Conjugation reactions involving maleimides and phosphorothioate oligonucleotides |
| |
Authors: | Sánchez Albert Pedroso Enrique Grandas Anna |
| |
Institution: | Departament de Química Orgànica and IBUB, Facultat de Química, Universitat de Barcelona , Martí i Franquès 1-11, 08028 Barcelona, Spain. |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|