Dr. Michael C. Pirrung
Professor
Presidential Chair, Chemistry

BA Chemistry with Highest Honors 1975 University of Texas, Austin
Ph.D. Organic Chemistry 1980 UC Berkeley
NSF Postdo Organic Chemistry 1980 Columbia University

CONTACT
Office : (951) 827-2722
Fax : (951) 827-2749
e-mail : michael.pirrung@ucr.edu
RESEARCH INTERESTS
Dr. Pirrung is an organic chemist with research in the areas of chemical biology, synthesis, and nucleic acids. He is a pioneer in the field of microarrays, which have important biological applications in genomics. Recent interests have included combinatorial chemistry, focused on solid-phase synthesis and natural products.

Our lab uses stem cell lines as model systems for the application of chemical biology to current problems in stem cell research. Efforts to direct stem cell differentiation can be based not only on biological mediators and the niche, but also on biologically active small organic molecules (drugs). A unique aspect of embryonic stem cells compared to essentially all other mammalian differentiated cells is that they are subject to post-transcriptional gene silencing (also known as RNA interference or RNAi). Thus, a chemical approach to steering ES cells in novel developmental directions is the knock down of specific genes using readily synthesized short interfering RNA (siRNA).

HONORS AND AWARDS
Phi Beta Kappa, December 1975.

Fannie and John Hertz Foundation Fellow, 1978-80.

Dreyfus Foundation Award for Newly-Appointed Faculty, 1982-87.

Eli Lilly Grantee, 1984-86.

Alfred P. Sloan Research Fellow, 1986-88.

NSF Presidential Young Investigator, 1985-90.

AAAS-Newcomb Cleveland Prize, 1991 (best paper in Science).

Intellectual Property Owners Distinguished Inventor Award, 1993.

John Simon Guggenheim Memorial Foundation Fellow, 1994-95.

Outstanding Young Texas Ex Award, University of Texas Ex-Student's Association, 1995.

Fellow of the AAAS, 1996.

Chemical Pioneer Award, American Institute of Chemists, 2004.

SELECTED PUBLICATIONS

See publications on PubMed

Michael C. Pirrung, Amy L. Odenbaugh, and Janice D. Davis, "Novel Reagents and Procedures for Immobilization of DNA on Glass Microchips for Primer Extension," Langmuir, 16, 2185 (2000).

Michael C. Pirrung and Tao Pei, Synthesis of (+)-Homohistidine," J. Org. Chem., 65, 2229 (2000).

Michael C. Pirrung and Krishna P. Kaliappan, "Dipolar Cycloaddition of Rhodium-generated Carbonyl Ylides with p-Quinones," Org. Lett., 2, 353 (2000).

Michael C. Pirrung, Richard V. Connors, Michael P. Montague-Smith, Amy L. Odenbaugh, Nathan G. Walcott, and Jeff J. Tollett, "The Arrayed Primer Extension Method for DNA Microchip Analysis. Molecular Computation of Satisfaction Problems," J. Am. Chem. Soc., 122, 1873 (2000).

Jane E. Jackman, Carol A. Fierke, L. Nathan Tumey, Michael Pirrung, Taketo Uchiyama, S. Hasan Tahir, Ole Hindsgaul, and Christian R. H. Raetz, "Antibacterial Agents that Target Lipid A Biosynthesis in Gram-negative Bacteria," J. Biol. Chem., 275, 11002 (2000).

Michael C. Pirrung, Sandra J. Drabik, Jasimuddin Ahamed, and Hydar Ali, "Caged Chemotactic Peptides," Bioconjugate Chem., 11, 679 (2000).

Michael C. Pirrung, Chris Silva, and John Jaeger, "Available Pathways Database: A Resource for Combinatorial Biology," J. Nat. Prod., 63, 1400 (2000).

Michael C. Pirrung and L. Nathan Tumey, "Oxazoline Synthesis from Hydroxyamides by Resin Capture and Ring-forming Release," J. Comb. Chem., 2, 675 (2000).

Michael C. Pirrung, Kenneth D. James, and Vipul S. Rana, "Thiophosphorylation of Histidine," J. Org. Chem., 62, 8448 (2000).

Michael C. Pirrung and Sunil Pansare, "Trityl Isothiocyanate Support for Solid-phase Synthesis," J. Comb. Chem., 3, 90-6 (2001).

Michael C. Pirrung, Kaapjoo Park, and Zhitao Li, "Synthesis of 3-Indolyl-2,5-Dihydroxybenzoquinones," Org. Lett., 3, 365-8 (2001).

Michael C. Pirrung, Laixin Wang, and Michael P. Montague-Smith, "3'-Nitrophenylpropyloxycarbonyl (NPPOC) Protecting Groups for High-fidelity Automated 5'->3' Photochemical DNA Synthesis," Org. Lett., 3, 1105 (2001).

Michael C. Pirrung, Lara Fallon, Jin Zhu, and Yong Rok Lee, "Photochemically-removable Silyl Protecting Groups, J. Am. Chem. Soc., 123, 3638 (2001).

John M. Shumaker, Jeffery J. Tollett, Kellie J. Filbin, Michael P. Montague-Smith, and Michael C. Pirrung, "APEX Disease Gene Resequencing: Mutations in Exon 7 of the p53 Tumor Suppressor Gene," Bioorg. Med. Chem., 9, 2269 (2001).

Michael C. Pirrung, Janice D. Worden, Joanne P. Labriola, Michael P. Montague-Smith, and Laura J. Weislo, “Solid-phase, Single Nucleotide Primer Extension of DNA/RNA Hybrids by Reverse Transcriptases,” Bioorg. Med. Chem. Lett., 11, 2437 (2001).

Michael C. Pirrung, Michael Wedel, and Yan Zhao, “7-Alkyl Indole Synthesis via a Convenient Formation/Alkylation of Lithionitrobenzenes and an Improved Bartoli Reaction,” Synlett, 143 (2002).

Michael C. Pirrung, Hao Liu, and Andrew T. Morehead, Jr., “Rhodium Chemzymes: Michaelis-Menten Kinetics in Dirhodium(II) Carboxylate-Catalyzed Carbenoid Reactions,” J. Am. Chem. Soc., 124, 1014 (2002).

Michael C. Pirrung, “How to Make a DNA Chip,” Angew. Chem., Int. Ed., 41, 1276 (2002).

Hyunsoo Kim and Michael C. Pirrung, “Arrayed Primer Extension Computing with Variant mRNA Splice Forms. Multiple Isoforms of CD44 in a Human Breast Tumor,” J. Am. Chem. Soc., 124, 4934 (2002).

John H. Reif, Thomas H. LaBean, Michael Pirrung, Vipul S. Rana, Bo Guo, Carl Kingsford, and Gene S. Wickham, “Experimental Construction of Very Large Scale DNA Databases with Associative Search Capability,” Jonoska, N., Seeman, N. C., Eds., DNA Computing (DNA7), Lecture Notes in Computer Science 2340, Springer, Heidelberg, 2002, p. 231.

Michael C. Pirrung, Kaapjoo Park, and L. Nathan Tumey, “19F Encoded Combinatorial Libraries: Discovery of Selective Metal-binding and Catalytic Peptoids,” J. Comb. Chem., 4, 329 (2002).

Michael C. Pirrung, Zhitao Li, Kaapjoo Park, and Jin Zhu, “Total Syntheses of Demethylasterriquinone B1, an Orally Active Insulin Mimetic, and Demethylasterriquinone A1,“ J. Org. Chem., 67, 7919 (2002).

Michael C. Pirrung, Xiadong Zhao, and Shannon V. Harris, "A Universal, Photocleavable DNA Base: Nitropiperonyl 2'-Deoxyriboside (dP*)," J. Org. Chem., 66, 2067 (2001).

Michael C. Pirrung, L. Nathan Tumey, Christian R. H. Raetz, Jane E. Jackman, Karnem Snehalatha, Amanda L. McClerren, Carol A. Fierke, Stephanie L. Gantt, and Kristin Rusche, “Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC). Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups,” J. Med. Chem., 45, 4359 (2002).

Michael C. Pirrung, Liu Deng, Zhitao Li, and Kaapjoo Park, “Synthesis of 2,5-Dihydroxy-3-(indol-3-yl)-benzoquinones by Acid-catalyzed Condensation,” J. Org. Chem., 67, 8374 (2002).

Michael C. Pirrung, L. Nathan Tumey, Amanda L. McClerren, and Christian R. H. Raetz, “High-Throughput Catch-and-Release Synthesis of Oxazoline Hydroxamates. Structure-activity Relationships of Novel Inhibitors of E. coli LpxC. in vitro Enzyme Inhibition and Antibacterial Properties,” J. Am. Chem. Soc., 125, 1575 (2003).

Nicholas J. G. Webster, Kaapjoo Park, and Michael C. Pirrung, “Signaling Effects of Demethylasterriquinone B1: a Selective Insulin Receptor Modulator (SIRM),” ChemBioChem, 4, 379 (2003).

Michael C. Pirrung and Hao Liu, “Parallel Synthesis and Screening of an Illudinoid Combinatorial Library,” Org. Lett., 6, 1983 (2003).

Jungsan Sohn, Brendan Kiburz, Zhitao Li, Liu Deng, Alexias Safi, Michael C. Pirrung, and Johannes Rudolph, “Inhibition of Cdc25 Phosphatases by Indolyldihydroxy-quinones,” J. Med. Chem., 46, 2580 (2003).

Michael C. Pirrung, Wolfgang Pieper, Krishna P. Kaliappan, and M. R. Dhananjeyan, "Combinatorial Discovery of Two-photon Photoremovable Protecting Groups," Proc. Natl. Acad. Sci. USA., 100, 12548 (2003).

Michael C. Pirrung and Koushik Das Sarma, “Multi-component Reactions Are Accelerated in Water,” J. Am. Chem. Soc., 126, 444 (2004).

Lyudmila Yakovleva, Christopher J. Handy, Jane M. Sayer, Michael Pirrung, Donald M. Jerina, and Stewart Shuman, “Benzo[c]phenanthrene Adducts and Nogalamycin Inhibit DNA Transesterification by Vaccinia Topoisomerase,” J. Biol. Chem., 279, 23335 (2004).

Michael C. Pirrung and Koushik Das Sarma, “beta-Lactam Synthesis by Ugi Reaction of beta-Ketoacids in Aqueous Solution,” Synlett, 1425 (2004).

The ENCODE Project Consortium, “The ENCODE (ENCyclopedia of DNA Elements) Project,” Science, 306, 636-640 (2004).

Michael C. Pirrung, Sunil V. Pansare, Koushik Das Sarma, Kathy A. Keith, and Earl R. Kern, “Combinatorial Optimization of Isatin-beta-Thiosemicarbazones as Anti-Poxvirus Agents,” J. Med. Chem., 47, 000 (2004).
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