Study of the Inducible Cross-Linking Reaction to mRNA and the Effect on the Translation

Chemical & Pharmaceutical Bulletin
Kenji KikutaShigeki Sasaki

Abstract

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-thiopyridinyl- and 2-thiopyrimidinyl T-vinyl derivatives were determined to be good candidates. The 2-thiopyrimidinyl T-vinyl 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.

References

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Aug 25, 2012·Organic & Biomolecular Chemistry·Atsuo ShigenoKenzo Fujimoto
Jun 25, 2015·Bioorganic & Medicinal Chemistry Letters·Kenji KikutaShigeki Sasaki
Nov 7, 2017·Muscle & Nerve·Neelam Goyal, Pushpa Narayanaswami
Dec 15, 2017·Nucleic Acids Research·Xiulong Shen, David R Corey
Jan 30, 2019·Annual Review of Medicine·C Frank Bennett

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