In this project, funded by the MPS-LEAPS (Launching Early-Career Academic Pathways) Program and The Chemistry of Life Processes (CLP) program in the Division of Chemistry (CHE) and managed by the Division of Chemistry (CHE), Professor Stack and his students at Providence College will study the chemical breakdown of azo-containing small molecules in the human gut. The trillions of microbes in the human gut can metabolize these compounds affecting their activity. However, the ongoing challenge is identifying which organisms and proteins are responsible and how quickly these transformations occur. Professor Stack and his students will examine the chemical requirements for bacterial enzymes and the hydrogen sulfide produced by bacteria to break the nitrogen-nitrogen double bond found in some drugs (such as sulfasalazine and phenazopyridine) and food dyes (like Red 40 and Yellow 4). This fundamental research could have potential broader impacts in future design of bioactive compounds with consideration of the influence of the gut microbiome. Additionally, this project provides undergraduate students with research opportunities through the work described above and by developing a Course-Based Research Experience in General Chemistry at Providence College. These experiences have potential to improve student retention in STEM fields and participation in scientific research. Professor Stack and his students will synthesize various azobenzene derivatives and evaluate their reduction