Presentation description

Cyclic peptides are important scaffolds for the discovery and design of metabolically stable peptide therapeutics. Inspired by Nature's oxidative means of cyclizing peptides, the Roberts group recently developed a chemical method to cyclize tyrosine-containing peptides. The method can be applied to form bioactive cyclic peptides from simple to prepare acyclic peptides. To generalize the oxidative method, I developed electrochemical conditions based on research from Alvarez-Dorta and coworkers that are milder and more tolerant of oxidation-sensitive residues (e.g., cysteine, methionine, tryptophan). Using electrochemistry we gain the ability to tune the oxidation potential and reduce undesired side reactions. The electrochemical method also allows for a one-pot synthesis of cyclic peptides, which contrasts the chemical method that requires separate solvents for oxidation and cyclization events, increasing the sustainability and viability of these syntheses. We are using the developed methods to create cyclic antimicrobial peptides.