University of Pittsburgh

Peter Wipf

Contact Info:

Department of Chemistry
Chevron Science Center
219 Parkman Avenue
Pittsburgh, PA 15260

Office: 758 CHVRN
Phone: 412-624-8606

Distinguished University Professor

Total Synthesis of Natural Products; Organometallic and Heterocyclic Chemistry; Medicinal 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

  • Edward W. Morley Award of the Cleveland Section of the ACS (2013)

  • ACS Pittsburgh Award (2012)

  • Fellow of the American Chemical Society (2010)

  • Ernest Guenther Award in the Chemistry of Natural Products (2009)

  • Associate Editor, ACS Medicinal Chemistry Letters (2009-present)

  • Organic Reactions, Inc. Board of Directors (2007-present)

  • 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)

Publications

[2,3]-Sigmatropic Rearrangements of 2-Phosphineborane 2-Propen-1-ols: Rapid Access to Enantioenriched Diphosphine Monoxide Derivatives,” Busacca, C. A.; Qu, B.; Farber, E.; Haddad, N.; Gret, N.; Saha, A. K.; Eriksson, M. C.; Wu, J.-P.; Fandrick, K. R.; Han, S.; Grinberg, N.; Ma, S.; Lee, H.; Li, Z.; Spinelli, M.; Gold, A.; Wang, Z.; Wang, G.; Wipf, P.; Senanayake, C.H., Org. Lett., Vol. 15, 2013, Pages (5),1136-1139, http://www.ncbi.nlm.nih.gov/pubmed/23427861
Hydrophosphination of Propargylic Alcohols and Amines with Phosphine Boranes,” Busacca, C. A.; Qu, B.; Farber, E.; Haddad, N.;Gret, N.; Saha, A. K.; Eriksson, M. C.; Wu, J.-P.; Fandrick, K. R.; Has, S.; Grinber, N.; Ma, S.; Lee, H.; Li, Z.; Spinelli, M.; Gold, A.; Wang, G.; Wipf, P.; Senanayake, C.H., Org. Lett, Vol. 15, 2013, Pages (5), 1132-1135, http://pubs.acs.org/doi/pdfplus/10.1021/ol400309y
Influence of Base and Structure in the Reversible Covalent Conjugate Addition of Thiol to Polycyclic Enone Scaffolds,” Rosenker, C. J.; Krenske, E. H.; Houk, K. N.; Wipf, P., Org. Lett., Vol. 15, 2013, Pages (5), 1076-1079, http://pubs.acs.org/doi/pdfplus/10.1021/ol400094k
Mitochondrial-derived Reactive Oxygen Species (ROS) Play a Causal Role in Aging-related Intervertebral Disc Degeneration,” Nasto, L. A.; Robinson, A.; Ngo, K.; Clausen, C. L.; Dong, Q.; St. Croix, C.; Sowa, G.; Pola, E.; Robbins, P. D.; Kang, J.; Niedernhofer, L. J.; Wipf, P.; Vo, M. V. , J. Orthopaed. Res. , 2013, http://www.ncbi.nlm.nih.gov/pubmed/23389888
Cycloadditions in Heterocycle and Alkaloid Synthesis,” Wipf, P.; Fang, Z.; Ferrié, L.; Ueda, M.; Walczak, M. A. A.; Yan, Y.; Yang, M., Pure Appl. Chem, Vol. 85, 2013, http://pac.iupac.org/publications/pac/pdf/asap/pdf/PAC-CON-12-09-03.pdf
Nanoassembly of Surfactants with Interfacial Drug-Interactive Motifs as Tailor-Designed Drug Carriers,” Gao, X.; Huang, Y.; Makhov, A. M.; Epperly, M.; Lu, J.; Grab, S.; Zhang, P.; Rohan, L.; Xie, X.-Q.; Wipf, P.; Greenberger, J.; Li, S., S. Mol. Pharm., Vol. 10, 2013, Pages 187-198, http://www.ncbi.nlm.nih.gov/pubmed/23244299
5-Hydroxyindoles by Intramolecular Alkynol-Furan Diels-Alder Cycloaddition,” LaPorte, M.; Hong, K. B.; Xu, J.; Wipf, P., J. Org. Chem. (Prof. Robert E. Ireland Memorial Issue), Vol. 78, 2013, Pages (1), 167-174, http://pubs.acs.org/doi/pdfplus/10.1021/jo3022605
Memory of Chirality in Rebound Cyclizations of α-Amide Radicals,” Sasmal, A.; Taniguchi, T.; Wipf, P.; Curran, D. P., Can. J. Chem. (Prof. Derrick Clive Special Issue), Vol. 91, 2013, Pages (1), 1-5, http://www.nrcresearchpress.com/doi/pdf/10.1139/v2012-085
In Vitro Cytotoxicity, Pharmacokinetics, Tissue Distribution, and Metabolism of Small-Molecule Protein Kinase D Inhibitors, kb-nb142-70 and kb-nb165-09, in Mice Bearing Human Cancer Xenografts,” Guo, J.; Clausen D. M.; Beumer J. H.; Parise R. A.; Egorin M. J.; Bravo-Altamirano, K.; Wipf, P.; Sharlow E. R.; Wang Q. J.; Eiseman J. L. , Cancer Chemother. Pharmacol, Vol. 71, 2013, Pages (2), 331-344, http://link.springer.com/article/10.1007%2Fs00280-012-2010-z?LI=true#page-1
New Calcium Channel Agonists as Potential Therapeutics in Lambert-Eaton Myasthenic Syndrome and other Neuromuscular Diseases,” Tarr, T. B.; Valdomir, G.; Liang, M.; Wipf, P.; Meriney, S. D., Ann. N. Y. Acad. Sci. , Vol. 1275, 2012, Pages (1), 85-91, http://www.ncbi.nlm.nih.gov/pubmed/23278582
Synthesis and Biological Evaluation of a Selective N- and P/Q-Type Calcium Channel Agonist,” Liang, M.; Tarr, T. B.; Bravo-Altamirano, K.; Valdomir, G.; Rensch, G.; Swanson, L.; DeStefino, N. R.; Mazzarisi, C. M.; Olszewski, R. A.; Wilson, G. M.; Meriney, S. D.; Wipf, P., ACS Me. Chem. Lett., Vol. 3, 2012, Pages (12), 985-990, http://pubs.acs.org/doi/pdfplus/10.1021/ml3002083
A Targeted Library Screen Reveals a New Inhibitor Scaffold for Protein Kinase D,” Tandon, M.; Wang, L.; Xu, Q.; Xie, X.; Wipf, P.; Wang, Q. J., PLoS One , Vol. 7, 2012, Pages (9), e44653, http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0044653
Targeting of XJB-5-131 to Mitochondria Suppresses Oxidative DNA Damage and Motor Decline in a Mouse Model of Huntington’s Disease,” Xun, Z.; Rivera-Sanchez, S.; Ayala-Penã, S.; Lim, J.; Budworth, H.; Skoda, E. M.; Robbins, P. D.; Niedernhofer, L. J.; Wipf, P.; McMurray, C. T. , Cell Rep. , Vol. 2, 2012, Pages (5), 1137-1142, http://www.ncbi.nlm.nih.gov/pubmed/23122961
Global Lipidomics Identifies Cardiolipin Oxidation as a Mitochondrial Target for Redox Therapy of Acute Brain Injury,” Ji, J.; Kline, A. E.; Amoscato, A.; Arias, A. S.; Sparvero, L. J.; Tyurin, V. A.; Tyrina, Y. Y.; Fink, B.; Cheng, J. P.; Alexander, H.; Clark, R. S. B.; Kochanek, P. M.; Wipf, P.; Kagan, V. E.; Bayir, H., Nat. Neurosci. , Vol. 15, 2012, Pages (10), 1407-1413, http://www.nature.com/neuro/journal/v15/n10/full/nn.3195.html?WT.ec_id=NEURO-201...
Structural Basis of Functional Group Activation by Sulfotransferases in Complex Metabolic Pathways,” Mccarthy, J. G.; Eisman, E. B.; Kulkarni, S.; Gerwick, L.; Gerwick, W. H.; Wipf, P.; Sherman, D. H.; Smith, J. L. , ACS Chem. Biol., Vol. 7, 2012, Pages (12), 1994-2003, http://www.ncbi.nlm.nih.gov/pubmed/22991895
Lipophilicity Screening of Novel Drug-Like Compounds and Comparison to cLog P,” Lu, D.; Chambers, P.; Wipf, P.; Xie, X.-Q.; Englert, D.; Weber, S. , J. Chromatogr. A, Vol. 1258, 2012, Pages 161-167, http://www.ncbi.nlm.nih.gov/pubmed/22939208
Synthesis of a Library of Tricyclic Azepinoisoindolinones,” Miller, B.; Mao, S.; Rosenker, K. M. G.; Pierce, J. G.; Wipf, P. , Beilstein J. Org. Chem. (Special Issue on Recent Developments in Chemical Diversity) , Vol. 8, 2012, Pages 1091-1097, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458725/
A Screen for Modulators of Large T Antigen’s ATPase Activity Uncovers Novel Inhibitors of Simian Virus 40 and BK Virus Replication,” Seguin, S. P.; Ireland, A. W.; Miyata, Y.; Wipf, P.; Pipas, J. M.; Gestwicki, J. E.; Brodsky, J. L., Antivir. Res. , Vol. 96, 2012, Pages 70-81, http://www.ncbi.nlm.nih.gov/pubmed/22898086
Geographic Variability and Anti-Staphylococcal Activity of the Chrysophaentins and Their Synthetic Fragments,” Keffer, J. L.; Hammill, J. T.; Lloyd, J. R.; Plaza, A.; Wipf, P.; Bewley, C. A., Mar. Drugs , Vol. 10, 2012, Pages (5), 1103-1125, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3397459/
A Bifunctional Dimethylsulfoxide Substitute Enhances the Aqueous Solubility of Small Organic Molecules,” Sprachman, M. M.; Wipf, P., ASSAY Drug Dev. Technol., Vol. 10, 2012, Pages (3), 269-277, http://www.ncbi.nlm.nih.gov/pubmed/22192308
Strategies for Discovery of Small Molecule Radiation Protectors and Radiation Mitigators,” Greenberger, J. S.; Clump, D.; Kagan, V.; Bayir, H.; Lazo, J. S.; Wipf, P.; Li, S.; Gao, X.; Epperly, M. W. , Front. Oncol. , Vol. 1, 2012, Pages Article 59, 1-12, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3356036/
Synthesis of 1,2,4-Triazines and the Triazinoisoquinolinedione DEF Ring System of Noelaquinone,” Cao, L.; Maciejewski, J. P.; Elzner, S.; Amantini, D.; Wipf, P., Org. Biomol. Chem. (Special 10 Year Anniversary Issue), Vol. 10, 2012, Pages 5811-5814, http://www.ncbi.nlm.nih.gov/pubmed/22473572
Selenosemicarbazones as Potent Cruzipain Inhibitors and Their Antiparasitic Properties against Trypanosoma cruzi,” Pizzo, C.; Faral-Tello, P.; Salinas, G.; Flo, M.; Robello, C.; Wipf, P.; Mahler, S. G. , MedChemComm, Vol. 3, 2012, Pages 362-368, http://pubs.rsc.org/en/content/articlepdf/2012/md/c2md00283c
Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres,” Skoda, E. M.; Davis, G. C.; Wipf, P. , Org. Proc. Res. Dev. , Vol. 16, 2012, Pages (1), 26-34, http://pubs.acs.org/doi/pdf/10.1021/op2002613
Genetically Encoded Redox Sensor Identifies the Role of ROS in Degenerative and Mitochondrial Disease Pathogenesis,” Liu, Z.; Celotto, A. M.; Romero, G.; Wipf, P.; Palladino, M. J., Neurobiol. Dis. , Vol. 45, 2012, Pages (1), 362-368, http://www.ncbi.nlm.nih.gov/pubmed/21889980
Structure-Activity Relationships amongst 4-Position Quinoline Methanol Antimalarials that Inhibit the Growth of Drug Sensitive and Resistant Strains of Plasmodium Falciparum.,” Milner, E.; McCalmont, W.; Bhonsle, J.; Caridha, D.; Carroll, D. W.; Gardner, S.; Gerena, L.; Gettayacamin, M.; Lanteri, C.; Luong, T.; Melendez, V.; Moon, J. K.; Roncal, N. E.; Sousa, J. C.; Tangteung, A.; Wipf, P.; Dow, G. S., Bioorg. Med. Chem. Lett., Vol. 20, 2010, Pages (4), 1347-1351, http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TF9-4Y3TX68-2-S&_cdi=5...
Regioselective Palladium-Catalyzed Cross-Coupling Reactions of 2,4,7-Trichloroquinazoline.,” Wipf, P.; George, K. M., Synlett (Special Issue Honoring G. Pattenden), 2010, Pages 644-648,
Screening of Antimicrobial Agents for In Vitro Radiation Protection and Mitigation Capacity, Including those Used in Supportive Care Regimens for Bone Marrow Transplant Recipients.,” Epperly, M. W.; Franicola, D.; Shields, D.; Rwigema, J.-C.; Zhang, X.; McBride, W.; Georges, G.; Wipf, P.; Greenberger, J. S. , In Vivo, Vol. 24, 2010, Pages (1), 9-19,
Transmetalation Reactions Producing Organocopper Compounds.,” Rosenker, C. J.; Wipf, P. In “Patai Series: The Chemistry of Functional Groups. The Chemistry of Organocopper Compounds”, Rappoport, Z.; Marek, I., Eds., Wiley Interscience, 2010, Pages Part 1, Chapter 10, pp 443-525,
Peptide-Like Molecules (PLMs): A Journey from Peptide Bond Isosteres to Gramicidin S Mimetics and Mitochondrial Targeting Agents,” Wipf, P.; Xiao, J.; Stephenson, C. R. J. , Chimia , Vol. 63, 2009, Pages 764-775,
Phosphatases as Targets for Cancer Treatment,” Lazo, J. S.; Wipf, P., Curr. Op. Invest. Drugs, Vol. 10, 2009, Pages 1297-1304,
Mitochondrial Targeting of Electron Scavenging Antioxidants: Regulation of Selective Oxidation vs Random Chain Reactions,” Kagan, V. E.; Wipf, P.; Stoyanovsky, D.; Greenberger, J. S.; Borisenko, G.; Belikova, N. A.; Yanamala, N.; Samhan Arias, A. K.; Tungekar, M. A.; Jiang, J.; Tyurina, Y. Y.; Ji, J.; Klein-Seetharaman, J.; Pitt, B. R.; Shvedova, A. A.; Bayir, H. , Adv. Drug Deliv. Rev, Vol. 61, 2009, Pages 1375-1385,
The Mitochondria-Targeted Nitroxide JP4-039 Augments Potentially Lethal Irradiation Damage Repair,” Rajagopalan, M. S.; Gupta, K.; Epperly, M. W.; Franicola, D.; Zhang, X.; Wang, H.; Zhao, H.; Tyurin, V. A.; Pierce, J. G.; Kagan, V. E.; Wipf, P.; Kanai, A. J.; Greenberger, J. S., In Vivo , Vol. 23, 2009, Pages 717-726,
Synthesis of Pyrrolo[1,3]diazepines by a Dipolar Cycloaddition – retro-Mannich Domino Reaction,” Liang, M.; Saiz, C.; Pizzo, C.; Wipf, P. , Tetrahedron Lett. , Vol. 50, 2009, Pages 6810-6813,
Reversible Thiazolidine Exchange: A New Reaction Suitable for Dynamic Combinatorial Chemistry,” Saiz, C.; Wipf, P.; Manta, E.; Mahler, G. , Org. Lett., Vol. 11, 2009, Pages 3170-3173,
Synthesis and Biological Evaluation of the First Pentafluorosulfanyl Analogs of Mefloquine,” Wipf, P.; Mo, T.; Geib, S. J.; Caridha, D.; Dow, G. S.; Gerena, L.; Roncal, N.; Milner, E. E. , Org. Biomol. Chem. , Vol. 7, 2009, Pages 4163-4165,
Evaluating b-Turn Mimics as b-Sheet Folding Nucleators,” Fuller, A. A.; Du, D.; Liu, F.; Davoren, J. E.; Bhabha, G.; Kroon, G.; Case, D. A.; Dyson, H. J.; Powers, E. T.; Wipf, P.; Gruebele, M.; Kelly, J. W. , Proc. Natl. Acad. Sci. USA , Vol. 106, 2009, Pages 11067-11072,
Optical Signatures of Molecular Dissymmetry: Combining Theory with Experiments to Address Stereochemical Puzzles,” Mukhopadhyay, P.; Wipf, P.; Beratan, D. N., Acc. Chem. Res. , Vol. 42, 2009, Pages 809-819,
Metamorphic Enzyme Assembly in Polyketide Diversification,” Gu, L.; Wang, B.; Kulkarni, A.; Geders, T. W.; Grindberg, R. V.; Gerwick, L.; Hakansson, K.; Wipf, P.; Smith, J. L.; Gerwick, W. H.; Sherman, D. H. , Nature , Vol. 459, 2009, Pages 731-735,
Nanoparticles in Cellular Drug Delivery,” Faraji, A. H.; Wipf, P., Bioorg. Med. Chem. , Vol. 17, 2009, Pages 2950-2962,
Cytochrome C/Cardiolipin Relations in Mitochondria: a Kiss of Death,” Kagan, V. E.; Bayir, H.; Belikova, N. A.; Kapralov, A.; Tyurina, Y. Y.; Tyurin, V. A.; Jiang, J.; Stoyanovsky, D.; Wipf, P.; Kochanek, P. M.; Borisenko, G. G.; Greenberger, J. S.; Shvedova, A. A.; Borisenko, G., G. Mol. Free Rad. Biol. Med. , Vol. 46, 2009, Pages 1439-1453,
Isolation, Biology and Chemistry of the Disorazoles: New Anti-Cancer Macrodiolides,” Hopkins, C. D.; Wipf, P. , Nat. Prod. Rep. , Vol. 26, 2009, Pages 585-601,
Select pyrimidinones inhibit the propagation of the malarial parasite, Plasmodium falciparum,” Chiang, A.N., Valderramos, J.-C., Balachandran, R., Chovatiya, R.J., Mead, B.P., Schneider, C., Bell, S.L., Klein, M.G., Huryn, D.M., Chen, X.S., Day, B.W., Fidock, D.A., Wipf, P., Brodsky, J.L., Bioorg. Med. Chem., Vol. 17, 2009, Pages 1527-1533,
Synthesis and Biological Evaluation of Inhibitors of Botulinum Neurotoxin Metalloprotease,” Wang, C.; Widom, J.; Petronijevic, F.; Burnett, J. C.; Nuss, J. E.; Bavari, S.; Gussio, R.; Wipf, P., Heterocycles (Special Issue Honoring J. Daly), Vol. 79, 2009, Pages 487-520,
A Microwave Assisted Intramolecular-Furan-Diels-Alder Approach to 4-Substituted Indoles,” Petronijevic, F.; Timmons, C.; Cuzzupe, A.; Wipf, P., Chem. Commun. , Vol. 1, 2009, Pages 104-106,
Triple Hybrids of Steroids, Spiroketals, and Oligopeptides as New Biomolecular Chimeras,” Banerjee, A.; Sergienko, E.; Vasile, S.; Gupta, V.; Vuori, K.; Wipf, P., Org. Lett. , Vol. 11, 2009, Pages 65-68,
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., Vol. 49, 2008, Pages 5986-5989,
Rhodium(I)-Catalyzed Cycloisomerizations of Bicyclobutanes,” Walczak, M. A. A.; Wipf, P., J. Am. Chem. Soc. , Vol. 130, 2008, Pages 6924-6925,
Targeting Mitochondria,” Hoye, A. T.; Davoren, J.; Wipf, P.; Fink, M. P.; Kagan, V. E. , Acc. Chem. Res., Vol. 41, 2008, Pages 87-97,