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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: 9774431
Publication DOI: 10.1074/jbc.273.43.28122
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: oholst

fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, D-23845 Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, DK-2500 Valby, Denmark, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Utrecht University,NL-3584 CA Utrecht, The Netherlands

For the first time, the tetrasaccharide Kdo a2→5 Kdo a2→5 (Kdo a2→4)Kdo (Kdo is 3-deoxy-Dmanno-oct-2-ulopyranosonic acid) has been identified in a bacterial lipopolysaccharide (LPS), i.e. in the core region of LPS from Acinetobacter baumannii NCTC 10303. The LPS was analyzed using compositional analysis, mass spectrometry, and NMR spectroscopy. The disaccharide DGlcpN b1→6 DGlcpN, phosphorylated at O-1 and O-4', was identified as the carbohydrate backbone of the lipid A. The Kdo tetrasaccharide is attached to O-6' of this disaccharide and is further substituted by short L-rhamnoglycans of varying length and by the disaccharide DGlcpNAc a1→4 DGlcpNA (GlcpNA, 2-amino-2-deoxy-glucopyranosuronic acid). The core region is not substituted by phosphate residues and represents a novel core type of bacterial LPS. The complete carbohydrate backbone of the LPS is shown in Structure I as follows: [see formula in text] where Rha is rhamnose. Except were indicated, monosaccharides possess the D-configuration. Sugars marked with an asterisk are present in non-stoichiometric amounts.

LPS, structure, core, acid, Acinetobacter, Acinetobacter baumannii, 3-deoxy-D-manno-oct-2-ulopyranosonic

Structure type: oligomer
Location inside paper: fig.1, oligosaccharide 1
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531

Methods: NMR-2D, NMR, MS, composition analysis
3D data: 3D data

Related record ID(s): 343, 5528, 5689, 5690, 5691, 5692, 5693, 5694
NCBI Taxonomy refs (TaxIDs): 470
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
4,4,2	Ac	175.3	22.8
4,4	aDGlcpN	97.8	54.5	71.6	70.5	72.5	60.9
4	aDGlcpNA	99.8	55.9	75.8	76.7	74.3	174.1
	aX2,7anhKdof	176.8	105.7	41.9	74.6	83.5	62.7	76.0	61.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
4,4,2	Ac	-	1.981
4,4	aDGlcpN	5.361	3.814	3.651	3.402	3.663	3.731
4	aDGlcpNA	4.873	2.712	3.681	3.681	3.972	-
	aX2,7anhKdof	-	-	2.222-2.671	4.512	4.421	3.675	3.475	3.611-3.792


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
4,4,2	Ac		22.8/1.981
4,4	aDGlcpN	97.8/5.361	54.5/3.814	71.6/3.651	70.5/3.402	72.5/3.663	60.9/3.731
4	aDGlcpNA	99.8/4.873	55.9/2.712	75.8/3.681	76.7/3.681	74.3/3.972	
	aX2,7anhKdof			41.9/2.222-2.671	74.6/4.512	83.5/4.421	62.7/3.675	76.0/3.475	61.7/3.611-3.792

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
4,4,2	Ac		1.981
4,4	aDGlcpN	5.361	3.814	3.651	3.402	3.663	3.731
4	aDGlcpNA	4.873	2.712	3.681	3.681	3.972
	aX2,7anhKdof			2.222 2.671	4.512	4.421	3.675	3.475	3.611 3.792

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
4,4,2	Ac	175.3	22.8
4,4	aDGlcpN	97.8	54.5	71.6	70.5	72.5	60.9
4	aDGlcpNA	99.8	55.9	75.8	76.7	74.3	174.1
	aX2,7anhKdof	176.8	105.7	41.9	74.6	83.5	62.7	76.0	61.7

There is only one chemically distinct structure:

CC(=O)N[C@H]1[C@@H](O[C@@H]2[C@@H](C(=O)O)O[C@H](O[C@@H]3C[C@]4(C(=O)O)O[C@H]3[C@H](O)[C@@H](CO)O4)[C@H](N)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize