Efficient Synthesis of 2’-O-Cyanoethylated Imidazole C-Ribonucleoside Phosphoramidite: A Practical Building Block for Probing the Catalytic Mechanism of Ribozymes

TY - JOUR

T1 - Efficient Synthesis of 2’-O-Cyanoethylated Imidazole C-Ribonucleoside Phosphoramidite

T2 - A Practical Building Block for Probing the Catalytic Mechanism of Ribozymes

AU - Araki, Lisa

AU - Zhao, Zheng-yun

AU - Lilley, David M. J.

AU - Harusawa, Shinya

PY - 2010/8/1

Y1 - 2010/8/1

N2 - 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.

AB - 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.

KW - Cyanoethyl

KW - Imidazole

KW - C-Ribonucleoside

KW - Phosphoramidite

KW - Ribozyme

KW - RNA

U2 - 10.3987/COM-10-11978

DO - 10.3987/COM-10-11978

M3 - Article

SN - 0385-5414

VL - 81

SP - 1861

EP - 1869

JO - Heterocycles

JF - Heterocycles

IS - 8

ER -