awards Howard Brenner. A colleague describes the volume as a "truly excellent textbook, combining microconstitutional equations with macroscopic phenomenological interfacial relationships." Wasan is the first chemical engineer to be the editor-in-chief of the Journal of Colloid & Interface Science, a position he ollowing is the final set of vignettes vided a new mechanism for stabilizing has held since 1993. He is the author or of recipients of awards administered dispersed-phase systems in applications coauthor of more than 280 refereed by the American Chemical Society ranging from shampoo to nuclear waste. journal publications and 22 book chapin 2000. An ankle on the 2000 Priestley Characteristic of his style of work is ters. He has edited six monographs and Medalist, Darleane C. Hoffman, is sched- to find technological applications for holds four patents. uled to appear in the March 27 issue. theoretical concepts. Wasan's research He received a B.S. degree in chemical Included in this set of vignettes are the has led to advances in several seeming- engineering from the University of Illiwinners of the Arthur C. Cope Award and ly diverse areas. For example, in early nois, Urbana-Champaign, in 1960 and a the Arthur C Cope Scholar Awards. The work, he co-invented two methods to Ph.D. degree in the same discipline from Cope Award recognizes and encourages ex-separate colloidal particles from syn- the University of California, Berkeley, in cellence in organic chemistry; it consists ofthetic fuels, and later investigations re- 1965. He then moved to Illinois Institute a medal, a personal cash prize of $25,000, sulted in a process for synthesizing he- of Technology as an assistant professor, and an unrestricted research grant of moglobin multiple emulsions for use as and he has progressed through the $150,000 to be assigned by the recipient to a red blood cell substitute. ranks, serving as department chairman any university or research institution. Wasan is especially proud of recent from 1971 to 1987. Wasan has also served Each Cope Scholar Award consists of work his group has done on thin liquid IIT as vice president for research and $5,000, a certificate, and an unrestricted films. Their discovery of oscillatory struc- technology (1988-91) and vice president research grant of $40,000. tural forces with a period of oscillation for academic affairs (1991-96). He has Most winners, including the Cope equal to the effective size of the particle held his current positions since 1996. Award recipient, will receive their awards arising from the self-organization of colOther universities have benefited during the ACS national meeting in San loidal particles in the confined geometry from Wasan's expertise as well; he has Francisco, March 26-30. However, the of thin liquid films such as those associat- been a special lecturer at many, includCope Scholars will receive their awards at ed with emulsions, foams, and other col- ing Yale University, Case Western Rethe ACS national meeting in Washington, loidal dispersions has opened up new vis- serve University, and UC Berkeley. D.C, Aug. 20-24. tas in dispersion science and technology. He has received a number of honors, This research, Wasan says, "is provid- among them the Boschasanwaisi Swaing significant new understanding of the minarayan Sanstha Pride of India Award phenomena of wetting, spreading, and (1994), the American Society for EngiACS Award in Colloid or Surface adhesion of colloidal particles on solid neering Education's 3M Lectureship Chemistry surfaces; oily soil removal; soil remedia- Award (1991), the National Science tion; and stability of emulsion- and foam- Foundation's Special Creativity Award Sponsored by Procter & Gamble Co. based products. For example, we have re- (1988 and 1986), and the Fine Particle Colleagues marvel at the depth of cently shown that the severe foaming Society's Hausner Award (1982). Wasan DARSH T. WASAN's work, yet still he problem encountered in the nuclear is also a fellow of the American Institute probes more deeply. They laud the waste sludge processing in the Defense of Chemical Engineers, and he has breadth of Wasan's contributions, even Waste Processing Facility at the Savan- served on the editorial board of a numas he focuses on distances spanning nah River Technology Center, Aiken, ber of scientific publications. S.C., is caused by structural forces of the only a few hundred nanometers. Robin Giroux Unlocking the secrets of how colloi- colloidal particles present in the sludge. A dal particles behave in confined geome- better understanding of these forces has tries is Wasan's passion. The Motorola led us to develop a new antifoaming agent James T. Grady-James H. Stack Professor of Chemical Engineering and to effectively treat these biphilic sludge vice president for international affairs at solids in the vitrification process for im- Award for Interpreting Chemistry for the Public Illinois Institute of Technology, Chica- mobilization of nuclear wastes." go, has clearly played a key role in unIn addition, the methods and instruderstanding interfacial transport phe- mentation that he and his students de- From the start of his career as a science nomena. A peer comments that Wasan veloped for thin liquid film research and writer, JEFF WHEELWRIGHT has was one of the first chemical engineers interfacial rheological measurements impressed scientists and peers alike to recognize the importance of colloidal have moved into wide use in industry. with his ability to combine pictures and phenomena in chemical engineering. Wasan incorporated nearly three de- text and to make complex science unWasan focused his attention on interfa- cades of his research efforts into his 1991 derstandable to lay readers. He has procial transport processes and rheology in graduate-level textbook, "Interfacial Trans- duced stories about dioxins, chemoindustrial applications. His discovery of port Processes and Rheology," which was therapy for cancer patients, air pollution ordered microstructures in thinning liq- coauthored by David A. Edwards—a and acid rain, and new materials used to uid foams, emulsions, and latexfilmspro- former graduate student of Wasan's—and make electrical superconductors.
2000 ACS National Award Winners
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awards
Wasan
Wheelwright
Starting in 1989, after stints in television and as science editor at Life magazine, his journalistic writing turned to an examination of the notion that substances in the environment pose a dire threat to human and ecological health. Some call his reporting "balanced," others, "contrarian." According to Smithsonian magazine editor Don Moser, who nominated Wheelwright for this award, several examples of his work stand out, such as "Degrees of Disaster" (1994), a book on the Exxon Valdez oil spill in Alaska's Prince William Sound. In it, Wheelwright attempts to explain the properties of crude oil and to put to rest fears about its lasting effects on the environment. Another achievement is "Atomic Overreaction," a 1995 piece for the Atlantic Monthly in which Wheelwright investigates the chemical and biological effects of plutonium—"the most toxic substance known to man." He has covered the subject of pollution from aging coke plants in the Czech Republic and a possible global ban of the soil fumigant methyl bromide—not because it is toxic but because of its effect on the ozone layer. 'Wheelwright's examination of the issue was extremely evenhanded," Moser says. He is currently working on a book about the illnesses among Persian Gulf War veterans, seeking to answer whether the mysterious conditions and illnesses developed by some of those veterans are due to chemical exposures or to psychological stress. Wheelwright received a B.A. degree in English from Yale University in 1969 and an M.S. degree in journalism in 1971 from Columbia University. He won the 1997 Overseas Press Club Award for "best reporting in any medium on international environmental issues." Wheelwright is a member of the National Association of Science Writers. William Schulz 120
FEBRUARY 14, 2000 C&EN
Wolynes
Peter Debye Award in Physical Chemistry Sponsored by DuPont Co. For more than 20 years, PETER G. WOLYNES, professor of chemistry, physics, and biophysics at the University of Illinois, Urbana-Champaign, has been a leading theoretical chemist and, most notably, a leading theorist in biophysical research. For example, he has been responsible for many conceptual breakthroughs in the fields of protein dynamics, electron transfer, and, most important, protein folding. "His work has had an enormous impact on the thinking and direction of experimental, theoretical, and computational research aimed at understanding the physics and physical chemistry of proteins," according to one colleague. Wolynes graduated with honors in chemistry from Indiana University in 1971 and obtained a Ph.D. degree in chemical physics at Harvard University in 1976. He was on the faculty at Harvard until 1980 and then moved to the University of Illinois, where he became professor in 1983. A central focus of his research has been on understanding and predicting the way that many-body phenomena modify the traditional areas of chemistry. "An overarching motivation in my research has been my belief that physical chemistry offers new 'emergent phenomena' for study that inspire the development of new general laws of manybody chemistry," he tells C&EN. Wolynes was one of the pioneers of the molecular theory of dynamics of solvation and of ion mobility. He also introduced the "random first-order transition" description of the glass transition. This theory provides a unified analysis of the low-temperature divergence of the viscosity that drives the transition and the intermediate-temperature mode-coupling
dynamics that account for the multiplicity of relaxation times. He has developed theories on the role of deviations from rapid randomization of energy in reaction rates, and he also has made novel predictions concerning energy localization and the rate of energy flow in molecules and concerning the transition to chaotic motion. A number of these predictions have been confirmed experimentally. His work on the conformational dynamics of proteins has not only provided an incisive interpretation of important experimental results in this area, but also has laid the groundwork for explaining a new generation of experiments—for example, femtosecond resolved spectroscopy of ligand and protein motions and single-molecule spectroscopy. Wolynes' "statistical energy landscape theory" of protein folding, which effectively supplants all previous pictures for the mechanism of protein folding, provides a comprehensive framework for interpreting experimental results. The theory connects the self-organization of biomolecules to the theory of spin glasses and phase transition. It explains kinetic heterogeneity, classifying folding kinetics into five "scenarios" that are determined by the relative location of glasslike traps and thermodynamic barriers. Recent experiments have confirmed the theory by providing many examples of the enormous acceleration in the rate of protein folding after modifying the protein structure to remove the source of the traps. "Understanding the folding problem has proved to be amazingly rich as an inspiration for new chemical physics, calling forth a set of ideas unifying biological evolution, the statistical mechanics of random systems, and modern condensedphase chemical kinetics," Wolynes says. Wolynes has received numerous awards and honors, including the ACS Award in Pure Chemistry in 1986. He has published more than 200 scientific papers and has been a member of the editorial advisory boards of several journals, including the Journal of Chemical Physics, Chemical Physics, and Chemical Physics Letters. "Wolynes, more than any other theorist, has been responsible for a turning point in the history of biochemistry, in which modern statistical mechanics is not only making major contributions to understanding biological problems of great importance, but it is also leading the way," his colleague concludes. Michael Freemantle
Arthur C. Cope Award In Evans' lab, the development of synthetic methods and the synthesis of new target molecules go hand-in-hand. Over the years, he has used the organic architecture of natural products to define the types of organic reactions needed to move the field of synthesis forward. "A characteristic of our work is that we develop most of the key bond construction ourselves and then incorporate it into our evolving natural product syntheses," Evans says. "I think we are making useful contributions to both natural product synthesis and also reaction design." Of the work currently going on in his laboratory, Evans says, "Many of the syntheses we are developing now have cata-
lytic processes as an integral part of the design." Evans was born in Washington, D.C., in 1941. He received a bachelor's degree from Oberlin College, Oberlin, Ohio, in 1963 and a doctorate degree from California Institute of Technology in 1967. That same year, he joined the chemistry faculty of the University of California, Los Angeles, becoming a full professor in 1973. Shortly afterward, he moved to Caltech, where he remained until 1983, when he joined the Harvard faculty. He was chairman of the department of chemistry and chemical biology at Harvard from 1995 to 1998. He is a member of the National Academy of Sciences and the American Academy of Arts & Sciences. Rebecca Rawls
Arthur C. Cope Scholars A 20-year quest to gain enantioselective control over the formation of carboncarbon bonds is producing a rich array of exquisite tools for organic synthesis in the laboratory of DAVID A. EVANS, Abbott & James Lawrence Professor of Chemistry at Harvard University. Among Evans' more recent and broadreaching tools are a family of chiral Cu(II) complexes that function as Lewis acid catalysts to induce spatial selectivity in many of the classic carbon-carbon bond-forming reactions of organic chemistry. The repertoire now includes catalysts that induce asymmetry in the DielsAlder and hetero Diels-Alder reactions, aldol additions, Michael additions, ene reactions, and enol aminations. In each of these cases, reaction enantioselectivity is greater than 95%, and many achieve this selectivity even when performed at room temperature. Developing the tools of stereoselective organic synthesis is only one part of the activity in Evans' lab. He and his students also apply their tools to the synthesis of medicinally useful natural products. In recent years, for example, they have synthesized the peptide antibiotic vancomycin, which is medically important because bacteria have not developed resistance to it. The Evans group has also developed the first synthesis for the spongipyran macrolide antibiotic altohyrtin C, a member of a class of antitumor agents produced by marine sponges, and for bryostatin, another marine natural product that is currently undergoing clinical trials in cancer patients.
JOHN E. BERCAW, Centennial Professor of Chemistry at California Institute of Technology's Arnold & Mabel Beckman Laboratories of Chemical Synthesis, is not particularly comfortable with classifying chemists as organic or inorganic—"a lot of chemists work at the interface," he says. Nonetheless, "it was a real surprise to me to receive a Cope Scholar Award, because these awards generally go to organic chemists," he says. "If push came to shove, I'd have to call myself an inorganic chemist. That's what I teach here at Caltech." Indeed, organic and inorganic chemistry have intertwined throughout much of Bercaw's research career. His recent work in polymerization catalysts—for which he received the Cope Scholar Award, as well as last year's George A. Olah Award in Hydrocarbon or Petroleum Chemistry—is a good example. An early feature of this endeavor was Bercaw's primary role in introducing into organometallic chemistry the pentamethylcyclopentadienyl ligand and demonstrating its utility in forming stable and characterizable derivatives. His work yielded not only a better understanding of mechanisms in organometallic reactions, but also commercially valuable metallocene and single-site catalysts for making polyolefins, such as polyethylene and polypropylene. "My interest has always been in the fundamental principles," he says of his research, which goes back to the early 1970s, when he first served as a re-
search fellow at Caltech and then joined the faculty in 1974. A number of ACS national awards trace the highlights of his research. Bercaw's early work on the activation and reduction of dinitrogen and carbon monoxide as well as his work on synthetic fuels brought him the ACS Award in Pure Chemistry in 1980. Work with organometallic compounds and his insertion of olefins into metal hydride bonds was recognized with the ACS Award in Organometallic Chemistry in 1990. His research and teaching accomplishments brought him ACS's Award for Distinguished Service in the Advancement of Inorganic Chemistry in 1997. And in 1999, the Olah Award recognized his work on single-site catalysts, especially his development of a new cyclopentadienyl ligand attached to an amide that together create a highly active and stereoselective catalyst center for olefin polymerization. His research and teaching have also been recognized by a number of other organizations, including the National Academy of Sciences, which elected him a member in 1990, and the American Academy of Arts & Sciences, which inducted him as a fellow in 1991. Born in Cincinnati, Bercaw, who is now 55, received a B.S. degree in chemistry from North Carolina State University in 1967 and a Ph.D. degree in chemistry from the University of Michigan in 1971. He served as postdoctoral research associate at the University of Chicago in 1971 and '72 and as Arthur FEBRUARY 14, 2000 C&EN
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awards Amos Noyés Research Fellow in Chem- ects his research adviser istry at Caltech from 1972 to 1974, when E. J. Corey had under he joined the faculty there. He became a way. Instead, Cane's thefull professor in 1979 and Centennial sis centered on the development of new reaction Professor of Chemistry in 1993. An avid photographer and hiker, Ber- methods, which he apcaw has also developed a reputation plied to the synthesis of a around Caltech for a tradition he started natural product. many years ago. Each summer, he leads That strong backmembers of his research group on a ground in mechanistic orbackpacking expedition into the Sierra ganic chemistry, stereoNevada Mountains, sometimes for as chemistry, and organic long as eight or nine days. "We carry synthesis has served our tents and food, and we interact in Cane well in his work fordifferent ways than in the laboratory," mulating mechanisms for Bercaw he says. "Everybody always gets back biosynthetic transformaalive. Nobody regrets going; it's always tions. His efforts led him to adopt the techniques of molecular biologists, as rewarding." Of his newest award, Bercaw is obvi- well. While studying pentalenene synously pleased with the accompanying thase, Cane and coworkers learned to isounrestricted research grant of $40,000 late and purify the enzyme and later to (in addition to the $5,000 award money). isolate, clone, and express its gene. "At 'The grant money is very welcome," he each stage, I learned to do things I couldn't do before," he says. "I can honsays, "and we can certainly use it." "You know," he adds, "it's a compli- estly say that, at one point, I didn't know ment to me to be considered an organic what a restriction enzyme was." chemist." Fruitful collaborations have enriched Ernest Carpenter Cane's career, he notes. His group and that of biochemistry professor Rodney It wasn't until his third year of graduate B. Croteau of Washington State Univerwork at Harvard University that DAVID sity, Pullman, together developed a genE. CANE—now Vernon K. Krieble Pro- eral stereochemical model of the way fessor of Chemistry and Professor of plants make terpenoids. "Between us, Biochemistry at Brown University— we did things that neither lab could developed a passion for understanding have done alone," Cane comments. how nature makes organic chemicals. Another rich collaborative effort has That's when he heard a series of lec- been with Chaitan Khosla, professor of tures by Duilio Arigoni of the Swiss Fed- chemical engineering, chemistry, and eral Institute of Technology, the biosyn- biochemistry at Stanford University and thesis expert with whom Cane later winner of ACS's Award in Pure Chemisspent two formative years as a postdoc- try for 2000 (C&EN, Jan. 24, page 59). toral fellow. Khosla and Cane focus on polyketide "Arigoni introduced me to the subject synthases, which catalyze the formation I've worked on ever since," Cane says. of hundreds of complex natural prodFirst with classical methods of feeding ucts, including important drugs like experiments and isotope incorporation erythromycin. The multifunctional, modusing stable-isotope NMR analysis, then ular enzymes carry out synthetic steps focusing on the enzymes of natural in sequence, using different active sites product biosynthesis, and most recently for each step. "Our work has gone a adding the tools of molecular biology, long way toward showing how nature Cane and his coworkers have elucidat- can carry out very complicated chemised the biosynthesis of important natural try using simple tools," Cane says. products, most notably terpenoids and In the future, Cane foresees chemispolyketides. try playing an important role in the revCane is "a vital and active scholar who olution genomics is initiating. As thoucontinues to redefine the fields of the sands of genes are identified, "a whole chemical inquiry in which he works," one treasure trove of new biochemical reacadmiring colleague writes. "He is one of tions" will also come to light, he says. the most accomplished scientists at the "There is a real challenge for people chemistry-biology interface." who do mechanistic studies on enzymes Ironically, when Cane began his grad- to develop methods to figure out not just uate studies, he simply wasn't interest- how a particular protein works, but what ed in the pioneering biosynthetic proj- it actually does in the first place."
Cane
Cane earned B.A., A.M., and Ph.D. degrees in chemistry from Harvard in 1966, 1967, and 1971. Of his many honors, he is especially proud of the ACS Ernest Guenther Award in the Chemistry of Natural Products (1985), the John Simon Guggenheim Memorial Foundation Fellowship (1990), and the Simonsen Lectureship of the Royal Society of Chemistry (1990-91). Pamela Zurer In an age when combinatorial chemistry has become crucial to the continued prosperity of the drug and materials industries, organic chemistry professor JONATHAN A. ELLMAN of the University of California, Berkeley, was the first to publish on small-molecule libraries, and he stands out as a developer of libraries targeted at specific enzyme or receptor classes, of new concepts that are widely useful in library synthesis, and of synthetic methods applicable to libraries and to general synthesis. That his methods are widely emulated by others is indicated in a fall 1998 Science Watch report published by the Institute for Scientific Information, Philadelphia. The report ranked Ellman as the sixth most highly cited researcher in chemistry or materials science between 1994 and 1996. One of his targeted libraries seeks to find inhibitors of cysteine proteases. These proteases, which are active in neurodegenerative diseases, osteoporosis, and programed cell death, begin by attack of the cysteine side-chain thiolate on the carbonyl carbon of an amide bond. So, when introduced into a nonpeptide inhibitor, a keto group serves as an ideal group to tie up the thiolate. Ellman's signature approach is to use the keto group to attach the substituted 3-amino-l-chloro-2-oxopropane scaffold of the intended inhibitor to the resin for FEBRUARY 14, 2000 C&EN
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awards solid-phase chemistry. The keto group is the one part of the molecule that is not to be combinatorially varied. In this way, every other part of the scaffold is available for substitution and is not "wasted" by binding to the resin. Two concepts that Ellman uses to generate libraries are "traceless" syntheses and the use of "safety-catch" links to the resin. Traceless syntheses are those that leave no functional groups on the compounds that are vestiges of attachment to the resin. Thus, every group on the molecule is there because of intentional combinatorial variation, and not because the chemist needed a handle. One resin for traceless syntheses is substituted with 3-chlorodimethylsilylpropyl groups. Ellman binds a lithiated aromatic ring to the silyl chloride as the starting point for synthesis. At the end, he cleaves the carbon-silicon bond with a fluoride salt, which leaves only hydrogen where the link to the resin was. A safety-catch linker survives even the severe reaction conditions used to synthesize the library. At its end, Ellman modifies the linker to "take off' the safety catch for release into the solution. Nucleophile-mediated cleavage of the compound from support allows further elements of diversity to be introduced in the cleavage step. The concept originated with organic chemistry professor G. W. Kenner at Liverpool University, England; but Ellman has made it more universally useful. One type of safety-catch resin is substituted with sulfonamide groups. The synthesis begins with alkylation of the sulfonamide nitrogen with the scaffold molecule. In Ellman's method, cyanomethylation of the nitrogen with a haloacrylonitrile at the end of the synthesis activates the N-sulfonamide for easy nucleophilic cleavage to provide diverse amides, esters, and acids. One of Ellman's synthetic methods that applies to traditional as well as combinatorial synthesis is use of singleisomer 2-methyl-2-propanesulfinamide, C 4 H 9 S(0)NH 2 , to make enantiomeric amines. A second method is the use of 3,3-di-teri-butylaziridine to convert alcohols to O-alkylhydroxylamines. Oximes of O-alkylhydroxylamines are prominent structural features of antibiotics such as aztreonam, ceftazidime, and roxithromycin. Ellman makes the O-alkylating aziridine reagent by treatment of di-tert-buty\ ketone imine with m-chloroperbenzoic acid. 124
FEBRUARY 14, 2000 C&EN
Ellman was born in 1962 in Los Angeles. He received a B.S. degree in chemistry from Massachusetts Institute of Technology in 1984 and a Ph.D. degree in organic chemistry from Harvard University in 1989. After a postdoc at Berkeley, he joined the faculty there in 1992. His interest in chemistry came late. "I was always interested in sci- Ellman ence," he says. "I chose to focus on chemistry upon taking a first- I year chemistry course at MIT that was taught by George Whitesides and Bill Roush." Stephen Stinson DANIEL HERSCHLAG is an outstanding physical organic chemist working in the interface area of biological chemistry. His research has already led to important insights in RNA chemistry, enzyme mechanisms, and hydrogen bonding and its importance in biological catalysis. Herschlag, an associate professor of biochemistry at Stanford University, uses physical organic chemistry to understand RNA catalysis. Most recently, he developed approaches to probe the properties of individual catalytic metal ions within the sea of metal ions bound to RNA. His studies of protein enzymes have revealed fundamental energetic principles of catalysis that are common to both protein and RNA enzymes. In addition, they have revealed features of the behavior of RNA as a macromolecule that are basic to its biological functions. For example, Herschlag and his coworkers have shown how a protein interacting transiently with an RNA structure can facilitate conformational and functional transitions of that RNA. These findings are seminal contributions because most RNAs work in concert with proteins in biology. Herschlag's careful analysis of the energetics of hydrogen-bond formation for organic compounds in aqueous and organic media has provided important models for understanding the potential contributions of hydrogen bonds in enzymatic catalysis. In addition, Herschlag's work has shown that understanding the transition states for nonenzymatic reactions can shed light on and help scientists evalu- I
Herschlag
ate the mechanisms used by enzymes in carrying out catalysis. His work has also addressed the nature of transition states for enzymatic reactions. Herschlag's research has covered diverse areas "without a hint of superficiality," one colleague notes. "Herschlag is the sort of scholar one rarely encounters, who approaches each subject with an original style and makes it his own." Herschlag is also an extraordinary teacher, "whose teaching does not stop at the doors of the classroom, but extends to all his interactions with students and faculty," says a colleague. Herschlag earned a B.S. degree in biochemistry from the State University of New York, Binghamton, in 1983 and a Ph.D. degree in biochemistry from Brandeis University, Waltham, Mass., in 1988. After this, he did three years of postdoctoral work at the University of Colorado under Thomas R. Cech, the distinguished professor of chemistry and biochemistry who won the Nobel Prize in Chemistry in 1989. Herschlag is the recipient of numerous research grants and awards, including ACS's Division of Biological Chemistry Pfizer Award in Enzyme Chemistry (1997), the David & Lucile Packard Fellowship in Science & Engineering (1995), and the Searle Scholar Award (1993-96). From 1990 until 1997, he was a Lucille P. Markey Scholar in Biomedical Science. Bette Hileman From the time he finished his first organic chemistry course in college, ERIC T. KOOL knew he was going to be a chemist. Chemistry fascinated him, he says, with its "amazing power to make molecules, not only ones that exist in nature, but even molecules that just exist in your mind. To me, that was incredibly appealing."
Kool
Padwa
ested in how proteins recognize and interact with DNA at specific sites. Using their nonnatural DNA bases, the group investigates the interactions between DNA and the polymerase enzymes that direct the accurate copying of the molecule. The chemists are also interested in using these probes to look at other DNA-protein interactions, such as the ones that regulate and direct gene expression. "Molecular recognition of DNAs is one of the most important problems in chemistry, and Eric Kool has made beautiful creative contributions to this area by designing and synthesizing novel molecules that are great improvements over simple complementary DNA strands," says Ronald Breslow, professor of chemistry at Columbia University, with whom Kool earned his Ph.D. degree in 1988. Born in 1960, Kool received a bachelor's degree in chemistry from Miami University, Oxford, Ohio, in 1982 before going to Columbia. Following two years of postdoctoral training at California Institute of Technology, he joined the faculty of the University of Rochester as an assistant professor of chemistry in 1990. He became a full professor there in 1997 and moved to Stanford University in September 1999. Rebecca Rawls
It's an appeal that has lasted. Kool, now professor of chemistry at Stanford University, is still hard at work imagining and then synthesizing interesting molecules that don't exist in nature. "Brilliant," "wonderfully creative," "intuitive," and having "a high level of craftsmanship in synthetic chemistry," are some of the ways colleagues describe Kool and his chemistry. He is probably best known for devising a set of nonnatural molecules that mimic some of the properties of the bases of DNA. His mimics match the shape of the natural bases but lack their polarity. This difference has allowed Kool and his colleagues to separate the role of base-pairing and hydrogen-bond formation from the other factors that contribute to the accuracy with which DNAreplicating enzymes make complimentary strands of DNA. His experiments, begun in 1997 while Kool was a professor of chemistry at the University of Rochester, have over- ALBERT PADWA is a skilled mounturned one of the dogmas of molecular tain climber. Over the past 20 years, he biology by showing that the hydrogen has made numerous climbs over 20,000 bonding between pairs of bases in DNA feet in the Andes region of South Amerthat Watson and Crick first described is ica as well as Mount Kilimanjaro in Afriactually not very important for the accu- ca. But he is also skilled at something rate replication of the molecule. else: chemistry. The work is part of a more general effort Padwa, professor of chemistry, joined in Kool's lab to try to understand biomolec- Emory University, Atlanta, in 1979, when ular recognition as it pertains to DNA He he accepted the post of William P. Timand his students want to understand what mie Professor in the department of chemholds the DNA helix together, for exam- istry. He has held the post ever since. ple, despite strong forces of entropy and He started his chemical studies at Coionic repulsion that work to break it apart. lumbia University, where he earned a Watson-Crick hydrogen bonds play an im- B.A degree in 1959 and a Ph.D. degree portant role here, Kool notes, but so do in 1962. Following that, he spent 1962stacking forces between the bases. 'We've 63 as a National Science Foundation done studies that give us more insight into postdoctoral fellow at the University of exactly what this base stacking is, how we Wisconsin, Madison. can stabilize it, and how we can design new From Wisconsin, he joined the faculmolecules that stack more strongly than ty at Ohio State University in 1963 as an the natural ones do," Kool says. assistant professor in the department of The group continues to be very inter- chemistry and worked there until 1966.
Subsequently, he was an associate professor in chemistry at the State University of New York, Buffalo, from 1966 to 1969. In 1969, Padwa was named professor of chemistry, a post he held until he went to Emory in 1979. He has held a number of visiting professorships over the years, such as a Humbolt senior scholar at the University of Wiirzburg, Germany; a Guggenheim fellow at the University of California, Berkeley; and a Fulbright-Hays Fellowship at Imperial College of Chemistry, London. His publications comprise an extensive list dating back nearly 40 years to his first cited effort in the Journal of the American Chemical Society in 1961. Padwa's scientific work reflects a career built upon complex structural chemistry. A specialty is cycloaddition chemistry as applied to organic natural products—in fact, one of his nominators termed him "the world leader" in such chemistry. He has developed new and useful synthetic methods using a wide range of reactive intermediates. Some of the methods include applications of photochemistry to organic synthesis, dipolar cycloaddition chemistry, smallring heterocyclic transformations, cyclization reactions of rhodium carbenoids for alkaloid synthesis, and domino cascade processes employing thionium ion intermediates. His early work, in the 1960s and 1970s, concentrated on photochemistry, especially the application of hydrogentransfer processes for organic synthesis. And he was among the first to demonstrate that synthetically useful and complex heterocycles could be prepared by excited-state chemistry. That work led to a study of the chemistry of various small-ring systems such as cyclopropenes, aziridines, and azirines. Padwa's group showed that suitable substituted three-ring systems undergo the "ene" reaction as well as 2+2 and 4+2 cycloadditions. In addition, his group was among the first to demonstrate that complexation of strained rings with transition metals results in synthetically useful transformations. By the late 1970s, he had turned his attention to the cycloaddition chemistry of 1,3-dipoles, culminating in his book, "Dipolar Cycloaddition Chemistry," in 1984. This has been described as "the most authoritative source in the field." For many years, his research group has been extensively involved in the development of new methods for formation of 1,3-dipoles and their use in synFEBRUARY14, 2000 C&EN
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awards thesis. A typical example from his laboratory involves nitrone cycloaddition with aliènes as a method for preparing alkaloids. His group was also involved in an extensive study of the chemistry of unsaturated sulfones as useful synthetic reagents for the assemblage of complex molecules. Over the past decade, he has published an extensive series of papers dealing with the cyclization reactions of metal carbenoids with carbonyl groups as a powerful method for synthesizing a wide variety of novel heterocycles. His recent investigations dealing with tandem Pummerer-Mannich cyclizations have added new dimensions to synthetic organic chemistry and have made it possible to prepare many alkaloids in a highly convergent manner. Padwa has made major contributions of time in the service of the organic chemical community. He has been chairman of the Gordon Research Conference on Heterocyclic Chemistry and has chaired the Organic Chemistry Division of ACS. He also has served as president of the International Society of Heterocyclic Chemistry, which presented him with its International Award in Heterocyclic Chemistry in 1999. He is credited with helping to build the national reputation of Emory's chemistry department. Its research profile was "marginal" when Padwa arrived, according to one colleague. "Padwa brought his program to the department and served as a role model for what could be done in the context of the resources available. He was proactive in faculty recruitment" and directly mentored young faculty on how to work with students and on what was necessary to build an externally funded research program. The result: There were about 30 graduate students in Emory's chemistry department when he came in 1979, and within a decade, Emory's graduate program grew to more than 120 graduate students. Patricia Short Of organic chemistry professor NED A. PORTER of Vanderbilt University, Nashville, a colleague says: "His research over the past 20 years has attempted to deal with the fundamental questions of structure and reactivity as they are manifested in free-radical and photochemical reactions in solution. In choosing research problems, he emphasized fundamental questions in free-radical chemistry and led the way in many important areas before they became popular with other groups around the world." 126
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One example of his photochemical clear to me what a 'chemist' did, and control of biological compounds and pro- that's the reason for my decision to macesses is the inhibition of enzymes with jor in engineering. I enjoyed the engineering courses, molecules that are photolytically cleavable. He demonstrates the method with and I believe that it is excellent training separation of thrombin and factor Xa, for someone interested in the chemical which are mediators of blood clotting; sciences, but I fell in love with organic they are serine proteases that cleave sub- chemistry when I took it as part of the strate peptide bonds adjacent to arginine. engineering curriculum." Stephen Stinson Porter's inhibitor is a substituted aryl cinnamate; the cinnamate ester acylates the two proteases at their active sites. He TIMOTHY M. SWAGER's "work has separates the two acylated enzymes and brought a new level of sophistication to cleaves the inhibitor. Light expels the en- the design of organic materials. Few inzyme from the cinnamoyl bond, and the dividuals in his age group can rival his cinnamate cyclizes to a coumarin. Porter accomplishments," according to a colsuggests that the method could serve as league. Swager, professor of chemistry a tool for exploring naturally occurring at Massachusetts Institute of Technolosources to discover new serine and cys- gy, is young—he's only 39 years old— but he's got a list of awards and fellowteine proteases associated with disease. In crafting the inhibitor to specificity for ships resembling that of some of his oldthrombin and factor Xa, he attaches a gua- er colleagues. Swager began collecting accolades in nidino group to the aryl ring in order to mimic the side chain of arginine. He has 1983, during his senior year at Montana screened a library of dipeptide derivatives State University, when he received the to hit upon an L-lysyl-L-tyrosinamide se- American Institute of Chemists' Most quence that must also be attached to the Outstanding Senior Chemistry Major Award and the Merck Index Undergradaryl ring for optimal specificity. An example of his free-radical mecha- uate Chemistry Award. Swager works in supramolecular and nistic work is his study of Lewis acidmediated atom-transfer free-radical ad- materials chemistry, but his primary inditions. These reactions may allow as- terests lie in the synthesis and construcsembly of complex structures with tion of functional assemblies. He and his simple, mild reactions that have high research group spend a great deal of their research time working in the realm diastereoselectivity. In the overall atom transfer, a radical of molecular recognition. His work with chemosensors—moleadds to an olefin double bond to generate an unpaired electron on the other carbon. cule-based devices used to detect specific That radical abstracts a halogen from a chemical signals—has focused on the desecond compound, converting that com- sign of amplification schemes that harpound into a radical for continuation of ness the unique transport properties of the chain reaction. Porter shows that conjugated polymers. In doing so, he has Lewis acids such as ytterbium trifluo- developed general concepts that are apromethanesulfonate speed up these plicable to many challenging and untransformations and permit atom-transfer solved sensing problems. His novel dereactions that would otherwise not occur signs are currently being put to the test in the search for a particularly menacing at room temperature. Porter was born in 1943 in Marion, compound: trinitrotoluene (TNT), the priOhio. He completed a B.S. degree in mary explosive used in land mines. chemical engineering summa cum laude Through innovative use of molecular from Princeton University in 1965 and a wires, or conjugated polymers, his system Ph.D. degree in organic chemistry from has been able to locate mines in the pres15 Harvard University in 1970. He joined the ence of as little as 10" g of TNT, a signifchemistry faculty at Duke University in icant advancement over the current tech1969 and moved to Vanderbilt University nology: dogs trained to sniff out TNT and DNT (dinitrotoluene). Vast numbers of in 1998. Of his interest in chemistry, Porter active land mines remain buried, particusays: "My father taught high-school larly in recent war zones such as Bosnia chemistry and physics, and that stimu- and Cambodia, and Swager's chemosenlated my early interests in the natural sors will reduce the risk for the people sciences. I thought I understood what a who inhabit the former battlefields. According to a colleague, this rechemical engineer did when I thought about a major in college, but it wasn't search is also significant in another way:
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awards "Here is a situation where the importance of organic chemistry can be clearly demonstrated both to the 'powers that be' and to the population at large." The young scientist has also brought the aging field of liquid-crystal chemistry a revitalizing boost through his endeavors with liquid crystals built from molecules with unusual shapes. His ability to control the association between molecules in the liquid-crystalline phase has led to elegant designs that are applicable to many systems, such as novel ferroelectric and chiral phases. Through his use of molecular recognition in calix[4]arenes, he has been able to answer old questions and break new ground in the construction of novel compounds. Following completion of a Ph.D. degree in chemistry from California Institute of Technology in 1988, where he studied under the direction of Robert H. Grubbs, Swager conducted a postdoctoral fellowship under Mark S. Wrighton at MIT. Prior to his first appointment at MIT, Swager received the Caltech chemistry department's Herbert Newby McCoy Award for Graduate Research (1988). In 1990, he started his independent career at the University of Pennsylvania, where, in 1996, he became a full professor. Swager returned to MIT shortly after his promotion. Swager has been an Office of Naval Research Young Investigator (1992-95), a National Science Foundation Young Investigator (1992-97), an Alfred P. Sloan Research Fellow (1994-96), and a Camille Dreyfus Teacher-Scholar (1995— 97). Other honors include the National Institutes of Health's Lawton Chiles Postdoctoral Fellowship in Biotechnology (1989), the DuPont Young Faculty Award (1993-96), the ACS Philadelphia Section Award (1996), and the Union Carbide Innovation Recognition Award (1997 and 1998). He currently serves on the editorial boards of Chemistry of Materials, Accounts of Chemical Research, the Journal of Polymer Science, and the Journal of the American Chemical Society. Kevin MacDermott DAVID L. VAN VRANKEN has been assistant professor of chemistry at the University of California, Irvine, only since 1994. Already, however, his colleagues say he has made his mark. The Cope Scholar Award is the latest addition to a list of accolades that include a National Science Foundation CAREER award, a Camille & Henry Dreyfus New Faculty Award, a Glaxo-Wellcome Chem128
FEBRUARY 14, 2000 C&EN
istry Scholar Award, and an Eli Lilly Faculty Grantee Award. A native of Missouri, Van Vranken received a B.S. degree in chemistry in 1987 from the University of Texas, Austin. He received a Ph.D. degree in chemistry in 1991 from Stanford University, where he did research work with Barry Trost. He followed that with a postdoc with Peter Schultz at the Porter University of California, Berkeley, and then joined the chemistry I faculty at UC Irvine. Since then, according to one nominator, he has established a dynamic independent research program at the interface of synthetic organic and bioorganic chemistry. He has carved out a research area that has major potential; it broadly focuses on the reactivity of tryptophan and carbon-carbon bond constructions through dearomatization processes. A major portion of Van Vranken's program focuses on the Mannich dimerization of tryptophan units of peptides and proteins. He has described oxidation of these tryptophan dimers to form fluorescent cross-links, which he calls ditryptophans. Ditryptophans are the third type of homodimeric cross-link to be discovered in the past 100 years of peptide chemistry; the other two—disulfides and dityrosines—are important in protein structure and protein aging, respectively. Van Vranken has shown that crosslinking occurs stereoselectively at the 2,2/-indolylindoline unit, and he was the first to report the reversibility of this dimerization. Either regioisomer of unsymmetrical indolo[2,3-tf]carbazoles can be accessed by carrying out intramolecular Mannich dimerization under either kinetic or thermodynamic conditions; this allows regiocontrolled access to the tjipanazoles, antifungal compounds from blue-green algae, and the AT2433 class of antitumor compounds from Actinomadura melliaura. As part of that work, his group has progressed from tryptophan dimerization to the related area of nonenzymatic protein aging, investigating the reactions by which proteins age. The group is searching peptide libraries for peptide sequences that are susceptible to fluorescent change through covalent modification. Such sequences may prove to be poten- I
Swager
tial hot spots for senescent change in human proteins. In his graduate research work, Van Vranken used palladium-catalyzed allylic alkylations in the synthesis of fivemembered-ring carbocyclic glycosidase inhibitors. Translating his racemic syntheses into asymmetric syntheses required the definition of new asymmetric ligands for palladium-catalyzed allylic alkylations. Van Vranken designed and implemented a topographically unprecedented, highly modular diphosphine ligand class that achieves high enantioselection in a wide variety of palladium-catalyzed allylic alkylation reactions. This work addressed the problem in which bondbreaking and bond-making do not occur at the metal but on the face of the organic substrate distal to the metal, so allylic alkylations have not succumbed to asymmetric induction, one nomination paper points out. In addition to demonstrating high levels of asymmetric induction, Van Vranken demonstrated a correlation of the stereochemistry of the chiral ligand with the stereochemistry of asymmetric induction. A colleague suggests that Van Vranken's design concepts may prove to be the most general practical approach for asymmetric induction in other transitionmetal-catalyzed reactions. Patricia Short If JEFFREY D. WINKLER were a composer, his music would not be heard in elevators—but it wouldn't be Jimi Hendrix-style either. It would use a synthesizer to compose a sound that melded instruments or notes in a combination that would seem familiar yet fresh. This is, in a way, what Winkler has accomplished in his chosen field of synthetic organic and bioorganic chemistry. In his research, Winkler—a professor of
Van Vranken
Winkler
chemistry at the University of Pennsylva nia—aims not for the total synthesis of complex organic molecules per se, but rather for the development of new strat egies in synthetic chemistry that will have applications beyond the construc tion of a particular class of natural prod ucts. For example, his group has recent ly developed a tandem Diels-Alder pro cess in which three new carbocyclic rings and four new stereogenic centers are formed in a single process.
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A colleague of Wink ler's at Columbia Univer sity calls the awardee "one of the most imagina tive and scholarly of our emerging leaders in syn thesis," pointing to his to tal synthesis of manzamine as well as his "bril liant efforts directed at the total synthesis of Taxol." Another colleague says Winkler is "one of those people whose work was always motivated by seeking the answer to significant questions of much impor tance to those, including himself, in volved in designing effective, novel, and elegant solutions to problems aris ing from targets carefully selected to offer serious synthetic challenges and the potential for making lasting contri butions to chemical architecture." The breadth of Winkler's research ac tivities is underscored by his recent ac complishments in three diverse areas: First is his highly selective approach to
the synthesis of polycyclic compounds from acyclic precursors based on the tandem Diels-Alder cycloaddition reac tion. Second is his development of a ste reoselective synthesis of methylphenidate (Ritalin). And third is his prepara tion of a series of dynamic systems that employ a spiro compound as a photoreversible switch. Before joining the University of Penn sylvania in 1990, Winkler had been an assistant professor of chemistry at the University of Chicago for seven years. He received an A.B. degree from Har vard College in 1977 and went on to re ceive an M.A degree in 1978, as well as M.Phil, and Ph.D. degrees in 1981 un der Gilbert Stork at Columbia Universi ty. He did postdoctoral work in Ronald Breslow's lab, also at Columbia. Currently, Winkler is a founding member of the University of Pennsylva nia's Center for Cancer Pharmacology and a member of the university's Can cer Center. Among his awards and hon ors are the American Cyanamid Young Faculty Award (1987-89), an NIH-NCI Research Career Development Award
The online ACS Directory of Graduate Research (DGRweb) is the most comprehensive source of information on chemical research and researchers in the US and Canada and it pro vides information on graduate programs from 12 disciplines within the chemical sciences.
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(1988-93), and an Alfred P. Sloan Research Fellowship (1987-89). In addition to teaching, Winkler gives many invited lectures and is the coauthor of more than 65 published journal articles. Arlene Goldberg-Gist
Mary Good honored by Heinz Family Foundation Chemist Mary Lowe Good, who will formally become president of the American Association for the Advancement of Science this week, and who served as president of the American Chemical Society in 1987, is one of five recipients of a 2000 Heinz Family Foundation Award. Good's award, which is the Prize for Technology, the Economy & Employment, consists of $250,000. The awards
are given annually in memory of Sen. John Heinz (R-Pa.), who was killed in an air crash in 1991. The award will be presented at private ceremonies later this year in Washington, D.C. Good has enjoyed distinguished careers in academia, industry, and government. In all of her roles, she has sought to harness advances in scientific knowledge to improve the economy, raise living standards, and generate resources with which to build a safer, cleaner, more just society. A native of Grapevine, Texas, Good received master's and Ph.D. degrees from the University of Arkansas. After more than 25 years of teaching, she moved into private industry, eventually becoming senior vice president of technology for AlliedSignal. Appointed to the National Science Board by President Jimmy Carter in 1980 and reappointed by President Ronald Reagan in 1986, Good also served four years in the Department of Commerce as undersecretary for technology in the Clinton Administration. Upon returning to her native South, Good helped establish the College of In-
formation Science & Systems Engineering at the University of Arkansas, Little Rock, where she now serves as dean. In that office, she has traveled extensively to recruit minorities and women to persuade them to study science and technology. She is now a managing partner of Venture Capital Investors, a group of Arkansas business leaders who foster economic growth through support of technology-based enterprises. "Good is a rare example of someone who is both firmly entrenched in the quantifiable, research-based world of science and technology, but whose every effort in those fields has been informed by an ethic of service to humanity," says Teresa Heinz, chairman of the Heinz Family Foundation. "Her contributions to the U.S. economy are well documented, but her contributions to our quality of life are only beginning to be appreciated. It is for these contributions, especially for her efforts to recruit young women and minorities into careers in science and technology, that the Heinz Award is so richly deserved." Linda Raber
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Biotechnology Catalysis Chemistry and Computers Chemistry in the Semiconductor Industry Environmental/Regulatory Issues Organic and Inorganic Materials Pharmaceuticals Chemistry in the 21st Century
