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Synthesis of Several Types of Bridged Nucleic Acids

 
09/01/2009

Synthesis of Several Types of Bridged Nucleic Acids

10/28/2014
Abstract

A number of bridged nucleic acids with conformationally locked sugar moiety were synthesized from the readily accessible sugar derivatives. The conformations of the sugar moiety of the bridged nucleic acids (BNAs) are locked to either N-type or S-type sugar puckering. This article summarizes the synthesis of these nucleic acid analogues.

Introduction

After the introduction of the first antisense drug phosphorothioate in 1998,1,2 tremendous attention has been focused on nucleic acid-based research and therapy. Numerous chemically modified nucleic acids have been designed, synthesized and their utility in various gene-silencing technologies such as antisense,3 antigene,4 and RNA interference5 have been investigated.4,6,7 A dramatic improvement in nucleic acids research and technology was achieved through synthesis of a bridged nucleic acid (BNA) in which the furanose conformation is locked to a definite form via bridging.8,9 Sugar conformation in A-form RNA exists predominantly as N-type whereas that in B-form DNA is S-type (Figure 1). Therefore, it is expected that modified nucleic acids possessing N-type or S-type sugar conformation will exhibit high binding affinity with complementary single-stranded RNA and single-stranded DNA, respectively. Based on this speculation, a number of BNAs were synthesized and their properties were investigated. Click on PDF icon to learn more about Bridged Nucleic Acids

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