J. Am. Chem. Soc., 130 (27), 87628768, 2008. 10.1021/ja801058h
Web Release Date: June 11, 2008

Copyright © 2008 American Chemical Society

Artificial DNA Made Exclusively of Nonnatural C-Nucleosides with Four Types of Nonnatural Bases

Yasuhiro Doi, Junya Chiba,* Tomoyuki Morikawa, and Masahiko Inouye*

Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama 930-0194, Japan

chiba@pha.u-toyama.ac.jp; inouye@pha.u-toyama.ac.jp

Received February 12, 2008

Abstract:

We describe a new class of DNA-like oligomers made exclusively of nonnatural, stable C-nucleosides. The nucleosides comprise four types of nonnatural bases attached to a deoxyribose through an acetylene bond with the β-configuration. The artificial DNA forms right-handed duplexes and triplexes with the complementary artificial DNA. The hybridization occurs spontaneously and sequence-selectively, and the resulting duplexes have thermal stabilities very close to those of natural duplexes. The artificial DNA might be applied to a future extracellular genetic system with information storage and amplifiable abilities.

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