Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: epidemic meningitis disease [ICD11:
1D01 
];
infection due to Neisseria meningitidis [ICD11:
XN1DV ]
NCBI PubMed ID: 30443159Publication DOI: 10.1002/ejoc.201801003Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: jjbarbero
cicbiogune.es
Institutions: Chemical Glycobiology Lab CIC bioGUNE Bizkaia Technology Park, Derio, Spain, Department of Organic Chemistry II Faculty of Science and Technology University of the Basque Country, EHU-UPV Leioa Spain, Atlas Molecular Pharma Bizkaia Technology Park, Derio, Spain, Departamento de Quimica Universidad de la Rioja Centro Cientifico Tecnologico Spain, Glycobiology Lab GSK Via Fiorentina 10 Siena Italy, Department of Chemistry and ISTM_CNR University of Milan Via Golgi 19 20133 Milan Italy, Basque Foundation for Science (IKERBASQUE), Bilbao, Spain
Neisseria meningitidis serogroup A (MenA) is an aerobic diplococcal Gram-negative bacterium responsible for epidemic meningitis disease. Its capsular polysaccharide (CPS) has been identified as the primary virulence factor of MenA. This polysaccharide suffers from chemical lability in water. Thus, the design and synthesis of novel and hydrolytically stable structural analogues of MenA CPS may provide additional tools for the development of therapies against this disease. In this context, the structural features of the natural phosphorylated monomer have been analyzed and compared to those of its carba-analogue, where the endocyclic oxygen has been replaced by a methylene moiety. The lowest energy geometries of the different molecules have been calculated using a combination of quantum mechanical techniques and molecular dynamics simulations. The predicted results have been compared and validated using NMR experiments. The results indicate that the more stable designed glycomimetics may adopt the conformation adopted by the natural monomer, although they display a wider flexibility around the torsional degrees of freedom.
structure elucidation, conformation analysis, chemical, natural products, synthesis design, Glycomimetics, LAB
Structure type: homopolymer
Location inside paper: p.4549, fig.1, N. meningitidis serogroup A
Compound class: CPS
Contained glycoepitopes: IEDB_1330666,IEDB_1330667,IEDB_1330668,IEDB_1330669,IEDB_1330670,IEDB_1330671,IEDB_149549,IEDB_149550,IEDB_149551,IEDB_149552
Methods: NMR, conformation analysis, chemical synthesis, MD simulations, computational methods
3D data: 3D data, molecular modeling
NCBI Taxonomy refs (TaxIDs): 65699
Show glycosyltransferases
There is only one chemically distinct structure:
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