Sánchez-Moya, AlbertPedroso Muller, EnriqueGrandas Sagarra, Anna2014-02-062014-02-062012-01-131043-1802https://hdl.handle.net/2445/49465Phosphorothioate 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.24 p.application/pdfeng(c) American Chemical Society , 2012OligonucleòtidsImmunologiaÀcids nucleicsBioquímicaProteïnesOligonucleotidesImmunologyNucleic acidsBiochemistryProteinsinfo:eu-repo/semantics/article6059702014-02-06info:eu-repo/semantics/openAccess22243598