Synthesis, characterization and hybridization studies of new nucleo-gamma-peptides based on diaminobutyric acid

J Pept Sci. 2006 Dec;12(12):829-35. doi: 10.1002/psc.819.

Abstract

In the present work, we report the synthesis and the characterization of a new chiral nucleoaminoacid, in which a diaminobutyric moiety is connected to the DNA nucleobase by an amidic bond, and its oligomerization to give the corresponding nucleo-gamma-peptide. The ability of this synthetic polymer to bind complementary DNA was studied in order to explore its possible use in antigene/antisense or diagnostic applications. Our interest in the presented DNA analogue was also supported by the importance of gamma-aminoacid-containing compounds in natural products of biological activity and by the known stability of gamma-peptides to enzymatic degradation. Furthermore, our work could contribute to the study of the role of nucleopeptides as prebiotic material in a PNA world that could successively lead to the actual DNA/RNA/protein world, as recently assumed.

MeSH terms

  • Aminobutyrates / chemistry*
  • Base Sequence
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Molecular Conformation
  • Molecular Structure
  • Nucleic Acid Probes / chemical synthesis
  • Nucleic Acid Probes / chemistry
  • Peptide Nucleic Acids / chemical synthesis
  • Peptide Nucleic Acids / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet
  • Temperature

Substances

  • Aminobutyrates
  • Nucleic Acid Probes
  • Peptide Nucleic Acids
  • 2,4-diaminobutyric acid