Quick Access to Nucleobase-Modified Phosphoramidites for the Synthesis of Oligoribonucleotides Containing Post-Transcriptional Modifications and Epitranscriptomic Marks.

ABSTRACT: Herein, we report a straightforward one-step procedure for modifying N-nucleophilic groups in the nucleobases of commercially available nucleoside phosphoramidites. This method involves the deprotonation of amide groups under phase-transfer conditions and subsequent reaction with electrophilic molecules such as alkyl halides or organic isocyanates. Using this approach, we obtained 10 different classes of modified nucleoside phosphoramidites suitable for the synthesis of oligonucleotides, including several noncanonical nucleotides found in natural RNA or DNA (e.g., m⁶A, i⁶A, m¹A, g⁶A, m³C, m⁴C, m³U, m¹G, and m²G). Such modification of nucleobases is a common mechanism for post-transcrip

SUBMITTER: Ziemkiewicz K 

PROVIDER: S-EPMC9361293 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature