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William Miles, professor and head of chemistry, received a $5,000 grant from Bristol-Myers Squibb Company to support student research.
The project supported by the grant was started this spring by April Pui-In Tang ’08 (Yuen Long N.T., Hong Kong), who is pursuing a B.S. chemistry and A.B. with a major in French. The grant also will support her work this summer.
“April is looking at the addition of reagents to gamma-hydroxybutenolides that will give compounds useful in the synthesis of antibiotic compounds. There are four possible products, with subtle but important differences in their molecular structure, in her reaction,” explains Miles. “Her goal is to find the reaction conditions that will give exclusive formation of one of the products. April has already made significant progress toward this goal. She also has to determine the identity of the compounds, which is a non-trivial task since the possibilities are so similar.”
For the past two years, Miles and his students have been investigating the stereoselective reactions of gamma-hydroxybutenolides, or the chemical transformation of gamma-hydroxybutenolides into new organic compounds with control of the three-dimensional structure of the resulting product.
Their initial study in this area, “Diastereoselective Addition of Organotitanium Reagents to Chiral Gamma-Hydroxybutenolides,” will soon be published in the journal Heterocyclic Communications.
Several of Miles’ students researched and contributed to the article, including biochemistry majors Daniela Duca ’09 (Chisinau, Moldova), Jaryd Freedman ’08 (Ambler, Pa.), and Elliot Goodzeit ’08 (Princeton, N.J.), and Chiquita Palha De Sousa ’08 (Harare, Zimbabwe), who is pursing a B.S. biology and A.B. with a major in art.
Biochemistry graduate Kristin Hamman ’07 and chemistry graduate Brandon Selfridge ’05 also assisted with the research.
The researchers use gamma-hydroxybutenolides as starting materials for other compounds, particularly antibiotic compounds. Miles explains that gamma-hydroxybutenolides are readily available compounds, but there have only been a few synthetic studies devoted to their use in organic chemistry.
Miles believes the grant allows the chemistry department to continue with its goal to expose students to scientific research.
“The Bristol-Myers Squibb Undergraduate Awards in Organic Chemistry is a wonderful program supporting undergraduate research in organic chemistry. The department of chemistry is very appreciative of Bristol-Myers Squibb support, since we feel programs like this further one of our most important goals: the involvement of Lafayette undergraduates in meaningful and significant research,” says Miles.
Though this is the first time Miles has received a grant from Bristol-Myers Squibb, chemistry students have received numerous other awards and opportunities.
“The chemistry department is proud of the number of students involved in our research program and the truly remarkable number of student co-authors on papers appearing in the best journals in chemistry,” he says. “The undergraduate research experience at Lafayette has helped our students be competitive for the most prestigious awards in science, such as the Goldwater Scholarship and National Science Foundation Pre-doctoral Fellowship, and have helped them with their pursuit for a Ph. D. in graduate programs at Harvard, Yale, Michigan, and Wisconsin; medical school; or careers in industry.”
Miles has published his research in 29 academic journal articles, given 21 presentations at scientific meetings, and participated in a dozen research seminars. He previously received three grants from the American Chemical Society and one from the National Science Foundation – for which he served as co-principal investigator with other Lafayette professors – that provided equipment for undergraduate laboratories. The Organic Division of the American Chemical Society honored him with a travel award, and he is a past recipient of the Marquis Distinguished Teaching Award.
He has served as a reviewer for Journal of the American Chemical Society, Organometallics,and several other journals since 1986. He has been a member of the Sigma Xi honor society for scientific and engineering research since 1994. He also belongs to the American Chemical Society and Council on Undergraduate Research. He was a member of the program committee and chairman of the Organic Division for the 24th Middle Atlantic Regional ACS Meeting.
Miles has been faculty adviser to Lafayette’s student chapter of the American Chemical Society since 1996.
He earned his Ph.D. in organic chemistry from the University of Wisconsin-Madison and a B. S. with distinction in chemistry from University of Delaware.
As a national leader in undergraduate research, Lafayette sends one of the largest contingents to the National Conference on Undergraduate Research each year. Twenty-one students have been accepted to present their research at this year’s conference.