Synthesis and hybridizing properties of isoDNAs including 3′-O,4′-C-ethyleneoxy-bridged 5-methyluridine derivatives

Publication date: Available online 26 May 2018
Source:Bioorganic & Medicinal Chemistry
Author(s): Takashi Osawa, Yuka Hitomi, Sawako Wakita, Han Kim, Yuta Ito, Yoshiyuki Hari
3′,4′-Ethyleneoxy-bridged 5-methyluridine derivatives with methyl groups in the bridge, (R)-Me-3′,4′-EoNA-T and (S)-Me-3′,4′-EoNA-T, were synthesized, and these two analogs and unsubstituted 3′,4′-EoNA-T were successfully incorporated into a 2′,5′-linked oligonucleotide (isoDNA). Their duplex-forming ability with complementary DNA and complementary RNA, and triplex-forming ability with double-stranded DNA, were evaluated by UV-melting experiments. The results indicated that isoDNAs, including these 3′,4′-EoNA analogs, could hybridize exclusively with complementary RNA. In particular, 3′,4′-EoNA-T and (R)-Me-3′,4′-EoNA-T modifications within isoDNA could stabilize the duplexes with complementary RNA compared with unmodified or 3′,4′-BNA-modified isoDNAs.

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