Artificial DNA made exclusively of nonnatural C-nucleosides with four types of nonnatural bases

J Am Chem Soc. 2008 Jul 9;130(27):8762-8. doi: 10.1021/ja801058h. Epub 2008 Jun 11.

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 beta-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / chemistry
  • Cytidine / analogs & derivatives*
  • Cytosine / analogs & derivatives*
  • DNA / chemical synthesis
  • DNA / chemistry*
  • Deoxyribose / chemistry
  • Hot Temperature
  • Hydrogen Bonding
  • Nucleic Acid Conformation*
  • Organophosphorus Compounds / chemistry
  • Thermodynamics

Substances

  • Organophosphorus Compounds
  • phosphoramidite
  • Deoxyribose
  • Cytidine
  • Cytosine
  • DNA
  • Acetylene