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

Reuben Ovadia | Zendy; Aurélien Lebrun | Zendy; Ivan Barvı́k | Zendy; JeanJacques Vasseur | Zendy; Carine Baraguey | Zendy; Karine Alvarez | Zendy

Open Access

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

Author(s) -

Reuben Ovadia,

Aurélien Lebrun,

Ivan Barvı́k,

JeanJacques Vasseur,

Carine Baraguey,

Karine Alvarez

Publication year - 2015

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/c5ob01604e

Subject(s) - chemistry , monomer , nucleic acid , isocyanide , combinatorial chemistry , nucleobase , peptide , peptide nucleic acid , amine gas treating , conformational isomerism , paraformaldehyde , solid phase synthesis , organic chemistry , dna , molecule , biochemistry , polymer

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.

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