Student researcher isolates aminoimine during summer chemistry project © July 23, 2010, Norwich University Office of Communications

Biology and premed student Anthony Sassi pours liquid nitrogen into acetone to make a bath that keeps a reaction temperature at -78 C.

photo by Jay EricsonBiology and premed student Anthony Sassi adds liquid nitrogen to acetone and dry ice to make a bath that keeps his reaction at a precise temperature.

As a student conducting organic chemistry research during his summer vacation, Anthony Sassi expects a certain measure of tedium, even when he finds the subject matter fascinating. He knows about repetition, washing racks of glassware and setting up chemical reactions that fail after a lot of work.

But one reaction, created in the summer of 2009 in a Norwich University chemistry lab, was anything but tedious.

Sassi, then an incoming junior from Woodbury, Vt., was participating in a project centered around compounds called 1, 2-diamines. In one of many experiments he set up, Sassi was able to isolate a solution of chemicals stable enough to form into amber crystals. He could scarcely believe the result.

“I was really excited when I found that,” said Sassi. “I didn’t know what it was. I brought it to Dr. [Natalia] Blank, and she said, ‘I think that’s the intermediate.’”

The “intermediate” Sassi isolated was a substance—sort of a waypoint—that forms during the five hours it takes to turn certain cheap and abundant chemicals into 1, 2-diamines, which are organic compounds used as building blocks of pharmaceuticals such as Tamiflu. Synthesis of these diamines is an expensive and time-consuming process. For several years Blank, an organic chemistry professor, has guided groups of students through research aimed at figuring out a better way to generate the final product.

“The process has a lot of potential in pharmaceuticals,” said Sassi, who continued his work on the project during the summer of 2010 with three other students on the Northfield, Vt., campus of Norwich, the country’s oldest private military college.

Blank described the intermediate as a product of the transformative process, which is generally elusive but useful in analyzing the reaction as a whole.

“You’re [usually] not able to touch them. You’re not able to see them,” she said.

By isolating the intermediate—they are calling it aminoimine—Sassi will help scientists study the chemical reaction and find more efficient ways to set it up. While intermediates have been discovered in many chemical processes, she doesn’t think it has happened for the synthesis of 1, 2-diamines.

“That’s quite exciting,” she said. “For that kind of reaction, I don’t think anyone has done that before.”

Sassi, thanks to a grant from the Vermont Genetics Network, is working to refine the reaction and synthesize enough aminoimine so results can be verified by a commercial lab with appropriate equipment.

For that kind of reaction, I don’t think anyone has done that before.”

~ Prof. Natalia Blank,
on student isolating
chemical compound

“We can’t publish this until we get [conclusions] backed by a neutral company,” he said.

The reactions Sassi runs begin in a nitrogen-only environment created by careful assemblage of flasks, tubes and gaskets, where chemicals are added to solvents, stirred and immersed in acetone and a dry-ice bath. The reaction is allowed to progress for five hours, and then halted by dousing the chemicals with methanol.

After that, chemicals are allowed to settle for a period before Sassi begins tests to analyze resulting compounds. Subsequent research will be determined by the data researchers collect.

“It probably takes about a week to do one reaction, unless you’re really pushing it,” he said.

Sassi enjoys the quiet of the laboratories in the summer, and the opportunity to work closely with his professor and other research assistants. He also had time to study for the Medical College Admissions Test, which he took during the summer, and learn a bit of Russian on the side. “I have the whole run of this place. There are only three or four of us here.”

Blank, who brought the idea for research on this particular reaction from her graduate school experience at Dartmouth College, said her role in this project is to make sure students are on the right path, to encourage them and oversee the big picture of the research project. Sassi tends to work well on his own, she said.

“He’s very detail oriented,” said Blank. “He’s very meticulous.”

Sassi spoke about his research in front of the National Conference on Undergraduate Research in Missoula, Mont., in April 2010, and that organization will also publish a paper he wrote on his findings. Sassi has made additional presentations on campus.

A biology major with pre-med concentration, Sassi actually doesn’t consider himself much of a chemistry expert. He enjoyed his organic chemistry classes, however, and signed on to learn about research and gain practical experience, particularly as a boost to his efforts to get into medical school. Blank said summer research is useful to all students, and teaches them to think about the design and implementation of a science experiment, and how to find meaning in the minutia of collected data.

“It will help them with whatever they do in the future,” she said.