Synthesis and structural characterization of monomeric and dimeric peptide nucleic acids prepared by using microwave-promoted multicomponent reactions

Abstract

A solution phase synthesis of peptide nucleic acid monomers and dimers was developed by using microwave-promoted Ugi multicomponent reactions. A mixture of a functionalized amine, a carboxymethyl nucleobase, paraformaldehyde and an isocyanide as building blocks generates PNA monomers which are then partially deprotected and used in a second Ugi 4CC reaction, leading to PNA dimers.

Conformational rotamers were identified by using NMR and MD simulations.

Keywords

• molecular-dynamics simulations
• liquid-phase synthesis
• multi component reactions
• protecting-group strategy
• pna-monomers
• phosphoramidate dinucleosides
• building-blocks
• nmr
• dna
• polyamide