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Chemical ligation of oligonucleotides using an electrophilic phosphorothioester.

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.

SUBMITTER: Maruyama H

PROVIDER: S-EPMC5499596 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Chemical ligation of oligonucleotides using an electrophilic phosphorothioester.

Maruyama Hideto H Oikawa Ryota R Hayakawa Mayu M Takamori Shono S Kimura Yasuaki Y Abe Naoko N Tsuji Genichiro G Matsuda Akira A Shuto Satoshi S Ito Yoshihiro Y Abe Hiroshi H

Nucleic acids research 20170701 12

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. ...[more]

PMID: 28520986

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