Light-Activated COS/H2S Donation from Photocaged Thiocarbamates

• DOI: 10.1021/acs.orglett.7b00808
• Publication Date: 2017-04-17T13:18:12Z
• Authors: Yu Zhao; Sarah G. Bolton; Michael D. Pluth
• Keywords: 01 natural sciences; 0104 chemical sciences

Hydrogen sulfide (H2S) is an important biomolecule, and responsive chemical tools for its delivery are needed. Here, we utilize the photocleavable o-nitrobenzyl group to unmask caged thiocarbamates and to access photoactivated H2S releasing molecules. These donors function by the initial release of carbonyl sulfide (COS), which is quickly hydrolyzed to H2S by carbonic anhydrase (CA). Our investigations demonstrate that o-nitrobenzyl-caged thiocarbamates can serve as a donor platform for the bio-orthogonal stimulated release of COS/H2S.