G--C quartet--a DNA-inspired Janus-GC heterocycle: synthesis, structural analysis, and self-organization

J Am Chem Soc. 2008 Oct 1;130(39):12860-1. doi: 10.1021/ja8047128. Epub 2008 Sep 4.

Abstract

In this communication we disclose the synthesis and characterization of a DNA-inspired self-complementary heterocycle that contains AAD-DAA H-bond acceptor/donor patterns. Whereas in the past such AAD-DAA self-complementarity has given rise to trimeric and hexameric rosettes, we now demonstrate that the same H-bonding scheme, when properly arrayed, can be used to program a tetrameric rosette, which unlike a G-quartet requires no metal binding or peripheral components for preorganization. Of note, we exploit both 2D-NOESY and DOSY 1H NMR to substantiate the tetrameric stoichiometry in this noncovalent rosette comprising 12 H-bonds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cytosine / analogs & derivatives*
  • Cytosine / chemical synthesis
  • DNA / chemistry*
  • Guanine / analogs & derivatives*
  • Guanine / chemical synthesis
  • Heterocyclic Compounds / chemical synthesis
  • Hydrogen Bonding
  • Nuclear Magnetic Resonance, Biomolecular / methods

Substances

  • Heterocyclic Compounds
  • Guanine
  • Cytosine
  • DNA