Study of the inducible cross-linking reaction to mRNA and the effect on the translation

Kenji Kikuta, Yosuke Taniguchi, Shigeki Sasaki

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1 Citation (Scopus)


The 4-vinylpyrimidin-2-one nucleoside (T-vinyl) forms a cross-link with the RNA containing uracil at the complementary site at a high reaction rate. To obtain the stable T-vinyl derivative so that its reactivity is protected until it access to the target site, several derivatives were investigated, and the 2-thiopyridinyland 2-thiopyrimidinyl T-vinyl derivatives were determined to be good candidates. The 2-thiopyrimidinyl Tvinyl derivative was found to more efficiently cross-link with mRNA albeit having a better stability than the 2-thiopyridinyl T-vinyl derivative. The investigation using the luciferase (Luc) mRNA, the synthetic mRNA and non-cellular translation system revealed that the translation is terminated at the end of the cross-linked duplex between the mRNA and the oligoribonucleotide (ORN). Thus, the 2-thiopyrimidinyl T-vinyl derivative has successfully demonstrated both a good stability and high efficiency for the cross-linking reaction, and expanded its applicability in biological applications.

Original languageEnglish
Pages (from-to)877-883
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Issue number8
Publication statusPublished - 2019

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery


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