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

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...

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Bibliographic Details
Published in:Tetrahedron letters 2012-10, Vol.53 (44), p.5891-5894
Main Authors: Harusawa, Shinya, Yoneyama, Hiroki, Fujisue, Daiki, Nishiura, Masayoshi, Fujitake, Mihoyo, Usami, Yoshihide, Zhao, Zheng-yun, McPhee, Scott A., Wilson, Timothy J., Lilley, David M.J.
Format: Article
Language:English
Subjects:
Acetal resins
Catalysis
Chemogenetic approach
Phosphoramidite
Protecting group
Ribonucleic acids
Ribozyme
Synthesis (chemistry)
Tetrahedrons
Tetrazole
Tetrazoles
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.08.082