Contribution to PNA–RNA Chimera Synthesis: One‐Pot Microwave‐Assisted Ugi Reaction to Obtain Dimeric Building Blocks. Issue 3 (30th December 2016)

• Record Type: Journal Article
• Authors: Ovadia, Reuben; Mondielli, Clémence; Vasseur, Jean‐Jacques; Baraguey, Carine; Alvarez, Karine
• Is Part Of: European journal of organic chemistry. Issue 3(2017)
• Page Start: 469
• Page End: 475
• Publication Date: 2016-12-30
• Subjects: Nucleotides -- Nucleosides -- Ribonucleosides -- RNA -- Amides -- Multicomponent reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601190
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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, paraformaldehyde, and N 4, 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. Abstract : An efficient, one‐step synthesis of chimeric PNA–RNA (PNA = peptide nucleic acid) dimers has been developed. This method, based on a Ugi reaction, gives rapid access to dimeric PNA–RNA building blocks with different sequences.