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Paper | Special issue | Vol 97, No. 1, 2018, pp.306-313
Published online, 14th February, 2018
DOI: 10.3987/COM-18-S(T)20
Synthesis and Properties of Oligonucleotides Containing 3′-O,4′-C-Ethyleneoxy-Bridged 5-Methyluridines

Takashi Osawa, Yuka Hitomi, Sawako Wakita, Han Kim, Masakazu Dohi, Masahiko Horiba, Yuta Ito, Satoshi Obika, and Yoshiyuki Hari*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan

Abstract

A phosphoramidite of 3ʹ-O,4ʹ-C-ethyleneoxy-bridged 5-methyluridine (3ʹ,4ʹ-EoNA-T) was successfully incorporated into oligonucleotides, and their abilities to form duplexes with RNA and DNA as well as triplexes with double-stranded DNA were evaluated. The stabilities of the duplexes formed between RNA and 3ʹ,4ʹ-EoNA-modified oligonucleotides were only slightly lower than those of the natural DNA–RNA duplex, while the duplexes formed between 3ʹ,4ʹ-EoNA-modified oligonucleotides and DNA were drastically less stable than the natural DNA–DNA duplex. Moreover, under the same conditions as the UV-melting experiments of the duplexes, 3ʹ,4ʹ-EoNA-modified oligonucleotides were unable to form triplexes with dsDNA. These results showed that oligonucleotides containing 3ʹ,4ʹ-EoNA-T had excellent RNA selectivity.