Benjamin List, who worked with a Brazilian researcher supported by FAPESP, won the prize for developing a cheap and eco-friendly class of catalysts (image: European Research Council)

Published on 10/25/2021

By José Tadeu Arantes  |  Agência FAPESP – Making chemicals green – reducing the environmental impact of the waste generated by industry and laboratories – was one of the criteria adopted by Sweden’s Royal Academy of Sciences in awarding this year’s Nobel Prize in Chemistry. Laureates Benjamin List, a German, and David MacMillan, a Scot, independently developed a third class of catalysts that are neither metals, widely used as catalysts in commercial products such as car batteries, which when used up and thrown away are a major source of pollution, nor enzymes, which are used by our bodies and other biological organisms to make the molecules necessary for life.

This third way, known as asymmetric organocatalysis, builds on small organic molecules. Organic catalysts have a stable framework of carbon atoms, which can bind to more active chemical elements, such as oxygen, nitrogen, sulfur or phosphorus. This means these catalysts are both environmentally friendly and cheap to produce. They are called asymmetrical because they can drive a chemical reaction that produces only the molecule of interest and not its chiral counterpart (another molecule whose structure is its mirror image, like our left and right hands). This precision is required in the manufacturing of pharmaceuticals, for example.

Longstanding collaboration

Born in 1968 and currently head of the Max Planck Institute for Coal Research in Mülheim, Germany, List has a long history of collaboration with the Natural Product and Drug Synthesis Laboratory (LSPNF) at the University of Campinas’s Institute of Chemistry (IQ-UNICAMP) in the state of São Paulo, Brazil. José Tiago Menezes Correia, currently a postdoctoral researcher at the Federal University of São Carlos (UFSCar), worked with List at the Max Planck Institute while he was doing his PhD at IQ-UNICAMP with a scholarship from FAPESP. His thesis advisor was Fernando Coelho, who is now UNICAMP’s Pro-Rector of Extension and Culture. 

Correia’s stay in Germany was funded by FAPESP via a Research Internship Abroad Scholarship. It resulted in an article signed by Correia, Coelho and List, and published in the journal Angewandte Chemie International Edition.

“We developed a methodology for catalytic addition of a class of substances called indolizines to unsaturated ketones. Until then there were no reports in the literature of asymmetric functionalization strategies for this class of molecules. We successfully catalyzed the reaction using organic chiral phosphoric acid, (S)-TRIP, one of the first asymmetric organocatalysts described by List’s group,” Correia told Agência FAPESP.

Coelho added that the nitrogenated heterocycles obtained with this asymmetric catalysis methodology were used as substrates for the synthesis of derivates that in later research displayed a good profile as selective inhibitors of tubulins (proteins that act as building blocks for microtubules, a major component of the skeletal system in living cells), and hence as potential candidates for novel selective anti-tumor agents.

“Professor List has come to see us here in Brazil several times. He’s an extremely cordial person and very good company. We’re preparing another student to work with him as a research intern at Max Planck,” Coelho said.

Correia confirmed these qualities of the Nobel laureate’s personality. “When I began working in Germany, he told me my limit would be my creativity. The structure of the institute and his lab would let me work with any chemistry I wanted,” Correia recalled. “The structure he set up at Max Planck is indeed a ‘dream lab’ for any researcher. And Ben, as we all called him, always had the patience and interest to talk to us about our progress.”

The article “Catalytic asymmetric conjugate addition of indolizines to alpha, beta-unsaturated ketones” is at: onlinelibrary.wiley.com/doi/abs/10.1002/anie.201700513. The Royal Swedish Academy of Sciences press release on the Nobel Prize in Chemistry 2021 is at: www.nobelprize.org/prizes/chemistry/2021/press-release/. 

 

Source: https://agencia.fapesp.br/37160