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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Brucella melitensis [ICD11: XN7ZW

]; infection due to Brucella abortus [ICD11: XN7A8

]; infection due to Brucella suis [ICD11: XN3UP

]

The structure was elucidated in this paper
NCBI PubMed ID: 23261780
Publication DOI: 10.1016/j.carres.2012.11.004
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: E. Vinogradov <evguenii.vinogradov

nrc.ca>
Institutions: Eunice Kennedy Shriver National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD, USA, National Research Council, Ottawa, ON, Canada K1A 0RA6

Brucella is an animal and human pathogen that expresses several virulence factors required for host cell invasion and intracellular survival. It produces LPS with unusually low toxicity, which hampers the detection of bacteria by the host immune system and thus provides resistance against intracellular antimicrobial mechanisms of the host. By chemical and spectroscopic methods we determined the structure of the LPS core and of a non-repetitive oligosaccharide fragment at the reducing end of the O-specific polysaccharide. These data should be useful for understanding the biological role of the Brucella LPS.

NMR, LPS, structure, Brucella, MS

Structure type: oligomer
Location inside paper: p.34, OS3
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_983930,SB_197,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GC-MS, NMR, sugar analysis, mild acid hydrolysis, CE-MS, reduction with NaBD4, MR-2D
Comments, role: Product of NaJO4 oxidation, NaBD4 reduction, AcOH hydrolysis of deformylated LPS.

Related record ID(s): 27226, 28439, 28440, 28441
NCBI Taxonomy refs (TaxIDs): 29459, 235, 29461
Show glycosyltransferases

NMR conditions: in D2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,3	aDManp	103.4	71.2	71.5	68.0	74.5	62.3
2,3	aDManp	102.1	71.1	79.2	66.7	74.6	61.8
2,2	Ac
2	bDQuipN	102.6	55.6	80.7	77.1	72.7	17.7
	x?1dEry-ol	62.0	82.9	71.5	63.5


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,3	aDManp	5.11	4.07	3.88	3.65	3.77	3.76-3.90
2,3	aDManp	5.25	4.17	3.88	3.81	3.60	3.83-3.83
2,2	Ac
2	bDQuipN	4.61	3.80	3.66	3.34	3.50	1.31
	x?1dEry-ol	3.72	3.70	3.78	3.52-3.71


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,3,3	aDManp	103.4/5.11	71.2/4.07	71.5/3.88	68.0/3.65	74.5/3.77	62.3/3.76-3.90
2,3	aDManp	102.1/5.25	71.1/4.17	79.2/3.88	66.7/3.81	74.6/3.60	61.8/3.83-3.83
2,2	Ac
2	bDQuipN	102.6/4.61	55.6/3.80	80.7/3.66	77.1/3.34	72.7/3.50	17.7/1.31
	x?1dEry-ol	62.0/3.72	82.9/3.70	71.5/3.78	63.5/3.52-3.71

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,3	aDManp	5.11	4.07	3.88	3.65	3.77	3.76 3.90
2,3	aDManp	5.25	4.17	3.88	3.81	3.60	3.83 3.83
2,2	Ac
2	bDQuipN	4.61	3.80	3.66	3.34	3.50	1.31
	x?1dEry-ol	3.72	3.70	3.78	3.52 3.71

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,3	aDManp	103.4	71.2	71.5	68.0	74.5	62.3
2,3	aDManp	102.1	71.1	79.2	66.7	74.6	61.8
2,2	Ac
2	bDQuipN	102.6	55.6	80.7	77.1	72.7	17.7
	x?1dEry-ol	62.0	82.9	71.5	63.5

There are 2 chemically distinct structures. Please, select:

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

SVG MW SMILES 3D mol Ionize