Bioactive natural products (also known as secondary metabolites) have an integral role in biology and ecology as well as modern drug discovery and medicine. The McKinnie lab is interested in understanding how natural products are biosynthesized by identifying and characterizing key enzymes involved in their construction. One particular enzyme family of interest is the vanadium-dependent haloperoxidases (VHPO); these enzymes catalyze the two-electron oxidation of aqueous halide ions to facilitate regio- and enantiospecific halogenation of organic substrates. Currently characterized actinobacterial VHPO homologs are involved in assembling the chemical scaffolds of a variety of meroterpenoid antibiotics with significant activities against multi-drug resistant bacterial pathogens. This seminar will highlight the chemical history of VHPO enzymes, give insight into the versatile range of chemical reactions catalyzed and variable distribution across biology, and suggest future directions towards their adaptation and evolution for chemoenzymatic syntheses.