Yuta Ito, Kazuki Yamamoto, Y. Hari
Sep 1, 2019
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Current Protocols in Nucleic Acid Chemistry
Abstract
This unit describes postsynthetic modification of oligonucleotides (ONs) containing 2′‐deoxy‐5‐trifluoromethyluridine and 2′‐deoxy‐5‐trifluoromethylcytidine. In ONs, the trifluoromethyl group at the C5 position of pyrimidine bases is converted into a variety of carboxylic acid equivalents using alkaline and amine solutions. In addition, treating fully protected and controlled pore glass (CPG)‐attached ONs with methylamine and sodium hydroxide aqueous solution results in deprotection of all protecting groups (except the 4,4′‐dimethoxytrityl group), cleavage from CPG, and simultaneous conversion of the trifluoromethyl group to afford the corresponding ONs containing 5‐substituted pyrimidine bases. © 2019 by John Wiley & Sons, Inc.