From Dr. Jakobsche’s Research at Clark:
(* = Clark University Student Coauthors)
18. A Versatile Platform for Adding Functional Properties
to Amyloid Fibrils
Org. Biomol. Chem.
2017 (15) 8023-8027 Link
This article describes a molecular design concept that enables the creation of various molecular tools that manipulate amyloid fibrils at the molecular level. This work opens the door to future directions in molecular medicine, nanotechnology, and chemical biology applications.
*D. F. A. Fontaine, *V. A. Ivancic, *M. B. Reardon, N. D. Lazo, C. E. Jakobsche
17. 6-Hydroxynorleucine: Syntheses and Applications
of a Versatile Building Block
Org. Prep. Proc. Int.
2017 (In Press)
This invited review article surveys a number of methods for synthesizing the unnatural amino acid 6-hydroxynorleucine along with a number of interesting synthetic target molecules that have been made using this compound.
*N. S. MacArthur, C. E. Jakobsche
16. Comparing Hydrazine-Derived Reactive Groups as Inhibitors of Quinone-Dependent Amine Oxidases
J. Enz. Inhib. & Med. Chem.
2017 (32) 496-503 Link
This study analyzes four chemical motifs as irreversible inhibitors of an enzyme that is relevant to cancer metastasis. Detailed studies of the kinetics of inhibition were performed to determine which of the structures is most promising for further development.
*A. A. Burke, *E. S. Severson, *S. Mool, *M. J. Solares Bucaro, F. T. Greenaway, C. E. Jakobsche
15. Bistability in Organic Magnetic Materials. A Comparative Study of the Key Differences between Hysteretic and Non-Hysteretic Spin Transitions in Dithiazolyl Radicals
Chemistry: A European Journal
2017 (23) 3479–3489 Link
This collaborative study explores the solid-solid, paramagnetic-diamagnetic phase transition in a family of stable organic radicals. Our group’s contribution was to synthesize the target compound and collect experimental data on its phase transition to support the theoretical and computational predictions made by Professor Novoa’s group.
S. Vela, *M. B. Reardon, C. E. Jakobsche, M. M. Turnbull, J. Ribas-Arino, J. J. Novoa
14. Long-Range Reactivity Modulations in Geranyl Chloride Derivatives
The Journal of Organic Chemistry
2016 (81) 10964-10974 Link
This study uses a combination of kinetics experiments and computational analyses to study how subtle changes to an electrophile’s structure can influence its reactivity despite being far from the reactive site. The results of these studies suggest that an interesting orbital mixing interaction contributes to these effects.
*M. B. Reardon, *M. Xu, *Q. Tan, *P. G. Baumgartel, *D. J. Augur, S. Huo, C. E. Jakobsche
13. A Regio- and Stereo-Selective Annulation
to Form the “Inside-Out” trans-Bicyclo[9.2.1]Tetradecane Ring System
Tetrahedron Letters
2016 (57) 2782–2785 Link
This study describes an approach to synthesizing trans-bicyclic structures by a selective intramolecular alkylation of a cyclopentanone intermediate.
*M. B. Reardon, *B. C. Yasgur, C. E. Jakobsche
12. A Simple Synthesis of 6-hydroxynorleucine
Based on the Rearrangement of an N-Nitrosodichloroacetamide
Tetrahedron Letters
2016 (57) 502-504 Link
This study describes an efficient synthetic sequence to convert L-Lysine into L-6-hydroxynorleucine, which is a broadly useful building block molecule for synthesizing numerous biologically active compounds.
*B. G. McCarthy, *N. S. MacArthur, C. E. Jakobsche
11. Using N-Nitroso-Dichloroacetamides to Conveniently
Convert Linear Primary Amines into Alcohols
Synthetic Communications
2015 (45) 2014-2021 Link
This study describes the development of a reaction sequence to transform amine functional groups into alcohols.
*N. S. MacArthur, *L. Wang, *B. G. McCarthy, C. E. Jakobsche
10. Overcoming the Inherent Alkylation Selectivity
of 2-3-trans-3-4-cis-Trisubstituted Cyclopentanones
2014 (46) 387–393 Link
This study describes a new synthetic strategy to construct a difficult-to-make ketone while controlling the site of reaction and the stereochemistry of the product.
*M. B. Reardon, *G. W. Carlson, C. E. Jakobsche
9. Biochemical Effects of Meditation:
A Literature Review
Scholarly Undergraduate Research Journal
2015 (1) 80–85 Link
This review, which resulted from a directed readings course, highlights some examples of how meditation can affect the body at the molecular level and how these molecular changes relate to physiological changes in the body.
*W. C. Daube, C. E. Jakobsche
From Dr. Jakobsche’s Postdoctoral Research:
8. Exploring Binding and Effector Function
of Natural Human Antibodies Using Synthetic Immunomodulators
ACS Chemical Biology
2013 (8) 2484-2492 Link
This study compares the abilities of various small-molecule motifs to bind antibodies found in non-immunized human serum and to utilize those antibodies to direct cytotoxic immune responses against cancer cells.
C. E. Jakobsche, C. G. Parker, R. N. Tao, M. D. Kolesnikova, E. F. Douglass Jr., D. A. Spiegel
7. Reprogramming Urokinase into an
Antibody-Recruiting Anticancer Agent
ACS Chemical Biology
2012 (7) 316-321 Link
This study describes a strategy to use synthetic organic molecules to direct components of the normal human immune system to identify and destroy human cancer cells.
C. E. Jakobsche, P. J. McEnaney, A. X. Zhang, D. A. Spiegel
6. Reprogramming Urokinase into an
Antibody-Recruiting Anticancer Agent
World Patent Application: WO 2013/070688-A1, May 16, 2013
D. A. Spiegel, C. E. Jakobsche

From Dr. Jakobsche’s Graduate Research:
5. npi* Interaction and n)(pi Pauli Repulsion
Are Antagonistic for Protein Stability
Journal of the American Chemical Society
2010 (132) 6651-6653 Link
This study describes a newly identified interaction between molecular orbitals that influences the conformation of proline-containing molecules.
C. E. Jakobsche, A. Choudhary, S. J. Miller, R. T. Raines
4. Functional Analysis of an Aspartate-Based
Epoxidation Catalyst with Amide-to-Alkene
Peptidomimetic Catalyst Analogues
Angewandte Chemie, International Edition
2008 (47) 6707-6711 Link
This study describes the synthesis and use of alkenes and fluoroalkenes to study how an epoxidation catalyst uses its amides to interact with its substrates.
C. E. Jakobsche, G. Peris, S. J. Miller
3. Selective Partial Reduction of Quinolines:
Hydrosilation versus Transfer Hydrogenation
Journal of Organometallic Chemistry
2008 (693) 1815-1821 Link
This study describes two new transition-metal-catalyzed reductions.
A. Voutchkova, D. Gnanamgari, C. E. Jakobsche, C. Butler, S. J. Miller, J. Parr, R. H. Crabtree
2. Aspartate-Catalyzed Asymmetric Epoxidation
Journal of the American Chemical Society
2007 (129) 8710-8711 Link
This study describes a new catalytic cycle for performing epoxidation reactions and its use for forming enentioenriched epoxides.
G. Peris, C. E. Jakobsche, S. J. Miller
From Dr. Jakobsche’s Undergraduate Research:
1. A Versatile Route to Benzocanthinones
2005 (61) 9102-9110 Link
This study describes the synthesis of several organic molecules that are non-natural analogues of medicinally interesting naturally occurring molecules.
J. H. Markgraf, A. D. Dowst, L. A. Hensley, C. E. Jakobsche, C. J. Kaltner, P. J. Webb, P.