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Research & teaching: Bonding pair in the hunt for new alkaloids

  • Scientist-teacher-mentor:
    Scientist-teacher-mentor:  Chemist Jonathan Scheerer was recently named a Henry Dreyfus Teacher-Scholar in recognition of the way in which he combines classroom instruction with laboratory experiences for his undergraduates.  Photo by Joseph McClain
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Alkaloids are members of a vast family of molecules that are chemically organic and also occur in nature. All forms of life have evolved ways to produce these useful chemicals.

Humans have long known that some of the alkaloids produced by plants, bacteria and fungi can be useful in our lives. Quinine is an alkaloid; the bitter taste of tonic water is one characteristic of these molecules that are carbon-based, but have a molecular structure that’s heavy on nitrogen atoms.

Some other famous members of the alkaloid clan are nicotine, morphine and cocaine. Like quinine, these drugs can be readily isolated from their plant origins. Jonathan Scheerer, an associate professor of chemistry at William & Mary, studies alkaloids. He is interested in the complex chemical process of alkaloid synthesis, making specific molecules in the lab.

Scheerer doesn’t work alone in the lab. He has assembled a group of William & Mary students, mostly undergraduates, to assist him in the quest to figure out the synthesis and bio-synthesis of various alkaloids. His success at integrating teaching and research has earned recognition in the form of the 2015 Henry Dreyfus Teacher-Scholar Award. It’s one of the top honors an American chemistry professor can receive.

“Research support at undergraduate institutions is very important,” stated Mark J. Cardillo, executive director of The Camille and Henry Dreyfus Foundation. “Nearly half the chemists who earn a doctorate degree receive their bachelor's degree from an undergraduate institution, and research is a fundamental part of chemistry education.”

The Camille and Henry Dreyfus Foundation is a leading non-profit organization devoted to the advancement of the chemical sciences. It was established in 1946 by chemist, inventor and businessman Camille Dreyfus, who directed that the foundation's purpose be "to advance the science of chemistry, chemical engineering and related sciences as a means of improving human relations and circumstances around the world."

Scheerer is one of seven U.S. Dreyfus Scholars for 2015. He is not the first Dreyfus Scholar from William & Mary’s Department of Chemistry.

“Being named a Dreyfus Scholar is a great honor, of course. It’s really a recognition of how we combine classroom instruction and laboratory research at William & Mary,” Scheerer said.

The Dreyfus Scholar Award comes with an unrestricted $60,000 grant. Scheerer plans to invest the money in his students, both to support them in research and for travel to professional conferences. Conferences provide Scheerer an opportunity to give his lab students a close look at the progress being made by the world’s other alkaloid scientists.

Scheerer explained that working to understand synthesis and bio-synthesis of various alkaloids offers solid background and opportunity for a young chemist. The potential that these molecules represent make alkaloid synthesis an excellent choice as a chemistry subspecialty. The molecules Scheerer investigates aren't related closely to household-name alkaloids such as LSD and cocaine, substances that chemists have been looking at thoroughly for decades.

“The low-hanging fruit, so to speak, among these molecules have been picked up long ago,” Scheerer said. The vast number of less-accessible alkaloids include some molecules that have tantalizingly attractive properties. There are alkaloids that show anti-parasitic properties. Others are effective natural vasodilators and could be used to increase blood flow to the brain or other tissues, a potential clinical strategy to combat neurodegenerative disease and age-related dementia.

One of Scheerer’s areas of study concerns alkaloids that are produced by fungi that live on certain grasses. The molecule is deadly to insects that might eat plants or fungus, but all indications show that it’s harmless to humans. It would make an excellent candidate for use as a natural insecticide, if only you could get enough of it.

“I don’t know how you’d grow enough of this fungus, since it lives on a plant,” Scheerer said. “So I have to figure out how to synthesize it in the lab.”

There are many paths that a William & Mary undergrad can take to get involved in a lab and get involved in work like helping Scheerer figure out how to synthesize the next big alkaloid.

The routes to the Scheerer Lab are much the same as they are for undergraduates seeking to work with other researchers in the natural sciences at William & Mary. Scheerer said some students read about his work on his web page. Faculty colleagues refer others. A fledgling chemist might first take interest in lab work in one of the classes Scheerer teaches. And there is always word of mouth; the science-major grapevine is quite efficient and Scheerer’s lab enjoys a continuing good reputation.

Like many scientists at William & Mary, Scheerer takes in students at any point from freshman to senior. Most join earlier rather than later in their college careers, and the labs often include one or more of the chemistry department’s graduate students. Participation in a lab is not an official requirement for chem majors, but most do choose do get involved with a professor’s research work.

“We usually have about 65 chemistry majors here in the department at any one time,” he said. “About 85 percent of the students are involved in chemistry research.”

Scheerer says that significant research experience is necessary to get a full understanding of the material taught in the classes. Gaining a full competency in a chemistry lab is a lengthy apprenticeship and requires time-management and problem-solving skills combined with physical dexterity.

Some students get it sooner than others, but Scheerer says that usually by the time he has a mentored a student to a point at which they could be considered a fully formed and competent chemist, they’re ordering a cap and gown.

Bringing along young scholar-scientists requires a lot of time on the faculty member’s part, as well. Mentoring lab members and other students occupies between 45 and 55 percent of Scheerer’s time, he estimates. “All the rest is teaching classes and prep,” he added.

Joining a lab means making a commitment to hours of work, but Scheerer points to a slate of compensations. In addition to obtaining a first-class apprenticeship in the rigorous and complex field of chemical analysis, many of Scheerer’s students end up as co-authors on papers published in the top peer-reviewed chemistry journals. In the past five years, he has published nine papers, which list 16 student co-authors. A tenth paper, with two additional student co-authors, has been accepted for publication.

“I have had student co-authors on every paper I’ve published here at William & Mary,” he said. “I put the student who was most involved in the work as the first author.”

In addition to delivering an immense amount of science cred, joining a laboratory is joining a community, Scheerer explained. Each lab develops its own character, a personality that changes from year to year as individual members join and others leave. Scheerer said that the lab members develop a bond, often acting like siblings.

“They have fun. There is a lot of sarcasm, usually,” he said. “We don’t have too many pranks, though.”