John W. Tomsho PhD

John Tomsho

John W. Tomsho PhD

Director, Graduate Programs in Chemistry, Biochemistry and Pharmacognosy
Co-Director, Chemistry Core Facility
NMR Facility Director
Associate Professor of Chemistry and Biochemistry

Education

BS Pharmaceutical Chemistry, University of the Sciences in Philadelphia

PhD Medicinal Chemistry, University of Michigan, Ann Arbor

Research Interests

  • Design, synthesis, and biological evaluation of novel chemical interventions for the treatment of infectious diseases
  • Expanding the use of boronic acids in bioorganic and medicinal chemistry
  • Developing peptides and peptidomimetics for the disruption of protein-protein interactions
  • Development of course-based undergraduate research experiences

Synopsis

The research in my group utilizes both chemical and biological tools for the development of new agents to study and treat infectious diseases including tuberculosis, malaria, HIV, and influenza. Currently, we are focused on the development of small molecules and peptides that target important processes in the organisms that cause infectious diseases. This goal is being pursued via two major research directions that reflect the areas of chemistry and biology and their interface. First is the use of boronic acid-containing compounds as potential small molecule pharmaceutical agents. Second is the development of new techniques for the generation of peptide libraries and the subsequent selection of active members that disrupt specific protein-protein interactions. In both cases, natural product chemistry plays an important role in providing target molecules and pathways.

Tomsho Laboratory: http://chemfaculty.usciences.edu/ChemFaculty/index.php/overviewtomsho
 

Chemistry Core Facility: https://sites.google.com/usciences.edu/chemistrycore/home
 

Selected Scholarly Activity

Trimpin S, Pophristic M, Adeniji-Adele A, Tomsho JW, McEwen CN. Vacuum matrix-assisted Ionization Source offering simplicity, sensitivity, and exceptional robustness in mass spectrometry. Analytical Chemistry. 90, 11188-11192 (2018).

Gamrat JM, Mancini G, Burke SJ, Colandrea RC, Sadowski NR, Figula BC, Tomsho JW. Protection of the Benzoxaborole Moiety: Synthesis and Functionalization of Zwitterionic Benzoxaborole Complexes. Journal of Organic Chemistry. 83(11), 6193-6201 (2018).

Burke SJ, Gamrat JM, Santhouse JR, Tomares DT, Tomsho JW. Potassium haloalkyltrifluoroborate salts: Synthesis, application, and reversible ligand replacement with MIDA. Tetrahedron Letters. 56(41), 5500-5503 (2015).

El-Mowafi SA, Sineva E, Alumasa JN, Nicoloff H, Tomsho JW, Ades SE, Keiler KC. Identification of inhibitors of a bacterial sigma factor using a new high-throughput screening assay. Antimicrobial Agents and Chemotherapy. 59, 193-205 (2015).

Liu CT, Tomsho JW, Benkovic SJ. The unique chemistry of benzoxaboroles: current and emerging applications in biotechnology and therapeutic treatments. Bioorganic and Medicinal Chemistry. 22(16):4462-73 (2014).

Tomsho JW, Benkovic SJ. Examination of the reactivity between benzoxaboroles and related compounds with a cis-diol. Journal of Organic Chemistry. 77(24), 11200-11209 (2012).

Tomsho JW, Benkovic SJ. Elucidation of the mechanism of the reaction between phenylboronic acid and a model diol, Alizarin Red S. Journal of Organic Chemistry. 77(5), 2098-2106 (2012).

Tomsho JW, Pal A, Hall DG, Benkovic SJ. Ring structure and aromatic substituent effects on the pKa of the benzoxaborole pharmacophore. ACS Medicinal Chemistry Letters. 3(1), 48-52 (2012).

Baker SJ, Tomsho JW, Benkovic SJ. Boron-containing inhibitors of synthetases. Chemical Society Reviews. 40(8), 4279-4285 (2011).

Patents

Tomsho JW, Gamrat JM. Protective groups and methods for protecting benzoxaboroles. PCT International Patent Application No. PCT/US2019/021552. March 1, 2019.

Tomsho JW, Gamrat JM. Protective groups and methods for protecting benzoxaboroles. U.S. Provisional Patent Application No. 62/640,916. March 9, 2018.

Benkovic S, Liu C, Tomsho JW. Boronic and boronic acid compounds as inhibitors of sulfenic acid-containing proteins. US 9,309,508. April 12, 2016.

Benkovic S, Liu C, Tomsho JW. Boronic and boronic acid compounds as inhibitors of sulfenic acid-containing proteins. US 8,980,544. March 17, 2015.

Professional Information

  • American Chemical Society, since 1997
  • Rho Chi, the Academic Honor Society in Pharmacy, since 2005
  • Sigma Xi, the Scientific Research Society, since 2005

Contact Information

Office location: Griffith Hall, Room 310A
Mailing address: Box # 48, Department of Chemistry and Biochemistry
University of Sciences
600 South 43rd Street
Philadelphia, PA 19104-4495
Office Phone: 215-596-7395
Email:

j [dot] tomsho [at] usciences [dot] edu