Conjugation reactions involving maleimides and phosphorothioate oligonucleotides
Contribuinte(s) |
Universitat de Barcelona |
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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 | |
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 |