Synthesis and structural characterization of monomeric and dimeric peptide nucleic acids prepared by using microwave-promoted multicomponent reactions. Issue 45 (23rd September 2015)

• Record Type: Journal Article
• Authors: Ovadia, Reuben; Lebrun, Aurélien; Barvik, Ivan; Vasseur, Jean-Jacques; Baraguey, Carine; Alvarez, Karine
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 45(2015)
• Page Start: 11052
• Page End: 11071
• Publication Date: 2015-09-23
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob01604e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A solution phase synthesis of peptide nucleic acid monomers and dimers was developed by using microwave-promoted Ugi 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.