Department of Chemistry DECEMBER 2009
Newsletter for Alumni and Friends
From the Department Chair... Greetings from the MSU Department of Chemistry. As we anxiously look forward to 2010, I was recently reminded of a conversation I had as a newly-appointed assistant professor in the early 1990’s. In this conversation, a senior faculty member discussed in great detail how the impact of Michigan’s economy was connected to the university. He pointed out that although the university is more John McCracken insulated from the economy than the private sector, the effects of an economic downturn would cascade to us after a delay of a couple of years. In 2009, we have seen this occur. All levels of the university are taking a proactive by using this as an opportunity to strategically shape our future and best position us behind our strengths. Chemistry has a solid track record at MSU in both research and teaching, and while the challenge is difficult and complex, I am optimistic as to our future role. The correct balance of research and teaching is crucial, and we remain focused on effectively providing some of the core courses of the university. The department’s operating budget was cut 5 percent this year and is being cut an additional 7 next year. Yet the demand for our courses remains and at the start of this fall semester, we had 8,047 students enrolled in chemistry classes. The faculty and staff have done an impressive job in meeting the demands of high enrollments. Everyone in the department has done a tremendous job of doing more with less while not letting the quality of coursework or research diminish. This passion and commitment is exemplified by two recent honors in the department. Nancy Lavrik, the course coordinator for organic chemistry, was selected as the 2009 recipient of the MSU Clerical Technical Recognition Award. Professor Amy Pollock, a teaching specialist in General Chemistry, received the 2009 Outstanding Academic Specialist Award from the Faculty Professional Women’s Association. This fall we had 30 doctoral students enter the program - 35 percent less than our average over the past five years. This is
due to budget reductions as we reduce the size of our graduate program from 220 to 160 over the next three years. The quality of our students remains high and I am proud to report that several of our graduate students received accolades for their research over the past year. Recent alumna Erin Vogel, who was a graduate student in the Baker lab, received the ICI Student Award in Applied Polymer Science at the 2009 national ACS meeting. Jeffrey Gour, a graduate student from the Piecuch lab, was invited to participate in the 59th Meeting of the Nobel Laureates held in Germany this past summer. Britt Vanchura, a graduate student in the Smith lab, won the Journal of Chemical Crystallography Prize for his poster at the American Crystallographic Association annual meeting. Finally, our Young Chemists Committee won an American Chemical Society ChemLuminary Award at the national ACS meeting for their outreach activities. Chemistry faculty have responded to the opportunities presented by the stimulus funds. The number of grants submitted by the department increased by 25 percent this year as compared to 2008. Overall, grant awards have followed this trend and research funding is up a proportional amount. Our junior faculty continue to set high standards. Xuefei Huang received the 2009 New Investigator Award from the American Chemical Society Carbohydrate Division for his promising work in carbohydrate synthesis and the development of applications for medical use. We also welcomed a new materials chemist, Viktor Poltavets, who is already busy teaching, establishing his lab and networking with scientists and engineers across campus. The chemistry faculty, staff and students are part of the strong foundation of MSU. I am optimistic about our future and hope you enjoy reading some of our highlights in the pages that follow. John McCracken Professor and Chair of Chemistry
W W W . C H E M I S T R Y. M S U . E D U
Discovery improves the manufacturing of anticancer drug A discovery by Assistant Professor Kevin Walker paves the way for more efficient production of cancer-fighting paclitaxels. The most common paclitaxel is the drug Taxol. Walker studies enzymes that assemble the Taxol molecule in Taxus plants. Taxol and its various formulations are top-selling cancer-fighting drugs used to fight ovarian and breast cancers. The drug is also used in the treatment of heart disease and is being developed for the management of Alzheimer’s disease and tuberculosis.
Assistant Professor Kevin Walker is paving the way for potentially cleaner, more efficient production of cancerfighting paclitaxel. A video of Kevin Walker explaining his research is online at http://bit.ly/kwalker.
The MSU Department of Chemistry newsletter is published annually by the College of Natural Science for alumni and friends. Copyright 2009 Michigan State University. MSU is an affirmative-action, equal-opportunity employer. Send correspondence to: Dept. of Chemistry, c/o College of Natural Science Advancement Office, 103 Natural Science Building, East Lansing, MI 48824-1115. Ph (517) 432-4561, E-mail: natsci4u@msu.edu Contributing writers: John McCracken, Gordon Shetler, and Mike Steger. Photography: Tom Carter, Dow Chemical, Marcos Dantus, Chao Li, Gordon Shetler, Mike Steger
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Walker’s method opens the door for employing effective Green Chemistry alternatives to assemble the drug in a way that minimizes the toxic chemical waste produced by the current synthetic production methods. Walker’s natural production process means pharmaceutical companies could reduce the steps involved in making the drug and reduce byproducts. “We have found that the NDTBT enzyme transfers a vast array of cyclic and non-cyclic pieces to the drug’s core to manufacture novel paclitaxels. The drug is modified naturally instead of synthetically,” Walker said. “This process is like painting from a palette. We can add select colors to the palette from which the enzyme chooses, so the molecule can be crafted in a variety of ways. The enzyme does all the work.” The enzyme used in Walker’s method foreseeably produces the desired molecule more directly than the synthetic methods, resulting in less waste in the environment. The traditional synthetic processes use chlorinated solvents or solvents derived from fossil fuels. Walker’s biosynthetic research involves a Taxus-derived enzyme N-benzoyltransferase, designated NDTBT, which was discovered to efficiently transfer novel side chains in place of the naturally occurring groups of paclitaxel. The discovery by Walker involves inserting the plant DNA, a template for making the NDTBT enzyme, into
a bacterium. The modified bacteria becomes the biological factory that produces abundant quantities of the enzyme needed to modify precursors of paclitaxel. These modifications occur at a specific site on the molecule. “A plant enzyme can do in one step what traditional synthetic construction does in multiples steps,” Walker added. “Under our process, the construction of Taxol uses a ‘biological assembly line’ where each enzyme does its job to create the final product.” Assisting Walker in the research are graduate students Danielle Nevarez, Yemane Mengistu and Irosha Nawarathne. The findings, “An N-Aroyltransferase of the BAHD Superfamily has Broad Aroyl CoA Specificity In Vitro with Analogs of N-Dearoylpaclitaxel,” were published in the April 2, 2009 edition of the Journal of the American Chemical Society. Walker’s research is funded by the Michigan Agricultural Experiment Station (MAES). “The science and technology of plants and natural systems is becoming increasingly relevant in human medicine as scientists look for greater efficiencies and ‘greener’ ways of manufacturing drugs and other health care products,” said MAES director Steve Pueppke. “Engaging in research that leads to improvements in human and animal health is a large and important part of the MAES mission.”
Scientists Developing More Efficient Solar Energy Solutions Developing cheaper, more efficient solar panels is the goal for a collaboration of chemists, mathematicians and engineers at MSU, and a recent $1.9 million grant from the National Science Foundation is moving their research forward. The 3-year grant, “Design and Development of Efficient Solid-State Dye-Sensitized Solar Cells,” is part of the American Recovery and Reinvestment Act and will provide the methods for making a new class of solar cells from cheaper materials. “For renewable energy to succeed, it has to get to a point where it is economically competitive with current technology,” said Chemistry professor James McCusker and leader on the grant. “This means we need totally transformational technologies.” The group is working on a solar cell based on a design introduced in 1991 which combines a dye with an inexpensive semiconductor, titanium dioxide, in place of silicon. Titanium dioxide is common in household products like paint, paper and many white materials. Using advanced materials and nano-particles makes the electron conduction more efficient. McCusker said the efficiency of these devices is around 11 percent, however, this currently requires using a liquid electrolyte. The NSF grant has the scientists using the same concept, but with a solid material versus a liquid. The scientists hope to develop a solid-state material which is more efficient than the liquid and cheaper to manufacture. Making new technologies means developing new approaches for converting sunlight into energy. This requires interaction among many different disciplines. Working on the project are chemical engineer Lawrence Drzal, chemists McCusker and Greg Baker, and mathematicians Keith Promislow and Andrew Christlieb. The mathematicians provide modeling to efficiently guide the chemists who experiment with the materials alongside the chemical engineers.
“Math is the steroids of experimental science,” Mathematics professor Keith Promislow said. “Nanoscale networks are key ingredients in the formation of efficient energy conversion devices as they are the infrastructure that does the ‘just-in-time’ delivery of reactants to catalyst sites, much like the interconnected networks of railroads, highways, and shipping lines deliver raw materials to a factory. Getting these networks to self-assemble, in an optimal way, is a fundamental challenge as there are millions of ways to build the networks. Mathematicians build, code, and analyze models which guide the experimental efforts by identifying the approaches most likely to succeed.”
Professor James McCusker has received several different grants involving fundamental research of solar cell technology. A video of McCusker explaining the issues surrounding his research is online at http://bit.ly/jmccusker.
McCusker leads a research group at MSU which is deeply involved in many areas of solar energy research. His research also receives funding from the Department of Energy which focuses on a different area of solar cell technology - using compounds based on abundant elements such as iron and copper as a replacement material. While different from the stimulus grant, both of these projects look toward providing energy solutions for the world. “To properly address the future demands of energy, we need to first solve the science in order to develop the technology for tomorrow,” said McCusker. “It takes a long time and much collaboration, but our job as scientists is to conquer the fundamental hurdles and address the scientific problems so companies can then build and develop the technologies needed based on the science.”
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Chemistry Faculty News Huang Receives New Investigator Award
New faculty member Victor Poltavets
Xuefei Huang was awarded the New Investigator Award from the Carbohydrate Division of the American Chemical Society in March of 2009. The New Investigator Award is given to acknowledge and encourage outstanding contributions to research in carbohydrate chemistry by scientists in their first independent faculty position.
Victor Poltavets joined the faculty in July as part of MSU’s effort to expand expertise in complex materials in energy.
Huang received the award for his Xuefei Huang contributions to synthetic carbohydrate chemistry. His research group has been developing novel methodologies to expedite the synthesis of complex oligosaccharides. “Traditional carbohydrate synthesis is very tedious and time consuming,” Huang said. “We have established two methods by which multiple glycosylation reactions can be carried out in the same reaction flask without the need to purify the intermediates. This greatly improved the overall synthetic efficiencies.” Recently, Huang has started investigating the utility of carbohydrates as sensors for pathogens and cancer cells as well as developing carbohydrate based anti-cancer vaccines.
Bickley studies reactions induced by rare isotope beams Abigail Bickley recently was awarded nearly $700,000 through the Major Research Instrumentation Program at NSF to build a Time Projection Chamber Detection system for her experiments at the National Superconducting Cyclotron Laboratory at MSU. She will be developing an Active Target-Time Projection Chamber (AT-TPC) to study reactions induced by rare isotope beams Abigail Bickley at the cyclotron and at the future Facility for Rare Isotope Beams (FRIB). Long-range research priorities for nuclear physics include work at rare isotope beam facilities to determine the properties of nuclei and nuclear matter in the unexplored domain of extreme isospin asymmetry. Knowledge of these properties will help answer questions about the nature of neutron stars and dense nuclear matter, the origin of elements in the cosmos and the nuclear reactions that drive stars and stellar explosions.
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Poltavets works with inorganic materials chemistry. His research interest is directed at the rational design of novel energy related materials, such as new battery, thermoelectric and strongly Victor Poltavets correlated electron materials. He received his Ph.D. in chemistry from Moscow State University. He previously worked at the Max Planck Institute for Solid State Research in Germany and also at Rutgers University.
McGuffin to retire after 25 years Victoria McGuffin will be retiring after 25 years of teaching and research at MSU. McGuffin’s research is related to the development of novel packed and open tubular capillary columns for liquid and supercritical fluid chromatography as well as electrophoresis. Her goal is to apply improved separation and detection techniques developed in the lab to problems of Victoria McGuffin environmental significance. Her specific areas of interest include the analysis and characterization of polycyclic aromatic hydrocarbons and perfluorinated surfactants. McGuffin received her B.A. from Eastern Michigan University in 1978 and her Ph.D. from Indiana University in 1983. After two years as a post-doctoral fellow at Stanford, she joined the faculty at MSU in 1985. During her time at MSU, she was an editorial board member of eight journals, wrote many papers, won the Outstanding Mentor Award through the Ronald E. McNair PostBaccalaureate Achievement Program. In 2006, she was awarded the Stephen Dal Nogare Award from the Chromatography Forum of Delaware Valley.
Accelerating analysis with mass spec If “Mass Spectrometry Guru” were a title at Michigan State, Dan Jones would have it. Jones, professor of chemistry and biochemistry, has spent four years at MSU involved in research projects across campus studying metabolomics. “Metabolomics is the crazy idea that we can study how organisms function by measuring as many different chemicals that they produce as possible,” Jones said. “For example, when you go to your physician, they will take some blood and measure your glucose or cholesterol. Based on a few measurements, they will tell you if you are healthy or not.”
plants will require as many as 20 tissue samples, which means hundreds of samples will be analyzed for more than 100 different chemical forms.
In a similar fashion, Jones uses a combination of mass spectrometry, liquid chromatography, and gas chromatography to characterize hundreds of compounds inside plant and animal tissues.
“This knowledge will improve plant production of a chemical or give us the ability to put these genes in yeast or bacteria, which will make it more efficient to harvest them,” Jones said. “Some of the chemicals we are testing now are effective cancer treatments, but they are expensive because they are difficult to produce.”
Jones’ lab has developed tools that enable them to test for more than 100 different chemicals from a single sample in less than one minute. “Only a few years ago, it would take an hour to test for 20 or 30 chemicals,” he said. His goal is to continue to make the technology more efficient so they can test more compounds on more samples, thereby enabling research that previously couldn’t even be imagined. Jones is involved in a recent National Institutes of Health grant to uncover how 14 medicinal plants make valuable compounds used to treat human disease. To decode the relationship between the genetic make up of these plants and the compounds they produce, scientists have several distinct tasks. They will understand the expression of genes in these plant tissues using transcriptomics and highthroughput DNA analysis. They will also create detailed chemical profiles of the same tissues. They are also generating databases of the chemical properties. Each of the 14
When the chemical profiles and genetic profiles are complete, they will be joined using bioinformatics to create a database that connects genetic information to chemical pathways.
Jones is also investigating how new chemicals attack cancer cells inside animal tissues. He is working with Babak Borhan, professor of chemistry, to investigate a plant-derived chemical that is a promising new cancer drug. They have sampled cells treated with traditional cancer treatments over time to see how their chemical composition changed and then compared it to Borhan’s new drug. Comparing the results allows them to determine how the cancer cells were killed. “We would like to understand how the chemicals Borhan synthesized kill cells,” Jones said. “If they kill cancer cells in a different way than other drugs, which preliminary results show that they do, then these chemicals could provide an additional mechanism for treating drugresistant cancers.” Jones has also developed a new tool to continue to improve mass spectrometry: mass spectrometry
These two mass spectrometry images from Dan Jones’ lab are of the leaf of a wild relative of tomato. They show the locations and amounts of two different metabolites present in the glandular trichomes of the leaf (detected at two different masses). Images were generated by chemistry graduate student Chao Li.
imaging which uses a laser to take samples at any point on an image. For example, the glands from a leaf can be transferred onto a specially tailored carbon surface and then use a laser to take 40 or 50 mass spectrometry readings. This new technology allows them to ask whether a particular cell in the edge of the leaf is doing similar things to a cell near a vein inside the leaf. “It turned out that location has a lot to do with chemistry, and when we take a sample of the whole leaf –we are taking the average of all the different cells there,” Jones said. Jones is involved in projects all across campus, but indicated that none of it could be done without MSU’s investment in core facilities. “MSU has long been a leading institution in mass spectrometry and we continue to be a leading institution,” Jones said. “We have fantastic experts and resources. A lot of that comes from phenomenal access to core facilities and instrumentation.”
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Alumna wins national ACS award Erin Vogel (Ph.D. Chemistry ’08) recently received the ICI Student Award in Applied Polymer Science from the the American Chemical Society (ACS) Division of Polymeric Materials: Science and Engineering. The national award recognizes outstanding graduate students of applied polymer science.
Erin Vogel received her Ph.D. in 2008 and is a senior chemist at Dow Chemical.
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Help Support Chemistry If you want to join me in supporting the long-term, financial viability of chemistry, I suggest contributions to the department’s discretionary endowment. Your gift will forever support essential components of the Department of Chemistry at Michigan State. Use the envelope provided or for a complete list of chemistry endowments and other funds, go to: http://bit.ly/msucem. Thank you. - John McCracken
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Vogel, a senior chemist at Dow Chemical, was selected for the award among six finalists who all presented papers at a symposium as part of the 2008 ACS Meeting. She received her award during the Spring 2009 ACS Meeting in Salt Lake City, Utah. “The award exemplifies my positive experiences at MSU,” Vogel said. “Professor Greg Baker always said our goal is to be scientists by understanding fundamentals and collaborating with our groups. I found it fun and enjoyable to work on materials used for something tangible.” Vogel’s award was for the paper titled “Unimolecular Biodegradable Nanoparticles from Comb Polymers.” Using a biodegradable polyglycolide scaffold, she prepared nanoparticles that self-assembled into unimolecular micelles in aqueous solution. The particles effectively encapsulated
and released a variety of molecules, showing thermoresponsive behavior, and were cross-linked to enhance stability. Originally from Grand Rapids, Vogel earned a B.S. in Chemistry and Teaching from Calvin College before coming to MSU in 2004. During her four years at MSU, she presented six papers at four ACS meetings and says she gained valuable experience giving talks and interacting with many scientists. She says the breadth of research and skills learned at MSU are what helped her land a position at Dow Chemical. She joined Dow in 2008 and is working to develop new polymeric materials for adhesive, coating, and elastomeric applications. Vogel said she enjoys being involved in project leadership and working on teams. “The environment at MSU really helped me collaborate with others and develop my skills in research and teamwork,” Vogel said. “I enjoy working with both research scientists and the business people who are on the front end. It is enjoyable to see how the science translates as meaningful to many others.”
Hupp to deliver alumni lecture Joseph Hupp will deliver the department’s annual Chemistry Alumni Lecture on April 15, 2010. Hupp is the Morrison Professor and Department Chair for the Department of Chemistry at Northwestern University. The lecture will begin at 4:10 p.m. and all alumni, students and faculty are invited. Hupp’s lab at Northwestern researches intra- and intermolecular energy and electron transfer. Many of the research projects in his lab revolve around a theme of studying materials for alternative energy applications. Hupp received his B.S. in chemistry from Houghton College and his Ph.D. in chemistry from Michigan State University in 1983. He joined the faculty at Northwestern in 1986. The Alumni Lecture Award was created by alumni of the Department of Chemistry to bring prominent scientists to campus where they present a series of lectures, participate in an instructional program and interact with faculty and students.
ALUMNI CLASS NOTES Karl Vorres, ’52, is retired and living in Tucson, Arizona. Wayne Wolsey, ’58, has retired as Professor of Chemistry at Macalester College in St. Paul, Minn. He is working on the 10th edition of Chemical Principles in the Laboratory (co-authored with Emil Slowinski). Richard Barnes, ’59, retired from a long career in international chemical sales and recently published a fictional thriller titled The Faircloth Reaction. Michael Hoechstetter, PhD ’60, retired after 15 years at Chemical Abstracts Service and 20 years at Ashland Chemical Company, and is now working part-time as an adjunct instructor in chemistry at Columbus State Community College. Bill Nickels, MS ’63, retired after 40 years of teaching college chemistry and is currently serving his 12th year as an elected Ypsilanti City Council member. Michael Powell, ’63, MS ’66, PhD ’69, retired several years ago from NASA’s Medical Sciences Division. Gary Steinman, MS ’63, is chairman of biochemistry of Touro College of Medicine in New York City. His area of research is spontaneous twinning and he was featured in an episode of on National Geographic Explorer which aired in November. David Taft, PhD ’63, continues as COO of Landec Corporation and is focused on developing new technology platforms for the company as well as spending a lot of field time exploring acquisitions. Floie Vane, PhD ’63, is enjoying retirement in Anacortes, Washington. Clare Moritz, ’66, retired in 2006 after teaching 40 years at Waverly Community Schools. Charles Yowler, ’73, is a professor of surgery at Case Western Reserve University and director of the Division of Trauma, Critical Care and Burns at MetroHealth Medical Center in Cleveland, Ohio.
Frederick Tehan, PhD ’74, after a successful career in the retail industry, has returned to teaching chemistry at Utica College of Syracuse University as a visiting assistant professor. Richard Yost, PhD ’79, is celebrating 30 years at the University of Florida and just graduated his 57th PhD student and has 13 more in his research group. He is the chairelect of the statewide faculty senate for the universities in Florida and will join the Board of Governors next summer. Michael Boska, ’80, is a professor of radiology and vice chairman for research at University of Nebraska Medical Center in Omaha, Nebraska. Damian Procari, ’81, is a patent attorney at Ford where he patents and enforces the work of others. Susan Werng Squiers, ’81, MS ’83, is retired from a career as a pharmacist. Michelle Brooks, ’85, MS ’93, PhD ’96, has recently taken a new position at the University of Maryland as the Assistant Director of the Biological Sciences Graduate Program. Scott Hanton, ’85, is a section manager in the Global Analytical Sciences department at Air Products and Chemicals and was recently named to the editorial board of the Journal of the American Society for Mass Spectrometry for his contributions to polymer mass spectrometry and matrixassisted laser desorption/ionization (MALDI) mass spectrometry. Michael Lombarski, PhD ’85, is in his 12th year as a Criminalist (forensic chemist) at the New York City Police Department’s Lab. Angela Fleming, ’86, is a teacher in California and recently published the book Teachers in Crisis: Why Do They Leave After an Average of Five Years in the Classroom? Eric Hudson, ’86, is a Principal Scientist at Lam Research Corp. in Fremont, California, working on plasma etch technology for the semiconductor industry. Recently he had
the honor of presenting a Plenary talk at the 31st International Symposium on Dry Process in Busan, South Korea. David Young, ’93, PhD ’97, is an applications software expert at the Alabama Supercomputer Center and in 2009 published his second book, Computational Drug Design; A Guide for Computational and Medicinal Chemists. LaRon Brown, ’95, is a Quality Engineer at Ford Motor Company, specializing in coating processes and injection molded plastics, and has received several Technical Achievement Award nominations for the launch and implementation for injection molded in color technologies on the 2007 Ford F-250 and 2010 Mustang, along with two SPE award nominations for Most Innovative Use of Plastics. Kira Christian, ’96, DVM ’05, is at the Centers for Disease Control and Prevention in Atlanta working in global disease detection and identifying animal to human transmission of international disease outbreaks that could affect the US. Dan Mindiola, ’96, is a professor of chemistry at Indiana University – Bloomington and received the 2009 National Fresenius Award. Deborah Marie Rathke Jenness, ‘98, is an elementary teacher and received the Office Max “A Day Made Better” Award. Prerna Goradia, PhD ’04, is the Manager of research and development for Grauer & Weil in India. Tina Martin Nguyen, ’06, is a Research Technologist at MSU’s Great Lakes BioEnergy Research Center working on Cell Wall Analysis as part of a biofuel project funded by the Department of Energy. Brooks Youngblood, ’06, is teaching high school chemistry in Forsyth County, Georgia. Tennille Jameson, ’07, is attending U of M Pharmacy School and will graduate in 2011.
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DEPARTMENT OF CHEMISTRY COLLEGE OF NATURAL SCIENCE 103 Natural Science Building East Lansing, MI 48824-1115
Laser imaging based on chemical composition Marcos Dantus received a $749,369 grant from the National Science Foundation for developing a new laser capable of imaging according to chemical composition. The grant, one of several Chemistry faculty have received as part of the American Recovery and Reinvestment Act, is for development of a phase and polarization modulated ultrafast laser source for nonlinear optical imaging and molecular identification. The system is based on robust ytterbium fiber technology and optical parametric amplification, allowing the generation of sub-5 fs pulses at 1040 nm. A new concept for manipulating ultrashort pulses is presented, enabling userdefined waveform generation for the synthesis of complex nonlinear optical measurements based on sequences of multiple phase-locked pulses. Pulse sequences with up to 180 sub-pulses will be possible, where each pulse in the sequence can be tailored to have a user-defined bandwidth, The Dantus Research Group specializes in controlling laser spectral phase, polarization and time delay. matter interactions. In this photograph from the Dantus lab, an invisible ultrafast laser with pulse duration of 30-millionths-of-aProjects the lab are working on include the real-time detec- billionth-of-a-second is used for machining the Spartan Block “S� tion of toxins and adulterants in food and depth resolved im- pattern. The ultrafast laser causes plasma ablation and white-light aging of heart tissue and the influence of high cholesterol di- formation at the focus and excites two-photon green fluorescence ets. The instrument will provide multimodal depth-resolved from the solution. imaging of bone, tendon and cartilages as well as other medical, food safety and homeland security applications.