Synthesis of novel tetrazole C5-linked C0- and C2-ribonucleoside phosphoramidites using MePOM and POM groups for probing RNA catalysis

Shinya Harusawa, Hiroki Yoneyama, Daiki Fujisue, Masayoshi Nishiura, Mihoyo Fujitake, Yoshihide Usami, Zheng-yun Zhao, Scott A. Mcphee, Timothy J. Wilson, David M.J. Lilley

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    Novel C5-linked C0- and C2-tetrazole ribonucleoside phosphoramidites were designed and synthesized via tetrazole C-nucleosides. Pivaloyloxymethyl (POM) and methyl-substituted POM (MePOM) groups were introduced as N-protecting groups in the tetrazole ring that can be readily removed under mild basic conditions. The phosphoramidites were successfully incorporated into the VS ribozyme substrate and hence providing a chemogenetic approach to determine which nucleobases of ribozymes function as the acid or base, in the studies of ribozyme general acid and base catalysis.
    Original languageEnglish
    Pages (from-to)5891-5894
    Number of pages4
    JournalTetrahedron Letters
    Volume53
    Issue number44
    DOIs
    Publication statusPublished - 2012

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