Phenylalkyl backbone modified oligodeoxynucleotides, their synthesis and the influence of the alkyl chain length

Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):1275-8. doi: 10.1081/NCN-100002535.

Abstract

Phenylalkyl modified phosphoramidites (alkyl chain length n = 1, 2, 3, 5; Fig. 1) were synthesised and incorporated into a DNA hexamer (5'-d(GCCp-GCG); p = place of modification). The obtained diastereomeres were separated by RP-HPLC. After hybridisation with the complementary DNA strand Tm-value and thermodynamic data were measured. The stability of duplexes depends on the linker length and the absolute configuration of the backbone modified oligodeoxynucleotides (Rp, Sp).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrocarbons, Aromatic / chemical synthesis
  • Hydrocarbons, Aromatic / chemistry
  • Nucleic Acid Conformation
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Structure-Activity Relationship

Substances

  • Hydrocarbons, Aromatic
  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite