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Our research program applies chemical probes and mass spectrometry-based proteomics to investigate and perturb protein activities in complex proteomes. In particular, we focus on understanding the role of cysteine-mediated protein activities in cancer and degenerative diseases associated with aging. These activities comprise proteases, oxidoreductases and metabolic enzymes that rely on cysteine residues for catalysis and regulation. Functional cysteine residues demonstrate heightened reactivity relative to non-functional cysteines, and are sensitive to a myriad of oxidative protein modifications that serve to regulate protein activity in vivo. In cancer and age-related degenerative diseases, the cellular redox homeostasis is severely disrupted and the resulting oxidative stress can have dramatic consequences on cysteine-mediated protein activities. Through a multidisciplinary approach that encompasses aspects of synthetic chemistry, cell biology, proteomics and mass spectrometry, we will investigate the dysregulation of cysteine-mediated protein activities to identify therapeutic targets and small-molecule drug-leads for the diagnosis and treatment of diseases such as cancer.