Contribution to PNA-RNA Chimera Synthesis: One-Pot Microwave-Assisted Ugi Reaction to Obtain Dimeric Building Blocks

Reuben Ovadia (1) , Clémence Mondielli (1) , Jean-Jacques Vasseur (2) , Carine Baraguey (2) , Karine Alvarez (1)

1 AFMB - Architecture et fonction des macromolécules biologiques
2 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

We report a solution-phase synthesis of dimeric PNA-RNA (PNA = peptide nucleic acid) building blocks by using a microwave-assisted Ugi four-component reaction. A mixture of a functionalized amine, a carboxymethyl nucleobase, para-formaldehyde, and N4,2'-O,3'-O-tribenzoyl-5'-deoxy-5'-isocyanocytidine generates the dimeric chimeras in one step. The method is simple, and gives rapid access (5 min) to diversity, as exemplified by the products described here.

Mots clés: SOLID-PHASE SYNTHESIS; MULTICOMPONENT REACTIONS; POLYAMIDE; CONTAIN; ANALOGS; DNA

Domaines: Chimie; Chimie organique; Chimie thérapeutique; Chimie analytique

Reuben Ovadia, Clémence Mondielli, Jean-Jacques Vasseur, Carine Baraguey, Karine Alvarez. Contribution to PNA-RNA Chimera Synthesis: One-Pot Microwave-Assisted Ugi Reaction to Obtain Dimeric Building Blocks. European Journal of Organic Chemistry, 2017, 2017 (3), pp.469-475. ⟨10.1002/ejoc.201601190⟩. ⟨hal-02197216⟩