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Title: | Conjugation reactions involving maleimides and phosphorothioate oligonucleotides |
Author: | Sánchez-Moya, Albert Pedroso Muller, Enrique Grandas Sagarra, Anna |
Keywords: | Oligonucleòtids Immunologia Àcids nucleics Bioquímica Proteïnes Oligonucleotides Immunology Nucleic acids Biochemistry Proteins |
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: http://dx.doi.org/10.1021/bc200598g |
It is part of: | Bioconjugate Chemistry, 2012, vol. 23, num. 2, p. 300-307 |
URI: | http://hdl.handle.net/2445/49465 |
Related resource: | http://dx.doi.org/10.1021/bc200598g |
ISSN: | 1043-1802 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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