CSDB: Search results

Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11: XN8LS

]

The structure was elucidated in this paper
NCBI PubMed ID: 11856300
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: oholst

fz-borstel.de
Institutions: Department of Chemistry, Carlsberg Laboratory, Valby, Copenhagen, Denmark

The chemical structure of the phosphorylated carbohydrate backbone of the lipopolysaccharide (LPS) from Acinetobacter baumannii strain ATCC 19606 was investigated by chemical analysis and NMR spectroscopy of oligosaccharides obtained after deacylation or mild acid hydrolysis. From the combined information the following carbohydrate backbones can be deduced: where R1 = H and R2 = α-Glcp-(1→2)-β-Glcp-(1→4)-β-Glcp-(1→4)-β-Glcp-(1 as major and R1 = Ac and R2 = H as minor products. All monosaccharides are d-configured. Also, smaller oligosaccharide phosphates were identified that are thought to represent degradation products of the above structures

Lipopolysaccharide, Acinetobacter baumannii, NMR spectroscopy, structural analysis, core region

Structure type: oligomer
Location inside paper: fig.1, oligosaccharide 2
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_137473,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_983931,SB_192

Methods: NMR-2D, NMR, chemical methods
Comments, role: Oligosaccharide was obtained from acetic acid degradation of the LPS and reduction.
3D data: 3D data

Related record ID(s): 5533, 5715, 5716, 5718, 5719, 5720
NCBI Taxonomy refs (TaxIDs): 575584
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
4,3,4,4,2	aDGlcp	98.2	72.1	73.5	70.1	72.4	61.1
4,3,4,4	bDGlcp	102.2	77.1	75.3	70.7	76.7	61.8
4,3,4	bDGlcp	103.2	73.5	74.5	76.6	75.7	60.8
4,3	bDGlcp	103.5	73.5	74.7	79.1	75.4	59.7
4,2	Ac
4,4	aDGalpN	96.7	51.5	68.5	68.7	71.7	61.3
4	aDGlcpNA	97.6	54.0	77.7	74.0	74.2	175.0
7	bDGlcpN	103.3	57.4	76.4	70.7	76.7	61.4
	xXKdo-ol	182.0	70.7	37.0	76.5	70.4	69.2	80.1	61.2


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
4,3,4,4,2	aDGlcp	5.34	3.51	3.73	3.43	4.04	3.75-3.78
4,3,4,4	bDGlcp	4.63	3.49	3.57	3.41	3.43	3.69-3.90
4,3,4	bDGlcp	4.50	3.34	3.64	3.75	3.63	3.85-3.96
4,3	bDGlcp	4.61	3.32	3.60	3.68	3.52	3.85-3.96
4,2	Ac
4,4	aDGalpN	5.74	3.26	3.87	3.96	3.92	3.68-3.68
4	aDGlcpNA	4.97	4.20	4.29	3.94	4.25	-
7	bDGlcpN	4.54	2.68	3.37	3.36	3.43	3.69-3.90
	xXKdo-ol	-	4.16	2.00-2.17	4.02	4.17	3.78	3.89	3.76-3.88


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
4,3,4,4,2	aDGlcp	98.2/5.34	72.1/3.51	73.5/3.73	70.1/3.43	72.4/4.04	61.1/3.75-3.78
4,3,4,4	bDGlcp	102.2/4.63	77.1/3.49	75.3/3.57	70.7/3.41	76.7/3.43	61.8/3.69-3.90
4,3,4	bDGlcp	103.2/4.50	73.5/3.34	74.5/3.64	76.6/3.75	75.7/3.63	60.8/3.85-3.96
4,3	bDGlcp	103.5/4.61	73.5/3.32	74.7/3.60	79.1/3.68	75.4/3.52	59.7/3.85-3.96
4,2	Ac
4,4	aDGalpN	96.7/5.74	51.5/3.26	68.5/3.87	68.7/3.96	71.7/3.92	61.3/3.68-3.68
4	aDGlcpNA	97.6/4.97	54.0/4.20	77.7/4.29	74.0/3.94	74.2/4.25	
7	bDGlcpN	103.3/4.54	57.4/2.68	76.4/3.37	70.7/3.36	76.7/3.43	61.4/3.69-3.90
	xXKdo-ol		70.7/4.16	37.0/2.00-2.17	76.5/4.02	70.4/4.17	69.2/3.78	80.1/3.89	61.2/3.76-3.88

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
4,3,4,4,2	aDGlcp	5.34	3.51	3.73	3.43	4.04	3.75 3.78
4,3,4,4	bDGlcp	4.63	3.49	3.57	3.41	3.43	3.69 3.90
4,3,4	bDGlcp	4.50	3.34	3.64	3.75	3.63	3.85 3.96
4,3	bDGlcp	4.61	3.32	3.60	3.68	3.52	3.85 3.96
4,2	Ac
4,4	aDGalpN	5.74	3.26	3.87	3.96	3.92	3.68 3.68
4	aDGlcpNA	4.97	4.20	4.29	3.94	4.25
7	bDGlcpN	4.54	2.68	3.37	3.36	3.43	3.69 3.90
	xXKdo-ol		4.16	2.00 2.17	4.02	4.17	3.78	3.89	3.76 3.88

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
4,3,4,4,2	aDGlcp	98.2	72.1	73.5	70.1	72.4	61.1
4,3,4,4	bDGlcp	102.2	77.1	75.3	70.7	76.7	61.8
4,3,4	bDGlcp	103.2	73.5	74.5	76.6	75.7	60.8
4,3	bDGlcp	103.5	73.5	74.7	79.1	75.4	59.7
4,2	Ac
4,4	aDGalpN	96.7	51.5	68.5	68.7	71.7	61.3
4	aDGlcpNA	97.6	54.0	77.7	74.0	74.2	175.0
7	bDGlcpN	103.3	57.4	76.4	70.7	76.7	61.4
	xXKdo-ol	182.0	70.7	37.0	76.5	70.4	69.2	80.1	61.2

There is only one chemically distinct structure:

CC(=O)N[C@H]1[C@@H](O[C@H](CC(O)C(=O)O)[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2N)O[C@H](C(=O)O)[C@@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2N)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize