Use of Dithiasuccinoyl-Caged Amines Enables COS/H₂ S Release Lacking Electrophilic Byproducts.

ABSTRACT: The enzymatic conversion of carbonyl sulfide (COS) to hydrogen sulfide (H₂ S) by carbonic anhydrase has been used to develop self-immolating thiocarbamates as COS-based H₂ S donors to further elucidate the impact of reactive sulfur species in biology. The high modularity of this approach has provided a library of COS-based H₂ S donors that can be activated by specific stimuli. A common limitation, however, is that many such donors result in the formation of an electrophilic quinone methide byproduct during donor activation. As a mild alternative, we demonstrate here that dithiasuccinoyl groups can function as COS/H₂ S donor motifs, and that these groups release two equivalents of COS/H₂ S and uncage an amine payload under physiological

SUBMITTER: Cerda MM 

PROVIDER: S-EPMC7182478 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature