Faculty

John Montgomery

Margaret and Herman Sokol Professor of Chemistry

Ph.D., Colorado State University
A.B., University of North Carolina - Chapel Hill

Research Focus: Biological Catalysis and Carbohydrate Chemistry

Phone: 734.764.4424
E-mail: jmontg@umich.edu

The general focus of the Montgomery group is the discovery and development of new catalytic reactions that enable the efficient assembly of bioactive structures. These efforts include the design and synthesis of new classes of transition metal catalysts, the discovery of new metal-catalyzed processes as enabling tools for organic synthesis, mechanistic and kinetic study of catalytic processes, and total synthesis of complex molecules.

A growing collaborative interest of our lab involves the development of biocatalysts as general tools in synthetic chemistry, particularly for the functionalization of unactivated C-H bonds. Our recent studies demonstrate that carefully designed substrate modifications enable improvements and/or reversals in site-selectivity of oxidations of a broad array of unnatural substrates using engineered cytochrome P450 enzymes. A high-throughput approach has been developed for the three-component assembly of oxidation substrates, providing an exceptionally versatile method for late-stage tailoring of complex structures and natural products. This strategy often offers selective access to several different mono-oxidized products starting from a single substrate.

Our laboratory is also focusing on the development of innovative catalytic methods for glycoside bond construction. A new class of carbohydrate-derived reagents, termed sugar silanes, was devised in our laboratory and enables sequential reductive conversions paired with an intramolecular glycosylation process. The available substrate classes include alcohols, ketones, and C-C bond forming processes, which provide the unprecedented opportunity to simultaneously build complexity within an aglycone while assembling the glycosidic bond.


Montgomery Research Group

 

Awards

2017
Rackham Distinguished Graduate Mentoring Award
2016 NIH Maximizing Investigators’ Research Award (MIRA)
2011 Fellow of the American Association for the Advancement of Science (AAAS)
2001 ACS Arthur C. Cope Scholar Award

 

Representative Publications

  1. Narayan, A. R. H.; Jimenez-Oses, G.; Liu, P.; Negretti, S.; Zhao, W.; Gilbert, M. M.; Ramabhadran, R. O., Yand, Y.-F.; Furan, L. R.; Li, Z.; Podust, L. M.; Montgomery, J.; Houk, K. N.; Sherman, D. H. “Enzymatic Hydroxylation of an Unactivated Methylene C-H Bond Guided by Molecular Dynamics Simulations,” Nat. Chem. 2015, 7, 653-660.

  2. Walk, J. T.; Buchan, Z. A.; Montgomery, J. “Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery,” Chem. Sci. 2015, 6, 3448-3453.

  3. Negretti, S.; Narayan, A. R.; Chiou, K. C.; Kells, P. M.; Stachowski, J. L.; Hansen, D. A.; Podust, L. M.; Montgomery, J.; Sherman, D. H. "Regioselective C-H Bond Oxidation by an Engineered P450 Monooxygenase Employing Simple Removable Directing Groups" J. Am. Chem. Soc. 2014, 136, 4901-4904.

  4. Partridge, K. M.; Bader, S. J.; Buchan, Z. A.; Taylor, C. E.; Montgomery, J. “A Streamlined Strategy for Aglycone Assembly and Glycosylation” Angew. Chem. Int. Ed. 2013, 52, 13647-13650.

 

 

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