97	72.1/3.88	67.8/4.41	16.5/1.16
2	Ac		23.2-23.6/1.97-2.04
	bDGlcpN	102.6/4.79	57.1/3.88	79.3/3.69	69.9/3.50	77.1/3.44	62.3/3.80-3.94

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,6	bDGlcp	4.51	3.49	3.49	3.38	3.40	3.71 3.89
3,3,2	Ac		1.97 2.04
3,3	aDGlcpN	5.01	3.96	3.76	3.77	3.84	3.97 4.08
3,2	Ac		1.97 2.04
3	aLFucpN	4.99	4.28	3.97	3.88	4.41	1.16
2	Ac		1.97 2.04
	bDGlcpN	4.79	3.88	3.69	3.50	3.44	3.80 3.94

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,6	bDGlcp	103.0	80.8	77.9	71.0	76.9	61.9
3,3,2	Ac	174.9 175.2	23.2 23.6
3,3	aDGlcpN	99.9	54.7	72.1	72.0	72.8	70.0
3,2	Ac	174.9 175.2	23.2 23.6
3	aLFucpN	98.7	49.7	75.0	72.1	67.8	16.5
2	Ac	174.9 175.2	23.2 23.6
	bDGlcpN	102.6	57.1	79.3	69.9	77.1	62.3

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize