2006 ACS National Awards Winners

Following is the final set of vignettes of recipients of awards administered by the American Chemical Society for 2006. An article on Paul S. Anderson, 2006 Priestley Medalist, is scheduled to appear in the March 27 issue of C&EN, along with his award address.

Peter G. Schultz, winner of the Arthur C. Cope Award, and most other national award winners will be honored at an awards ceremony that will be held on Tuesday, March 28, in conjunction with the 231st ACS national meeting in Atlanta. The Arthur C. Cope Scholar awardees will be honored at the 232nd ACS national meeting in San Francisco, Sept. 10-14.

The Cope Award recognizes and encourages excellence in organic chemistry; it consists of a medal, a cash prize of $25,000, and an unrestricted research grant of $150,000 to be assigned by the recipient to any university or research institution. Each Cope Scholar Award consists of $5,000, a certificate, and an unrestricted research grant of $40,000. Arthur C. Cope and Arthur C. Cope Scholar Awards are sponsored by the Arthur C. Cope Fund.

Arthur C. Cope Award

Peter G. Schultz has been called "the most creative and insightful organic chemist of his generation." Because of the range of his discoveries and potential contributions to medicine and biology, he is "truly one of the most outstanding chemists of our time," says Peter B. Dervan, professor of chemistry at California Institute of Technology. "His work exemplifies the tremendous opportunities at the interface of chemistry and biology," explains Jonathan A. Ellman, chemistry professor at the University of California, Berkeley.

In recent years, one of Schultz's primary contributions has been the development of technology that enables the systematic expansion of the genetic codes of living organisms to include unnatural amino acids. Another has been his discovery that small molecules can be used to control stem cell proliferation, differentiation, and dedifferentiation. These molecules will likely provide new insights into stem cell biology and may eventually contribute to medicines for tissue repair and regeneration.

Early in his career, Schultz, along with Richard A. Lerner, created the field of antibody catalysis. They demonstrated that antibodies could be used to selectively catalyze chemical reactions. Schultz also pioneered the field of combinatorial materials science. He developed a new approach for the parallel synthesis, processing, and screening of large libraries of solid-state inorganic and organic materials for new properties. His methods have resulted in the discovery of novel magnetoresistive, luminescent, and ferroelectric materials.

Schultz is the Scripps Family Professor of Chemistry at Scripps Research Institute and director of the Genomics Institute of the Novartis Research Foundation (GNF), both in La Jolla, Calif. Born in Cincinnati, Ohio, in 1956, he received a B.S. in chemistry in 1979 and a Ph.D. in organic chemistry in 1984 from Caltech. After a year of postdoctoral work at Massachusetts Institute of Technology, he joined the chemistry faculty at the University of California, Berkeley, where he became full professor in 1989. He became a principal investigator at Lawrence Berkeley National Laboratory in 1985 and a member of Howard Hughes Medical Institute in 1994. In 1999, Schultz moved to Scripps Research Institute and also founded GNF, now one of the major functional genomics institutes, with about 500 employees. Initially, what convinced Schultz to specialize in chemistry was the "terrific" freshman chemistry course at Caltech taught by David A. Evans, who is now at Harvard University.

In addition, Schultz has founded seven technology companies-Affymax Research Institute to search for new drugs; Symyx Technologies to develop advanced materials; and Syrrx, Kalypsys, Phenomix, Ambrx, and Ilypsa to develop small and macromolecular drugs for cancer, metabolic diseases, and inflammation. He finds it satisfying to combine basic research with preclinical drug discovery efforts.

For years, scientists have created peptides with unnatural amino acids in the lab, but Schultz was the first to find a way to get organisms to add an unnatural amino acid to their genetic codes. This allows the organisms to mass-produce proteins with unnatural amino acids. With rare exceptions, all known forms of life use the same common 20 amino acids to make proteins. Schultz and his colleagues have made organisms with 21 or more amino acids. They have genetically encoded more than 30 unnatural amino acids-including glycosylated, photoreactive, chemically reactive, fluorescent, and metal-binding amino acids-in bacteria, yeast, and mammalian cells.

"In nature, there are 20 amino acids in the genetic code," Schultz says. "The question is, 'Why 20? What would we look like if God had worked on the seventh day?' The question we are trying to get at is 'What would life have looked like and would it be more evolvable if it had more building blocks?' "

Ambrx is using this technology to create new drugs. It is introducing unnatural amino acids into human growth hormone, interferons, and various antibodies. An Investigational New Drug Application on one of these drugs will probably be filed with the Food & Drug Administration this year, Schultz says.

Another of Schultz's recent breakthroughs was the discovery of a synthetic small molecule-reversine-that can turn differentiated cells into progenitor cells (C&EN, Jan. 5, 2004, page 9). Reversine reverts mouse myoblast cells into multipotent progenitor cells that can differentiate into a variety of cells-fat, bone, muscle, or cartilage. Schultz and his coworkers are now looking for molecules that cause dedifferentiation in other cell types.

Eventually, molecules like reversine could be used to produce progenitor cells to use in place of stem cells in regenerative medicine-generating new tissue for human therapy.

A further advance made by Schultz's group was the identification of small molecules that differentiate stem cells, both embryonic and adult, into specific cell lines called lineages. "This research has generated a lot of interest and excitement in the stem cell community because it's probably one of the most straightforward ways to translate stem cell biology into human therapeutics," Schultz says.

Throughout his career, Schultz has trained many successful academics. Altogether, he has had about 300 coworkers and roughly 50 of them now have university positions. Some examples are UC Berkeley's Ellman, Thomas Scanlan and Kevan M. Shokat at UC San Francisco, Linda Hsieh-Wilson at Caltech, David R. Liu and Nathanael S. Gray at Harvard, Alice Y. Ting and Stuart S. Licht at MIT, and Floyd Romesberg and Sheng Ding at Scripps. "Having had the opportunity to work with some of the best people in science is probably the most rewarding part of this job," Schultz says.

Schultz has received numerous awards including the National Science Foundation Alan T. Waterman Award (1988), the ACS Award in Pure Chemistry (1990), the UC Berkeley College of Chemistry Teaching Award (1992), the Wolf Prize in Chemistry (1994), the ACS Alfred Bader Award in Bioorganic Chemistry (2000), and the Paul Ehrlich & Ludwig Darmstaedter Award (2002). He is a member of the National Academy of Sciences and the Institute of Medicine.

Outside his very busy and productive work life, Schultz enjoys boating, fishing, scuba diving, surfing, and racquetball.-Bette Hileman

Arthur C. Cope Scholar Awards

Eric V. Anslyn chose to pursue a career in chemistry at an unusual stage in his academic studies-during his first semester of medical school. "I went to medical school for two weeks," Anslyn recalls, "but those two weeks were enough to convince me that I should be a chemist."

But then Anslyn is a go-kart racer, so a quick route change of this sort probably felt natural to him. Now, 24 years and more than 130 publications later, it's clear that Anslyn, 45, took the right road.

Currently the Norman Hackerman Professor of Chemistry at the University of Texas, Austin, Anslyn is recognized as a world leader in sensor design using principles of supramolecular chemistry. He has also pioneered the field of differential sensing techniques. Dennis A. Dougherty, a chemistry professor at California Institute of Technology who coauthored the textbook "Modern Physical Organic Chemistry" with Anslyn, calls him one of the brightest, most creative organic chemists of his generation.

Taking such praise in stride, Anslyn explains that his chemical research basically boils down to taking physically oriented topics and applying them to organic chemistry. It's an approach that has interested him since his graduate school days at Caltech. Working in Robert H. Grubbs's lab, Anslyn did mechanistic and theoretical studies of olefin metathesis and ring-opening metathesis.

Since moving to UT in 1989, Anslyn has used his organic and physical chemistry know-how to marry supramolecular chemistry and pattern recognition. As a result, Anslyn has created sensors based on molecular recognition that can make in situ chemical measurements in complex environments such as blood, saliva, and wine. In one specific example, Anslyn quantified tannic acids in Scotch whiskies. He was able to correlate the concentration of these compounds with the potables' age.

"Although the use of synthetic receptors in sensing applications has been explored for decades, Anslyn has set a high bar for contemporary work in the area," notes Stephen F. Martin, Anslyn's colleague at UT. "His work established a new standard for the supramolecular community for sensor creation."

In collaboration with his UT colleagues John T. McDevitt, Dean P. Neikirk, and Jason B. Shear, Anslyn is developing an electronic taste chip (C&EN, Jan. 30, page 37). "Much of the inspiration for how our sensors work comes from how our senses of taste and smell operate," he says.

Anslyn's pioneering work with indicator displacement assays (IDA) for sensor creation is now routinely used in laboratories around the world. Whereas many sensors require a chromophore or fluorophore to be covalently incorporated into a receptor, Anslyn's sensors simply self-assemble when the indicators and receptors are mixed.

Martin points out that Anslyn recently introduced an IDA method for enantioselective sensing. The technique displays different colors for enantiomers of common organic functional groups. The method has drawn much interest from the pharmaceutical industry, where it could be used in high-throughput screening.

"Anslyn has shown that the recognition principles he has developed can be translated to sensors that could actually be used in the real world, as evidenced by his extensive list of patents," Dougherty says. "I can think of no other chemist in America who has so successfully merged scholarly research with goals that are relevant to the real world."

Martin adds, "His discoveries, which are already beginning to have far-reaching effects, set the standards for excellence and creativity in the sensing community."-Bethany Halford

Robert K. Boeckman Jr. remembers standing in the quad at Pittsburgh's Carnegie Institute of Technology as a freshman, soaking up the campus atmosphere. The life of a professor must be great, he thought. After all, they only teach three hours a week.

Now Marshall D. Gates Jr. Professor of Chemistry and chairman of the chemistry department at the University of Rochester, Boeckman long ago learned the truth about the rigors of academia. "But by then I was so enthralled with science that I would have worked for free," he says.

Boeckman's passion is for organic chemistry, where in his research, he applies the principles and analytical skills of physical organic chemistry to synthetic problems. "His efforts have always attempted to incorporate tests of physical principles and theory in order to provide deeper insights into the design and implementation of stereocontrolled synthetic reactions," says Steven M. Weinreb, professor of chemistry at Pennsylvania State University. "He brings an innovative and creative touch to the art of organic synthesis."

The total synthesis of complex natural products is where Boeckman has made his most significant contributions, notes Rick L. Danheiser, professor of chemistry at Massachusetts Institute of Technology. "In this research, Boeckman has defined the scope and limitations of the field and demonstrated new strategic approaches to several important classes of naturally occurring molecules," Danheiser says. "On a number of occasions, his lab was the first to complete the total synthesis of a formidable target attracting the interest of a number of research groups around the world."

Boeckman picks problems where conformational analysis can play an important role in the solution. "Many compounds I've synthesized have medium-sized rings with seven to 10 atoms," he says. "Modern conformational theory helps us to understand the spatial relationships and unique reactivity of functional groups in medium rings."

Among Boeckman's notable achievements are syntheses of the eremantholides, a group of natural products with antitumor activity. The compounds have a complex architecture with a highly functionalized 10-membered ring. Another remarkable accomplishment was synthesis of the antibiotic pleuromutilin, whose unique structure includes a single carbon common to three rings, through a novel application of the anionic oxy-Cope rearrangement. Boeckman's group has just submitted for publication its tetronolide synthesis, the second total synthesis of this structurally complex aglycon of the tetrocarcins, a group of related spirotetronate antitumor agents.

Recently, Boeckman and his coworkers have been developing chiral auxiliaries and ligands derived from camphor. "We tailor the molecules so we can use them to control specific stereochemical relationships in a target," he says. "The next stage is to employ these molecules as controllers of chirality in a catalytic sense."

Boeckman, 61, graduated from Carnegie Tech (now Carnegie Mellon University) in 1966. He obtained his Ph.D. from Brandeis University in 1971, working with James B. Hendrickson. Boeckman went on to a National Institutes of Health postdoctoral fellowship at Columbia University with Gilbert Stork, then joined Wayne State University in Detroit as an assistant professor in 1972. After rising through the ranks at Wayne State, he moved to Rochester in 1980. Boeckman has given more than 150 invited lectures and seminars since 1990 and is a consultant to a number of pharmaceutical companies. He is an associate editor of the Journal of Organic Chemistry.

In addition to chemistry, Boeckman has a passion for sports. He is an avid golfer and plays in an adult table tennis league. He and his wife, Mary H. Delton, who is also a Ph.D. organic chemist, breed horses, one of which was a reserve national champion.-Pamela Zurer

Since the late 1960s, the laboratory of Franklin A. Davis, now a professor of chemistry at Temple University, in Philadelphia, has been a focal point for the design and synthesis of new organic reagents. He has focused on the chemistry of lesser known combinations of functionalities and on bringing these reactions to a level of practical utility for the synthetic organic community.

Davis' most acclaimed work has been the development of the chemistry of N-sulfonyloxaziridines, now known as Davis reagents. This class of reagents oxidizes enolates to α-hydroxy carbonyl compounds, sulfides and selenides to the corresponding oxides, and organometallic reagents to the corresponding alcohols. Through the use of these reagents, highly enantioselective syntheses of homoisoflavanones and several anthracycline antitumor antibiotics were achieved in the Davis laboratory. Because of their aprotic nature and high selectivity, the reagents are finding wide use and are principally responsible for the more than 750 citations of Davis' work in the past five years.

A key area of research for Davis, 66, has concerned the chemistry of sulfinyl amide and sulfinyl imine derivatives. "Much of what is known about the fundamental chemistry of these functionalities was learned in his early studies," says colleague K. Barry Sharpless, a professor of chemistry at Scripps Research Institute. Particularly important in his early work was the silver-assisted synthesis of N-sulfinyl imines, now considered the most general route to these materials.

More recently, Davis took advantage of chirality at sulfur and at sulfur-substituted carbon centers to develop asymmetric versions of his reagents and synthetic intermediates. His group was the first to introduce the use of N-sulfinyl imines as chiral building blocks for the asymmetric synthesis of the amine derivatives found in many bioactive materials. This provided a general solution to the problem of adding organometallic reagents to chiral imines.

Also important is Davis' work in fluorine chemistry, where he devised reagents capable of selectively inserting a fluorine atom via site-specific fluorination of carbanions and enolates. Using these reagents, his team developed general methodology for enantioselective synthesis of α-fluorocarbonyl compounds, important building blocks for the asymmetric synthesis of pharmacologically active compounds such as fluorosugars.

After earning a B.S. in chemistry at the University of Wisconsin, Madison, Davis went on to Syracuse University, in New York, where he was awarded a Ph.D. in organic chemistry in 1966. He did postdoctoral work at the University of Texas, Austin, before moving to Drexel University, in Philadelphia, as an assistant professor in 1968. At Drexel, he rose to become the George S. Sasin Professor of Organic Chemistry. He moved on to Temple in 1995.

In addition to his research and teaching work, Davis has served as national program chair (1988-91), chairman (1994), and councilor (1999-2002, 2003-06) of the ACS Division of Organic Chemistry, where he continues to serve on the executive committee. He has also served on the editorial boards of Organic Letters and the Journal of Phosphorus, Sulfur & Silicon.

Davis chaired the 1998 Gordon Conference on Stereochemistry and was appointed to a four-year term on the NIH Medicinal Chemistry Study Section. In addition to numerous reviews and book chapters, he has written approximately 215 research papers.-MELISSA KUHNELL

Michael P. Doyle, professor of chemistry and chair of the department of chemistry and biochemistry at the University of Maryland, College Park, achieved his top position in organic chemistry through groundbreaking research and outstanding professional leadership. His accomplishments, combined with his service to the chemistry community, make him one of the discipline's most prolific contributors.

Doyle discovered and developed chiral dirhodium(II) carboxamidate catalysts, which bear his name, and directed their applications in diverse metal carbene and Lewis acid transformations that are characterized by exceptional stereocontrol and high turnover numbers.

Doyle's logical development of chemo-, regio-, and diastereoselective metal carbene transformations is a model for catalyst development. His most recent work provides catalytic metal carbene reactions that produce intramolecular ring formations and carbon-hydrogen insertions that routinely provide products with greater than 90% enantioenrichment.

He has also contributed practical organosilane reductions, in situ arenediazonium ion generation and processes, and basic understanding of nitric oxide and nitrite reactions with metalloproteins. Most recently, he has been working in the area of catalytic asymmetric synthesis.

Doyle's development of asymmetric macrocyclization methodology is particularly notable. His development of asymmetric ylide chemistry using chiral catalysts is opening a new methodology that has been recently applied to biologically important compounds. His work with asymmetric hetero Diels-Alder reactions is of notable utility, and his catalysts are produced commercially.

In addition to the impact his research has had for its own sake, his work has had an important influence on the development of the more than 130 undergraduate coauthors on his papers. More than 90% of his undergraduate coauthors have gone on to obtain advanced degrees in chemistry or medicine; more than 50 have Ph.D.s or M.D./Ph.D.s. His work in educating students was recognized by the ACS George C. Pimentel Award in Chemical Education in 2002.

Doyle, 63, received a bachelor's degree in chemistry at the College of St. Thomas, St. Paul, Minn., in 1964, and a Ph.D. from Iowa State University, Ames, in 1968. After a year as a postdoc and instructor at the University of Illinois, Chicago Circle, he joined the faculty at Hope College, Holland, Mich. In 1984, he went to Trinity University, San Antonio, where he was D. D. R. Semmes Distinguished Professor of Chemistry.

Doyle joined Research Corporation as vice president in 1997 and served as president in 2002. While there, he held a joint appointment as a professor in the department of chemistry at the University of Arizona, Tucson. He joined the University of Maryland faculty in 2003.

A member of the ACS Council since 1990, Doyle has served on various ACS committees, including stints as chair of the Joint Board-Council Committee on Publications, the C&EN Editorial Board, and the Membership Affairs Committee.

Among his other awards are the ACS Award for Research at Undergraduate Institutions (1988), the ACS Northeastern Section James Flack Norris Award for Outstanding Achievements in the Teaching of Chemistry (1995), and the ACS Division of Organic Chemistry Paul G. Gassman Distinguished Service Award (1998).-LINDA RABER

Shu Kobayashi, a professor in the graduate school of pharmaceutical sciences at the University of Tokyo, is widely acclaimed for his work on using water instead of organic solvents in organic reactions. His contributions have opened the door to new areas of research and are finding applications in green chemistry.

"My work is important for two basic reasons," Kobayashi says. "It has environmentally friendly applications, and it advances our understanding of enzymatic reactions in water."

Kobayashi started the formal study of water's potential as a solvent in 1991, when he became a lecturer at the Science University of Tokyo-a small institution, Kobayashi says-at the comparatively young age of 32. He explains that because he was in a private university, his position allowed him to engage in independent research, something that most academics in Japan cannot officially undertake until a later stage in their career.

Kobayashi had observed that the human body does not require organic solvents to accomplish enzymatic reactions. It was therefore likely, he surmised, that enzymatic reactions could be conducted in water in the lab.

Kobayashi and his group then achieved a world first: They used Lewis acids as catalysts in water reactions. The trick was to use as Lewis acids rare-earth metal compounds that were, in contrast with other Lewis acids, unlikely to decompose in water. The rare-earth compounds used were metal trifluoromethanesulfonates, also called triflates.

Major advantages of Kobayashi's metal triflates are that only a small quantity is enough for the reaction and that they can be recovered and reused. This is unusual as Lewis acids had been known to deactivate when hydrolyzed. Moreover, until Kobayashi's discoveries, more than stoichiometric amounts of Lewis acids such as titanium tetrachloride, tin tetrachloride, and aluminum trichloride were required for promoting the reactions.

For organic reactions in water, low solubility and low stability of substrates and reagents can be serious problems. To address this issue, Kobayashi also developed surfactant-type catalysts that react efficiently in water.

The discoveries made by Kobayashi have inspired others. There have so far been more than 600 reports published about rare-earth metal triflates. Industry is also showing much interest in their potential for green production processes.

Pharmaceutical producers and materials makers are the most likely industries to implement his discoveries commercially, Kobayashi says. But he is not sure how far along industry is in making use of his work because corporate labs tend not to reveal exactly what they're working on.

His research in another area, the immobilization of catalysts, is more obviously finding favor with companies commercializing green chemical products. Wako Pure Chemical and Strem Chemicals have launched microencapsulated osmium tetroxide, a material he developed. Osmium tetroxide is a useful but toxic catalyst. With Kobayashi's microencapsulation technique, it can be easily removed after the reaction. Kobayashi has also microencapsulated and incarcerated several polymer-supported catalysts such as scandium, osmium tetroxide, palladium, and ruthenium.

Kobayashi is also noted for his work in asymmetric catalysis. He was the first person to demonstrate catalytic asymmetric Mannich and aza Diels-Alder reactions. Later, he developed highly efficient asymmetric carbon-carbon bond-forming reactions in aqueous media.

Over the past few years, Kobayashi has been awarded prestigious prizes. Last year, he won the Japan Society for the Promotion of Science Award. Also in 2005, along with Harvard University chemistry professor Eric N. Jacobsen, he won the Mitsui Chemicals Catalysis Science Award. In 2001, he won the IBM Science Award.

Kobayashi is an advisory board member of the journal Chemical Reviews and was from 1999 to 2003 an associate editor of the Journal of Combinatorial Chemistry, for which he remains a consulting editor.-Jean-François Tremblay

From his group's research lab at the University of Toronto, where he is AstraZeneca Professor of Organic Synthesis and NSERC/Merck Frosst Industrial Research Chair, Mark Lautens goes about his acclaimed work that spans the fields of organic synthesis, asymmetric catalysis, and organometallic chemistry.

Canadian-born Lautens, 46, has won numerous awards for using metals as catalysts to prepare new molecular structures that have valuable biological activity. He has been recognized by the Natural Sciences & Engineering Research Council (NSERC) as an E. W. R. Steacie Fellow; by the Canadian Society for Chemistry as an R. U. Lemieux & Alfred Bader Award winner; and by the Royal Society of Canada, which elected him as a fellow and awarded him the Rutherford Memorial Medal.

Lautens holds a B.S. in chemistry from the University of Guelph, in Ontario, and a Ph.D. in chemistry from the University of Wisconsin, Madison. He came to Toronto after postdoctoral studies at Harvard University.

Two of Lautens' key discoveries, says a colleague, have allowed the preparation of high-value-added compounds for the pharmaceutical industry: the identification of oxabicyclics as a simple starting material for complex molecule synthesis and the development of unique catalytic reactions of such systems.

The colleague says Lautens' efficient carbometallation chemistry has applications to the synthesis of bioactive molecules. He adds that Lautens' recent work involving catalytic, enantioselective carbometallation reactions (with Sheldon Hiebert and Jean-Luc Renaud) is the culmination of visionary thinking shared by only a few groups years ago. Now, this field has flourished "to become a theme central to synthetic chemistry. The reaction methods [Lautens] has developed stand singularly as the best in their class and as one of the classics of asymmetric catalysis," explains the colleague.

Stephen L. Buchwald, professor of chemistry at Massachusetts Institute of Technology, points out Lautens' "sensational work on the asymmetric ring-opening reactions of cyclic ethers" as one of the most important of all Lautens' contributions. It began with Lautens' work, in conjunction with Tomislav Rovis (now on the faculty at Colorado State University), on the Ni-BINAP-catalyzed reductive ring opening of oxacycloheptenes and oxanorbornadienes.

A pivotal discovery, with Keith Fagnou (now on the faculty at the University of Ottawa, in Ontario), was asymmetric desymmetrization utilizing alcohols, amines, and carboxylates. It has led to rapid access to enantiomerically pure substituted hydronaphthalenes, which are important to the pharmaceutical industry. Commercialization of this chemistry is under way by Solvias AG.

Buchwald cites the "elegant" desymmetrization process as one of the reasons Lautens has become viewed as one of the top synthetic organic chemists in the world. Lautens' total synthesis of the polyether antibiotic ionomycin was, according to Buchwald, "a beautiful demonstration" of the utility of desymmetrization. Other applications include syntheses of Zoloft, an antidepressant marketed by Pfizer, and of a family of diaminohydronaphthalenes as potential agents to treat pain.

Lautens mentors a group of 22 to 26 coworkers each year. An energetic speaker with more than 240 lectures to his credit, he has also produced more than 170 published papers. His current research interests include investigations into new synthetic methods using multicomponent couplings and the synthesis of both natural products and pharmaceutically important molecules.-Deanna Miller

At age 13, Lanny S. Liebeskind fell in love. "I always had a passion for chemistry, and my parents were very helpful in setting up a full lab in my basement, with a Bunsen burner and everything," he says. "It is amazing that I didn't burn the house down."

As a professor in the chemistry department and director of science strategies at Emory University, in Atlanta, Liebeskind encourages his students to be curious. And he warns against scheduling too many meetings. "What's really very important is having unstressful time to think and to read." He has found time around 4 AM.

Liebeskind, 55, is "one of the top practitioners in the world in this field," says Stephen L. Buchwald, a chemistry professor at Massachusetts Institute of Technology. "The novelty of Liebeskind's work serves to differentiate it from most others in organic synthesis using transition metals," Buchwald says. "Furthermore, he has not shied away from working with highly functionalized compounds."

Many of his organometallic discoveries have found applications in medicinal chemistry. For example, early in Liebeskind's career, he "devised an ingenious route to quinines employing the combination of maleoyl- and phthaloylmetal complexes with alkenes," which he later used for synthesizing the antitumor antibiotic (+/-) nanomycin A and a natural product called royleanone, explains Buchwald.

Then Liebeskind became interested in cross-coupling chemistry, part of which became a classic paper by Vittorio Farina and Liebeskind on the copper-enhanced rate of Stille couplings.

His interest in coupling expanded to relevant processes in bioorganometallic chemistry. "He has established a new concept for the formation of carbon-carbon bonds," notes Buchwald. Liebeskind discovered the first-generation coupling of thiol esters with boronic acids under neutral reaction conditions.

"Liebeskind has also undertaken the design and development of easily prepared, enantiomerically pure molybdenum π-complexes of unsaturated oxygen and nitrogen heterocycles," which can have medicinal value," Buchwald adds.

"His approach is very insightful, grounded in a firm understanding of organic and metal-based reactivity," says Gregory C. Fu, also a professor at MIT.

That grounding likely came from spending as much time in the snow as in the South. Raised in Buffalo, Liebeskind graduated from the State University of New York, Buffalo, with a B.S. in chemistry in 1972. He received a Ph.D. in 1976 from the University of Rochester, where he worked with Andrew S. Kende. He spent a year at MIT as a National Science Foundation postdoctoral fellow and a year at Stanford University as a National Institutes of Health postdoctoral fellow, both in the laboratories of K. Barry Sharpless.

In 1978, Liebeskind became an assistant professor at Florida State University. He was promoted to associate professor in 1983 and left for Emory in 1985. In 1988, he was awarded the Samuel Candler Dobbs Chair in Chemistry. He chaired the department from 1996 to 2000. In addition, he consults with Johnson & Johnson and Janssen Pharmaceuticals.

He chaired the NIH Medicinal Chemistry Study Group for two years and has served as an associate editor of Organometallics for the past 16 years. He was a member of the advisory board for the ACS Petroleum Research Fund.

Liebeskind also likes ballroom dancing with his wife, whom he married three months after they met 26 years ago.-Rachel Petkewich

The golden age of chemistry sets had come and gone by the time Brian M. Stoltz was old enough to express an interest in chemists' favorite childhood toy. But that didn't stop the budding scientist, now 35, from mixing up some creative concoctions anyway. Mrs. Stoltz gave young Brian free rein over her spice rack, and he says that combining baking soda, vinegar, and various herbs and spices into a "dark, smoking, smelly mess" never lost its allure.

Now an associate chemistry professor at California Institute of Technology, Stoltz still finds himself drawn to synthetic chemistry. These days, however, Stoltz's syntheses are notable for their elegance, rather than their odor. In fact, colleagues have recognized Stoltz with a Cope Award "for his development of highly original methods for the synthesis of chiral organic molecules and multistep routes for the synthesis of several complex bioactive natural products."

Kitchen chemistry aside, Stoltz says his interest in organic synthesis was sparked during his undergraduate studies at Indiana University of Pennsylvania in Indiana, Pa. In particular, he credits his undergraduate chemistry professor for igniting his interest in synthesis. "It was a type of problem-solving that really was a perfect fit for me," Stoltz recalls. "I was very interested in nonmathematical types of puzzles. Yet there was plenty of room to be creative.

"Synthesis is a lot of design and creation," he adds. "Chemistry is really unique in the sciences. So much of science is observational. But in synthetic chemistry, you can make new things. Physicists can't make a new planet."

But chemistry wasn't the sole focus of Stoltz's undergraduate studies. He also majored in German. Stoltz made the most of his dual interests by doing an internship with Bayer in Leverkusen, Germany; the experience, he says, ultimately cemented his decision to be a chemist. Stoltz also devoted some of his time in Germany to one of his nonscientific passions, baseball. Playing third base, he led one of the local teams on to victory at the Bavarian championships.

As a graduate student, Stoltz's aptitude for organic synthesis quickly became apparent. In John L. Wood's lab at Yale University, Stoltz developed a concise total synthesis of the protein kinase C inhibitors staurosporine and K252a. He then worked as a National Institutes of Health postdoctoral research fellow with E. J. Corey at Harvard University. There, Stoltz accomplished the first total synthesis of the nicandrenones, a class of complex, bioactive natural products.

"All through his graduate and postdoctoral years, Stoltz had a record of generating brilliant ideas leading to important innovations in synthetic methodologies," Corey notes. "Stoltz is everything that one would like to see in a young synthetic chemist venturing into the next millennium."

Stoltz has also made remarkable contributions to the field of organic synthesis in the five years he's headed his own laboratory at Caltech. Corey points out that "his development of a highly enantioselective method for the Pd-catalyzed aerobic chemical oxidation to effect kinetic resolution of racemic secondary alcohols represents a remarkable advance not only as a method, but because of the beautiful demonstration of reaction mechanism."

Larry E. Overman, a chemistry professor at the University of California, Irvine, also points out Stoltz's natural talent as a research mentor. "I have had the opportunity to get to know several of his graduate and postdoctoral coworkers," Overman says. "The striking feature they share is their unabashed excitement about chemistry."-BETHANY HALFORD

Five years ago, when F. Dean Toste applied for a postdoc position in Robert G. Bergman's laboratory at the University of California, Berkeley, he didn't get the job. His recommendations from the likes of Stanford University's Barry M. Trost, developer of the synthesis efficiency framework known as "atom economy," were, in Bergman's words, "off the charts." "But at the time," laments Bergman, "I didn't have the money."

Toste didn't end up in the street. He was snatched by California Institute of Technology's Robert H. Grubbs, the metathesis pioneer who was fated to become a cowinner of the 2005 Nobel Prize in Chemistry for his pioneering work in that versatile strategy of molecule making. In the summer of 2002, Bergman and his Berkeley colleagues finally got what they wanted: They hired Toste as an assistant professor specializing in organic chemistry.

"His research has gotten off to a faster start than almost anyone else we have ever had on our organic chemistry staff," says Bergman. "He is clearly on the fast track to becoming one of the leaders in organic chemistry in his generation, and his work will have an enormous impact on synthetic organic chemistry and the companies that utilize it, such as those in the pharmaceutical industry."

Toste is known for the development of rhenium-based metal-oxo complexes that can catalyze a variety of reactions under unusually mild and convenient conditions that require fewer steps, yield one enantiomer or the other, and produce environmentally more benign by-products, such as water, compared with other synthetic routes for achieving the same products. He also has been extending the boundaries of gold-catalyzed reactions, including ones that introduce ring structures or rearrange existing ones. As an unintended nod to the namesake of the award he is receiving this year from ACS, Arthur C. Cope, some of Toste's cationic gold complexes can catalyze Cope rearrangements, in which multiple double bonds in a structure shift places, a fundamental step for creating many specific structures. Only 34 years old and at the start of his career, Toste has reported this portfolio of research in nearly 50 papers in major chemistry journals.

For Toste, the joy of chemistry is in discovering new reactivity and new types of chemical transformation. "This gives you opportunities to put new molecules together in ways you hadn't done before," he says. And that, he adds, is perhaps the only way to eke out more from the periodic table, whose ingredients are the basis for every chemical or material thing that can be.

Superimposed on this search for new reactivity and his quest to understand reaction mechanisms, a pair of interests that he attributes to his association with Grubbs, Toste incorporates a sense of synthetic efficiency and waste reduction, a practical and "green" mind-set that he says he absorbed from Trost.

Calling himself a late bloomer, Toste recalls that as an undergraduate he was taken with "stuff like DNA" and thought he was on his way to a career as a biologist. It was when he took his first organic chemistry class during his sophomore year at the University of Toronto that he turned toward the "central science," as chemists are apt to call their field. He was grabbed, he says, "by the logic of reactions." It was so grabbing that he stayed at Toronto long enough to earn a master's degree in organic chemistry. In 1995, he moved from there to Stanford, where he earned a Ph.D. under Trost's supervision. Immediately following an 18-month stint as a postdoc in Grubbs's lab at Caltech in 2001 and 2002, he accepted the assistant professor position he now holds at the University of California, Berkeley.

To be recognized by his peers with this award so early in his career is particularly thrilling, says Toste. "Early on when you are just starting out, the impact is greater."-Ivan Amato

Since joining the University of Illinois, Urbana-Champaign, only eight years ago, Wilfred A. van der Donk has established an exceptionally broad and internationally recognized research program at the interface between chemistry and biology. His field encompasses mechanistic enzymology, bioorganic and bioinorganic chemistry, and bioengineering. In fact, "mechanistic enzymology is a common thread that runs through van der Donk's work," a colleague notes.

His areas of interest include enzymology of lantibiotic biosynthesis, the mechanism of prostaglandin H synthase, the enzymology of phosphorus redox chemistry, the use of intein methods to incorporate selenocysteine into proteins, and the reductive dechlorination of chloralkenes by cobalamins.

The main point of his research has been to combine in creative ways the tools and thinking of organic and inorganic chemistry with enzymology and to provide insight into the mechanisms of these enzyme-catalyzed reactions.

According to one colleague, van der Donk's most outstanding research accomplishment to date has been in the area of antibiotic synthesis, where he achieved the in vitro reconstitution of the biosynthesis of the lantibiotic lacticin 481. The lantibiotics-used for four decades in food preservation-are of increasing importance because there are no known examples of bacterial resistance against them.

In work related to this project, he put together the synthetic organic chemistry methodology to allow preparation of dehydroalanine and dehydrobutyrine residues in oligopeptide substrates. He also used synthetic peptides with cloned lantibiotic biosynthetic enzymes and mutants to reengineer the biosynthesis of lantibiotics to produce chimeric and other novel variants that could prove to be novel products of pharmaceutical importance.

Van der Donk has received Burroughs-Wellcome and Beckman Young Investigator Awards, an Alfred P. Sloan Fellowship, and a Camille Dreyfus Teacher-Scholar Award. In 2004, he also won the Pfizer Award in Enzyme Chemistry given by ACS's Biochemistry Division.

Not only has he been productive, a colleague says, "but the breadth and depth of his interests in science are truly amazing, and his enthusiasm for science is infectious. These characteristics have provided him with the ability to marshal whatever technique or reaction is necessary to solve the problem at hand."

That enthusiasm also shows in his teaching: He has been included in 1998, 1999, 2000, and 2003 among "Teachers ranked as excellent by their students," published by the university's daily newspaper, the Daily Illini. The list consists of the top 10% of instructors in all disciplines across campus, based on student evaluations.

One supporter is particularly enthusiastic about van der Donk's "beautiful experiments with prostaglandin synthase. To determine the structure of enzyme-bound radical intermediates in the cyclooxygenase reaction, he developed practical syntheses of several deuterated derivatives of arachidonic acid." He then used these compounds in electron paramagnetic resonance experiments with the enzyme to determine the electron spin density at critical carbon atoms in the chain of the fatty acid substrate. "The result," says the colleague, "provides a much clearer picture of the structures of the free radicals that had been previously proposed as intermediates in the cyclization."

Van der Donk received his B.Sc.-M.Sc. degree from Leiden University, in the Netherlands, in 1989. He then went to Rice University in Houston, earning a Ph.D. in 1994. His thesis tackled transition-metal-catalyzed hydroborations.

Following a postdoc at Massachusetts Institute of Technology from 1993 to 1997, van der Donk joined the University of Illinois as an assistant professor in the department of chemistry. In 2003, he was named an associate professor and, in 2005, Lycan Professor of Chemistry.-Patricia Short