Gustaf H. Carlson School of Chemistry

Charles Jakobsche

Charles Jakobsche, Ph.D.

Organic Chemistry, Chemical Biology, Chemistry of Medicine

Assistant Professor
Carlson School of Chemistry and Biochemistry
Clark University
Worcester, MA 01610-1477

Phone: 508-793-8866

Curriculum Vitae
Research Lab Website


Postdoctoral Fellow, Yale University, 2009-2012
Ph.D. Yale University, 2009
B.A. Williams College, 2004

Current Research Interests

Professor Jakobsche brings a wide range of interests and expertise to his research. The group's research projects typically embody the following major themes:

  1. Using synthetic organic chemistry to make target molecules, whether they are structures derived from natural products or artificial compounds created through rational design
  2. Designing functional probe molecules that have well defined interactions with particular proteins or other biological structures and that can be used for chemical biology analysis of these systems
  3. Developing new organic chemistry reactions that can help enable more efficient synthesis of target molecules
  4. Performing detailed analysis of reactions or molecular structures to better understand the properties and reactivities of unusual organic molecules
  5. Using chemistry to learn about biological systems that are relevant to diseases, medicines, or the immune system

More details about specific projects can be found on his group's webpage.

Selected Publications

"6-Hydroxynorleucine: Syntheses and Applications of a Versatile Building Block" (Invited Review)
            N. S. MacArthur, C. E. Jakobsche
            Org. Prep. Proc. Int. 2017 – In Press

"Comparing Hydrazine-Derived Reactive Groups as Inhibitors of Quinone-Dependent Amine Oxidase"
            A. A. Burke, E. S. Severson, S. Mool, M. J. Solares Bucaro, F. T. Greenaway, C. E. Jakobsche
            J. Enz. Inhib. & Med. Chem. 2017, 32, 496–503
"Long-Range Reactivity Modulations in Geranyl Chloride Derivatives"
            M. B. Reardon, M. Xu, Q. Tan, P. G. Baumgartel, D. J. Augur, S. Huo, C. E. Jakobsche
            J. Org. Chem. 2016, 81, 10964–10974
"A Regio- and Stereo-Selective Annulation to Form the "Inside-Out" trans-Bicyclo[9.2.1]Tetradecane Ring System"
            M. B. Reardon, B. C. Yasgur, C. E. Jakobsche
            Tetrahedron Lett. 2016, 57, 2782–2785
"A Simple Synthesis of 6-Hydroxynorleucine Based on the Rearrangement of an N-Nitrosodichloroacetamide"
            B. G. McCarthy, N. S. MacArthur, C. E. Jakobsche
            Tetrahedron Lett. 2016, 57, 502–504
"Overcoming the Inherent Alkylation Selectivity of 2–3-trans-3–4-cis-Trisubstituted Cyclopentanones"
            M. B. Reardon, G. W. Carlson, C. E. Jakobsche
            Synthesis 2014, 46, 387–393
"Exploring Binding and Effector Functions of Natural Human Antibodies Using Synthetic Immunomodulators"
            C. E. Jakobsche, C. G. Parker, R. N. Tao, M. D. Kolesnikova, E. F. Douglass, D. A. Spiegel
            ACS Chem. Biol. 2013, 8, 2484–2492
“Reprogramming Urokinase into an Antibody-Recruiting Anticancer Agent”
            C. E. Jakobsche, P. J. McEnaney, A. X. Zhang, D. A. Spiegel
            ACS Chem. Biol. 2012, 7, 316–321
“n-->p* Interaction and n)(p Pauli Repulsion Are Antagonistic for Protein Stability”
            C. E. Jakobsche, A. Choudhary, S. J. Miller, R. T. Raines
            J. Am. Chem. Soc. 2010, 132, 6651–6653

“Aspartate-Catalyzed Asymmetric Epoxidation Reactions”
            G. Peris, C. E. Jakobsche, S. J. Miller
            J. Am. Chem. Soc. 2007, 129, 8710–8711