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Get the most interesting and important stories from the University of Pittsburgh.Organic chemistry is serious business. But as you spend time reading about molecules and reactions, you’ll notice some less-than-serious nicknames — like MOM, DEAD, TiPSY and even BArF. So when Pitt PhD student Ashlyn Bohn was brainstorming a name for her own new chemical discovery, she wanted to have some fun with it.
Eventually, she struck on an acronym that paid homage to Pitt’s most striking building: CAATHy.
“I was glad to be able to name something after the institution we represent,” Bohn said. “There’s a lot of cool chemistry going on at Pitt.”
Bohn is a chemistry PhD student studying in the lab of Distinguished University Professor Peter Wipf in the Kenneth P. Dietrich School of Arts and Sciences. The team conducts what’s known as natural products synthesis, or taking useful molecules from nature and finding ways to create them or their building blocks in the lab. When she joined the group, Bohn took the reins of a project left by a former student and sought to find a simpler, easier-to-reproduce path to a particularly useful molecule.
After lots of trial and error, she came across the transformation that would become CAATHy: a method that’s more efficient, uses more affordable inputs and results in fewer unwanted byproducts than previous techniques. She and her lab mate Benjamin Cipriano published the paper on their new technique in January in the journal Synthesis.
Building CAATHy
CAATHy stands for “chiral auxiliary-assisted asymmetric transfer hydrogenation” — intimidating if you’ve never sat through an organic chemistry lecture, but it can be broken down piece by piece.
The auxiliary is a part of the molecule that Bohn added to make the reaction work, a menthol group (a compound most well-known for being responsible for the smell of peppermint). Much like one of your own hands, this group is chiral: It’s different from its mirror image no matter how you turn it around in 3D space. That choice helped create an asymmetric reaction, one that produces more of the correct molecule and less of its not-as-useful mirror image. The process passes a hydrogen atom from one molecule to another, a transfer hydrogenation.
The result of CAATHy and the rest of the team’s process is the core of a natural product called macroline: a scaffold of atoms that’s the basis for hundreds of molecules derived from snakeroot and other related plants. Many of these molecules have antimicrobial, anticancer or other useful properties.
Bohn describes the process of their research as being much like cooking from scratch — all the way from scratch, if you had to grow the wheat for your flour from seed. Cipriano likens the process to playing with Lego bricks (albeit, higher-stakes and with a bigger impact). When they find a new pathway for getting to an important molecule, it can make it easier for others to produce new medicines and other useful substances.
“We need novel ways to prepare these molecules, especially once you get to more complex compounds,” said Cipriano. “Very small changes in molecules can actually have a huge impact on how you make them.”
Coming up with one of these novel mechanisms also means they get the right to name their discovery. The name went through several iterations, like AAATH (too awkward) and CAATH (not catchy enough). Bohn’s stroke of genius was borrowing the lowercase “y” from “hydrogen.” Creative acronym magic is yet another tool in the organic chemist’s toolbox.
The name simplifies what would otherwise be a mouthful and pays homage to a building that both students have affection for. Bohn fondly remembers long nights spent studying for PhD exams in the Commons Room, and when Cipriano gets to work early on Saturdays, he likes to watch the sun rise by the building from a Chevron Hall balcony.
And hopefully, says Bohn, the name will give people a reason to learn a bit more about the importance of a discipline that’s famous largely for striking fear in the hearts of undergrads.
“Chemists, we have fun, too,” said Bohn. “And our methodology, CAATHy, could be used in medicinal chemistry and could be used to make really important molecules.”
Photography by Aimee Obidzinski