Post-synthetic modification of oligonucleotides containing 5-trifluoromethylpyrimidine bases. Issue 47 (22nd November 2018)

• Record Type: Journal Article
• Authors: Ito, Yuta; Matsuo, Misaki; Yamamoto, Kazuki; Yamashita, Wakana; Osawa, Takashi; Hari, Yoshiyuki
• Is Part Of: Tetrahedron. Volume 74:Issue 47(2018)
• Page Start: 6854
• Page End: 6860
• Publication Date: 2018-11-22
• Subjects: 5-Trifluoromethylpyrimidine nucleobase -- 5-Substituted pyrimidine nucleobase -- Nucleoside -- Oligonucleotide -- Post-synthetic modification; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.10.006
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: