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Arthur C. Cope Scholar Awards

by Carmen Drahl
February 25, 2008 | APPEARED IN VOLUME 86, ISSUE 8

Credit: Michael Rommel
Credit: Michael Rommel

In the four short years since Jeffrey W. Bode began his independent research career, his work has challenged convention in small-molecule and biomolecule synthesis. The potential applications of his strategies extend from materials to molecular biology.

Bode, 34, is an associate professor of chemistry at the University of Pennsylvania. According to Samuel H. Gellman, Ralph F. Hirschmann Professor of Chemistry at the University of Wisconsin, Madison, Bode "thinks about organic reactivity and the design of new reaction processes in a highly original and inspiring way." Colleagues praise Bode's work in two areas-new catalytic methods mediated by heterocycles and amide bond formation.

Amides play fundamental roles in chemistry, biology, and biomaterials. Bode sought to overcome limitations that hamper amide construction, such as excess reagents and unwanted by-products. According to Craig J. Hawker, director of the Materials Resource Laboratory and professor of chemistry, biochemistry, and materials at the University of California, Santa Barbara (UCSB), Bode's approach "is among the most significant and far-reaching discoveries in synthetic chemistry in the past decade."

Bode's method forges amide bonds between α-keto carboxylic acids and N-alkyl hydroxylamines. The reaction occurs selectively in the presence of amines and carboxylic acids, the traditional amide ligation partners. It proceeds in water without catalysts or other reagents, with by-products of water and carbon dioxide.

When chemically synthesizing large proteins, amide bond-making typically requires a cysteine at the end of one of the reaction partners. The new reaction may "lead to something peptide chemists have wanted for a while, which is ligating any two unprotected peptide fragments together," Bode says. Though more work is warranted, Bode's reaction potentially delivers that kind of versatility, according to Stephen B. H. Kent, professor of chemistry at the University of Chicago.

While thinking about better ways to make amides, Bode also explored organocatalysis. He transformed aldehydes into activated carboxylic acids poised for amide bond formation catalytically, with reactive species arising from nontoxic heterocycles. He also made other functional groups such as esters, lactones, and lactams from aldehydes in this way. Bode eventually extended this concept to carbon-carbon bond formation. His team recently achieved an enantioselective Diels-Alder reaction that employs an unusually small amount of the catalyst. That result "challenges the entrenched view" that organocatalytic processes require high catalyst loadings to be viable, Hawker says.

Bode first encountered chemistry through what he calls "a freak registration accident." Initially a philosophy major at Trinity University, he signed up for Michael P. Doyle's organic chemistry course to fill a vacant slot. Doyle encouraged creativity in class and in the lab, inspiring Bode to pursue chemistry. He earned bachelor's degrees in chemistry and philosophy at Trinity in 1996 and earned a doctorate of natural science in chemistry degree from the Swiss Federal Institute of Technology, Zurich, in 2001, where he worked for Erick M. Carreira. After a postdoctoral fellowship with Keisuke Suzuki at Tokyo Institute of Technology, in Japan, Bode accepted a faculty position at UCSB in 2003. In September 2007, he moved his group to the University of Pennsylvania.

Bode has received many prestigious awards, including the Beckman Young Investigator Award, the Research Corporation Cottrell Scholar Award, and the David & Lucille Packard Foundation Fellowship, all in 2006.



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