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Synthesis

2005 ACS National Award Winners

Recipients are honored for contributions of major significance to chemistry

January 31, 2005 | A version of this story appeared in Volume 83, Issue 5

Following is the fifth set of vignettes of recipients of awards administered by the American Chemical Society for 2005. C&EN will publish the vignettes of the remaining recipients in successive February issues. An article on George A. Olah, 2005 Priestley Medalist, is scheduled to appear in the March 14 issue of C&EN along with his award address.

Most of the award recipients will be honored at an awards ceremony, which will be held on Tuesday, March 15, in conjunction with the 229th ACS national meeting in San Diego. However, the Arthur C. Cope Scholar awardees will be honored at the 230th ACS national meeting in Washington, D.C., Aug. 28-Sept. 1.

Nakanishi Prize
Alfred Bader Award in Bioinorganic or Bioorganic Chemistry
Gabor A. Somorjai Award for Creative Research in Catalysis
National Fresenius Award
Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator
ACS Award in Organometallic Chemistry
ACS Award for Encouraging Women into Careers in the Chemical Sciences


Nakanishi Prize


Sponsored by the Nakanishi Prize Endowment

Benkovic
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Stephen J. Benkovic's accomplishments have had a profound impact on the way scientists think about how proteins function as catalysts. A colleague notes, "What is most impressive is the breadth of techniques and the freshness of his ideas--generated by his remarkable sense of which questions to ask--that continually place his work at the forefront of chemistry being done at the chemistry/biology interface."

Benkovic, 66, is Evan Pugh Professor and Eberly Chair in Chemistry at Pennsylvania State University. He received a bachelor's degree with concentrations in English literature and chemistry from Lehigh University in 1960 and a Ph.D. in organic chemistry from Cornell University in 1963. After a postdoctoral appointment at the University of California, Santa Barbara, he joined the faculty of Penn State in 1965.

His career began auspiciously with the joint authorship in 1966 of the now classic two-volume set of texts entitled "Bioorganic Mechanisms," which was the first authoritative review of this subject. From that time, Benkovic has pioneered numerous developments in the rapidly evolving field, changes that are reflected in his own work as it progressed from model studies for phosphate transfer through investigations of the mechanism of action of specific enzymes to the examination of complex, multifunctional enzyme assemblies and to efforts to create novel, biologically based catalysts.

In mechanistic enzymology, Benkovic has made ingenious use of transient kinetic techniques (and in doing so, establishing an experimental framework now widely practiced) to solve key biochemical puzzles and to provide deep insights into how enzymes function. His experiments are far from one-dimensional: They are enriched by challenging organic syntheses; by stereochemical analysis; by NMR monitoring of isotopically enriched substrates; and by recombinant techniques that include cloning, expression, and site-specific mutagenesis.

In the investigation of complex multiprotein assemblies, Benkovic is internationally recognized for his beautiful, clean, and painstaking reconstruction in vitro of the T4 replication machine. Benkovic and his colleagues have taken the eight separate proteins that constitute the T4 system and defined the pathway of how these separate proteins assemble through the use of ATP hydrolysis into the four units that carry out leading and lagging strand synthesis at a replication fork. The combination of methodologies is dazzling: time-independent and -dependent fluorescence energy transfer measurements, specific cross-linking through mutagenesis, ultracentrifugation, isothermal calorimetry, rapid quench kinetics, and unique DNA structures, to name a few.

In the embryonic field of protein-based catalyst development, Benkovic's work plays a key role in understanding the mode of action of catalytic antibodies and their relationship to enzymes. Recently, he and his group pioneered several novel approaches to catalytic design to overcome the limitations imposed by the antibody framework and to surpass the topological span explored by DNA shuffling. The recombination of gene-derived fragments from selected gene pairs promises a means for creating novel chimeric enzymes. These will be used to test a major interest of Benkovic's research--the relationship between enzyme conformational motion and catalysis.

The award address will be presented before the ACS Division of Organic Chemistry.--LINDA RABER

 

Alfred Bader Award in Bioinorganic or Bioorganic Chemistry


Sponsored by Alfred Bader

Like many child chemistry enthusiasts, curiosity trumped safety in Sir Alan R. Fersht's earliest experiments.

"When I was 11 years old, I saw an advertisement in the local newsagent's for chemical equipment, and my father bought me a box," he says. "In those days, the local chemist's shop stocked a wide range of chemicals--all the common acids, sulfur, phosphorus, organic and inorganic compounds. The chemist was not at all put out by a 12-year-old spending his pocket money on sulfuric acid and would allow me to search his shelves.

"I first did all of the simple experiments, such as making gases, heating iron filings with sulfur, and adding dilute acid to make H2S," he says. "This was rather tame, so I graduated to poisons and explosives. I read that Carl Scheele had died after making prussic acid from potassium ferrocyanide and dilute sulfuric acid, so I made some at the back of the garden, carefully. I did my first organic synthesis there as well: picric acid from nitric acid and phenol, as the French used it as a shell filling. The only near miss I had was from a rocket motor I made from a metal tube filled with potassium chlorate and sulfur; it exploded instead of propelling a truck. At that point, I had the sense to take up chess."

Fersht, 61, is Herchel Smith Professor of Organic Chemistry at Cambridge University and director of its Centre for Protein Engineering; he is also the first non-American to receive the Alfred Bader Award, being recognized for pioneering work that combined molecular biology and physical organic chemistry techniques to study enzymatic catalysis, protein folding, and protein stability.

Torn between physics and chemistry as an undergraduate, Fersht was taken with the physical organic chemistry research of Tony Kirby, one of his chemistry supervisors. "So I did my Ph.D. with him and never regretted it since," Fersht says. "It was like playing chess with chemistry: arguing logically from fundamental principles combined with leaps of the imagination to devise novel experiments."

Since then, Fersht has originated methods for studying transition states in biological processes, including analysis of how aminoacyl-tRNA synthetases use binding energy to catalyze their reactions and also achieve extreme specificity in amino acid binding. "It is not often one is presented with the opportunity to pioneer a new field," he says.

Fersht also introduced the use of site-directed mutagenesis to change protein structure for mechanistic study, and he is most proud of his work on *-value analysis, which allows scientists to reconstruct the transition states of proteins during folding. His subsequent work on the tumor suppressor p53 has led to promising insights into cancer and diseases of protein folding and unfolding.

Fersht received both a bachelor's degree in natural sciences (majoring in physical chemistry) in 1965 and a Ph.D. in organic chemistry in 1968 from Cambridge. After serving as a postdoctoral fellow at Brandeis University, he worked on the scientific staff for Cambridge's MRC Laboratory for Molecular Biology. In 1978, he started as a professor of biological chemistry at London College and then served briefly as a visiting professor at Stanford University. He returned to Cambridge in 1988.

The award address will be presented before the Division of Biological Chemistry.--AALOK MEHTA

 

Gabor A. Somorjai Award for Creative Research in Catalysis


Sponsored by the Gabor A. & Judith K. Somorjai Endowment Fund

Goodman
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Credit: PHOTO BY AMY LIU
Credit: PHOTO BY AMY LIU

 Ask D. Wayne Goodman about his interests and you have as much chance hearing about aviation as surface chemistry. "Ever since I can remember, I was interested in flying," says Goodman, who holds the Robert A. Welch Chair in chemistry at Texas A&M University.

In his grade-school days, Goodman befriended a crop duster, who gave the young boy flying lessons in exchange for helping with chores at the airport in Greenville, Miss. The friend also worked as a stunt pilot on weekends, and as Goodman recalls, "on Saturday mornings, he'd pick me up and we would fly aerobatics together."

Asked how he managed to convince his parents to let him tag along for the ride while the pilot flew stunt maneuvers, Goodman answers, "I don't believe they knew." But they probably would have been supportive because enthusiasm for flying runs through the family. For example, Goodman's father--now 83 years old--continues to work as a flying instructor and aerial photographer.

At age 59, the younger Goodman also continues to fly. But most of his time during the past four decades has been devoted to science. In 1968, Goodman graduated from Mississippi College in Clinton with a bachelor's degree in chemistry. Six years later, he earned a Ph.D. degree in physical chemistry from the University of Texas, Austin.

Goodman's keen interest in surface science was cultivated at the National Bureau of Standards (now the National Institute of Standards & Technology, NIST), where he served first as a postdoctoral associate and later as a staff scientist. Goodman notes that, while at NIST, he had the good fortune to work under the direction of two leading figures in surface science, both of whom are now professors of chemistry and physics. Some 25 years have passed since Goodman worked at NIST with John T. Yates Jr., now at the University of Pittsburgh, and Theodore E. Madey of Rutgers University, Piscataway, N.J., but Goodman continues to express great admiration and fondness for his mentors.

In 1980, Goodman accepted a position as a research scientist at Sandia National Laboratories, and from 1985 to 1988 he served as head of Sandia's Surface Science Division. In 1988, he moved to Texas when he was appointed professor of chemistry at Texas A&M.

With more than 400 scientific publications to his credit, Goodman's contributions to surface science cover a broad range of topics. Early in his career, he developed techniques that made it possible to combine measurements of high-pressure reaction kinetics and high-vacuum surface analysis. The studies, which are often cited as textbook examples, led to a fundamental understanding of the roles of carbidic and graphitic forms of carbon in surface catalysis.

Goodman has also elucidated basic mechanisms through which small quantities of impurities can serve as catalyst poisons or promoters. He has also been a leader in the study of bimetallic catalysts and in developing procedures for applying high-resolution electron energy-loss spectroscopy and infrared reflection-absorption spectroscopy.

Experts worldwide regard Goodman as a scientific trendsetter. As a recent example, Charles T. Campbell, a chemistry professor at the University of Washington, Seattle, points to Goodman's work on the size-dependent catalytic behavior of 2- to 3-nm gold particles. Campbell asserts that Goodman's studies "caught the attention of the surface-science community and led to an explosion" of research in that subject.

The award address will be presented before the Division of Colloid & Surface Chemistry.--MITCH JACOBY

 

National Fresenius Award


Sponsored by Phi Lambda Upsilon

Long
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Credit: PHOTO BY LIANNE M. C. BELTRAN
Credit: PHOTO BY LIANNE M. C. BELTRAN

Technological advances are often enabled by painstaking, systematic research in basic chemistry. In the positive sense of the word, Jeffrey R. Long, associate professor of chemistry at the University of California, Berkeley, is an enabler. His research focuses on developing rational and general methods for the synthesis of inorganic clusters and solids with targeted physical properties, and his work sets the foundations for the design on increasingly complex materials that function as catalysts; sensors; and electronic, magnetic, and computing components.

At the heart of Long's research lies a determination to refine and extend the basic principles of inorganic chemistry. His group is involved in establishing predictive solid-state reaction schemes, including an approach called dimensional reduction, which is a high-temperature method for dismantling binary solid frameworks. To help others use this method in the synthesis of new solids, Long and his coworkers have compiled a database of more than 3,000 structures that is available on the Internet. In addition, he has shown how this technique can be applied to cluster-containing solids, in which case the composition of the cluster core itself can even be used to manipulate framework connectivity.

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Long and his group have also shown how octahedral cluster units can be used to expand the crystal structures of simple coordination solids, such as the dye Prussian blue. The resulting materials present a series of stable microporous solids that behave as sieves, sensors, and ion-exchange materials. He has been working toward synthesis of a porous magnet capable of performing magnetic separations and sees further application in the generation of hydrogen storage materials. The Department of Energy also sees the potential and is funding Long's project.

Another area that attracted Long's attention is single-molecule magnets, and he has focused on developing rational approaches to their synthesis. Single-molecule magnets are unusual species that, because of a combination of properties, can reverse magnetization within individual clusters. They are of widespread interest for possible future use in high-density information storage and even quantum computing.

Although he joined the chemistry faculty at UC Berkeley in 1997, Long arrived at the department in 1996 as a postdoc in A. Paul Alivisatos' lab. Long made a lasting impression. "Long has a deep and genuine devotion to the discipline of solid-state inorganic chemistry," Alivisatos says. "His work on the synthesis of solids through dimensional reduction and cluster fusion leads to more systematic solid state synthesis. His work on designed cluster molecules with controlled magnetic properties shows great promise. He is making truly outstanding contributions to the subject, and he is highly valued for the quality of his scholarship. He is also much appreciated for his dedication and service to the community."

Long earned a B.A. in chemistry and mathematics from Cornell University in 1991, and he completed a Ph.D. at Harvard University in 1995.

He has received awards for both research and teaching; among them are a 1998 Research Corporation Research Innovation Award, a 1999 Hellman Family Faculty Award, a 2000 Camille Dreyfus Teacher-Scholar Award, a 2001-03 Alfred P. Sloan Research Fellowship, the 2002 Wilson Prize from Harvard, and a 2002 TR100 Award from MIT's Technology Review magazine.--ROBIN GIROUX

 

Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator


Sponsored by the Pfizer Endowment Fund

In a little over five years as an independent researcher, David W. C. MacMillan's impressive accomplishments have made him a leader in his field. MacMillan, a professor of chemistry at California Institute of Technology, has focused his work on the development of strategies for enantioselective catalysis using organic chemicals as reaction catalysts.


MacMillan

"The organocatalytic, asymmetric, carbon-carbon bond-forming reactions that MacMillan is developing are truly spectacular. They entail a fundamentally new design strategy, and the chemistry is eminently practical," says Larry E. Overman, a professor of chemistry at the University of California, Irvine. "I have never seen anyone accomplish in such a short time what he has."

MacMillan hypothesized that the reversible formation of iminium ions by *,ß-unsaturated aldehydes and amines might emulate the equilibrium dynamics inherent to Lewis acid catalysis. Thus, chiral amines might function as enantioselective catalysts for transformations that traditionally utilize metal salts. He first demonstrated the viability of this concept in 2000 by showing that amino-acid-derived imidazolidinones can function as highly enantioselective catalysts for the Diels-Alder reaction.

In 2002, MacMillan outlined the first general approach to asymmetric catalysis of the Diels-Alder reaction of ketone dienophiles, a long-standing goal in the field. His research group has now developed more than 20 asymmetric reactions using iminium catalysis.

Other accomplishments include the design and development of new Lewis-acid-catalyzed [3,3]-sigmatropic rearrangements. He was the first to recognize the role that Lewis acids play in the Claisen rearrangement and to use it for the enantioselective synthesis of complex acyclic units.

Also, he recently described a simple procedure that enables aryl trialkylammonium salts to function as electrophilic partners for Suzuki cross-coupling reactions. This nickel-catalyzed coupling sequence allows anilines that readily participate in organocatalytic Friedel-Crafts chemistry to be converted to substrates for transition-metal-catalyzed coupling sequences.

MacMillan is now investigating the use of these new asymmetric reaction technologies in the construction of molecules found throughout nature and pharmaceuticals. Current total synthesis targets include diazonamide A, littoralisone A, and callipeltoside A.

"I have been extraordinarily fortunate to work with an amazing group of coworkers," says MacMillan. "It is through their innovation and determination that we have been able to rapidly develop this chemistry. That being said, we still have an awful lot of work left to do."

MacMillan received a B.S. degree in chemistry from the University of Glasgow, Scotland, in 1991, and a Ph.D. from the University of California, Irvine, in 1996. He then went on to join UC Berkeley as an assistant professor in 1998 and was promoted to associate professor in 2000. He moved to Caltech in 2003 as a professor of chemistry.

His many honors include the GlaxoSmithKline Chemistry Scholar Award, the Michigan Distinguished Lecturer Award, the Cottrell Scholar Award, the Lilly New Investigator Award, the Bristol-Myers Squibb Award for Chemical Synthesis, and the Camille Dreyfus Teacher-Scholar Award.

The award address will be presented before the Division of Organic Chemistry.--MELISSA BRADDOCK

 

ACS Award in Organometallic Chemistry


Sponsored by Dow Chemical Co.

Jack R. Norton, 59, professor of chemistry at Columbia University, is best known for his work on the properties and reactions of transition-metal hydrides. It is work that has had a far-reaching impact on many of the most important processes in organometallic chemistry.

Norton's work on the kinetic and thermodynamic acidity of metal hydrides helped exploit the reactivity of metal hydrides as proton donors. He also carried out definitive studies of the kinetics of hydrogen atom transfer reactions of many of these same metal hydrides.

He has found examples of H+, H·, and H transfer processes and has studied how the rates of all three depend upon acidity (pKa), bond strength, and other thermodynamic parameters. He developed the first general procedure for measuring the pKa values of transition-metal hydrides and compared these thermodynamic acidities with the rates of proton transfer reaction of these hydrides.

He learned that metal acids behave much like carbon acids, with their proton transfer reactions proceeding slowly, owing to the requirement of substantial steric and electronic rearrangement.

Norton was among the first to demonstrate that the elimination of alkanes from some alkyl hydride complexes proceeds through a transient intermediate in which the alkane is coordinated to the transition metal. Such C–H complexes are pertinent to activation and functionalization of alkane C–H bonds by transition metals.

He provided early examples of cooperativity between metal centers in a cluster. Norton has used bimetallic systems to bridge the gap between homogenous and heterogeneous catalysts. He prepared a 1,2-dimetallacyclobutane and confirmed the prediction that ethylene elimination could not occur symmetrically.

One of his colleagues notes, "A hallmark of Norton's research is that he does not shy away from challenging problems. ... He is assiduous in seeking comprehensive explanations for how reactions work."

A Dallas native, Norton received a B.A. in chemistry from Harvard University in 1967 and a Ph.D. in chemistry from Stanford University in 1972. His first academic position was at Princeton University, where he was an assistant professor of chemistry from 1973 to 1979. He was an associate professor of chemistry and then a professor of chemistry at Colorado State University between 1979 and 1997. In 1997, he joined Columbia's faculty.

Norton has received a number of honors. In 1976, he was named a Dreyfus Foundation Teacher-Scholar. Between 1977 and 1981, he was an Alfred P. Sloan Fellow; in 1989, he became a Guggenheim Fellow; and in 1999, he became a fellow of the American Association for the Advancement of Science. He also received an Innovation Recognition Award from Union Carbide in 1985 and a Humboldt Research Award for Senior U.S. Scientists in 1993. In 1997, he received a Japan Society for the Promotion of Science Fellowship.

Norton was a member of the editorial advisory board for Organometallics between 1990 and 1994. He was treasurer of ACS's Division of Inorganic Chemistry between 1988 and 1991. From 1992 to April 2003, he served as an associate editor of the Journal of the American Chemical Society.

The award address will be presented before the Division of Inorganic Chemistry.--MARC S. REISCH

 

ACS Award for Encouraging Women into Careers in the Chemical Sciences


Richmond
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Credit: PHOTO BY JACK LIU
Credit: PHOTO BY JACK LIU

Sponsored by the Camille & Henry Dreyfus Foundation Inc.

Every morning, Geraldine L. Richmond, 52, wakes up around 4 AM and goes out for a 5- to 6-mile run in the dark. With darkness to block out distractions, Richmond's runs are when she thinks best. And Richmond keeps on thinking throughout the rest of her day. One of her ideas is the reason she is being honored.

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Richmond, the Richard M. & Patrice H. Noyes Professor of Chemistry at the University of Oregon, Eugene, saw the need to develop a program to help women trying to pursue chemistry careers. "I was increasingly concerned about the stories I was hearing from women chemists about their inability to achieve their goals at the level that they were seeing their male colleagues achieve them," says Richmond.

One day, Richmond heard a neighbor talking about her group of senior-level women in computer information science. The group met periodically and discussed how to advance women in their field. Richmond thought such a group would be perfect for chemistry. In 1998, the Committee on the Advancement of Women Chemists (COACh) was born.

COACh provides skills development workshops; research on gender issues; consulting services; and coaching, mentoring, and networking activities for women chemists at all levels in their careers. The program has now expanded into other fields including physics, math, computer science, and biology.

The success of COACh has Richmond both "thrilled to death" and stunned. "I'm stunned because what it demonstrates is the overwhelming need for the kind of programs that COACh is developing--far beyond what I initially anticipated."

Richmond does consider herself a role model to some extent, but she doesn't think she's "the recipe for how be a successful woman chemist." She thinks everyone should take pieces and parts from different role models to create a personalized one. "I just think I have some pieces and parts that have worked that other women might find helpful."

One of those "pieces and parts" is to consider alternatives to current standards of developing a career. In her own career, Richmond has been able to make her family a priority while also running a successful lab specializing in the structure and reactivity of complex surfaces and interfaces.

In 1975, Richmond received a B.S. in chemistry from Kansas State University. After graduating in 1980 with her Ph.D. in physical chemistry from the University of California, Berkeley, Richmond began her academic career at Bryn Mawr College, in Pennsylvania, as an assistant professor. She has been at the University of Oregon since 1985.

Throughout her career, Richmond has received several awards for her work on behalf of women, including the ACS Women Chemists Committee Contributions to Diversity Award (2002), Soroptimist International's Women Helping Women Award (1998), the National Science Foundation's ADVANCE Leadership Award (2001-03), and the Presidential Award for Excellence in Science & Engineering Mentoring (1997).

While Richmond is excited to receive the ACS award, she believes the award also honors the women around her who have given her energy and support. "I really stand on the shoulders of all those women who make me look good," she says. Some of those women include former students from Bryn Mawr and Oregon; the women in COACh; and her mother, Lucille.

The award address will be presented before the Division of Chemical Education.--RACHEL SHEREMETA PEPLING

 

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