Efficient Synthesis of 2’-O-Cyanoethylated Imidazole C-Ribonucleoside Phosphoramidite: A Practical Building Block for Probing the Catalytic Mechanism of Ribozymes

Lisa Araki, Zheng-yun Zhao, David M. J. Lilley, Shinya Harusawa

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    11 Citations (Scopus)

    Abstract

    A high-yielding synthetic route leading to new 2'-O-cyanoethylated imidazole C-ribonucleoside phosphoramidite (PA) 1 has been developed (41% overall yield in ten steps). This has resulted in a marked improvement of yield compared to unstable 2'-O-TBDMS PA 2. The new synthon PA 1 enables the imidazole moiety to be incorporated into any RNA sequence in principle, and has been used as a practical building block for probing the catalytic mechanism of a ribozyme.

    Original languageEnglish
    Pages (from-to)1861-1869
    Number of pages9
    JournalHeterocycles
    Volume81
    Issue number8
    DOIs
    Publication statusPublished - 1 Aug 2010

    Keywords

    • Cyanoethyl
    • Imidazole
    • C-Ribonucleoside
    • Phosphoramidite
    • Ribozyme
    • RNA

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