Fox, Joseph - University of Delaware - Department of Chemistry & Biochemistry

个人简介

Joseph M. Fox is Professor of Chemistry in the Department of Chemistry and Biochemistry, where he also is the Director of the NIH-funded Center of Biomedical Research Excellence on Molecular Discovery. A native of Philadelphia, Pennsylvania, Fox received his bachelor’s degree from Princeton University, where he conducted undergraduate research as a Pfizer fellow with Maitland Jones Jr. He completed graduate studies under Thomas Katz at Columbia University, where he developed a combined interest in materials science and the synthesis of challenging targets. He studied organometallic chemistry with Stephen Buchwald at MIT as an NIH postdoctoral fellow, where he worked on Pd-catalyzed ketone arylation and devised a synthesis of phosphine ligands that is now used commercially. In 2001, Fox joined the faculty at UD, and he has built a multidisciplinary program that centers on the development of new types of chemical reactions. His group has developed new syntheses and transformations of chiral cyclopropenes and trans-cycloalkenes, and a new type of bioorthogonal reaction that allows for extremely rapid conjugation to biological macromolecules. Applications of this work include synthesis of naturally occurring and designed molecules with biological function, and in the use of design concepts in organic synthesis for applications in biology, radiochemistry, imaging, therapy and materials science.

研究领域

Research in the Fox group centers on the development of new types of chemical reactions, the application of these new reactions to the synthesis of natural occurring and designed molecules with biological function, and in the use of design concepts in organic synthesis for applications in materials science. The nature of the research program is highly multidisciplinary, and involves active collaborations with groups in peptide chemistry, bioorganic chemistry, surface science, computational chemistry, materials science, and radioimaging. Our work focuses on the idea of using strain as a design principle in synthesis. The basic concept is that high energy molecules have unusual— and therefore interesting— reactivity. To this end, the Fox group has developed a number of new reactions and transformations of chiral cyclopropenes, methylenecyclopropenes and trans-cycloalkenes. The applications extend into natural products synthesis and pharmaceutical research. A new type of strain driven bioorthogonal ligation further extends the applications to bioorganic chemistry, and molecular imaging. Our group is interested in the design and utilization of new catalyst types. In one area, we have developed the first general conditions for Rh-catalyzed intermolecular reactions of alkyldiazo compounds. Ordinarily, intermolecular chemistry of carbenoids from alkyldiazo compounds isprecluded by beta-hydride elimination. Current interests include the development of new classes of Rh-catalysts for enantioselective transformations of alkyldiazo compounds. Our group is also actively investigating the origin of asymmetric induction in salen-based catalysis. To this end, we have designed a novel class of metallofoldamers. We have shown how these macromolecules can provide unusual insight into the conformation of salenmetal complexes and the mechanisms by which they induce asymmetr

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Selvaraj, R.; Chintala, S. R.; Taylor, M. T.; Fox, J. M. Org. Synth. 3-Hydroxymethyl-3-phenylcyclopropene. in press Darko, A.; Wallace, S.; Dmitrenko, O.; Machovina, M. M.; Mehl, R. A.; Chin, J. W.; Fox, J. M. Conformationally strained trans-cyclooctene with improved stability and excellent reactivity in tetrazine ligation Chemical Science 2014, Advance Article. DOI: 10.1039/C4SC01348D Zhang, H.; Dicker, K. T.; Xu, X.; Jia, X.; Fox, J. M. Interfacial Bioorthogonal Cross-Linking ACS Macro Letters 2014, 3, 727. http://pubs.acs.org/doi/abs/10.1021/mz5002993 Fox, J. M.; Robillard, M. In vivo chemistry - pushing the envelope Curr. Opin. Chem. Biol. 2014, in press. DOI: 10.1016/j.cbpa.2014.07.07 Selvaraj, R.; Fox, J. M. An efficient and mild oxidant for the synthesis of s-tetrazinesTetrahedron Lett. 2014, 55, 4795–4797. DOI: 10.1016/j.tetlet.2014.07.012 Selvaraj, R.; Fox, J. M. trans-Cyclooctene- a stable, voracious dienophile for bioorthogonal labeling Curr. Opin. Chem. Biol. 2013, 17, 753-760. http://dx.doi.org/10.1016/j.cbpa.2013.07.031 Panish, R.; Chintala, S. R.; Boruta, D. T.; Fang, Y.; Taylor, M. T.; Fox, J. M., Enantioselective Synthesis of Cyclobutanes via Sequential Rh-catalyzed Bicyclobutanation/Cu-catalyzed Homoconjugate Addition. J. Am. Chem. Soc. 2013, 135, 9283-9286. DOI: 10.1021/ja403811t Xie, X.; Fox, J. M., Diastereoselective Syntheses of Highly Substituted Methylenecyclopropanes via Copper- or Iron-Catalyzed Reactions of 1,2-Disubstituted 3-(Hydroxymethyl)cyclopropenes with Grignard Reagents. Synthesis 2013, ASAP. DOI: 10.1055/s-0033-1338876 Xie, X.; Fox, J.; Li, Y., Selective Syntheses of Δα,β and Δβ,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements. Org. Lett. 2013, 15, 1500–1503 http://dx.doi.org/10.1021/ol400264a. Fisher, L. A.; Smith, N. J.; Fox, J. M. Chiral Cyclopropenyl Ketones— Reactive and Selective Diels-Alder Dienophiles J. Org. Chem. 2013, 78, 3342–3348. Wu, Z., Liu, S., Hassink, M., Nair, I., Park, R., Li, L., Todorov, I., Fox, J. M., Li, Z., Shively, J. E., Conti, P. S., Kandeel, F. Development and Evaluation of 18F-TTCO-Cys40-Exendin-4: A novel PET probe for transplanted islets imaging Journal of Nuclear Medicine, 2013, 54, 244-251. Liu, S., Hassink, M., Selvaraj, R., Yap, L.-P., Park, R., Wang, H., Chen, X., Fox, J., Li, Z., Conti, P.S. Efficient 18F labeling of cysteine containing peptides and proteins using the tetrazine-trans-cyclooctene ligation Molecular Imaging, 2013, 12, 121-8. Tarwade, V.; Selvaraj, R.; Fox, J. M. Facially Selective Cu-Catalyzed Carbozincation of Cyclopropenes Using Arylzinc Reagents Formed by Sequential I/Mg/Zn Exchange. J. Org. Chem. 2012, 77, 9900–9904. DeAngelis, A.; Dmitrenko, O.; Fox, J. M. Rh-Catalyzed Intermolecular Reactions of Cyclic α-Diazocarbonyl Compounds with Selectivity over Tertiary C–H Bond Migration J. Am. Chem. Soc., 2012, 134, 11035–11043 . Lang, K.; Davis, L.; Wallace, S.; Mahesh, M.; Cox, D. J.; Blackman, M. L.; Fox, J. M.; Chin, J. W. Genetic encoding of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via fluorogenic Diels-Alder reactions. J. Am. Chem. Soc. 2012, 134, 10317-10320. Hassink, M. D.; Fox, J. M. Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes Synthesis, 2012, 44, 2843-2850. NIHMS387488, PMC3128944. Boruta, D. T.; Dmitrenko, O.; Yap, G. P. A.; Fox, J. M. Rh2(S-PTTL)3TPA—a mixed-ligand dirhodium(II) catalyst for enantioselective reactions of α-alkyl-α-diazoesters. Chemical Science, 2012, 3, 1589-1593 Seitchik, J. L; Peeler, J. C.; Taylor, M. T.; Blackman, M. L.; Rhoads, T. W.; Cooley, R. B.; Refakis, C.; Fox, J. M.; Mehl, R. A. Genetically Encoded Tetrazine Amino Acid Directs Rapid Site-Specific in Vivo Bioorthogonal Ligation with trans-Cyclooctenes. J. Am. Chem. Soc., 2012, 134, 2898–2901. D. S. Liu, A. Tangpeerachaikul, R. Selvaraj, M. T. Taylor, J. M. Fox, and A. Y. Ting. Diels-Alder cycloaddition for fluorophore targeting to specific proteins inside living cells. J. Am. Chem. Soc. 2012, 134, 792-795. Royzen, M.; Taylor, M. T.; DeAngelis, A.; Fox, J. M. “Total Synthesis of Hyacinthacine A2: Stereocontrolled 5-aza-cyclooctene Photoisomerization and Transannular Hydroamination with Planar-to-Point Chirality Transfer” Chemical Science 2011, 2, 2162.