A Synthetic Supramolecular Receptor for the Hydrosulfide Anion. (11th August 2016)

• Record Type: Journal Article
• Authors: Hartle, Matthew D.; Hansen, Ryan J.; Tresca, Blakely W.; Prakel, Samuel S.; Zakharov, Lev N.; Haley, Michael M.; Pluth, Michael D.; Johnson, Darren W.
• Is Part Of: Angewandte Chemie. Volume 128:Number 38(2016)
• Page Start: 11652
• Page End: 11656
• Publication Date: 2016-08-11
• Subjects: Anionenbindung -- Gasotransmitter -- Molekulare Erkennung -- Sulfid -- Supramolekulare Chemie; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201605757
• Languages: English
• ISSNs: 0044-8249

Abstract

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.