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

doi:10.1016/j.tetlet.2012.08.082

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 journal › Article › peer-review

17 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 language	English
Pages (from-to)	5891-5894
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2012.08.082
Publication status	Published - 2012

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10.1016/j.tetlet.2012.08.082

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

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.",

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

year = "2012",

doi = "10.1016/j.tetlet.2012.08.082",

language = "English",

volume = "53",

pages = "5891--5894",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Synthesis of novel tetrazole C5-linked C0- and C2-ribonucleoside phosphoramidites using MePOM and POM groups for probing RNA catalysis

AU - Harusawa, Shinya

AU - Yoneyama, Hiroki

AU - Fujisue, Daiki

AU - Nishiura, Masayoshi

AU - Fujitake, Mihoyo

AU - Usami, Yoshihide

AU - Zhao, Zheng-yun

AU - Mcphee, Scott A.

AU - Wilson, Timothy J.

AU - Lilley, David M.J.

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

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U2 - 10.1016/j.tetlet.2012.08.082

DO - 10.1016/j.tetlet.2012.08.082

M3 - Article

AN - SCOPUS:84866746906

SN - 0040-4039

VL - 53

SP - 5891

EP - 5894

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

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

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Fluorescence Resonance Energy Transfer as a Rich Source of Orientational Information in Nucleic Acid Structure

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

Abstract

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Fluorescence Resonance Energy Transfer as a Rich Source of Orientational Information in Nucleic Acid Structure

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