Sarah Reisman: Better synthesis of natural compounds

Chemist hunts for recipes to brew seemingly impossible-to-synthesize molecules

Sarah Reisman headshot

CREATIVE CHEMISTRY  Sarah Reisman spends her days thinking about innovative ways to build complicated chemical compounds that could lead to new drugs for numerous ills.

S. Reisman

Sarah Reisman, 36
Caltech | Organic Chemistry
Graduate school: Yale

Organic chemistry haunts most pre-med students, but not Sarah Reisman. The two-semester class was so invigorating that she abandoned her pre-med major to pursue chemistry.

“Organic chem presented me with this idea that we could do things that are new,” says Reisman, who heads a lab at Caltech. “The idea that I could design a brand new way to make a molecule, there was this real creative component,” she says.

Reisman got the science bug in high school through a program that paired local students with scientists at the MDI Biological Laboratory in Bar Harbor, Maine. As an undergraduate at Connecticut College in New London, she worked in the lab of chemist Timo Ovaska. He asked Reisman and three other undergrads to make various fragments of the ringed molecule phorbol, a difficult task.

Structural scribbles adorn the fume hood during synthesis of a plant-derived natural product. S. Reisman

“We never made that molecule, but he had a plan and some naïve students that were happy to try,” she says. “It taught us how to think about making these products and to be ambitious.”

While getting her Ph.D. at Yale in the lab of John Wood, Reisman dived into synthesis strategies and new reactions, a focus that continued during a postdoc at Harvard. Today she keeps a running list of seemingly impossible-to-synthesize molecules, ones that many chemists steer clear of. “We try to look at molecules that we don’t know how to make,” she says. “What are the reactions that we wish we had?”

Many of these molecules are made by plants, fungi or bacteria and have interesting biological activities that could prove useful in drug development. The molecules typically have elements of asymmetry, dangling reactive chemical groups, and a backbone of many rings. (A motif that Reisman sees everywhere: “A piece of abstract art in an airport looks like benzene rings to me.”)

She has already developed several new synthesis strategies, including a way to make the fungal metabolite acetylaranotin and its chemical relatives. These compounds are potential cancer therapeutics, but difficult to work with.

Without feasible ways to make these molecules, scientists can’t generate quantities large enough for study. Enter Reisman. “There’s still so much important chemistry to do.”

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