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A Strategy for Multivalent Presentation of Carba Analogues from N. meningitidis A Capsular Polysaccharide
Author(s) -
Ramella Daniela,
Polito Laura,
Mazzini Stefania,
Ronchi Silvia,
Scaglioni Leonardo,
Marelli Marcello,
Lay Luigi
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402701
Subject(s) - neisseria meningitidis , immunogenicity , chemistry , polyclonal antibodies , microbiology and biotechnology , polysaccharide , linker , conjugated system , bacteria , antigen , combinatorial chemistry , biochemistry , biology , polymer , immunology , organic chemistry , genetics , computer science , operating system
Neisseria meningitidis is a Gram‐negative encapsulated bacterium that is a major cause of meningitis and meningococcal septicemia. Serogroup A (MenA) is most often implicated in epidemic disease in the sub‐Saharan region of Africa. However, the development and manufacture of an efficient polysaccharide‐based vaccine against MenA is greatly hampered by the poor immunogenicity and instability of its capsular polisaccharide (CPS). We report the synthesis of stable MenA CPS carba analogues, and an easy strategy to access multivalent carbohydrate structures based on iron oxide nanoparticles (SPIONs). A 1‐ O ‐tetraethyleneglycol‐phosphate linker attached to the carba analogues was used to attach them to the metal surface. We evaluated the positive multivalent effect of the antigen presentation by MRI analysis, which showed that the conjugated monomer and dimer analogues could be recognised by the polyclonal anti‐MenA antibody.