Arthur C. Cope Scholar: Donald S. Matteson

Donald S. Matteson’s friends dubbed him “The Mad Chemist” when he was a boy. “By the time I was 11 or 12, I was making things like sodium-lead alloy and thiokol rubber,” he recalls. His father, a high school biology teacher, nurtured the boy’s scientific interest. After a jar of home-canned plums spoiled, “my dad said, ‘If you let it sit around a week or two, it will ferment some more and you can distill alcohol out of it.’ So I did.”

That playful and relaxed attitude toward experimentation has stayed with Matteson throughout his career and governed the way he ran his lab. Now 80, he is a chemistry professor at Washington State University (WSU), Pullman.

“Students can’t really learn chemistry from lectures; they learn it by doing it,” Matteson maintains. He encouraged his grad students and postdocs to test out their hypotheses in the lab, reasoning that even if they didn’t synthesize the anticipated products, the team would still gain some chemical insights.

In fact, when his first grad student, Raymond W. H. Mah, obtained an unexpected product, Matteson’s efforts to work out the rearrangement that had occurred led to his discovery of α-haloalkylboronic ester chemistry. “The most important discoveries I’ve made since have all been based on that chemistry,” he says.

Matteson “is best known for his seminal developments in the fields of boronic ester chemistry and asymmetric synthesis,” a method that controls the chirality of reaction products, says his Pullman colleague Philip P. Garner. “He has developed reactions that provide precise and general tools for stereoselective and asymmetric syntheses,” including the Matteson α-haloalkylboronate alkylation reaction.

“Don and his coworkers have utilized this chemistry for the synthesis of a wide range of biologically interesting compounds with very high enantioselectivity: use of carbon nucleophiles for synthesizing pheromones, oxygen nucleophiles for synthesizing carbohydrate derivatives, and nitrogen nucleophiles for synthesizing amino acid analogs,” notes William R. Roush, a chemistry professor and executive director of medicinal chemistry at Scripps Research Institute, in Florida.

“The latter work is particularly significant,” Roush adds. Matteson’s studies of α-amino boronic acids and his methodology for their synthesis laid the foundation for Millennium Pharmaceuticals to develop Velcade, a treatment for patients with multiple myeloma, Roush explains. “Velcade contains a boronic acid analog of leucine, which serves as the electrophilic center that interacts with the proteasome—Velcade’s biological target. This amino acid analog is synthesized as a single enantiomer on very large scale using Don’s α-alkylboronate alkylation technology.”

Matteson earned a bachelor’s degree in chemistry in 1954 from the University of California, Berkeley, and a doctorate in organic chemistry in 1957 from the University of Illinois, Urbana-Champaign, where he studied with Harold Snyder. Matteson joined WSU’s chemistry faculty in 1958 and attained the rank of professor in 1969. He is the author of two books, coinventor on five patents, and author or coauthor of 203 technical articles.

His awards include an Alfred P. Sloan Foundation Research Fellowship in 1966 and the Boron USA Award in 1992.