4.4 Article

Post-synthetic modification of oligonucleotides containing 5-trifluoromethylpyrimidine bases

Journal

TETRAHEDRON
Volume 74, Issue 47, Pages 6854-6860

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.10.006

Keywords

5-Trifluoromethylpyrimidine nucleobase; 5-Substituted pyrimidine nucleobase; Nucleoside; Oligonucleotide; Post-synthetic modification

Funding

  1. Japan Society for the Promotion of Science (JSPS) KAKENHI Grant [JP17K15431]

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A practical and operationally simple post-synthetic modification of oligonucleotides containing 5-trifluoromethylpyrimidine bases is described. Trifluoromethyl group was used as a post-synthetic precursor and 5-trifluoromethylpyrimidine bases within oligonucleotides were converted into the corresponding 5-carboxy-, 5-cyano-, 5-amidinyl-, and 5-carbamoyl derivatives by treatment with an alkaline solution and amines. Moreover, post-synthetic treatment of fully protected and controlled pore glass (CPG)-attached oligonucleotides proceeded successfully with the simultaneous removal of all protecting groups, cleavage from CPG, and conversion of the trifluoromethyl group to afford the corresponding modified oligonucleotides. (C) 2018 Elsevier Ltd. All rights reserved.

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