Solid support post-conjugation of amino acids and a phenanthroline derivative to a central position in peptide nucleic acids

Nucleosides Nucleotides Nucleic Acids. 2007;26(10-12):1485-9. doi: 10.1080/15257770701542819.

Abstract

A solid phase synthesis strategy for post-conjugation of amino acids and a phenanthroline derivative to peptide nucleic acids is described. The peptide nucleic acids, synthesized by 9-fluorenylmethyloxycarbonyl chemistry on TentaGel S Rink Amide resin, have an internally placed unit carrying an amino linker with 4-methyltrityl protection. Methyltrityl removal by mild acidic conditions and conjugation of amino acids or a phenanthroline derivative, via an amide or urea linker, was performed on-resin after completion of the chain assembly. This solid phase methodology resulted in excellent purities of the crude conjugates.

MeSH terms

  • Amino Acids / chemistry*
  • Peptide Nucleic Acids / chemical synthesis*
  • Peptide Nucleic Acids / chemistry
  • Phenanthrolines / chemistry*
  • Polystyrenes / chemistry

Substances

  • Amino Acids
  • Peptide Nucleic Acids
  • Phenanthrolines
  • Polystyrenes
  • Tentagel resin