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Peer reviewed
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Hara, Rintaro Iwata; Saito, Tatsuya; Kogure, Tomoki; Hamamura, Yuka; Uchiyama, Naoki; Nukaga, Yohei; Iwamoto, Naoki; Wada, Takeshi
Journal of organic chemistry, 06/2019, Volume: 84, Issue: 12Journal Article
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.
