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Updated: Jan 5, 2026

Sequence-specific Labeling of Nucleic Acids and Proteins with Methyltransferases and Cofactor Analogues
Published on: November 22, 2014
Synthesis of selenomethylene-locked nucleic acids (SeLNA) nucleoside unit bearing an adenine base
Yoshihiro Moai1, Hidekazu Hiroaki1, Saoshi Obika2
1Graduate School of Pharmaceutical Sciences, Nagoya University, Nagoya, Aichi, Japan.
Abstract:
Synthesis of selenomethylene-locked nucleic acids nucleoside bearing an adenine base (SeLNA-A) was investigated. We first examined the stereoinversion reaction at 2'-positions of a 5',3'-O-TIPDS-protected 4'-C-(hydroxymethyl)ribosyladenine derivative to give the corresponding arabinosyladenine. After triflation, treatment of the arabinosyladenine derivative with a mixture of selenium and sodium borohydride in ethanol managed to construct the desired SeLNA skeleton. Finally, removal of TIPDS by treating with fluoride gave the SeLNA-A nucleoside. In this study, we found the heat-labile property of SeLNA-A. It is necessary to know more precise characteristics of SeLNA to achieve its oligonucleotides synthesis.
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