Abstract:

Teixobactin is a cyclodepsipeptide natural product with excellent antibiotic activity against drug-resistant bacterial pathogens, and its unique mechanism of action appears to preclude the development of antibiotic resistance. But what is a “cyclodepsipeptide,” and how do we advance teixobactin from an interesting natural product to a clinically viable antibiotic drug? In this talk, I will discuss fundamental principles in peptide chemistry and how those principles influence the creative molecular design of new antibiotic molecules. This includes the development of “swapmer” antibiotics inspired by, but structurally dissimilar to, teixobactin, and structure-activity relationship studies of the related antibiotic clovibactin. Time permitting, I will also discuss an education research project in which an undergraduate Learning Assistant program was implemented in non-chemistry major organic chemistry laboratory courses for the first time at UC Irvine to address the lack of hands-on experience among students during COVID-19 teaching disruptions.