Last summer, when David Reilley was funded by the Koshland Integrated Natural Sciences Center to conduct research in William Lubell’s lab at the Université de Montréal in Quebec, he noted that the experience felt like “the capstone of his studies at Haverford.” So it was appropriate that, when he returned to campus, his actual capstone project—his senior thesis—was related to the work he did on that internship.
A chemistry major with a concentration in scientific computing, Reilley worked on the mechanism of cyclization of macrolactams, the building blocks of molecules that can function as proteins and are typically used in pharmaceuticals, in Lubell’s lab last summer, and learned that the professor had a computational obstacle. Inspired by an interest in organic chemistry and mechanisms, Reilley’s thesis, “A Computational Study of the Stereospecificity of the Lubell Method for the Synthesis of Azabicycloalkanone Amino Acids,” aimed to rectify that problem.
Reilley is now continuing his chemistry studies at the University of California, Los Angeles, where he is pursuing a Ph.D. and working in the lab of Dr. Anastassia Alexandrova.
How did your advisor help you develop your topic, conduct your research, or interpret your results?
My thesis advisor was [Associate Professor of Chemistry] Joshua Schrier. He is the only computational chemist in our department and tends to study problems in the area of materials chemistry. I was involved on a project in this area my first three years at Haverford College. However, I had thoroughly enjoyed the theory involved in my organic chemistry courses and wished to pursue computational research in that area. Josh helped me form a connection with Dr. William Lubell at the Université de Montréal who works in organic synthesis, but who had a computational problem. Since I have worked on the project, both of these professors have acted as my advisors in their respective subject areas. Josh has helped me consider what questions I should ask to challenge my hypotheses and navigate the new computational methods I used to do this, their implementation, and their use. Bill helped me better understand the underlying organic chemistry of the problem.
What are the implications for this research?
My thesis research will help the Lubell group in their syntheses of azabicycle-based drugs, making their syntheses more precise and effective at producing new compounds. Ultimately, this will help the lab in their goal of developing peptidomimetic drugs to treat conditions like pre-term labor. However, more work will need to be done on the project until these benefits will be seen.
“What They Learned” is a blog series exploring the thesis work of recent graduates.
Photo by Jim Roese