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Synthesis of novel tetrazole C5-linked C0- and C2-ribonucleoside phosphoramidites using MePOM and POM groups for probing RNA catalysis |
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| Authors: | Shinya Harusawa Hiroki YoneyamaDaiki Fujisue Masayoshi NishiuraMihoyo Fujitake Yoshihide UsamiZheng-yun Zhao Scott A McPheeTimothy J Wilson David MJ Lilley |
| Institution: | a Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan b School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK c CR-UK Nucleic Acid Structure Group, MSI/WTB Complex, University of Dundee, Dundee DDI 5EH, UK |
| 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. |
| Keywords: | Tetrazole Phosphoramidite Protecting group Chemogenetic approach Ribozyme |
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