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3'-Amino-2',4'-BNA: novel bridged nucleic acids having an N3'-P5' phosphoramidate linkage

Satoshi Obika, et al.
05/22/2014
Novel oligonucleotide analogues, containing a 3A-amino- 2A,4A-BNA unit, were successfully synthesized, and they showed superior duplex and triplex forming ability as well as BNA itself, along with remarkable enzymatic stability.

Introduction

Oligonucleotides for practical antisense and/or antigene molecules should fulfil some requirements, such as a high binding affinity for the target ssRNA or dsDNA, high sequence selectivity, and sufficient enzymatic stability. During the past decade, various chemically modified oligonucleotides have been synthesized, and their properties have been investigated; 1–5 however, an ideal antisense or antigene molecule is still lacking. We recently achieved the first synthesis of a novel nucleoside with a fixed N-type conformation,6 2A-O,4A-Cmethylene bridged nucleic acid (2A,4A-BNA)7,8 (Fig. 1) and found that 2A,4A-BNA modified oligonucleotides exhibited strong hybridization ability with complementary strands of RNA and DNA.9,10 Moreover, these 2A,4A-BNA oligonucleotides appeared to possess high affinity for dsDNA forming a stable DNA triplex.10–15.

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