title: Hetero-Selective DNA-Like Duplex Stabilized by Donor-Acceptor Interactions.
abstract: We report on the characterization of a novel hetero-selective DNA-like duplex of pyrene and anthraquinone pseudo base pairs. The pyrene/anthraquinone pairs showed excellent selectivity in hetero-recognition and even trimers were found to form a hetero-duplex. Pyrene and anthraquinone moieties were tethered on acyclic D-threoninol linkers and linked to adjacent residues by using standard phosphoramidite chemistry. When pyrene and anthraquinone were incorporated at pairing positions in complementary strands of natural DNA oligonucleotides, the duplex was stabilized significantly. Moreover, a pyrene hexamer and an anthraquinone hexamer formed a stable artificial hetero-duplex without the assistance of natural base pairs. The pyrene/anthraquinone pair was so stable that even trimers formed a hetero-duplex under conditions in which natural DNA strands of three residues do not.
authors.affiliation: Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603 (Japan).
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Doi
authors.affiliation: Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603 (Japan).
authors.forename: Takumi
authors.initials: T
authors.lastname: Sakakibara
authors.affiliation: Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603 (Japan).|PRESTO (Japan) Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012 (Japan).
authors.forename: Hiromu
authors.initials: H
authors.lastname: Kashida
authors.affiliation: Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai 980-8577 (Japan).
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Araki
authors.affiliation: Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai 980-8577 (Japan).
authors.forename: Takehiko
authors.initials: T
authors.lastname: Wada
authors.affiliation: Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603 (Japan). asanuma@mol.nagoya-u.ac.jp.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Asanuma
mesh_terms: D000880:Anthraquinones / Q000737:chemistry*; D020029:Base Pairing; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D009690:Nucleic Acid Conformation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry* / Q000378:metabolism; D009841:Oligonucleotides / Q000737:chemistry* / Q000378:metabolism; D011721:Pyrenes / Q000737:chemistry*
chemical_list: D000880:Anthraquinones; D009692:Nucleic Acid Heteroduplexes; D009841:Oligonucleotides; D011721:Pyrenes; D004247:DNA
keywords: DNA structures; charge transfer; donor-acceptor systems; helical structures; pi interactions