Oligonucleotide cyclization: The thiol-maleimide reaction revisited

A novel method to synthesize cyclic oligonucleotides (5- to 26-mer) using the thiol-maleimide reaction is described. The target molecules were obtained after subsequent removal of thiol and maleimide protecting groups from 5′-maleimido-3′-thiol-derivatized linear precursors. Retro-Diels-Alder condit...

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Detalhes bibliográficos
Autores: Sánchez-Moya, Albert, Pedroso Muller, Enrique, Grandas Sagarra, Anna
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2013
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/50383
Acesso em linha:https://hdl.handle.net/2445/50383
Access Level:Acceso aberto
Palavra-chave:Bioquímica
Àcids nucleics
Bacteris
Microbiologia
Ciclització (Química)
Biochemistry
Nucleic acids
Bacteria
Microbiology
Ring formation (Chemistry)
Descrição
Resumo:A novel method to synthesize cyclic oligonucleotides (5- to 26-mer) using the thiol-maleimide reaction is described. The target molecules were obtained after subsequent removal of thiol and maleimide protecting groups from 5′-maleimido-3′-thiol-derivatized linear precursors. Retro-Diels-Alder conditions deprotecting the maleimide simultaneously promoted cyclization cleanly and in high yield.