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

2012; Elsevier BV; Volume: 53; Issue: 44 Linguagem: Inglês

10.1016/j.tetlet.2012.08.082

1873-3581

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,

Chemical Synthesis and Analysis

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.