Oligonucleotides containing a new type of acyclic, achiral nucleoside analogue: 1-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]thymine

Bioorg Med Chem Lett. 2003 Mar 10;13(5):847-50. doi: 10.1016/s0960-894x(03)00008-8.

Abstract

An achiral, acyclic nucleoside analogue has been incorporated once or twice in oligodeoxyribonucleotides by the phosphoramidite method, and conditions found which allow deprotection of the oligonucleotides containing a sensitive modified allylic unit. The binding affinity of the modified oligonucleotides towards complementary DNA and RNA was reduced compared to unmodified DNA (DeltaT(m) -2 to -6.5 degrees C). An oligonucleotide with two modifications at the 3'-end showed considerable resistance towards cleavage with a 3'-exonuclease.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Base Sequence
  • DNA, Complementary / chemistry
  • DNA, Complementary / metabolism
  • Nucleic Acid Denaturation
  • Nucleic Acid Heteroduplexes / chemistry
  • Nucleic Acid Hybridization
  • Oligonucleotides / chemistry*
  • Phosphoric Diester Hydrolases / metabolism
  • RNA / chemistry
  • RNA / metabolism
  • Snake Venoms
  • Temperature
  • Thymine / analogs & derivatives*
  • Thymine / metabolism

Substances

  • DNA, Complementary
  • Nucleic Acid Heteroduplexes
  • Oligonucleotides
  • Snake Venoms
  • RNA
  • Phosphoric Diester Hydrolases
  • Thymine