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Paper | Regular issue | Vol 81, No. 8, 2010, pp.1861-1869
Published online, 23rd June, 2010
DOI: 10.3987/COM-10-11978
■ Efficient Synthesis of 2’-O-Cyanoethylated Imidazole C-Ribonucleoside Phosphoramidite: A Practical Building Block for Probing the Catalytic Mechanism of Ribozymes

Lisa Araki, Zheng-yun Zhao, David M. J. Lilley, and Shinya Harusawa*

*Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan

Abstract

A high-yielding synthetic route leading to new 2’-O-cyanoethylated imidazole C-ribonucleoside phosphoramidite (PA) 1 has been developed (41% overall yield in ten steps). This has resulted in a marked improvement of yield compared to unstable 2’-O-TBDMS PA 2. The new synthon PA 1 enables the imidazole moiety to be incorporated into any RNA sequence in principle, and has been used as a practical building block for probing the catalytic mechanism of a ribozyme.