People | Faculty | Peter Wipf
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Peter Wipf Department of Chemistry |
Total Synthesis of Natural Products Total Synthesis encompasses all aspects of organic chemistry: The development of new methodology, mechanistic and physical organic experiments, conformational and configurational analysis by spectroscopic and computational methods, and bioorganic and medicinal chemistry. Total Synthesis is also one of the broadest and most rewarding educational experiences for aspiring synthetic chemists.
Organometallic Chemistry Organometallic Chemistry will provide most of new revolutionary techniques for C,C and C-heteroatom bond formations and asymmetric catalysis. Our group has had a long tradition in synthetic applications of transition metals.
Heterocyclic Chemistry More than half of all known organic compounds, and the vast majority of drugs, are heterocyclic. We are interested in the development of new stereoselective methods for the preparation of highly functionalized heterocycles. In particular, we have developed novel protocols for five-membered heterocycle synthesis that have been widely adopted in industry and academe.
Combinatorial Synthesis & Medicinal Chemistry We apply combinatorial chemistry and solid phase synthesis methods for reagent and catalyst design in organometallic and heterocyclic chemistry, and for the structure-activity analysis of bioactive natural products. Specifically, we are involved in collaborative drug discovery and development. Some of these projects take advantage of the infrastructure of the Combinatorial Chemistry Center (CCC).
Computational Prediction of Macroscopic Properties In another exciting interdisciplinary collaboration, we have joined forces with the Beratan group for the computational assignment of the relative and absolute stereochemistry of organic molecules of organic molecules and the theoretical prediction of chiroptical phenomena.
Awards
- Ernest Guenther Award in the Chemistry of Natural Products (2009)
- Chancellor's Distinguished Research Award (2008)
- Faculty of 1000 Biology (2006-present)
- Novartis Chemistry Lectureship (2005)
- Fellow of the Royal Society of Chemistry (FRSC, 2004)
- Visiting Professor (Professeur Associé), École Supérieur de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI), Paris, France (September 2004)
- Long Range Planning Committee, ACS Division of Medicinal Chemistry (2004-2006)
- ISHC Katritzky Award in Heterocyclic Chemistry (2003)
- Fellow of the American Association for the Advancement of Science (AAAS, 2002)
- Chair, Gordon Research Conference on Stereochemistry, Salve Regina University, Newport, Rhode Island (June 9-14, 2002)
- Visiting Professor (Professeur Associé), Université de Paris-Sud, Orsay, France (November 2001)
- Member-at-Large, Organic Division Executive Committee of the ACS (2001-2003)
- Novartis Research Award (2000, 2001)
- Japan Society for the Promotion of Science Fellow (2000)
- Akron Section ACS Award (1998)
- Arthur C. Cope Scholar Award (1998)
- NIH Medicinal Chemistry Study Section, Member, 1998-2003, Chairman, 2001-2003
- Chancellorís Distinguished Research Award (1997)
- Phi Eta Sigma, Honorary Member (1996)
- Merck Young Investigator Award (1995)
- Zeneca Award for Excellence in Chemistry (1995)
- Camille Dreyfus Teacher-Scholar Award (1995)
- UCI-Allergan Visiting Lecturer, University of California, Irvine, California (May, 1995)
- NSF Presidential Faculty Fellow (1994-1999)
- ETH Ruzicka Award (1994)
- Alfred P. Sloan Research Fellow (1994-1996)
- American Cyanamid Faculty Award (1994)
- Eli Lilly Grantee (1993-1995)
- University of Zürich, Distinguished Dissertation Award (1987).
Selected Publications
"Formal Alder-Ene Reaction of a Bicyclo[1.1.0]butane in the Synthesis of the Tricyclic Quaternary Ammonium Core of Daphniglaucin." Ueda, M.; Walczak, M. A. A.; Wipf, P. Tetrahedron Lett. 2008, 49, 5986-5989.
"Computational Design, Synthesis and Biological Evaluation of para-Quinone-Based Inhibitors for Redox Regulation of the Dual-Specificity Phosphatase Cdc25B." Keinan, S.; Paquette, W. D.; Skoko, J. J.; Beratan, D. N.; Yang, W.; Shinde, S.; Johnsoton, P. A.; Lazo, J. S.; Wipf, P. Org. Biomol. Chem. 2008, 6, 3256-3263.
"Rhodium(I)-Catalyzed Cycloisomerizations of Bicyclobutanes." Walczak, M. A. A.; Wipf, P. J. Am. Chem. Soc. 2008, 130(22), 6924-6925.
"A Cell-Active Inhibitor of Mitogen-Activated Protein Kinase Phosphatases Restores Paclitaxel-Induced Apoptosis in Dexamethasone-Protected Cancer Cells." Vogt, A.; McDonald, P. R.; Tamewitz, A.; Sikorski, R. P.; Wipf, P.; Skoko, J. J.; Lazo, J. S.Mol. Cancer Ther. 2008, 7(2), 330-340.
"A Mitochondria-Targeted Nitroxide/Hemigramicidin S Conjugate Protects Mouse Embryonic Cells Against Gamma Irradiation." Jiang, J.; Belikova, N.; Hoye, A. T.; Zhao, Q.; Epperly, M. W.; Greenberger, J. S.; Wipf, P.; Kagan, V. E. Int. J. Radiat. Oncol. Biol. Phys. 2008, 70(3), 816-825.
"An Experimental Survey of the Transition between Two-State and Downhill Protein Folding Scenarios." Feng, L.; Du, D.; Fuller, A. A.; Davoren, J. E.; Wipf, P.; Kelly, J. W.; Gruebele, M. Proc. Natl. Acad. Sci. USA 2008, 105(7), 2369-2374.
"Tubulin-Perturbing Naphthoquinone Spiroketals." Balachandran, R.; Hopkins, T. D.; Thomas, C. A.; Wipf, P.; Day, B. W. Chem. Biol. Drug Design 2008, 71(2), 117-124.
"Exploring the Optical Activity Tensor by Anisotropic Rayleigh Optical Activity Scattering." Zubar, G.; Wipf, P.; Beratan, D. N. ChemPhysChem 2008, 9(2), 265-271.
"Pyrimidinone-Peptoid Hybrid Molecules with Distinct Effects on Molecular Chaperone Function and Breast Cancer Cell Proliferation." Wright, C. M.; Chovatiya, R. J.; Jameson, N. E.; Turner, D. M.; Zhu, G.; Werner, S.; Huryn, D. M.; Pipas, J. M.; Day, B. W.; Wipf, P.; Brodsky, J. L. Bioorg. Med. Chem. 2008, 16, 3291-3301.
"Targeting Mitochondria." Hoye, A. T.; Davoren, J.; Wipf, P.; Fink, M. P.; Kagan, V. E. Acc. Chem. Res. 2008, 41(1), 87-97.
"Chiral Ligand Optimization in the Asymmetric Zirconium-Zinc Transmetalation Aldehyde Addition Reaction." Wipf, P.; Jayasuriya, N. Chirality (Special Issue Honoring N. Berova), 2008, 20(1), 425-430.
"Natural Product Chemistry and Anticancer Drug Discovery." Huryn, D. M.; Wipf, P. In "Cancer Drug Design and Discovery", Neidle, S., Ed.; Academic Press, 2008, Part II, Chapter 5, pp 107-130.
"Contribution of a Solute's Chiral Solvent Imprint to Optical Rotation." Mukhopadhyay, P.; Zuber, Wipf, P.; Beratan, D. N. Angew. Chem., Int. Ed. 2007, 46(34), 6450-6452.
Structure-Activity and High-Content Imaging Analyses of Novel Tubulysins." Wang, Z.; McPherson, P. A.; Raccor, B. S.; Balachandran, R.; Zhu, G.; Day, B. W.; Vogt, A.; Wipf, P. Chem. Biol. Drug Design 2007, 70(2), 75-86.
Synthesis of (+/-)-thio-Halenaquinone by Iterative Metalations of Thiophene." Wakefield, B.; Halter, R. J.; Wipf, P. Org. Lett. 2007, 9(16), 3121-3124.
"Selective Compounds Define Hsp90 as a Major Inhibitor of Apoptosis in Small Cell Lung Cancer." Rodina, A.; Vilenchik, M.; Moulick, K.; Aguirre, J.; Kim, J.; Chiang, A.; Litz, J.; Clement, C. C.; She, Y.; Wipf, P.; Massague, J.; Jiang, X.; Broadsky, J. L.; Krystal, G. W.; Chiosis, G. Nature Chem. Biol. 2007, 3(8), 498-507.
"Total Synthesis of N14-Desacetoxytubulysin H." Wipf, P.; Wang, Z. Org. Lett. 2007, 9(8), 1605-1607.
"Treatment with a Novel Hemigramicidin-TEMPO Conjugate Prolongs Survival in a Rat Model of Lethal Hemorrhagic Shock." Macias, C. A.; Chiao, J. W.; Xiao, J.; Arora, D. S.; Tyurina, Y. Y.; Delude, R. L.; Wipf, P.; Kagan, V. E.; Fink, M. P. Ann. Surg. 2007, 245(2), 305-314.
"Mitochondrial Targeting of Radioprotectants Using Peptidyl Conjugates." Kanai, A.; Zabbarova, I.; Amoscato, A.; Epperly, M.; Xiao, J.; Wipf, P. Org. Biomol. Chem. 2007, 5(2), 307-309.
"Inhibition of Metalloprotease Botulinum Serotype A: From a Pseudo-Peptide Binding Mode to a Small Molecule that is Active in Primary Neurons." Burnett, J. C.; Ruthel, G.; Stegmann, C. M.; Panchal, R. G.; Nguyen, T. L.; Hermone, A. R.; Stafford, R. G.; Lane, D. J.; Kenny, T. A.; McGrath, C. F.; Wipf, P.; Stahl, A. M.; Schmidt, J. J.; Gussio, R.; Brunger, A. T.; Bavari, S. J. Biol. Chem. 2007, 282(7), 5004-5014.
"Structural Requirements for Optimized Delivery, Inhibition of Oxidative Stress and Anti-apoptotic Activity of Targeted Nitroxides." Jiang, J.; Kurnikov, I.; Belikova, N. A.; Xiao, J.; Zhao, Q.; Amoscato, A. A.; Braslau, R.; Studer, A.; Fink, M. P.; Greenberger, J. S.; Wipf, P.; Kagan, V. E. J. Pharm. Exp. Ther. 2007, 320(3), 1050-1060.
"Spiroketals via Oxidative Rearrangement of Enol Ethers." Waller, D. L.; Stephenson, C. R. J.; Wipf, P. Org. Biomol. Chem. 2007, 5, 58-60.
"HPLC Determinations of Enantiomeric Ratios." Wipf, P.; Werner, S.; Twining, L. A.; Kendall, C. Chirality 2007, 19, 5-9.
"Independent Mechanistic Inhibition of Cdc25 Phosphatases by a Natural Product Caulibugulone." Brisson, M.; Foster, C.; Wipf, P.; Joo, B.; Tomko, R. J.; Nguyen, T.; Lazo, J. S. Mol. Pharm. 2007, 71(1), 184-192.