Hetero-Selective DNA-Like Duplex Stabilized by Donor-Acceptor Interactions

Tetsuya Doi, Takumi Sakakibara, Hiromu Kashida, Yasuyuki Araki, Takehiko Wada, Hiroyuki Asanuma

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)15974-15980
Number of pages7
JournalChemistry - A European Journal
Issue number45
Publication statusPublished - 2015 Nov 1


  • DNA structures
  • charge transfer
  • donor-acceptor systems
  • helical structures
  • pi interactions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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