Synthesis and Antisense Properties of 2'β-F-Arabinouridine Modified Oligonucleotides with 4'-C-OMe Substituent.

ABSTRACT: A novel 2'-F,4'-C-OMe⁻arabinouridine (araU) was successfully synthesized and introduced into oligonucleotides. The oligonucleotide containing 2'-F,4'-C-OMe⁻araU exhibited improved nuclease resistance and RNA hybridizing selective ability relative to 2'-F⁻araU. In particular, when 2'-F,4'-C-OMe⁻araU inserted into C⁻H⋯F⁻C bonding-favorable 5'⁻uridine⁻purine⁻3' steps, the modified oligonucleotide showed remarkable binding affinity and selectivity to RNA complements. Thus, 2'-F,4'-C-OMe⁻araU has valuable antisense properties and can be used as novel chemical modification for antisense therapeutic strategy.

SUBMITTER: He XY 

PROVIDER: S-EPMC6225415 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature