Chemical synthesis and properties of modified oligonucleotides containing 5′-amino-5′-deoxy-5′-hydroxymethylthymidine residues

Abstract

In this study, we designed 5′-amino-5′-deoxy-5′-hydroxymethylthymidine as a new oligonucleotide modification with an amino group directly attached to the 5′-carbon atom. We successfully synthesized two isomers of 5′-amino-5′-deoxy-5′-hydroxymethylthymidine via dihydroxylation of the 5′-vinyl group incorporated into 5′-deoxy-5′-C-methenylthymidine derivative. Moreover, it was found that the nuclease resistance, binding selectivity to single-stranded RNA, and triplex-forming ability of an oligonucleotide containing RT residues of the new compound were higher than those of the unmodified oligonucleotide.