mechanism | organic synthesis | chemical biology
Organosulfur Chemistry
Organosulfur compounds often engage in reactivity that defies the conventional intuition of organic chemists, making it good fun for the most adventurous of us - on top of being a fertile playground for new reactivity. Our group first became enamored by the magic of sulfur while studying the antioxidant activity of allicin, the origin of garlic’s characteristic odour. We have since pursued a variety of projects aimed at understanding the H-atom transfer activity of organosulfur compounds (some of which are among the most potent known) and radical substitution chemistry on polysulfide species, which has enabled synthetic method development and clarified the basis of their important antioxidant activity. We have also aimed to shed light on the various mechanisms by which thiols undergo oxidation, as this is key to the role of amino acid cysteine in protein structure/function and cell signaling.
Check out some representative work from our lab:
Photocatalytic C-S Bond Formation Using N-Thio and N-Perthio Phthalimide Derivatives
Hsin-Ju Huang, Zijun Wu & Derek A. Pratt*
ACS Catalysis 2023, 13, 13912-13919
Radical Approaches to C-S Bonds
Zijun Wu & Derek A. Pratt*
Nature Reviews Chemistry 2023, 7, 573-589
A Divergent Strategy for Site-Selective Radical Disulfuration
of Carboxylic Acids with Trisulfide-1,1-Dioxides
Zijun Wu & Derek A. Pratt*
Angewandte Chemie International Edition 2021, 60, 15598-15605
Radical Substitution on Tetrasulfides: A Unique Route to Disulfides
Zijun Wu & Derek A. Pratt*
Journal of the American Chemical Society 2020, 142, 10284-10290
The Hydrogen Atom Transfer Reactivity of Sulfinic Acids
Markus Griesser, Jean-Philippe R. Chauvin & Derek A. Pratt*
Chemical Science 2018, 9, 7218-7229
On the Mechanism of Thiol, Sulfenic and Sulfinic Acid Oxidation
by Hydrogen Peroxide
Jean-Philippe R. Chauvin & Derek A. Pratt*
Angewandte Chemie International Edition 2017, 56, 6255-6259
