American Chemical Society
jo9b00658_si_001.pdf (8.95 MB)

Stereocontrolled Synthesis of Boranophosphate DNA by an Oxazaphospholidine Approach and Evaluation of Its Properties

Download (8.95 MB)
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 Wada
In 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.