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Title: Conjugation reactions involving maleimides and phosphorothioate oligonucleotides
Author: Sánchez-Moya, Albert
Pedroso Muller, Enrique
Grandas Sagarra, Anna
Keywords: Oligonucleòtids
Àcids nucleics
Nucleic acids
Issue Date: 13-Jan-2012
Publisher: American Chemical Society
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.
Note: Versió postprint del document publicat a:
It is part of: Bioconjugate Chemistry, 2012, vol. 23, num. 2, p. 300-307
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ISSN: 1043-1802
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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