Synlett 2014; 25(11): 1499-1510
DOI: 10.1055/s-0033-1341060
account
© Georg Thieme Verlag Stuttgart · New York

Development of External Stimuli-Responsive Nucleic Acids by Sugar, Backbone, and Nucleobase Modification

Kunihiko Morihiro
a   Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan   Fax: +81(6)68798204   Email: obika@phs.osaka-u.ac.jp
b   National Institute of Biomedical Innovation (NIBIO), 7-6-8 Saito-Asagi, Ibaraki, Osaka 567-0085, Japan
,
Tetsuya Kodama
c   Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan
,
Satoshi Obika*
a   Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan   Fax: +81(6)68798204   Email: obika@phs.osaka-u.ac.jp
b   National Institute of Biomedical Innovation (NIBIO), 7-6-8 Saito-Asagi, Ibaraki, Osaka 567-0085, Japan
› Author Affiliations
Further Information

Publication History

Received: 26 January 2014

Accepted: 18 February 2014

Publication Date:
03 April 2014 (online)


Abstract

Nucleic acids are the principal materials for the preservation and flow of genetic information. The control of the properties of nucleic acids by using external stimuli is important for regulating biological processes and for the possibility of developing unique molecular machines. This account summarizes the development of external stimuli-responsive nucleic acids by our group. Our external stimuli-responsive nucleic acids are designed and synthesized through sugar, backbone, and nucleobase modifications. Various external stimuli, such as light, acids, or oxidants/reductants can trigger changes in nucleic acid structure. By means of such structural alterations, various properties of nucleic acid, including their hybridization ability, nuclease resistance, backbone degradability, and base-recognition ability, can be changed.

1 Introduction

2 External Stimuli-Responsive Nucleic Acids

2.1 2′,4′-Bridged Nucleic Acid Analogues Bearing External Stimuli-Responsive Bridged Moieties

2.2 Oligonucleotides Containing a P–N Phosphoramidite Linkage for Double-Stranded DNA-Templated Digestion

2.3 Light-Triggered Change in the Hydrogen-Bonding Pattern of a Nucleobase Analogue Enables a Strand-Exchange ­Reaction

3 Conclusions