A constrained tricyclic nucleic acid analogue of α-L-LNA: investigating the effects of dual conformational restriction on duplex thermal stability

J Org Chem. 2013 Sep 20;78(18):9064-75. doi: 10.1021/jo401170y. Epub 2013 Sep 4.

Abstract

A constrained tricyclic analogue of α-L-LNA (2), which contains dual modes of conformational restriction about the ribose sugar moiety, has been synthesized and characterized by X-ray crystallography. Thermal denaturation experiments of oligonucleotide sequences containing this tricyclic α-L-LNA analogue (α-L-TriNA 2, 5) indicate that this modification is moderately stabilizing when paired with complementary DNA and RNA, but less stabilizing than both α-L-LNA (2) and α-L-TriNA 1 (4).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Conformation
  • Nucleic Acid Denaturation
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Temperature*

Substances

  • Oligonucleotides
  • locked nucleic acid