A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition

Taiho Park, Eric M. Todd, Shoji Nakashima, Steven C. Zimmerman

Research output: Contribution to journalArticle

Abstract

An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (Kassoc ≈ 5 × 107 M-1) for the UG·DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (Kdimer < 10 M-1) and UG (Kdimer ca. 200-300 M-1) means that the UG·DAN complex forms with unparalleled fidelity.

Original languageEnglish (US)
Pages (from-to)18133-18142
Number of pages10
JournalJournal of the American Chemical Society
Volume127
Issue number51
DOIs
StatePublished - Dec 28 2005

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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