Solid-phase synthesis of novel peptide nucleic acids

Abstract

Novel peptide nucleic acids with configurationally and conformationally constrained glycylproline backbones have been synthesized by the solid-phase method from the Fmoc-protected dipeptide building blocks. Three decathymine peptide nucleic acids with different stereochemistry at the proline ring (cis-L, trans-D, cis-D) and mixed sequences in the cis-D series have been efficiently synthesized. In addition, oligothymine peptide nucleic acids with a conformationally flexible glycyl-N-ethylglycine backbone have also been synthesized from stepwise coupling of the Boc-protected monomer.