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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: meningitis [ICD11: 1D01

]; neonatal necrotising enterocolitis [ICD11: KB88

, Life stage: neonatal]

The structure was elucidated in this paper
NCBI PubMed ID: 25723620
Publication DOI: 10.1016/j.carres.2015.01.020
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: zbigniew.kaczynski

ug.edu.pl (Z. Kaczyński)
Institutions: Faculty of Chemistry, University of Gdansk, Gdansk, Poland, School of Science and Technology, Nottingham Trent University, Clifton Lane, Nottingham NG11 8NS, United Kingdom, Department of Medical Microbiology, Medical University of Gdansk, Do Studzienki 38, 80-227 Gdansk, Poland

The O-polysaccharide (OPS) of Cronobacter sakazakii NTU 696 (Sequence Type 12) from a case of neonatal necrotizing enterocolitis was isolated from the polysaccharide fraction obtained after lipopolysaccharide (LPS) hydrolysis. Purified OPS was analyzed by NMR spectroscopy ((1)H, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC experiments) and chemical methods. Obtained monosaccharide derivatives analyzed by gas chromatography and gas chromatography-mass spectrometry allowed the identification of six sugar components. Performed experiments enabled to establish a structure of the OPS repeating unit of C. sakazakii NTU 696, as: [structure: see text].

NMR, structure, O-polysaccharide, Cronobacter sakazakii

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.57
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_885822,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GC-MS, acid hydrolysis, GLC, composition analysis, NMR-1D, GPC

Related record ID(s): 30812
NCBI Taxonomy refs (TaxIDs): 28141
Show glycosyltransferases

NMR conditions: in D2O at 308 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,2,2,3,2	Ac	175.67	23.42
6,2,2,3,6	aDGlcp	100.33	72.56	74.51	70.79	73.45	61.86
6,2,2,3	aDGalpN	98.08	50.99	68.25	77.69	71.20	66.91
6,2,2,2	Ac	175.11	23.90
6,2,2	bDGlcpN	102.59	55.78	79.47	72.13	76.99	62.06
6,2	bDGlcp	101.60	82.65	77.81	71.51	77.27	62.61
6,3	lR3HOBut	174.73	46.22	66.28	23.59
6	bDFucp3N	103.96	74.77	55.97	71.86	73.11	16.52
2	Ac	175.42	23.35
	aDGlcpN	99.58	55.38	71.74	70.43	72.42	69.34


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,2,2,3,2	Ac	-	2.058
6,2,2,3,6	aDGlcp	4.795	3.580	3.666	3.462	3.680	3.782-3.854
6,2,2,3	aDGalpN	5.541	4.272	3.905	4.117	4.033	3.599-3.854
6,2,2,2	Ac	-	2.061
6,2,2	bDGlcpN	4.817	3.750	3.734	3.695	3.405	3.754-3.908
6,2	bDGlcp	4.688	3.486	3.491	3.388	3.389	3.740-3.915
6,3	lR3HOBut	-	2.481	4.246	1.269
6	bDFucp3N	4.545	3.881	4.181	3.644	3.851	1.242
2	Ac	-	2.106
	aDGlcpN	4.946	3.957	3.872	3.883	4.238	3.915-4.026


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,2,2,3,2	Ac		23.42/2.058
6,2,2,3,6	aDGlcp	100.33/4.795	72.56/3.580	74.51/3.666	70.79/3.462	73.45/3.680	61.86/3.782-3.854
6,2,2,3	aDGalpN	98.08/5.541	50.99/4.272	68.25/3.905	77.69/4.117	71.20/4.033	66.91/3.599-3.854
6,2,2,2	Ac		23.90/2.061
6,2,2	bDGlcpN	102.59/4.817	55.78/3.750	79.47/3.734	72.13/3.695	76.99/3.405	62.06/3.754-3.908
6,2	bDGlcp	101.60/4.688	82.65/3.486	77.81/3.491	71.51/3.388	77.27/3.389	62.61/3.740-3.915
6,3	lR3HOBut		46.22/2.481	66.28/4.246	23.59/1.269
6	bDFucp3N	103.96/4.545	74.77/3.881	55.97/4.181	71.86/3.644	73.11/3.851	16.52/1.242
2	Ac		23.35/2.106
	aDGlcpN	99.58/4.946	55.38/3.957	71.74/3.872	70.43/3.883	72.42/4.238	69.34/3.915-4.026

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,2,2,3,2	Ac		2.058
6,2,2,3,6	aDGlcp	4.795	3.580	3.666	3.462	3.680	3.782 3.854
6,2,2,3	aDGalpN	5.541	4.272	3.905	4.117	4.033	3.599 3.854
6,2,2,2	Ac		2.061
6,2,2	bDGlcpN	4.817	3.750	3.734	3.695	3.405	3.754 3.908
6,2	bDGlcp	4.688	3.486	3.491	3.388	3.389	3.740 3.915
6,3	lR3HOBut		2.481	4.246	1.269
6	bDFucp3N	4.545	3.881	4.181	3.644	3.851	1.242
2	Ac		2.106
	aDGlcpN	4.946	3.957	3.872	3.883	4.238	3.915 4.026

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,2,2,3,2	Ac	175.67	23.42
6,2,2,3,6	aDGlcp	100.33	72.56	74.51	70.79	73.45	61.86
6,2,2,3	aDGalpN	98.08	50.99	68.25	77.69	71.20	66.91
6,2,2,2	Ac	175.11	23.90
6,2,2	bDGlcpN	102.59	55.78	79.47	72.13	76.99	62.06
6,2	bDGlcp	101.60	82.65	77.81	71.51	77.27	62.61
6,3	lR3HOBut	174.73	46.22	66.28	23.59
6	bDFucp3N	103.96	74.77	55.97	71.86	73.11	16.52
2	Ac	175.42	23.35
	aDGlcpN	99.58	55.38	71.74	70.43	72.42	69.34

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize