University Directory

John W. Tomsho, PhD

 Professor

John Tomsho

Department

Chemistry and Biochemistry

Office

Griffith 310A

Phone

215-596-7395
Contact

The research in Dr. Tomsho's 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.

    • BS in Pharmaceutical Chemistry, University of the Sciences in Philadelphia
    • PhD in Medicinal Chemistry, University of Michigan, Ann Arbor
    • Postdoctoral Research in Chemistry, Pennsylvania State University, University Park

  • Selected Publications

    • Trimpin S, Inutan, ED, Pagnotti VS, Karki S, Marshall DD, Hoang K, Wang B, Lietz CB, Richards AL, Yenchick FS, Lee C, Lu C, Fenner M, Madarshahian S, Saylor S, Chubatyi ND, Zimmerman T, Moreno-Pedraza A, Wang T, Adeniji-Adele A, Meher A, Madagedara H, Owczarzak Z, Musavi A, Hendrickson TL, Peacock PM, Tomsho JW, Larsen BS, Prokai L, Shulaev V, Pophristic M, McEwen CN. Direct Sub-Atmospheric Pressure Ionization Mass Spectrometry: Evaporation/Sublimation-Driven Ionization is Amazing, Fundamentally and Practically. Journal of Mass Spectrometry. 59, 6, e5018 (2024). DOI: 10.1002/jms.5018.
    • Alhthlol LM, Orme CL, Jefferis BS, Herter SA, Kemper HE, Tomsho JW. Synthesis of boron-containing nucleoside analogs. Journal of Organic Chemistry. 89, 3, 1556-1566 (2024). DOI: 10.1021/acs.joc.3c02179.
    • Burke SJ, Alhthlol LM, Gamrat JM, Mancini G, Orme CL, Santhouse JR, Tomares DT, Tomsho JW. Synthesis of Potassium 5-Bromopentyltrifluoroborate via Hydroboration of a Haloalkene. Organic Syntheses. 100, 218-233 (2023). DOI: 10.15227/orgsyn.100.0218.
    • Mancini G, Bouda M, Gamrat JM, Tomsho JW. Synthesis and antimicrobial evaluation of γ-borono phosphonate compounds in Escherichia coli and Mycobacterium smegmatis. ACS Omega. 4, 14551-14559 (2019). DOI: 10.1021/acsomega.9b01774 
    • 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, 19, 11188-11192 (2018). DOI: 10.1021/acs.analchem.8b03378.
    • 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). DOI: 10.1021/acs.joc.8b00677.
    • 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). DOI: 10.1016/j.tetlet.2015.08.012.
    • 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, 1, 193-205 (2015). DOI: 10.1128/AAC.03979-14.
    • 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, 4462-4473 (2014). DOI: 10.1016/j.bmc.2014.04.065.
    • 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). DOI: 10.1021/jo302264g.
    • 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). DOI: 10.1021/jo202250d
    • 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). DOI: 10.1021/ml200215j.
    • Baker SJ, Tomsho JW, Benkovic SJ. "Boron-containing Inhibitors of Synthetases." Chemical Society Reviews. 40, 8, 4279-4285 (2011). DOI: 10.1039/C0CS00131G.

    Patents

    • Tomsho JW, Gamrat JM. Protective groups and methods for protecting benzoxaboroles or oxaboroles. US 11,773,114. October 3, 2023.
    • Tomsho JW, Gamrat JM. Protective groups and methods for protecting benzoxaboroles or oxaboroles. US 11,427,603. August 30, 2022.
    • Tomsho JW, Gamrat JM. "Protective Groups and Methods for Protecting Benzoxaboroles." PCT International Patent Application No. PCT/US2019/021552. March 1, 2019.
    • 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.
    • 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
    • American Chemical Society, since 1997
    • Rho Chi, the Academic Honor Society in Pharmacy, 2005-2021
    • Sigma Xi, the Scientific Research Society, 2005-2022