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The Synthesis of a Thymine Containing E-Olefinic Peptide Nucleic Acid (OPA) Monomer

Christopher D. Roberts, Rolf Schütz, Christian J. Leumann

Abstract

All articles of this category A monomeric unit of a conformationally constrained PNA analog, E -olefinic peptide nucleic acid ( E -OPA) containing the base thymine was synthesized in 14 steps. The key step involved a palladium (0) catalyzed cross-coupling reaction utilizing a Reformatsky reagent as nucleophile. A protecting group regime that is compatible with solid-phase PNA and DNA chemistries was chosen. OPA - PNA - Reformatsky - DNA-analog - antisense

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Key concepts: Chemistry, Peptide nucleic acid, Thymine, Nucleic acid, Monomer, Nucleic acid analogue, Nucleophile, Combinatorial chemistry