Jacobsen Reaches for the Stars in Chemistry

In the world of organic chemistry, few scientists have accomplished so much so fast as Professor of Chemistry Eric N. Jacobsen.

A specialist in organo-metallic catalysts, Jacobsen is best known among undergraduates for teaching Chemistry 20, "Organic Chemistry."

But he has also gained international acclaim by leading the first group to develop an epoxide-forming reaction. An epoxide is a ring-shaped organic molecule consisting of an oxygen atom and two carbon atoms bonded together.

This reaction occurs in living organisms only when the enzymes which perform the reaction are too slow and inefficient for laboratory usage, Jacobsen says.

Thus, Jacobsen's development allows scientists to use the catalyst in the lab, and is currently being used by drug companies like Merck to produce drug candidates to fight AIDS.

Jacobsen says most scientists marvel at how quickly we have learned about AIDS.

"Scientists are impressed that things have progressed as [fast] as they have," he says.

Scientists now understand most of the molecular mechanism of AIDS, although they have only known of the disease for about 15 years, Jacobsen says.

But the general public does not understand the rate of scientific advancement, he says, a problem he attributes to a failure to communicate on the part of scientists.

"The attitude has been, 'don't talk to us until we have an answer,'" he said, adding that public expectation might be more realistic if scientists were better at giving progress reports.

He says he believes chemists and biologists have not been as good as NASA at capturing the public's imagination.

"The closer we got to the moon during the Apollo missions, the more the public thought that anything was possible even though we weren't really landing on the moon," he says. "With AIDS, every step is just as exciting, though not as useful as the final answer."

Interest

Jacobsen says the most important element of his research is studying chemical reactions for their interest value alone.

He says genuine interest in the subject matter is directly responsible for the success of the Jacobsen Group. "When we started research, we started with the notion that we wanted to study interesting reactions," he says.

According to Jacobsen, maintaining interest in the research under study is the key to being productive.

"Many times, interesting things turn out to be useful," he says. When practicality is the only concern of research, Jacobsen says, there is a tendency to miss both that which is useful and that which is interesting.

Jacobsen points to the development of magnetic resonance imaging (MRI) as an example of interesting research that later led to important developments. MRI is the use of a nuclear magnetic resonance spectrometer to produce electronic images of human cells, tissues and organs.

MRI has become an important tool in the battle against cancer because the pictures produced by MRI help detect clusters of cancerous cells and tumors.

Jacobsen cites MRI as a classic example of a basic, fundamental research which has led to something practical and useful.

"This is a case where the scientists doing this research really had no idea what its practical applications would be," he said. It wasn't until later that people discovered the practical applications of MRI.

Jacobsen says MRI indicates the importance of doing research which is interesting although not necessarily practical.

"The connection between fundamental research and real-life applications isn't always obvious," he says. "What we've tried to do [in the Jacobsen Group] is develop very practical reactions from things that are interesting."

Catalysts

Although Jacobsen emphasizes the importance of studying chemical reactions for their interest value, it is practical research which marks the foundation of Jacobsen's career.

Much of his research focuses on the design and development of catalysts for industrial use. Catalysts are substances, usually used in small amounts relative to the starting materials, which increase the rate of a reaction without being consumed in the process.

Jacobsen says his main concern is the study of catalysts with chirality, or handedness. A catalyst with this quality is capable of distinguishing between molecules which are mirror images of each other in the same way that a person's left and right hand are mirror images.

A catalyst without this quality can only distinguish between two completely different molecules in the same way that a rubber ball feels differently into a hand or foot, but fits the same in the left or right hand.

The professor is currently working to synthesize new catalysts using combinatorial chemistry.

He said it took him and his group more than three years to produce about 200 epoxidation catalysts before finding a workable design for use in the epoxide-forming reaction. A Harvard postdoctoral researcher recently synthesized more than 1,200 simpler molecules in one week using the techniques of combinatorial chemistry, Jacobsen said.

He said combinatorial chemistry allows scientists to quickly produce every possible permutation of a catalyst with many interrelated components. The compounds form on microscopic "beads" and can be studied individually under a microscope.

"Combinatorial chemistry is a technique for studying molecules that completely changes the rules," Jacobsen says. He says he believes that the techniques of combinatorial chemistry hold great potential for organic chemists although he says they are still too immature for applied research.

Background

Jacobsen accepted a tenured position at Harvard in 1993, only seven years after receiving his doctorate from the University of California at Berkeley.

From 1986 to 1988, he worked as a postdoctoral fellow at the National Institutes of Health at MIT, before joining the faculty of the University of Illinois.

There, he won a number of awards for teaching and research, including the Dreyfus Teacher-Scholar award. He has also worked as a consultant for the Exxon Corporation, Sepracor and Ethyl Corporation.

Future

Jacobsen says he is also working on designing reaction which produce as little waste byproduct as possible.

"Traditionally, waste hasn't been a big issue in organic chemistry," he says. "A big question now is how to design reactions with as little waste as possible."

He points to environmental and economic considerations which have forced the elimination of waste to the forefront of chemistry.

Jacobsen says scientists must now be aware of the environmental consequences of disposing waste byproducts, as well as the rising costs associated with this disposal.

He recently designed a reaction in which salt water is the only byproduct, and he is currently developing a reaction in which 100 percent of the product is useful and no byproduct is produced.

Jacobsen says he foresees learning more about chemical relativity and selectivity during the rest of his career. He says he hopes that lifetime scientists will be able to understand chemical systems and predict whether a reaction or catalyst will work.

"There is still a tremendous element of luck associated with discovering reaction in organic chemistry," he says. "We're at an information gathering period. We've advanced to the point [in organic chemistry] where we know how much more there is to learn."