Conjugation reactions involving maleimides and phosphorothioate oligonucleotides


Autoria(s): Sánchez, Albert; Pedroso Muller, Enrique; Grandas Sagarra, Anna
Contribuinte(s)

Universitat de Barcelona

Resumo

Phosphorothioate diester oligonucleotides proved to be fully compatible with maleimides in the context of two different conjugation reactions: (a) reaction of 5′diene-[phosphorothioate oligonucleotides] with maleimido-containing compounds to afford the Diels-Alder cycloadduct; (b) conjugation of 5′maleimido-[phosphorothioate oligonucleotides] with thiol-containing compounds. No evidence of reaction between phosphorothioate diesters and maleimides was found in any of these processes. Importantly, in the preparation of 5′maleimido-[phosphorothioate oligonucleotides] from [protected maleimido]-[phosphorothioate oligonucleotides], which requires the maleimide to be deprotected by retro-Diels-Alder reaction (heating for 3-4 h in toluene at 90 °C), no addition of phosphorothioate diester to the maleimide was found either. Finally, maleimide-[phosphorothioate monoester] conjugation was also explored for comparison purposes.

Identificador

http://hdl.handle.net/2445/49465

Idioma(s)

eng

Publicador

American Chemical Society

Direitos

(c) American Chemical Society , 2012

info:eu-repo/semantics/openAccess

Palavras-Chave #Oligonucleòtids #Immunologia #Àcids nucleics #Bioquímica #Proteïnes #Oligonucleotides #Immunology #Nucleic acids #Biochemistry #Proteins
Tipo

info:eu-repo/semantics/article

info:eu-repo/semantics/acceptedVersion