title: A cyclopentane conformational restraint for a peptide nucleic acid: design, asymmetric synthesis, and improved binding affinity to DNA and RNA.
abstract: [structure: see text] 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.
authors.affiliation: Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
authors.forename: Michael C
authors.initials: MC
authors.lastname: Myers
authors.forename: Mark A
authors.initials: MA
authors.lastname: Witschi
authors.forename: Nataliya V
authors.initials: NV
authors.lastname: Larionova
authors.forename: John M
authors.initials: JM
authors.lastname: Franck
authors.forename: Russell D
authors.initials: RD
authors.lastname: Haynes
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Hara
authors.forename: Andrzej
authors.initials: A
authors.lastname: Grajkowski
authors.forename: Daniel H
authors.initials: DH
authors.lastname: Appella
mesh_terms: D000478:Alkylation; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000378:metabolism*; D004247:DNA / Q000378:metabolism*; D015195:Drug Design; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000378:metabolism*; D012313:RNA / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D020135:Peptide Nucleic Acids; D012313:RNA; D004247:DNA