Chimeric RNA Oligonucleotides Incorporating Triazole-Linked Trinucleotides: Synthesis and Function as mRNA in Cell-Free Translation Reactions

Tomoko Fujino, Takeru Suzuki, Koudai Okada, Kanako Kogashi, Ken Ichi Yasumoto, Kazuhiro Sogawa, Hiroyuki Isobe

    Research output: Contribution to journalArticlepeer-review

    5 Citations (Scopus)

    Abstract

    A method for the synthesis of chimeric oligonucleotides was developed to incorporate purine nucleobases and multiple triazole linkers in natural, phosphate-linked structures of RNA. A solution-phase synthesis method for triazole-linked RNA oligomers via copper-catalyzed azide-alkyne cycloaddition reaction was optimized and tolerated purine nucleobases and protecting groups for further transformations. Three TLRNA trinucleotides with 5′-protected hydroxy and 3′-phosphoramidite groups were prepared, and one congener with a representative sequence was subjected to automated, solid-phase phosphoramidite synthesis. The synthesis allowed the efficient preparation of 13-mer chimeric RNA oligonucleotides with two triazole linkers, ten phosphate linkers and purine/pyrimidine nucleobases. The chimeric oligonucleotide was found applicable to a cell-free translation system as mRNA and provided the genetic code for dipeptide production.

    Original languageEnglish
    Pages (from-to)8967-8976
    Number of pages10
    JournalJournal of Organic Chemistry
    Volume81
    Issue number19
    DOIs
    Publication statusPublished - 2016 Oct 7

    ASJC Scopus subject areas

    • Organic Chemistry

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