Issue Date: July 11, 2011
In 1929, researchers descended on Prince-ton University for the third biennial Symposium on Organic Chemistry. Back then, Princeton’s Frick Chemical Laboratory was a just-built, state-of-the-art brick facility on the ivy-covered campus. Last month, the same meeting—now in its 42nd incarnation and known as the National Organic Chemistry Symposium or NOS—returned to Princeton for the first time, just months after Princeton’s chemistry department left that aging facility for a spanking new Frick building, resplendent in glass and metal.
The organic chemists of yesteryear could no more fathom a laboratory like the new Frick than they could imagine the advances happening inside it. But it’s clear that some things about their field haven’t changed. As a story about the 1929 meeting in the News Edition of Industrial & Engineering Chemistry (the forerunner of C&EN) put it, “Once again it was shown that organic chemists can get an unbelievable amount of pleasure and profit out of three solid days of nothing but organic chemistry, with even food and sleep cut to a minimum in order to allow more time for more organic chemistry” (I&EC, Jan. 10, 1930, page 8).
It’s true that the symposium, which is sponsored in part by the American Chemical Society’s Division of Organic Chemistry (ORGN), takes up several very long days. But afternoons are dedicated to sports and activities so that the upwards of 700 attendees can get to know each other. Poster sessions are major social events. And the meeting is designed without concurrent talks so that everyone has a shared experience. For the students in attendance, the meeting is designed to welcome them into the organic chemistry family. For established researchers and academics, it’s a family reunion.
“At NOS there are opportunities for everybody to meet everybody,” said Cornell University chemist Geoffrey W. Coates, one of 14 invited speakers at this year’s conference. Smaller conferences might achieve a similar informal vibe, “but you wouldn’t have the kind of breadth that the NOS does, you wouldn’t learn as much about what else is out there.”
Faculty at primarily undergraduate institutions flock to NOS to build ties with each other and with the field, said Carolyn E. Anderson, an assistant professor of chemistry at Michigan’s Calvin College. “At bigger meetings we wave to each other and keep going,” she explained. “For us, this is the meeting. This is where we get to hang out, to interact.”
“It’s like adult summer camp,” said Jennifer Howell, a fifth-year graduate student in John Wood’s group at Colorado State University. “We learn about chemistry and then we get to go play softball.”
This year's lineup of speakers was designed to showcase the diversity of research in organic chemistry. But talks were more than a recounting of research results. Speakers described challenges in their fields that they believe organic chemists have the power to solve. Introductions highlighted challenges and brought up economic issues that affect chemists. And talks were sprinkled with a healthy dose of humor. “Everybody brings their ‘A’ game to NOS,” said Gary A. Molander, University of Pennsylvania chemistry professor and 2011 chair of ORGN. “It’s one of the most important things we do as a division.”
Boston College chemistry professor Amir H. Hoveyda started off the meeting by discussing a new tungsten catalyst that can perform ring-closing olefin metathesis to form large rings, or macrocycles, with selectivity for Z olefins. “We have done a lot in catalysis, and we have not done much in catalysis,” he told C&EN. His group and others have made strides in developing metathesis catalysts that can selectively churn out Z olefins (C&EN, March 28, page 9; May 23, page 33). But E-olefin selective meta-thesis catalysts are far from a done deal, he said. More broadly, organic chemists still need to worry about the vast quantities of waste that result from a typical synthesis and to come up with ways to do textbook reactions more efficiently, he added.
In a talk describing improvements in the industrial-scale route to the diabetes medication Januvia, Joseph D. Armstrong III, senior director for RNAi and discovery process chemistry at Merck Research Laboratories, echoed the call for more work in catalysis because of the accompanying potential for waste reduction. “The footprint of pharma is shrinking, but there will be opportunities in green chemistry and green technology,” he said.
Nobel Laureate Robert H. Grubbs also spoke more generally about challenges for catalysis in the symposium’s keynote address. Grubbs, of California Institute of Technology, is a pioneer in metathesis (see page 25) and is the winner of this year’s ACS Roger Adams Award in Organic Chemistry, an award traditionally celebrated at NOS. He noted that the vast majority of catalysts are designed to add functional groups to a molecule of interest. “We need chemistry to take functionality out as well,” he said.
“Both Joe Armstrong and Bob Grubbs had excellent points regarding challenges for catalysis,” Vy Dong of the University of Toronto, who presented her own team’s work in catalysis inspired by large rings, told C&EN after the meeting. “In fact, the two points are related in an emerging area of green chemistry that aims to transform renewable biomass into more simple alkanes, making products that would normally be derived from petroleum cracking.”
Leaders in the field of chemical biology also issued challenges to the audience. For example, the University of California, Berkeley’s Carolyn R. Bertozzi had advice for aspiring reaction developers—come up with chemistries that can be done amid the complexity of biology. Bertozzi is well-known for developing azide- and alkyne-containing tools to probe biological events that involve cell-surface sugars called glycans. “I don’t have to sing the praises of the azide to this crowd,” Bertozzi quipped. But one chemical tool can’t tackle all of biology alone, she stressed. “For students looking for research questions, inventing new bio-orthogonal reactions would be really high impact.”
Prior to Bertozzi’s talk, Scripps Research Institute chemical biologist Benjamin F. Cravatt III called for more chemists to deposit their compounds in public compound libraries such as those run by the National Institutes of Health.
“The beauty of academic organic chemistry is that we can make molecules for no particular reason other than that they’re interesting structures or challenging to make,” Cravatt said in Princeton. But submitting compounds to libraries lets chemical biologists unlock the potential of such unusual compounds, he added. In fact, his team found promising inhibitors for a protein with roles in cancer and neurodegeneration from compounds Massachusetts Institute of Technology chemist Gregory C. Fu submitted to just such a library (C&EN, March 14, page 13). The Fu team’s molecules are chiral aza-β-lactams, which Cravatt says occupy an unusual portion of structural space that is rarely found in commercial compound collections.
“We’re beholden to academic chemists for providing the tools that could ultimately lead to new druggable disease targets,” said Christopher B. Cooper, senior director of chemistry for the Global Alliance for TB Drug Development, who attended the symposium. “The field of TB is suffering from a lack of pharmacologically validated targets,” and chemical biology has the potential to remedy the situation, he added.
Pfizer’s senior vice president and head of worldwide medicinal chemistry Tony Wood added to the chorus calling for more chemical tools to probe biology, using the flourishing drug target class of kinases as an example. Medicinal chemists have yet to develop selective inhibitors for the vast majority of kinases, and it’s often not clear which of a kinase’s many forms is most relevant to a disease, he told C&EN. Chemical biology tools from several labs have made strides in understanding kinase biology, but the picture is far from complete, Wood said. “There’s a role for synthetic chemists to provide tools to understand pharmacology. I see huge opportunities there.”
However, some chemists at the meeting wanted to go beyond abstract research opportunities and discuss the concrete reality of the economy. After Wood’s talk, University of Delaware adjunct professor Albert S. Matlack stood to say that “many of us are disappointed” with downsizing in the industry, prompting applause from attendees.
“There’s one thing on the minds of the 16,000 chemists in the Organic Chemistry Division—where are the jobs going to be in a few years?” said University of Pennsylvania professor Marisa C. Kozlowski during her introduction of materials-focused chemists Coates and Colin Nuckolls of Columbia University.
“Jobs are what everyone is talking about. If you listen at poster sessions, there’s a lot of discussion about what folks’ plans are,” Kozlowski, a member of ORGN’s executive committee, told C&EN. “There is so much angst among so much talent.”
Because of layoffs in the pharmaceutical industry “the landscape of employment in organic chemistry in this country has changed, and it’s not clear whether that’s permanent or not,” Kozlowski said. The speakers at NOS can’t change the economy single-handedly, but the inclusion of talks focused on materials and green chemistry makes it clear that organic chemistry is useful outside the traditional employment channels, Kozlowski said.
After four jam-packed days of organic chemistry, it’s safe to say that even the hungriest NOS attendee went home sated. But William J. Greenlee, senior director of chemistry at Merck and the executive officer of the symposium, hoped they also went home inspired. “I hope that the attendees, especially the many students, took away a sense of the many areas of science where organic chemistry plays an important role,” he said.
The next NOS will be held at the University of Washington, Seattle, from Sunday, June 23, through Wednesday, June 26, 2013.
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