SAN FRANCISCO, CA--Using a specially prepared chemical "key," University of Delaware researchers have set the stage to unlock the secrets of five unique compounds derived from red sea algae, according to an April 14 presentation at the American Chemical Society meeting.
The marine-based compounds, known in research circles by the lengthy handle, "halogenated nonisoprenoid sesquiterpenes," might someday prove useful to pharmaceutical companies, says P. Andrew Evans, an assistant professor of chemistry at UD.
Evans says he hopes his work will inspire other researchers to identify a variety of practical uses for the structurally diverse compounds, by making them easier to synthesize in large quantities. The compounds currently have "undetermined biological activity," Evans says. "But," he adds, "this strategy will allow significant quantities of these agents to be prepared and assayed."
With graduate student Jamie D. Roseman, a recipient of the coveted ACS graduate fellowship sponsored by Rohm & Haas, Evans has thus far used the new technique to synthesize kumausallene (pronounced koo-MOW-sa-leen). The compound was first synthesized by Larry Overman, distinguished professor of chemistry at the University of California-Irvine, Evans notes.
The chemical key that makes kumausallene accessible to UD researchers is a "bicyclic lactone," an organic compound featuring a ring of atoms common to kumausallene and each of its family members.
Evans and Roseman first prepared the bicyclic lactone using technology pioneered at UD--a process based on a chemical species known as an acyl radical. The seven-step process converts an "optically active" substance (diol) into the lactone with a yield of roughly 60 percent. The lactone is then further manipulated to produce the natural product in a total of 15 steps, Evans reports. The synthesis involves introducing a component of kumausallene, bromoallene, in a "biomimetic" fashion, mimicking the way it would have been introduced in nature. Surprisingly, Evans says, "The bromoallene functionality is more robust than one would have thought."
In summary, "The bicyclic lactone allows us to access the entire family of these halogenated nonisoprenoid sesquiterpenes in an enantioselective and highly efficient manner," Evans says. "We think our process is a viable alternative to existing technologies."
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Ginger Pinholster / Beth Thomas
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ACS presentation information - P. Andrew Evans:
Moscone Center, Room 110, Exhibit Level
Monday, April 14, 1997, 9:40 a.m. (Pacific Time)