CAREER: Fostering Innovative Scientists Through Development of Biomimetic Catalysts for Discovery of New Medicines.

Bowdoin College, Brunswick ME

Investigators

Abstract

Life is one of the most powerful forces shaping our planet. Thus, mimicking the molecules of life (one of the NSF "Grand Challenges" for 21st century science) presents an opportunity to controllably harness this power to benefit humanity. Currently, many medicines are adaptations of molecules produced by living organisms. By constructing artificial analogs of the enzymes that Nature uses to build molecules, new potential medicines may be discovered. In this project, Dr. Gorske is developing enzyme mimics to accomplish this goal. The design of these enzyme mimics is allowing undergraduates to construct them with minimal training. This is enabling students to gain experience conducting meaningful research prior to choosing a major. Such early access to these research experiences, which include both summer research internships and course-related laboratories, is stimulating interest in pursuing science as a career. Especially, underprepared and underrepresented students and groups are being exposed to STEM fields. In the process, students are contributing directly to the development of new technology for facilitating the discovery of urgently needed medicines. With support from the Chemical Catalysis Program of the Chemistry Division, Dr. Gorske of Bowdoin College is developing biomimetic catalysts for nucleophilic trifluoromethylations that deliver enantiopure alpha-trifluoromethyl alcohol and beta-trifluoromethyl carbonyl subunits for construction of new biological probes and medicines. These studies are elucidating the structural design parameters of peptidomimetic catalysts that maintain their competency in polar solvents and facilitate nucleophilic trifluoromethylation reactions. In turn, the results of these investigations are informing iterative cycles of catalyst design and structure-activity relationship analysis that aim to produce highly enantio- and regio-selective nucleophilic trifluoromethylation catalysts with wide substrate scope. More broadly, a new class of structured catalyst scaffolds designed to be generally applicable to a wide range of reactions is being realized, while simultaneously providing early but authentic research experiences for undergraduates. These experiences are specifically designed to enhance learning outcomes and enthusiasm for pursuit of STEM careers, especially among members of underrepresented groups in STEM fields that are identified through partnerships with both internal and local external organizations. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.