Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability

Nucleic Acids Res. 1992 Sep 25;20(18):4711-6. doi: 10.1093/nar/20.18.4711.

Abstract

Oligonucleotides containing 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (2) and 1-(3,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (3) were synthesized on a solid support using the phosphoramidite approach. The properties of these oligonucleotides were compared with the earlier reported characteristics of oligonucleotides containing 1-(2,3-dideoxy-beta-D-erythro-hexopyranosyl) thymine (1). The order in enzymatic stability of end-substituted oligonucleotides is 3 greater than 1 much greater than 2. The hybridization properties of the modified oligonucleotides are in reverse order: 2 much greater than 1 greater than 3.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaline Phosphatase / metabolism
  • Base Composition
  • Base Sequence
  • Hexoses*
  • Hydrogen Bonding
  • Indicators and Reagents
  • Molecular Structure
  • Nucleic Acid Conformation
  • Nucleic Acid Denaturation
  • Nucleosides*
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry*
  • Phosphodiesterase I
  • Phosphoric Diester Hydrolases / metabolism
  • Structure-Activity Relationship
  • Thymine

Substances

  • Hexoses
  • Indicators and Reagents
  • Nucleosides
  • Oligonucleotides
  • Alkaline Phosphatase
  • Phosphoric Diester Hydrolases
  • Phosphodiesterase I
  • Thymine