Phe and Asn side chains in DNA double strands

Bioorg Med Chem Lett. 2000 Jul 3;10(13):1417-20. doi: 10.1016/s0960-894x(00)00231-6.

Abstract

The contribution of amino acid side chains to the recognition of DNA by peptides or proteins is evaluated by substituting single nucleobases of a DNA double strand by amino acid side chains. C-nucleosides with the side chains of phenylalanine and asparagine were synthesized and incorporated in DNA. This modification should allow to keep the double strand conformation. Hydrogen bonds, pi-pi-interactions and solvation have an influence on the double strand stability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Asparagine / analogs & derivatives*
  • Asparagine / chemical synthesis*
  • Base Pair Mismatch
  • DNA / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Nucleic Acid Conformation
  • Nucleosides / chemistry*
  • Peptide Nucleic Acids / chemistry
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemical synthesis*

Substances

  • Nucleosides
  • Peptide Nucleic Acids
  • Phenylalanine
  • Asparagine
  • DNA