Unexpectedly stable artificial duplex from flexible acyclic threoninol

J Am Chem Soc. 2010 Oct 27;132(42):14702-3. doi: 10.1021/ja105539u.

Abstract

A new foldamer, acyclic threoninol nucleic acid (aTNA), has been synthesized by tethering each of the genetic nucleobases A, G, C, and T to d-threoninol molecules, which were then incorporated as building blocks into a scaffold bearing phosphodiester linkages. We found that with its fully complementary strand in an antiparallel fashion, the aTNA oligomer forms an exceptionally stable duplex that is far more stable than corresponding DNA or RNA duplexes, even though single-stranded aTNA is rather flexible and thus does not take a preorganized structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemistry*
  • Butylene Glycols / chemistry*
  • Circular Dichroism
  • Models, Molecular

Substances

  • Amino Alcohols
  • Butylene Glycols
  • threoninol