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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: neonatal necrotising enterocolitis [ICD11: KB88

, Life stage: neonatal]; meningitis [ICD11: 1D01

]; septicemia [ICD11: MA15.Y

]

The structure was elucidated in this paper
NCBI PubMed ID: 20206918
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: Z. Kaczynski <zbyszek

chem.univ.gda.pl>
Institutions: Faculty of Chemistry, University of Gdansk, Gdansk, Poland

The Cronobacter spp., previously known as Enterobacter sakazakii, are Gram-negative enterobacterial pathogens that can cause necrotizing enterocolitis, meningitis, and septicemia with a high mortality rate in neonates. The O-specific polysaccharide (O-PS) was isolated from Cronobacter sakazakii strain 767 and structurally characterized using 1H and 13C NMR spectroscopy, including two-dimensional DQF-COSY, TOCSY, ROESY, HSQC, andHMBC experiments. Further compositional determination was undertaken using classical chemical methods followed by GLC, and GLC-MS analysis. The repeating unit of O-PS isolated from C. sakazakii 767 was a branched heptasaccharide composed of L-Rha, D-Glc, D-GlcNAc, and D-GalA, and had the structure shown below. One of the Rha residues was partially O-acetylated at C-4. C. sakazakii 767 was originally isolated from a fatal neonatal meningitic case, and the structure of its O-PS significantly differs from the O-PS structures previously described for Cronobacter spp.

Lipopolysaccharide, O-antigen, NMR spectroscopy, bacterial polysaccharide structure, Cronobacter sakazakii, Enterobacter sakazakii

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.911
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, GLC, NMR-1D

Related record ID(s): 25337
NCBI Taxonomy refs (TaxIDs): 28141
Reference(s) to other database(s): GTC:G20299ZC
Show glycosyltransferases

NMR conditions: in D2O at 327 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,4,3,2	Ac	174.53	23.93
2,4,3,4	aDGlcp	98.97	72.63	74.14	70.65	74.05	61.83
2,4,3	bDGlcpN	102.82	56.66	81.59	75.76	76.36	62.73
2,4,2,4	aLRhap	101.66	71.77	71.45	73.61	69.99	17.87
2,4,2	aDGalpA	97.50	69.30	71.75	77.52	72.88	175.01
2,4,4	50%Ac	174.21	21.90
2,4	aLRhap	98.56	75.30	76.75	74.18	68.61	17.56
2	aDGlcp	98.89	72.63	72.75	78.76	71.94	61.52
	aLRhap	99.25	78.07	70.78	73.33	71.64	17.97


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,4,3,2	Ac	-	2.046
2,4,3,4	aDGlcp	5.427	3.576	3.670	3.456	3.693	3.790-3.880
2,4,3	bDGlcpN	4.736	3.689	4.126	3.850	3.577	3.833-3.881
2,4,2,4	aLRhap	5.288	4.076	3.822	3.383	3.806	1.266
2,4,2	aDGalpA	5.076	3.943	4.179	4.545	4.699	-
2,4,4	50%Ac	-	2.211
2,4	aLRhap	5.071	4.309	4.148	4.966	4.212	1.174
2	aDGlcp	5.026	3.591	3.842	3.655	4.129	3.787-3.837
	aLRhap	5.142	3.927	3.896	3.511	3.906	1.315


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,4,3,2	Ac		23.93/2.046
2,4,3,4	aDGlcp	98.97/5.427	72.63/3.576	74.14/3.670	70.65/3.456	74.05/3.693	61.83/3.790-3.880
2,4,3	bDGlcpN	102.82/4.736	56.66/3.689	81.59/4.126	75.76/3.850	76.36/3.577	62.73/3.833-3.881
2,4,2,4	aLRhap	101.66/5.288	71.77/4.076	71.45/3.822	73.61/3.383	69.99/3.806	17.87/1.266
2,4,2	aDGalpA	97.50/5.076	69.30/3.943	71.75/4.179	77.52/4.545	72.88/4.699	
2,4,4	50%Ac		21.90/2.211
2,4	aLRhap	98.56/5.071	75.30/4.309	76.75/4.148	74.18/4.966	68.61/4.212	17.56/1.174
2	aDGlcp	98.89/5.026	72.63/3.591	72.75/3.842	78.76/3.655	71.94/4.129	61.52/3.787-3.837
	aLRhap	99.25/5.142	78.07/3.927	70.78/3.896	73.33/3.511	71.64/3.906	17.97/1.315

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,4,3,2	Ac		2.046
2,4,3,4	aDGlcp	5.427	3.576	3.670	3.456	3.693	3.790 3.880
2,4,3	bDGlcpN	4.736	3.689	4.126	3.850	3.577	3.833 3.881
2,4,2,4	aLRhap	5.288	4.076	3.822	3.383	3.806	1.266
2,4,2	aDGalpA	5.076	3.943	4.179	4.545	4.699
2,4,4	50%Ac		2.211
2,4	aLRhap	5.071	4.309	4.148	4.966	4.212	1.174
2	aDGlcp	5.026	3.591	3.842	3.655	4.129	3.787 3.837
	aLRhap	5.142	3.927	3.896	3.511	3.906	1.315

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,4,3,2	Ac	174.53	23.93
2,4,3,4	aDGlcp	98.97	72.63	74.14	70.65	74.05	61.83
2,4,3	bDGlcpN	102.82	56.66	81.59	75.76	76.36	62.73
2,4,2,4	aLRhap	101.66	71.77	71.45	73.61	69.99	17.87
2,4,2	aDGalpA	97.50	69.30	71.75	77.52	72.88	175.01
2,4,4	50%Ac	174.21	21.90
2,4	aLRhap	98.56	75.30	76.75	74.18	68.61	17.56
2	aDGlcp	98.89	72.63	72.75	78.76	71.94	61.52
	aLRhap	99.25	78.07	70.78	73.33	71.64	17.97

There is only one chemically distinct structure:

*O[C@H]1[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](CO)O[C@@H](O[C@@H]2[C@@H](OC(C)=O)[C@H](C)O[C@@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@H]4[C@H](*)O[C@@H](C)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@@H]2O[C@H]2O[C@H](C(=O)O)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize