Chemical ligation of oligonucleotides using an electrophilic phosphorothioester

Nucleic Acids Research
Hideto MaruyamaHiroshi Abe

Abstract

We developed a new approach for chemical ligation of oligonucleotides using the electrophilic phosphorothioester (EPT) group. A nucleophilic phosphorothioate group on oligonucleotides was converted into the EPT group by treatment with Sanger's reagent (1-fluoro-2,4-dinitrobenzene). EPT oligonucleotides can be isolated, stored frozen, and used for the ligation reaction. The reaction of the EPT oligonucleotide and an amino-modified oligonucleotide took place without any extra reagents at pH 7.0-8.0 at room temperature, and resulted in a ligation product with a phosphoramidate bond with a 39-85% yield. This method has potential uses in biotechnology and chemical biology.

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Citations

May 6, 2020·Chemical Communications : Chem Comm·Kosuke NakamotoHiroshi Abe
Feb 2, 2019·Scientific Reports·Anastassia Kanavarioti
Feb 17, 2021·Nucleic Acids Research·Zenita AdhireksanCurt A Davey
Aug 18, 2020·ACS Sensors·Elia JanettChristian G Bochet
Sep 15, 2021·Chembiochem : a European Journal of Chemical Biology·Kazuki YamaokaHiroshi Abe

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