Article

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

Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama 930-0194, Japan
J. Am. Chem. Soc., 2008, 130 (27), pp 8762–8768
DOI: 10.1021/ja801058h
Publication Date (Web): June 11, 2008
Copyright © 2008 American Chemical Society

Abstract

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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.

Synthetic details, Scheme S1, and Figures S1−13. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 3,450 Times
Received 12 February 2008
Published online 11 June 2008
Published in print 1 July 2008
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