jo9b00658_si_001.pdf (8.95 MB)
Stereocontrolled Synthesis of Boranophosphate DNA by an Oxazaphospholidine Approach and Evaluation of Its Properties
journal contribution
posted on 2019-05-29, 00:00 authored by Rintaro Iwata Hara, Tatsuya Saito, Tomoki Kogure, Yuka Hamamura, Naoki Uchiyama, Yohei Nukaga, Naoki Iwamoto, Takeshi WadaIn
this paper, we
describe the first stereocontrolled synthesis and properties of boranophosphate
DNA (PB-DNA), which contains all of the four nucleobases longer than
10mer. Synthesis was accomplished via an oxazaphospholidine approach
combined with acid-labile protecting groups on nucleobases. It was
demonstrated that there were significant differences between all-(Rp)- and all-(Sp)-PB-DNA in terms of the
duplex-formation ability, nuclease resistance, and ribonuclease H
(RNase H) activity. In particular, all-(Sp)-PB-DNA
was demonstrated to show a duplex-formation ability with RNA and RNase
H activity, both of which are necessary for antisense-type nucleic
acid therapeutics.