Saneyoshi Hisao, Seio Khoji, Sekine Mitsuo
Department of Life Science, Tokyo Institute of Technology.
Nucleic Acids Symp Ser (Oxf). 2005(49):125-6. doi: 10.1093/nass/49.1.125.
A new method for the synthesis of natural RNAs was developed via 2'-O-cyanoethylated RNA derivatives as available precursors. It was found that the cyanoethyl groups of 2'-O-cyanoethylated RNAs could be removed by use of the reverse reaction of the Michael addition of alcohols with acrylonitrile to afford 2'-unprotected RNAs. In addition, new ribonucleoside 3'-phosphoramidite building blocks having the cyanoethyl group as the 2'-hydroxyl protecting group have sterically less hindered circumstance around the 3' reaction site than the commercially available phosphoramidite building blocks.
通过使用2'-O-氰基乙基化的RNA衍生物作为可用前体，开发了一种合成天然RNA的新方法。研究发现，2'-O-氰基乙基化RNA的氰基乙基可以通过醇与丙烯腈的迈克尔加成反应的逆反应去除，从而得到2'-未保护的RNA。此外，以氰基乙基作为2'-羟基保护基团的新型核糖核苷3'-亚磷酰胺构建模块在3'反应位点周围的空间位阻环境比市售的亚磷酰胺构建模块更小。
