Title:
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Conjugation reactions involving maleimides and phosphorothioate oligonucleotides
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Author:
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Sánchez, Albert; Pedroso Muller, Enrique; Grandas Sagarra, Anna
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Other authors:
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Universitat de Barcelona |
Abstract:
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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. |
Subject(s):
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-Oligonucleòtids -Immunologia -Àcids nucleics -Bioquímica -Proteïnes -Oligonucleotides -Immunology -Nucleic acids -Biochemistry -Proteins |
Rights:
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(c) American Chemical Society , 2012
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Document type:
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Article Article - Accepted version |
Published by:
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American Chemical Society
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