Synthesis and structural characterization of monomeric and dimeric peptide nucleic acids prepared by using microwave-promoted multicomponent reactions†,10.1039/C5OB01604E

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

Reuben Ovadia,Aurélien Lebrun,Ivan Barvik,Jean-Jacques Vasseur,Carine Baraguey,Karine Alvarez

Organic & Biomolecular Chemistry Pub Date : 09/10/2015 00:00:00 , DOI:10.1039/C5OB01604E

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.