Peptide Nucleic Acid with a Lysine Side Chain at the β-Position: Synthesis and Application for DNA Cleavage

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  • Sugiyama Toru
    Faculty of Pharmaceutical Sciences, Teikyo University
  • Kuwata Keiko
    Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University
  • Imamura Yasutada
    Faculty of Engineering, Kogakuin University
  • Demizu Yosuke
    Division of Organic Chemistry, National Institute of Health Sciences, Ministry of Health and Welfare
  • Kurihara Masaaki
    Division of Organic Chemistry, National Institute of Health Sciences, Ministry of Health and Welfare
  • Takano Masashi
    Faculty of Pharmaceutical Sciences, Teikyo University
  • Kittaka Atsushi
    Faculty of Pharmaceutical Sciences, Teikyo University

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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.

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