Dr. John Gupton
Floyd D. and Elisabeth S. Gottwald Professor of Chemistry
Profile
Dr. Gupton's primary research interests involve developing new organic reactions that can be applied to the synthesis of bioactive compounds in agriculture and medicine. More specifically, he has studied for some time the preparation and reactions of novel vinylogous iminium salts as building blocks for the construction of highly functionalized heterocycles. In recent years this work has focused on the preparation of pyrroles by this methodolgy and the subsequent application to the synthesis of bioactive marine natural products which contain the pyrrole ring system.
Awards
In 2008, Dr. Gupton was recognized by the American Chemical Society as the winner of the ACS Award for Research at an Undergraduate Institution, sponsored by Research Corporation.
Publications
Articles
J. Gupton, S. Clough, C. Hickenboth*, I. Bluhn Chertudi*, S. Cutro*, S. Petrich, F. Hicks*, D. Wilkinson* and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to the Regiocontrolled Preparation of Heterocyclic Appended Pyrazoles", Tetrahedron, 58, 5467-5474 (2002).
J. Gupton, S. Clough, R. Miller, J. Lukens*, C. Henry*, R. Kanters and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to the Synthesis of Ningaline B Hexamethyl Ether", Tetrahedron, 59, 207-215 (2003).
H. Yamanaka, K. Kase, M. Katayama, T. Ishihara, T. Konno and J. Gupton, "Reaction of ß-Trifluoroethoxy Vinamidinium Salts with Carbon Nucleophiles", J. of Fluorine Chem., 120, 33-39 (2003).
B. Burnham, M. Evans, D. Smith, J. Holub, A. Argenti, M. Hoff, G. Daglish, D. Wilson, B. Taylor, J. Berkowitz, K. Krumpe, J. Gupton, T. Scarleet, R. Durham and I. Hall, "Synthesis and Cytotoxicity of Substituted Ethyl-2-Phenacyl-3-phenylpyrrole-4-carboxylates", Arch. Pharm. Pharm. Med. Chem., 336, 181-190 (2003).
S. Clough, J. Gupton, K. Griffin*, A. Hewitt*, M. Hudson*, A. Ligali*, S. Mulcahey*, M. Roberts*, R. Miller and B. Norwood, "Extension of ß-Chloroenals to Ethyl 5-Chloro-2,4-pentadienoates Using Wadsworth-Emmons Reactions: Subsequent Conversions to 5-Aryl-5-chloro-2,4-pentadienoic Acids and 5-Aryl-2-penten-4-ynoic Acids", Tetrahedron, 60, 10165-10169 (2004).
J. Gupton, R. Miller, S. Clough, K. Krumpe, E. Banner, R. Kanters, K. Du, K. Keertikar, N. Lauerman*, J. Solano*, B. Adams*, D. Callahan*, B. Little*, A. Scharf*, and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to an Efficient Relay Synthesis of the Pyrrole Containing Alkaloids Polycitone A and B", Tetrahedron, 61, 1845-1854 (2005).
S. Clough, J. Gupton, A. Ligali*, M. Roberts*, D. Driscoll*, S. Annett*, A. Hewitt*, M. Hudson*, E. Jackson*, R. Miller, B. Norwood, R. Kanters, H. Wyre* and H. Petruzzi*, "Reactions of (Z)-3-Aryl-3-chloropropenals with Nucleophiles: Stereoselective Formation of (E)-Vinylogous Esters, (E)-Vinylogous Amides and Vinamidinium Salts", Tetrahedron, 61, 7554-7561 (2005).
J. Gupton, E. Banner, A. Scharf*, B. Norwood, R. Kanters, R. Dominey, J. Hempel*, A. Kharlamova*, I. Bluhn-Chertudi*, C. Hickenboth*, B. Little*, M. Coppock*, K. Krumpe, B. Burnham, H. Holt., K. Du, K. Keertikar, A. Diebes, S. Ghassemi and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to an Efficient Synthesis of the Pyrrole Containing Alkaloids Rigidin and Rigidin E", Tetrahedron, 62, 8243-8255 (2006).
S. Arimitsu, T. Konno, T. Ishihara, H. Yamanaka and J. Gupton, "Synthetic Application of Fluorinated Vinamidinium Salts: Synthesis of Fluorinated 1,3-butadienylphosphonates by the Reaction With Horner-Wadsworth-Emmons Reagents", J. of Fluorine Chem., 127, 1235-1241 (2006).
S. Mooberry, K. Wiederhold, S. Dakshanamurthy, E. Hamel, E. Banner, A. Kharlamova*, J. Hempel*, J. Gupton and M. Brown,  "Identification and Characterization of a New Tubulin-Binding Tetrasubstituted Brominated Pyrrole", Molecular Pharmacology, 72 (1), 132-140 (2007).
C. Arthur, J. Gupton, G. Kellog, A. Yeudall and D. Gewirtz, "Autophagic Cell Death, Polyploidy and Senescence Induced in Breast Tumor Cells by the Substituted Pyrrole JG-03-14, a Novel Microtubule Poison", Biochemical Pharmacology, 74, 981-991 (2007).
A. Tripathi, M. Fornabaio, G. Kellogg, J. Gupton, D. Gewirtz, W. Yeudall, N. Vega and  S. Mooberry,    "Docking and Hydropathic Scoring of Polysubstituted Pyrrole Compounds with Anti-Tubulin Activity", Biorganic and Medicinal Chemistry, 16, #5, 2235-2242 (2008).
J. Gupton, E. Banner, M. Sartin*, M. Coppock*, J. Hempel*, A. Kharlamova*, D. Fisher*, B. Giglio*, K. Smith*, M. Keough*, T. Smith, R. Kanters, R. Dominey and J. Sikorski, "Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products", Tetrahedron, 64, 5246-5243 (2008).

J. Gupton, B. Giglio*, J. Eaton*, E. Rieck*, K. Smith*, M. Keough*, P. Barelli*, L. Firich*, J. Hempel*,T. Smith and R. Kanters, R., "The Application of Vinylogous Iminium Salt Derivatives to Efficient Formal Syntheses of the Marine Alkaloids Lamellarin G trimethylether and Ningalin B", Tetrahedron,65, 4283-4292 (2009).

N. Dalyot-Herman, F. Delgado-Lopez, D. Gewirtz, J. Gupton and E. Schwartz, "Interference with Endothelial Cell Function by JG-03-14, an Agent That Binds to the Colchicine Site on Microtubules", Biochemical Pharmacology, 78 (9), 1167-1177 (2009).
J. Gupton, N. Telang, E.Banner, E. Kluball*, K. Hall*, K. Finzel*, X. Jia*, S. Bates*, S. Welden*, B. Giglio*, J. Eaton*, P. Barelli*, L. Firich*, J. Stafford*, M. Coppock*, E. Worral*l, R. Kanters, K. Keertikar and R. Osterman, "The Application of (Z)-Haloenoic Acids to the Synthesis of (Z)-5-Benzylidene-4-arylpyrrol-2(5H)-ones", Tetrahedron, 66, 9133-9122 (2010).
J. Gupton, N. Telang, X. Jia*, B. Giglio*, J. Eaton*, P. Barelli*, M. Hovaizi*, K. Hall*, S. Welden*, M. Keough*, E. Worral*l, K. Finzel*, E. Kluball*, R. Kanters, S. Smith, S. Nunes*, M. Wright* and J. Birnstihl, "Further Studies on Vinamidinium Salt Amine Exchange Reactions, Borohydride Reductions and Subsequent Transformations", Tetrahedron, 66, 8485-8493 (2010).
Chenxiao Da, Nakul Telang, Peter Barelli*, Xin Jia*, John T. Gupton, Susan L. Mooberry, and Glen Kellogg, “Pyrrole-Based Antitubulin Agents: Two Distinct Binding Modalities are Predicted for C-2 Analogs in the Colchicine Site”, ACS Med. Chem. Lett., 3, 53-57 (2012).
J. Biggers, T. Nguyen, X. Di, J. Gupton, S. Henderson, Emery, S., Alotaibi, M., White, K., Almenera, J. and D. Gewirtz, “Autophagic Cell Death and Sustained Senescence Arrest in B16/F10 Melanoma Cells and HCT 116 Colon Carcinoma Cells in Response to the Novel Microtubule Poison, JG-03-14”, Cancer Chemotherapy and Pharmacology, 71, 441-455 (2013).
Chenxiao Da, Nakul Telang, Kayleigh Hall*, Emily Kluball*, Peter Barelli*, Kara Finzel*, Xin Jia*, John T. Gupton, Susan L. Mooberry and Glen E. Kellogg, “Developing novel C-4 analogues of pyrrole-based antitubulin agents: weak but critical hydrogen bonding in the colchicine site”, Med. Chem. Commun., 4, 417-421 (2013).
J. Gupton, N. Telang, D. Gazzo*, P. Barelli*, K. Lescalleet*, J. Fagan*, B. Mills*, K. Finzel*, R. Kanters, K. Crocker*, S. Dudek*, C. Lariviere*, S. Smith, K. Keetrikar, C. Warme and W. Zhong., “Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles”, Tetrahedron,69, 5829-5840 (2013).
C. Da, S. Mooberry, J. Gupton and G. Kellogg, “How to Deal with Low Resolution Target Structures: Using SAR, Ensemble Docking, Hydropathic Analysis and 3D-QSAR to Definitively Map the α,β-Tubulin Colchicine Site”, J. Med. Chem., 56,7382-7395 (2013).
J. Gupton, N. Telang, M. Wormald*, K. Lescalleet*, J. Patteson*, W. Curry*, A. Harrison*, M. Hoerrner*, J. Sobieski*, M. Kimmel*, E. Kluball* and T. Perry*, “Formal Group Activation of a Bromopyrrole Ester in Suzuki Cross-Coupling Reactions: Application to a Formal Synthesis of Polycitone A and B and Polycitrin A”, Tetrahedron,70, 2738-2745 (2014).
J. Gupton, N. Telang, J. Patteson*, K. Lescalleet*, S. Yeudall*, J. Sobieski*, A. Harrison* and W. Curry*, "The Application of Formyl Group Activation of Bromopyrrole Esters to Formal Syntheses of Lycogarubin C, Permethyl Storniamide and Lamellarin G Trimethyl Ether", Tetrahedron, 70, 9759-9767 (2014).
C. Rohena, N. Telang, C. Da, A. Risinger, J. Sikorski, G. Kellogg, J. Gupton and S. Mooberry,”Biological Characterization of an Improved Pyrrole-Based Colchicine Site Agent Identified Through Structure-Based Design”,  Mol. Pharm., 89, 287-296 (2016)
J. Ciemniecki*, C. Lewis*, J. Gupton and K. Fischer-Stenger, “Effects of a Pyrrole-Based, Microtubule-Depolymerizing Compound  on RAW 264.7 Macrophages”, Chemico-Biological Interactions, 246, 63-68, (2016).
Chapters
J. Gupton, "Pyrrole Natural Products with Antitumor Properties", Chapter. 2, pp 53-92  in "Heterocyclic Antitumor Antibiotics: Topics in Heterocyclic Chemistry, Vol.2", Ed. by M. Lee, Springer-Verlag, Berlin/Heidelberg, 2006: ISBN # 3-540-30982-9.

Education
Ph.D., Georgia Institute of Technology
Contact Information
(804) 287-6498
(804) 287-1897 (Fax)
Areas of Expertise
Organic Chemistry