Richard C. Bunt

Assistant Professor of Chemistry

Department of Chemistry and Biochemistry

Middlebury College

Middlebury, VT  05753

Office: (802) 443-2559

Fax: (802) 443-2072

Email: rbunt@middlebury.edu

Web: http://community.middlebury.edu/~rbunt

 

Education

            Massachusetts Institute of Technology, Cambridge, MA.

            Postdoctoral Fellow, Department of Chemistry, April 1996-August 1998.

            Advisor: Professor JoAnne Stubbe.

            Stanford University, Stanford, CA.

            Doctor of Philosophy, Department of Chemistry, April 1996.

            Advisor: Professor Barry M. Trost.

            Northwestern University, Evanston, IL.

            Bachelor of Arts and Master of Science in Chemistry, with distinction, departmental honors, June 1990.

 

Teaching

            Middlebury College

            Assistant Professor of Chemistry and Biochemistry, September 1998-present.

            General Chemistry (CHEM 0103)

            Organic Chemistry (CHEM 0241, CHEM 0242)

            Advanced Inorganic and Physical Chemistry Laboratory (CHEM 0312)

            Seminar in Chemical Research (CHEM 0400)

            Organic Mechanisms of Enzyme Catalysis (CHEM 0441)

            First-Year Seminar: Modern Age of Science (FYSE 1007, Fall '03)

            First-Year Seminar: Science Risk, Reward and Public Policy (FYSE 1008, Fall '99)

            Stanford University

            Acting Instructor–Graduate. January-March 1995.

            Synthesis Laboratory (CHEM 136)

 

Research

            Middlebury College

            Assistant Professor of Chemistry and Biochemistry, September 1998-present.

            · Synthesis and studies of electronically modified phosphinooxazoline chiral ligands to investigate the mechanism of stereochemical induction in palladium-catalyzed allylic-alkylation reactions.

            · Synthesis and NMR study of 5'-modified nucleoside analogs to investigate DNA base-flipping processes used by many DNA repair enzymes and DNA methylases.

            Massachusetts Institute of Technology

            Postdoctoral research with Professor JoAnne Stubbe, April 1996-August 1998.

            · Synthesized site-specific DNA lesion in short oligonucleotide, determined structure of DNA lesion by 2D NMR, studied binding and cleavage of lesion by metallo-Bleomycins.

            · Directed undergraduate in synthesis of isotopically labeled inhibitors of ribonucleotide reductase for EPR spectroscopy and radiolabeling studies.

            Stanford University

            Graduate research with Professor Barry M. Trost, September 1990-March 1996.

            · Developed new methodologies and chiral ligands for enantioselective π‑allylpalladium catalysis, established novel features of palladium catalyzed allylic alkylation reaction mechanisms and ion pair structures, discovered new method for determining absolute configuration of primary amines.

            · Directed undergraduates in total synthesis and methodology projects resulting in publications.

            Kraft General Foods

            Research intern with Dr. Rich Fisher, June-September 1989.

            · Accomplished synthesis, purification, molecular modeling, and structure‑activity relationship analysis of flavor compounds.

            Northwestern University

            Undergraduate research with Professor Joseph B. Lambert, September 1988-June 1990.

            · Performed synthesis and small-molecule NMR binding studies of aza-crown ethers.

 

Honors and Awards

            Damon Runyon–Walter Winchell Cancer Research Fellow, MIT, 1996-1999.

            The Roche Award for Excellence in Organic Chemistry, Hoffmann-La Roche Inc.,1994.

            Franklin Veatch Memorial Fellow, Stanford University, 1993-1994.

            National Science Foundation Predoctoral Fellow, Stanford University, 1990-1993.

            Linus Pauling Award, Stanford University, 1990.

            Marple-Schweitzer Memorial Award, Northwestern University, 1990.

            Phi Beta Kappa, Northwestern University,1989.

            National Merit Scholar, Northwestern University, 1986-1990.

 

Grants in Support of Undergraduate Research

Vermont Genetics Network (NIH-BRIN), Equipment Grant for "A Solvent Purification System" Co-PI with Jeff Byers ($24,700, 2005).

National Institutes of Health (NIH-AREA), "Mechanism of Base-Flipping by DNA Modifying Enzymes" ($137,971, 2003-2006).

Vermont Genetics Network (NIH-BRIN), Partial Sabbatical Leave Support for "Altering the Rate of Base Flipping in DNA" ($20,000, 2002-2003).

Pfizer Summer Undergraduate Research Fellowship for Sarah S. Goodwin ($5,000, 2003).

American Chemical Society-Petroleum Research Fund, Type G, "Probing the Electronic Origins of Chiral Ligand Asymmetry in Palladium-Catalyzed Allylic-Alkylation Reactions" ($25,000, 2001-2004).

Cottrell College Science Award from Research Corporation, "Probing the Electronic Origins of Chiral Ligand Asymmetry in Palladium-Catalyzed Allylic-Aklylation Reactions" ($41,381, 2001-2005).

Pfizer Summer Undergraduate Research Fellowship for Agnes Makingwe ($5,000, 2000).

VT EPSCoR Award, "Electronic Control of Chiral Ligand Asymmetry" ($5,500, 2000).

Camille and Henry Dreyfus Faculty Start-up Grant, "The Mechanism of Base-Flipping in DNA Repair Enzymes," ($20,000, 1998-2003).

 

Publications

            # Denotes Middlebury College undergraduate co-authors.

            14. Paul B. Armstrong,# Lisa M. Bennett, Ryan N. Constantine,# Jessica L. Fields,# Jerry P. Jasinski, Richard J. Staples, Richard C. Bunt “Hammett 13C NMR and X-ray studies of allylpalladium phosphinooxazoline chiral ligand complexes” Tetrahedron Lett. 2005, 46, 1441-1445.

            13. Sunhee Choi, Richard B. Cooley,# Amanda S. Hakemian, # Yuna C. Larrabee, Richard C. Bunt, Stéphane D. Maupas, James G. Muller, and Cynthia J. Burrows, “Mechanism of Two-Electron Oxidation of Deoxyguanosine 5'-Monophosphate by a Platinum(IV) Complex” J. Am. Chem. Soc. 2004, 126, 591.

            12. Ryan N. Constantine,# Naomi Kim,# and Richard C. Bunt, “Hammett Studies of Enantiocontrol by PHOX Ligands in Pd-Catalyzed Allylic Substitution Reactions” Org. Lett. 2003, 5, 2279.

            11. Hans-Dieter Junker, Silvia T. Hoehn, Richard C. Bunt, Vasilios Marathius, Jingyang Chen, Christopher J. Turner, and Joanne Stubbe “Synthesis, Characterization and Solution Structure of Tethered Oligonucleotides Containing an Internal 3'-Phosphoglycolate, 5'‑Phosphate Gapped Lesion” Nucleic Acids Res. 2002, 30, 5497.

            10. Silvia T. Hoehn, Hans-Dieter Junker, Richard C. Bunt, Christopher J. Turner, and Joanne Stubbe “Solution Structure of Co(III)-Bleomycin-OOH Bound to a Phosphoglycolate Lesion Containing Oligonucleotide: Implications for Bleomycin-Induced Double-Strand DNA Cleavage,” Biochemistry 2001, 40, 5894.

            9. Barry M. Trost, Richard C. Bunt, Reme C. Lemoine, and Trevor L. Calkins “Dynamic Asymmetric Transformation of Butadiene Monoepoxide. A Practical Asymmetric Synthesis of Vinylglycinol, Vigabatrin, and Ethambutol,” J. Am. Chem. Soc. 2000, 122, 5968.

            8. Lisa A. Marzilli, Richard C. Bunt, JoAnne Stubbe, Paul Vouros, and Andreas Harsch “Accurate and Rapid Modeling of Iron-Bleomycin Induced DNA Damage Using Tethered Oligonucleotides and Electrospray Ion Trap Mass Spectrometric Analysis,” Nucleic Acids Res. 2000, 28, 1978.

            7. Barry M. Trost and Richard C. Bunt “On the Effect of the Nature of Ion Pairs as Nucleophiles in a Metal Catalyzed Substitution Reaction,” J. Am. Chem. Soc. 1998, 120, 70.

            6. Barry M. Trost, A. Chris Kruger, Richard C. Bunt, and Jorge Zambrano “On the Question of Asymmetric Induction with Acyclic Allylic Substrates. An Asymmetric Synthesis of (+)‑Polyoxamic Acid,” J. Am. Chem. Soc. 1996, 118, 6520.

            5. Barry M. Trost and Richard C. Bunt “On the Question of the Symmetry of Formally Symmetrical π‑(Allyl)palladium Cationic Intermediates in Allylic Alkylations,” J. Am. Chem. Soc. 1996, 118, 235.

            4. Barry M. Trost and Richard C. Bunt “On Ligand Design for Outer Sphere Catalytic Reactions. A Simple Asymmetric Synthesis of Vinylglycinol,” Angew. Chem., Int. Ed. Engl. 1996, 35, 99.

            3. Barry M. Trost, Richard C. Bunt, and Shon R. Pulley "On the Use of O‑Methylmandelic Acid for the Establishment of Absolute Configuration of a‑Chiral Primary Amines," J. Org. Chem. 1994, 59, 4202.

            2. Barry M. Trost and Richard C. Bunt "Asymmetric Induction in Allylic Alkylations of 3‑Acyloxycycloalkenes," J. Am. Chem. Soc. 1994, 116, 4089.

            1. Barry M. Trost and Richard C. Bunt "On the Nature of the Ion Pair as a Nucleophile in Pd Catalyzed Alkylations with Dienyl Carboxylates," Tetrahedron Lett. 1993, 34, 7513.

 

Patents

            Barry M. Trost, David L. van Vranken, and Richard C. Bunt “Asymmetric Ligands Useful for Transition Metal Catalyzed Bond Forming Reactions” 1998 U.S. Patent 5,739,396.

 

Presentations and Talks

            “Hammett Studies of Phosphinooxazoline Chiral Ligands in Pd-Catalyzed Allylic Substitutions”, Invited talk at College of Charleston, Charleston, SC, March 25, 2004.

            “Hammett Studies of Phosphinooxazoline Chiral Ligands in Pd-Catalyzed Allylic Substitutions”, Invited talk at Smith College, Northampton, MA, March 4, 2004.

            “Hammett Studies of Phosphinooxazoline Chiral Ligands in Pd-Catalyzed Allylic Substitutions”, Invited talk at Merck Process Research, Rahway, NJ, July 11, 2003.

            “Hammett Studies of Enantiocontrol by PHOX Ligands in Pd-Catalyzed Allylic Substitution Reactions”, Paul B. Armstrong,# Ryan N. Constantine,# Naomi Kim# and Richard C. Bunt, Poster Presentation at National Organic Symposium, Bloomington, IN, June 11, 2003.

            “DNA Base-Flipping and Hammett Studies of Asymmetric Palladium Catalysis”, Invited talk at Chiron Corporation, Emeryville, CA, June 14, 2001.

 

Senior Thesis Projects Supervised

            11. “Base Pair Flipping: The Kinetics and Dynamics of a Modified G:U Mismatch in the Dodecamer 5’-d(CGCGAATTU*GCG)-3’,” Sarah S. Goodwin, 2004.

            10. “The Mechanism of Asymmetric Induction by Chiral PHOX Ligands in Pd-Catalyzed Allylic Substitution Reactions,” Paul B. Armstrong, 2004.

            9. “Synthesis of Modified 5’C of Deoxyuridine: Study of Base-Flipping Mechanism in DNA,” Agnes Mwakingwe, 2002.

            8. “Rates of Imino Proton Exchange in 5’-d(CGCGAATTUGCG)-3’ Containing a G-U Mismatch: Kinetic Studies of Base Flipping Dynamics,” Nicole R. LeBoeuf, 2002.

            7. “Palladium-Catalyzed Allylic-Alkylation Reactions: Using Modified Phophinooxazline Ligands to Understand Enantiocontrol,” Ryan N. Constantine, 2002.

            6. “Kinetics and Energetics of Base-Pair Opening in the 5’-d(CGCGAATTUGCG)-3’ Dodecamer Containing a GU Mismatch,” Fritzline L. Montalmant, 2001.

            5. “Hammett Studies of Pd-Chiral Ligand Complexes by 13C NMR,” Jessica L. Fields, 2001

            4. “5’-Modification of Deoxyuridine to Aid in Kinetic Studies of Uracil-DNA Glycosylase,” Michael R. Cooley, 2001.

            3. “The Addition of a Methyl Group to a Deoxyribose Sugar with the Goal of Studying the DNA Repair Enzyme Uracil DNA-Glycosylase,” Charlene M. Weigel, 2000.

            2. “Addition of a Uracil Base to a Deoxyribose Sugar to Study the Mechanism of DNA Repair by Uracil-DNA Glycosylase,” Rachel T. Davis, 2000.

            1. “Synthesis of Nucleoside Analogs with Restricted Backbone Conformation,” Suzanne M. Muchene, 1999.