Open AccessA new method for RNA synthesis by use of the cyanoethyl group as the 2′-hydroxyl protecting group
Author(s) -
Hisao Saneyoshi,
Khoji Seio,
Mitsuo Sekine
Publication year - 2005
Publication title -
nucleic acids symposium series
Language(s) - English
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/49.1.125
Subject(s) - protecting group , group (periodic table) , chemistry , rna , combinatorial chemistry , biochemistry , organic chemistry , gene , alkyl
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.
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