title: Peptide Nucleic Acid with a Lysine Side Chain at the β-Position: Synthesis and Application for DNA Cleavage.
abstract: This paper reports the synthesis of new β-Lys peptide nucleic acid (PNA) monomers and their incorporation into a 10-residue PNA sequence. PNA containing β-Lys PNA units formed a stable hybrid duplex with DNA. However, incorporation of β-Lys PNA units caused destabilization of PNA-DNA duplexes to some extent. Electrostatic attractions between β-PNA and DNA could reduce this destabilization effect. Subsequently, bipyridine-conjugated β-Lys PNA was prepared and exhibited sequence selective cleavage of DNA. Based on the structures of the cleavage products and molecular modeling, we reasoned that bipyridine moiety locates within the minor groove of the PNA-DNA duplexes. The lysine side chain of β-PNA is a versatile handle for attaching various functional molecules.
authors.affiliation: Faculty of Pharmaceutical Sciences, Teikyo University.
authors.forename: Toru
authors.initials: T
authors.lastname: Sugiyama
authors.forename: Keiko
authors.initials: K
authors.lastname: Kuwata
authors.forename: Yasutada
authors.initials: Y
authors.lastname: Imamura
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Demizu
authors.forename: Masaaki
authors.initials: M
authors.lastname: Kurihara
authors.forename: Masashi
authors.initials: M
authors.lastname: Takano
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kittaka
mesh_terms: D053837:DNA Cleavage / Q000187:drug effects*; D008239:Lysine / Q000737:chemistry*; D008968:Molecular Conformation; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D020135:Peptide Nucleic Acids; D008239:Lysine