Radicals in Synthesis

Oxidation of the lipids that comprise our cell membranes, as well as the membranes of the various organelles and components of our cells, has long been implicated in the pathogenesis of a wide variety of degenerative diseases, as well as cancer and aging. To better understand the part lipid oxidation products play in these processes, we study the mechanisms by which lipids oxidize, as well as the mechanisms by which the oxidation products interact with other cellular constituents. Moreover, we synthesize what we believe to be particularly relevant oxidation products, and/or specifically-derivatized versions thereof, in order to probe their roles in cell and animal models of disease. Lipid classes currently under active investigation in the laboratory include plasmalogens, sterols and polyunsaturated fatty acids. Researchers pursuing projects in this area train in organic synthesis and kinetic and mechanistic studies, and may gain additional experience in the analysis of cell and tissue extracts with state-of-the-art UPLC with  tandem mass spectrometry, molecular and cell biology, and cell imaging.

 

 

 

 

 

 

 

 

For more info, please check out some of our recent work in this area:

 

Synthesis of Vitisin A & D: Thermal Isomerization Enabled by a Persistent Radical Equilibrium

Kevin J. Romero, Mitchell H. Keylor, Markus Griesser, Xu Zhu, Ethan J. Strobel, Derek A. Pratt* & Corey R. J. Stephenson*

Submitted (deposited on chmrxiv at https://doi.org/10.26434/chemrxiv.10294826.v1).

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

Kevin J. Romero, Matthew S. Galliher, Mark A. R. Raycroft, Jean-Philippe R. Chauvin, Irene Bosque, Derek A. Pratt* & Corey R. J. Stephenson* Angewandte Chemie International Edition 201857, 17125-17129.

Radicals in Natural Product Synthesis

Kevin J. Romero, Matthew S. Galliher, Derek A. Pratt* & Corey R. J. Stephenson*

Chemical Society Reviews 2018, 47, 7851-7866.

Synthesis of Resveratrol Tetramers via a Stereoconvergent Radical Equilibrium

Mitchell H. Keylor, Bryan S. Matsuura, Markus Griesser, Jean-Philippe R. Chauvin, Ryan A. Harding, Mariia S. Kirillova, Xu Zhu, Oliver J. Fischer, Derek A. Pratt* & Corey R. J. Stephenson*
Science 
2016354, 1260-1265.

A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities

Bryan S. Matsuura, Mitchell H. Keylor, Bo Li, YuXuan Lin, Shelby Allison, Derek A. Pratt* & Corey R. J. Stephenson*

Angewandte Chemie International Edition 2015, 54, 3754-3757.