Students Synthesize Newly-Discovered Molecule
Professor Robin Kinnel has recently discovered the chemical compound dichlorobouillonamide, which is released by a cyanobacteria in the Lyngbya family. The chemical has never been studied in depth, and it is possible that dichlorobouillonamide has potential applications in pain treatment. This summer Aaron Danilack ’13 and Jeffrey “Miles” Blackburn ’13 are working with Kinnel, the Silas D. Childs Professor of Chemistry Emeritus and Lecturer in Environmental Studies, to carry out a laboratory synthesis of dichlorobouillonamide.
Danilack’s and Blackburn’s summer research was funded through the Edward and Virginia Taylor Fund for Student/Faculty Research in Chemistry, established in 2008 through a gift from Ted ’46 and Virginia to inspire students interested in chemical research and to facilitate their work with outstanding faculty.
The cyanobacteria that creates dichlorobouillonamide grows naturally at the Palmyra Atoll, southwest of Hawaii, and can also be grown in culture. Professor Kinnel believes that the compound may be bioactive and potentially useful in medicine. While he does not believe that the compound is applicable to cancer treatment, its structure is similar to compounds that have cannabinomimetic activity and may have potential to aid medical researchers interested in treating pain.
To test dichlorobouillonamide for its possible uses, there is a need for a larger sample of the chemical, which presently is available only in submilligram quantities and would be difficult and tedious to obtain from the original cyanobacterium. Furthermore, some features of the structure are still somewhat ambiguous, so Danilack and Blackburn are attempting to synthesize the molecule in the lab.
The project consists of connecting several building blocks through a series of chemical reactions. With compounds as elaborate as dichlorobouillonamide, the process can be intricate and slow. Each piece of the molecule is put together in a specific order, and certain elements of the structure must be protected while others are attached or removed. Furthermore, the results of each step can be difficult to interpret because unwanted side reactions can introduce contaminants into the sample.
Danilack and Blackburn are each responsible for synthesizing half of the molecule, and they hope that ultimately it will be possible to join the two completed halves without difficulty. Though they have a general outline of reactions to complete, the students frequently try running the same reaction in different ways to see which method gives the best yields. They rely on Hamilton’s NMR instrument to show how their results are structured and LC-MS chromatography techniques to separate products from solution. So far, Blackburn and Danilack have obtained some promising results, but they believe that the overall synthesis is too complex to complete over the summer, and they expect another group to finish the project at a later time.
Danilack, a chemistry major with a mathematics minor, says that he enjoyed his organic chemistry courses at Hamilton, and was looking forward to doing research in that area over the summer. He finds the project interesting despite the occasional setbacks, and he says that he is learning a lot from working with Professor Kinnel. In his free time, Danilack plays for the club ice hockey team.
Blackburn, majoring in math and chemistry, was interested in the potential biological implications that this project might have. He is considering attending graduate school after Hamilton, and he enjoys gaining lab experience through his summer work. Outside the lab Blackburn is a member of the Hamilton track team and he is looking forward to working at the Quantitative Literacy Center as a chemistry and mathematics tutor.
Jeffrey Blackburn is a graduate of Milbrook High School (N.Y.) Aaron Danilack is a graduate of Crestwood High School in Mountaintop, Pa.