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A Synthetic Supramolecular Receptor for the Hydrosulfide Anion.

  • Author(s): Hartle, Matthew D;
  • Hansen, Ryan J;
  • Tresca, Blakely W;
  • Prakel, Samuel S;
  • Zakharov, Lev N;
  • Haley, Michael M;
  • Pluth, Michael D;
  • Johnson, Darren W
  • et al.
Abstract

Hydrogen sulfide (H2 S) has emerged as a crucial biomolecule in physiology and cellular signaling. Key challenges associated with developing new chemical tools for understanding the biological roles of H2 S include developing platforms that enable reversible binding of this important biomolecule. The first synthetic small molecule receptor for the hydrosulfide anion, HS(-) , using only reversible, hydrogen-bonding interactions in a series of bis(ethynylaniline) derivatives, is reported. Binding constants of up to 90 300±8700 m(-1) were obtained in MeCN. The fundamental science of reversible sulfide binding, in this case featuring a key CH⋅⋅⋅S hydrogen bond, will expand the possibility for discovery of sulfide protein targets and molecular recognition agents.

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