Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea

Hugo C. Ong, Steven C. Zimmerman

Research output: Contribution to journalArticlepeer-review

Abstract

UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligomerization of UG (Kassoc ∼ 230 M-1, CDCl 3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (>10-fold higher Kassoc for DeUG-DAN vs UG-DAN) but also dimerizes more strongly (Kdim = 880 ± 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.

Original languageEnglish (US)
Pages (from-to)1589-1592
Number of pages4
JournalOrganic Letters
Volume8
Issue number8
DOIs
StatePublished - Apr 13 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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