Kyle Biegasiewicz is an Assistant Professor in the School of Molecular Sciences at Arizona State University. He received his Bachelor of Science (BS) in Chemistry from Niagara University in 2010, conducting undergraduate research with Professor Ronny Priefer where he established a general approach for the synthesis of the isoflavone class of natural products. He then pursued graduate studies in synthetic organic chemistry with Professor Robert K. Boeckman, Jr. at the University of Rochester. His graduate studies featured the development of an organocatalyzed asymmetric hydroxymethylation reaction that ultimately enabled a gram-scale synthesis of the apoptosis inducer (-)-rasfonin. Upon completion of his Doctor of Philosphy (PhD) in Chemistry, he moved to Princeton University as Postdoctoral Research Associate working with Professor Todd K. Hyster. His postdoctoral work broadly involved the expansion of the synthetic repertoire of enzymes through photoexcitation with visible light. Capitalizing on the photophysical properties of enzymes with redox active cofactors (namely nicotinamide and flavin), this work has begun to address longstanding challenges in selective hydrogen atom transfer and radical carbon-carbon bond forming reactions. His current work aims to capitalize on the unique catalytic capabilities of underexplored enzyme classes to achieve rapid construction of complex molecular architectures and/or the selective installation of structural entities that are highly desired in early and late stage organic synthesis.
Ph.D., University of Rochester 2016
B.S., Niagara University 2010
Our group is interested in the efficient and selective catalytic construction of molecular complexity in synthetic organic chemistry. While numerous methods have been developed to solve some of the grand challenges in chemical synthesis with small molecule catalysts, enzymes remain one of the most selective and tunable platforms for catalysis to date. However, a majority of synthetically useful enzymes have strictly been utilized for the reactions they are known to perform in nature. Our research group aims to expand the synthetic repertoire of enzymes by capitalizing on the unique catalytic capabilities of underexplored enzyme classes to achieve rapid construction of complex molecular architectures and/or the selective installation of structural entities that are highly desired in early and late stage organic synthesis. These applications will range from the synthesis of medicinally relevant core architectures to natural products.
Students and postdocs that join the Biegasiewicz group should expect to gain expertise in state of the art techniques in organic synthesis and molecular biology. Through a combination of new reaction discovery and directed evolution of enzymes, we envision designing synthetic sequences that operate under mild conditions, enable better step and atom economy, and lower waste production in comparison to current chemocatalytic alternatives.
Nakano, Y.; Black, M.J.; Meichan, A.J.; Sandoval, B.A.; Chung, M.; Biegasiewicz, K.F.; Zhu, T.; Hyster, T.K. “Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using 'Ene'-Reductases with Photoredox Catalysts,” Angewandte Chemie-International Edition Early Access 4/1/2020.
Black, M.J.; Biegasiewicz, K.F.*; Meichan, A.J.*; Oblinsky, D.G.*; Kudisch, B. Scholes, G.D.; Hyster, T.K. “Asymmetric redox-neutral radical cyclization catalysed by flavin-dependent ‘ene’-reductases,” Nat. Chem., 2019, In Press.
Biegasiewicz, K.F.*; Cooper, S.J.*; Gao, X.*; Oblinsky, D.G.; Kim, J.; Garfinkle, S.E.; Joyce, L.A.; Sandoval, B.A.; Scholes, G,D.; Hyster, T.K. “Photoexcitation of flavoenzymes enables a stereoselective radical cyclization,” Science 2019, 364, 1166-1169.
Sandoval, B.A.; Kurtoic, A.I.; Chung, M.; Biegasiewicz, K.F.; Hyster, T.K. “Photoenzymatic Catalysis Enables Ketone Reduction in Ene-Reductases,” Angew. Chem. Int. Ed., 2019, 58, 8714-8718.
Nakano, Y.; Biegasiewicz, K.F.; Hyster, T.K. “Biocatalytic Hydrogen Atom Transfer: An Invigorating Approach to Free-Radical Reactions,” Curr. Opin. Chem. Biol., 2019, 49, 16-24.
Boeckman, R.K., Jr.; Niziol, J.; Biegasiewicz, K.F. “Scalable Synthesis of (-)-Rasfonin Enabled by a Convergent Enantioselective a-Hydroxymethylation Strategy,” Org. Lett., 2018, 20 (16), 5062.
Biegasiewicz, K.F.*; Cooper, S.J.*; Emmanuel, M.A.; Miller, D.C.; Hyster, T.K. “Catalytic promiscuity enabled by photoredox catalysis in nicotinamide-dependent oxidoreductases,” Nat. Chem., 2018, 10, 770.
Concepcion, A.B.; Yamamoto, H.; Boeckman, R.K.; Biegasiewicz, K.F.; Tusch, D.J. “Formaldehyde,” e-EROS Encyc. Reagents Org. Synth., 2018, doi:10.1002/047084289X.rf018.pub2
Boeckman, R.K. Jr.; Tusch, D.J.; Biegasiewicz, K.F. “Organocatalyzed Direct Asymmetric α-Hydroxymethylation of Aldehydes,” Org. Synth., 2015, 92, 320.
Boeckman, R.K. Jr.; Tusch, D.J.; Biegasiewicz, K.F. “(S)-1,1-Diphenylprolinol Trimethylsilyl Ether,” Org. Synth., 2015, 92, 309.
Boeckman, R.K. Jr.; Biegasiewicz, K.F.; Tusch, D. J.; Miller, J.R. “Organocatalytic Enantioselective a-Hydroxymethylation of Aldehydes: Mechanistic Aspects and Optimization,” J. Org. Chem. 2015, 80 (8), 4030.
Biegasiewicz, K.F.; Griffiths, J. R.; Savage, G.P.; Tsanaktsidis, J.; Priefer, R. “Cubane: 50 Years Later,” Chem. Rev. 2015, 115 (14), 6719.
Biegasiewicz, K. F.; Gordon IV, J. S.; Rodriguez, D.A.; Priefer, R. "Development of a general approach to the synthesis of a library of isoflavonoid derivatives," Tetrahedron Lett., 2014, 55, 5210.
Carroll, V. M.; St. Denis, J. D.; Biegasiewicz, K. F. “Chemistry and Synthesis of Daidzein and its Methylated Derivatives: Formononetin, Isoformononetin, and Dimethyldaidzein,” Food Nutr. Compon. Focus 2013, 5 (isoflavones), 61.
Biegasiewicz, K. F.; Ingalsbe, M. L.; St. Denis, J. D.; Gleason, J. L.; Ho, J.; Coote, M.L.; Savage, G.P.; Priefer, R. “Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions,” Beilstein J. Org. Chem., 2012, 8, 1814.
Biegasiewicz, K. F.; St. Denis, J. D.; Carroll, V. M.; Priefer, R. “An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin,” Tetrahedron Lett., 2010, 51, 4408.