A Cyclopentane Conformational Restraint for a Peptide Nucleic Acid: Design, Asymmetric Synthesis, and Improved Binding Affinity to DNA and RNA

A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding properties were determined. The cyclopentane ring leads to a significant improvement in the binding properties of the resulting PNA to DNA and RNA.