Basic tool for making organic molecules wins chemistry Nobel

Three researchers get prize for methods used to make drugs, electronics, plastics

The 2010 Nobel Prize in chemistry goes to one American- and two Japanese-born scientists for devising means for spurring extraordinarily useful and efficient reactions that coax carbon-containing molecules to bond with each other. The reactions are some of the most widely used in chemistry, yielding plastics, better light-emitting diodes for computer screens, and numerous medications, including drugs for fighting cancer, asthma and HIV.

Three chemists win for developing palladium-catalyzed reactions that combine carbon atoms. Univ. of Delaware; Purdue Univ; Hokkaido Univ.

Three scientists will share the prize: Richard Heck, who retired in 1989 from the University of Delaware in Newark, Ei-ichi Negishi of Purdue University in West Lafayette, Ind., and Akira Suzuki, of Hokkaido University in Sapporo, Japan.

“This is fundamental carbon chemistry at its best,” says Joseph Francisco, also of Purdue and president of the American Chemical Society in Washington, D.C.

All three scientists figured out ways to make chemical reactions go by using the metal palladium as a hand-holder to connect and disconnect particular atoms with speed and efficiency, and often under mild conditions. Generally known as palladium-catalyzed cross-coupling reactions, different versions of the reactions already bear the names of each Nobel winner and are familiar to organic chemistry students, as well as to those in industry and academia. The Heck reaction, for example, is a key step in making steroids, strychnine and the herbicide prosulfuron.

The research that led to the prizes began back in the 1950s and is now part of the standard toolkit of chemists, says synthetic chemist Jeremy Berg, director of the National Institute of General Medical Sciences in Bethesda, Md.

“This is textbook stuff, it’s really part of the fabric of organic chemistry,” says Berg. “It was a very active area when it began, but that was just the tip of the iceberg.”

Carbon-carbon bonds are stable, strong and plentiful. That means trying to connect two specific carbon atoms, each held in its own elaborate molecule, can be difficult.

Enter palladium, the coordinator of who will partner up with whom. The metal elegantly connects carbon compounds with little waste. Such palladium-employing reactions have proven useful for mimicking the complex molecules found in nature, such as discodermolide, first isolated from a sponge in the Caribbean Sea and now being explored as a cancer drug.

In a more basic application, the Suzuki reaction was used in 1994 to make palytoxin, a naturally occurring poison and a spectacularly large compound that is considered one of synthetic chemistry’s crowning achievements. The enormous molecule comprises 129 carbon atoms, 223 hydrogen atoms, three nitrogen atoms and 54 oxygen atoms.

Negishi, speaking at an October 6 press conference, said there is no one molecule that stands out as particularly special in his career. “My research goal,” he said, “is to be able to synthesize any molecule in the best possible way.”

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