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Issue 69, 2013
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A post-synthetic approach for the synthesis of 2′-O-methyldithiomethyl-modified oligonucleotides responsive to a reducing environment

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Abstract

Based on a novel concept, a Reducing-Environment-Dependent Uncatalyzed Chemical Transforming RNA, “REDUCT RNA”, we established a post-synthetic approach for the synthesis of 2′-O-methyldithiomethyl-modified oligonucleotides from 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-oligonucleotides by treatment with dimethyl(methylthio)sulfonium tetrafluoroborate. 2′-O-methyldithiomethyl oligonucleotides were easily converted into 2′-hydroxy oligonucleotides under reducing conditions, such as those found in the intracellular environment.

Graphical abstract: A post-synthetic approach for the synthesis of 2′-O-methyldithiomethyl-modified oligonucleotides responsive to a reducing environment

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Publication details

The article was received on 17 May 2013, accepted on 25 Jun 2013 and first published on 27 Jun 2013


Article type: Communication
DOI: 10.1039/C3CC43725F
Citation: Chem. Commun., 2013,49, 7620-7622
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    A post-synthetic approach for the synthesis of 2′-O-methyldithiomethyl-modified oligonucleotides responsive to a reducing environment

    Y. Ochi, O. Nakagawa, K. Sakaguchi, S. Wada and H. Urata, Chem. Commun., 2013, 49, 7620
    DOI: 10.1039/C3CC43725F

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