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Conjugation reactions involving maleimides and phosphorothioate oligonucleotides
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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.
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SÁNCHEZ-MOYA, Albert, PEDROSO MULLER, Enrique, GRANDAS SAGARRA, Anna. Conjugation reactions involving maleimides and phosphorothioate oligonucleotides. _Bioconjugate Chemistry_. 2012. Vol. 23, núm. 2, pàgs. 300-307. [consulta: 23 de gener de 2026]. ISSN: 1043-1802. [Disponible a: https://hdl.handle.net/2445/49465]