Art Meets Science
“Bench-Stable 2-Halopyridinium Ketene Hemiaminals as Reagents for the Synthesis of 2-Aminopyridine Derivatives” describes a new method for making 2-aminopyridines, an important class of compound found in many biologically active compounds, including FDA-approved drugs. Organic Letters is a leading organic chemistry journal.
Majireck said the project published in the Nov. 22, 2024, issue of Organic Letters took about five years to complete. “The organic synthesis was a long-standing problem — how to make our key chemical reagent on a large scale — that we had worked on here and there since 2016, so it took quite a while to perfect that recipe,” he explained. “This new synthesis method is likely to find ready use in the design of new pharmaceutical agents for a range of disease types. In the meantime, it garnered enough interest that our central reagent is now manufactured by a major chemical vendor as ‘Majireck’s reagent.’”
Covering chemistry
Early this semester prior to the issue’s publication, Majireck shared with Crespo, a biochemistry & molecular biology major and art minor, the opportunity to make a visual for the cover of Organic Letters. “Naturally I took up the opportunity,” she said.
Crespo described her design: “The piece itself has three parts. The orange background is a drawing of a real organic synthesis bench top during the peak of research. It’s quite messy, but this is really normal: the mark of a lab that is producing results! (Although at the end of projects we always ensure we are practicing proper OSHA compliance procedures when cleaning.) For some reason, I found the messiness of the lab benches eye-catching.
“All the different glassware in the picture are parts of various students’ projects. Everyone in the Majireck lab is working on something interesting, from sonically activating compounds by blasting sound waves at little glass tubes or trying to build compounds of medicinal nature only found in the wild. It’s really all very exciting.
“The lab equipment and specific reaction structures/reactants at the foreground are details of the optimized reaction the students, myself included, of the Majireck lab ‘Pyridine group’ have been working on.”
Crespo plans to continue doing research before going on to medical school. “Of course, naturally, between all the science, I will weave art right into my plans” she said.
Five years of researchers
Student and alumni members of Majireck’s research group who contributed to the Organic Letters article include:- Bella Bote ’22
- Zoe Krevlin ’22
- Chrissy Crespo ’25
- Prim Udomphan ’26
- Carolyn Levin ’26
- Christie Lam ’26
- Amy Glanzer ’21
- Holly Hutchinson ’21
- Danielle L. McConnell ’20
- Alisha M. Blades ’20
- Crystal Lin ’22
- John Frank ’24
- Will Strutton ’25
- Jordan Merklin ’26
- Beau Sinardo ’26
- Khady Gueye ’23
- Karly Leiman ’21
- Ashley Thayaparan ’21
- Joel Adade ’22
- Nestor Martinez ’25
The Majireck Group’s Organic Synthesis Research
Organic chemistry is the study of carbon-based compounds, which include many molecules of life like proteins and DNA, or valuable chemicals like medicines and polymers. Organic synthesis pertains to creating these types of chemicals from scratch in the lab, akin to building structures but on the molecular scale. Instead of bolts and beams, bonds are created between atoms using chemical reactions as the main set of tools. It takes a lot of planning, testing, and tinkering to build the desired type of molecule.
In Majireck’s work, the researchers focused on a ring structure called pyridine that is commonly found in bioactive and/or medicinal molecules. They developed a set of new chemical reactions (new tools for the organic synthesis tool box) as well as a new chemical reagent (like a versatile building block) that installs a pyridine ring on to many other different types of medically relevant molecules.
At first, they could only make tiny quantities (a few hundred milligrams) of the compound, but professional medicinal chemists would need a lot more material if this were to be incorporated into the synthesis of a new drug.
Their paper in the Organic Letters paper outlines a new protocol for making multigram quantities of the compound, and Oakwood Chemical quickly followed up with a kilogram scale procedure. So now, any practicing synthetic chemist in the world can use the Majireck compound to aid their research.
Time will tell, but the Hamilton researchers expect to see their methods and reagents used by medicinal chemists in the synthesis of drug candidates for many types of diseases. For example, pyridine rings are a key structural element in a range of cancer drugs and antibiotics.
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