Alpha-LNA (locked nucleic acid with alpha-D-configuration): synthesis and selective parallel recognition of RNA

Chemistry. 2002 Feb 2;8(3):712-22. doi: 10.1002/1521-3765(20020201)8:3<712::AID-CHEM712>3.0.CO;2-0.

Abstract

Alpha-LNA is presented as a stereoisomer of LNA (locked nucleic acid) with alpha-D-configuration. Three different approaches towards the thymine alpha-LNA monomer as well as the 5-methylcytosine alpha-LNA monomer are presented. Different alpha-LNA sequences have been synthesised and their hybridisation with complementary DNA and RNA has been evaluated by means of thermal stability experiments and circular dichroism spectroscopy. In a mixed pyrimidine sequence, alpha-LNA displays unprecedented parallel-stranded and selective RNA binding. Furthermore, a remarkable selectivity for hybridisation with RNA over DNA is indicated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • DNA / chemistry
  • DNA / metabolism
  • Drug Stability
  • Hot Temperature
  • Nucleic Acid Conformation
  • Nucleic Acid Hybridization*
  • Nucleosides / chemistry*
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Oligodeoxyribonucleotides / chemistry
  • Oligodeoxyribonucleotides / metabolism
  • RNA / chemistry
  • RNA / metabolism
  • Stereoisomerism

Substances

  • Nucleosides
  • Oligodeoxyribonucleotides
  • RNA
  • DNA