title: 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.
authors.affiliation: Laboratoire d'Architecture et Fonction des Macromolécules Biologiques, Université Aix-Marseille UMR CNRS 7257, Equipe "Antiviral Medicinal Chemistry", Parc scientifique de Luminy, 163 av. de Luminy, 13288 Marseille Cedex 9, France. karine.alvarez@afmb.univ-mrs.fr.
authors.forename: Reuben
authors.initials: R
authors.lastname: Ovadia
authors.forename: Aurélien
authors.initials: A
authors.lastname: Lebrun
authors.forename: Ivan
authors.initials: I
authors.lastname: Barvik
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Vasseur
authors.forename: Carine
authors.initials: C
authors.lastname: Baraguey
authors.forename: Karine
authors.initials: K
authors.lastname: Alvarez
mesh_terms: D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry; D019281:Dimerization; D005557:Formaldehyde / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D056004:Molecular Dynamics Simulation; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D003486:Cyanides; D020135:Peptide Nucleic Acids; D011108:Polymers; D005557:Formaldehyde; C003043:paraform