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ACS Award For Creative Work In Fluorine Chemistry

by Stephen K. Ritter
January 21, 2013 | A version of this story appeared in Volume 91, Issue 3

Ojima
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Credit: Courtesy of Iwao Ojima
Photo of State University of New York, Stony Brook, professor Iwao Ojima.
Credit: Courtesy of Iwao Ojima

Sponsored by Honeywell

Fluorine’s versatility as a substituent in bioactive compounds is legend—strategic placement of fluorine improves the bioavailability, metabolic stability, and efficacy of many drugs. One chemist to thank for that is State University of New York, Stony Brook, professor Iwao Ojima.

“Ojima is a pioneer in bridging the gap between fluorine chemistry and medicinal chemistry and establishing an essential interdisciplinary field,” comments medicinal fluorine chemist Robert Filler, an emeritus professor at Illinois Institute of Technology. “A hallmark of Ojima’s contributions is his deft and creative use of fluorine as a key marker to open new vistas in medicinal research.”

Ojima has a long list of chemical firsts to his credit. “In the early 1980s, his seminal application of transition-metal catalysis for functionalizing readily available fluorinated alkenes and arenes led to the synthesis of fluorinated amino acids and heterocycles,” notes John T. Welch, a fluorine chemist at the State University of New York, Albany. These methods were timely inventions that spurred interest in incorporating the fluorinated compounds into biologically active peptides and proteins, Welch says.

For example, Ojima invented a process to synthesize 5-trifluoromethyluracil via palladium-catalyzed reactions. The process was commercialized to produce the antiviral drug trifluridine, which is used to treat herpesvirus, in particular in eye infections. He also developed fluorinated versions of captopril, an angiotensin-converting enzyme inhibitor used to treat high blood pressure, as well as fluorinated enkephalins, which are analgesic brain peptides.

Another first was the synthesis of fluorinated taxoids, which are derivatives of the cancer drug Taxol. His group used these compounds as molecular probes to identify bioactive conformations of Taxol and taxoids via 19F nuclear magnetic resonance spectroscopy. The fluorinated taxoids have been used as “warheads” in tumor-targeting drug delivery systems.

Ojima received B.S. (1968), M.S. (1970), and Ph.D. (1973) degrees, all from the University of Tokyo. After a decade of research at Sagami Institute of Chemical Research in Japan, Ojima joined the faculty at Stony Brook in 1983. He was the founding director of and continues to lead the university’s Institute of Chemical Biology & Drug Discovery.

Ojima has mentored nearly 300 graduate students, postdoctoral researchers, undergraduates, and high school students. He has also served in editorial capacities for numerous journals, served on National Institutes of Health and National Science Foundation committees and review panels, chaired an array of scientific conferences, and served as a consultant for several chemical and pharmaceutical companies.

Among his career awards, Ojima received an Arthur C. Cope Scholar Award in 1994 and the E. B. Hershberg Award for Important Discoveries in Medicinally Active Substances in 2001, both from ACS. He received the Chemical Society of Japan Award in 1999 and was named a fellow of the John Simon Guggenheim Memorial Foundation in 1995, the American Association for the Advancement of Science in 1997, and the New York Academy of Sciences in 2000. In addition, Ojima was inducted into the ACS Division of Medicinal Chemistry Hall of Fame in 2006 and named an ACS Fellow in 2010.

Ojima will present the award address before the ACS Division of Fluorine Chemistry.

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