DEREK A. PRATT by lanyuehua

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									                                          DEREK A. PRATT
                                       Assistant Professor &
                           Canada Research Chair in Free Radical Chemistry

                                         Department of Chemistry
                                             Queen’s University
                                         Kingston, Ontario, Canada
                                                 K7L 3N6
                                              T: 613.533.3287
                                              F: 613.533.6669
                                         E: pratt@chem.queensu.ca


EDUCATION & RESEARCH EXPERIENCE
  •   July 2005 – Present, Assistant Professor & Canada Research Chair (Tier II), Queen’s University
  •   Aug. 2003 – Jun. 2005, Post-Doctoral Fellow, University of Illinois, Urbana (Prof. Wilfred van der Donk)
  •   Sept. 1999 – Dec. 2003, Ph.D., Organic Chemistry, Vanderbilt University (Prof. Ned A. Porter)
  •   Sept. 1995 – Jun. 1999, B.Sc., Chemistry with Highest Honours, Carleton University (Dr. Keith U. Ingold)

SELECTED HONOURS & AWARDS
  •   41st National Science Foundation Workshop on Organic Synthesis and Natural Products Chemistry (2010)
  •   10th Organic Workshop for Leading Young Canadian Chemists (2010)
  •   John Charles Polanyi Prize in Chemistry, Ontario Council on Graduate Studies (2007)
  •   Early Researcher Award, Ontario Ministry of Research and Innovation (2006)
  •   Journal Award, Thieme-Verlag Publishers (2006)
  •   Canada Research Chair in Free Radical Chemistry (2005)
  •   Jane Coffin Childs Fund for Medical Research Post-Doctoral Fellowship (2004)
  •   Warren Graduate Research Fellowship (2002)
  •   Julie Payette NSERC Post-Graduate Scholarship B (2001)
  •   NSERC Post-Graduate Scholarship A (1999)
  •   U.S. Graduate Assistance in Areas of National Need (1999)
  •   Senate Medal for Outstanding Academic Achievement (1999)
  •   President’s Scholarship (1995, 1996, 1997, 1998)

SELECTED PROFESSIONAL ACTIVITIES
  • Member, American Chemical Society, Canadian Society for Chemistry
  • Manuscript Reviewer, Journal of the American Chemical Society, Angewandte Chemie, Canadian Journal
    of Chemistry, Accounts of Chemical Research, Journal of Organic Chemistry, Journal of Physical
    Chemistry A, Organic Letters, Inorganic Chemistry, Lipids, European Journal of Organic Chemistry,
    Chemical Research in Toxicology, ChemBioChem, Journal of Agricultural and Food Chemistry, Journal
    of Chemical Information and Computer Sciences, Environmental and Molecular Mutagenesis
  • Grant Reviewer, Natural Sciences and Engineering Research Council (Discovery Grants Program,
    Collaborative Research and Development Program), U.S. Civilian Research and Development Foundation
  • Co-organizer, “Organic Free Radicals Ottawa”, an international meeting on organic free radical chemistry
    in the style of a Gordon Research Conference. Ottawa, ON (July, 2009)
  • Organizer, “Bio-organic Mechanisms” Symposium of the 90th Canadian Chemistry Conference and
    Exhibition. Winnipeg, MB (May, 2007)
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PUBLICATIONS
While a Faculty Member at Queen’s
(45) Susheel J. Nara, Luca Valgimigli, Gian Franco Pedulli & Derek A. Pratt* Unnatural Amino Acids for
     Probing Radical Transfer in Peptides and Proteins. Journal of the American Chemical Society 2010, 132, 863-872.
(44) Tae-Gyu Nam, Susheel J. Nara, Thomas Cooper, Luca Valgimigli, Johan A. Oates, Ned A. Porter, Olivier
     Boutaud & Derek A. Pratt* Pyridine and Pyrimidine Analogs of Acetaminophen as Inhibitors of Lipid
     Peroxidation and Cyclooxygenase and Lipoxygenase Catalysis. Organic and Biomolecular Chemistry 2009, 7,
     5103-5112 (selected as a hot paper by the publisher)
(43) Luca Valgimigli, Riccardo Amorati, Silvia Petrucci, Gian Franco Pedulli, Di Hu, Jason J. Hanthorn &
     Derek A. Pratt* Unexpected Acid Catalysis in Reactions of Peroxyl Radicals with Phenols. Angewandte
     Chemie International Edition 2009, 48, 8348-8351.
(42) Matthew D. Morrison, Jason J. Hanthorn & Derek A. Pratt* Synthesis of Pyrrolnitrin and Related
     Halogenated Phenylpyrroles. Organic Letters 2009, 11, 1051-1054.
(41) Vipraja Vaidya, K. U. Ingold & Derek A. Pratt* Garlic: Source of the Ultimate Antioxidants – Sulfenic
     Acids. Angewandte Chemie International Edition 2009, 48, 157-160. (highlighted by media around the globe)
(40) Susheel J. Nara, Mukund Jha, Johan Brinkhorst, Tony J. Zemanek & Derek A. Pratt* A Simple Cu-
     Catalyzed Coupling Approach to Substituted 3-Pyridinol and 5-Pyrimidinol Antioxidants. Journal of Organic
     Chemistry 2008, 73, 9326-9333.
(39) Johan Brinkhorst, Susheel J. Nara & Derek A. Pratt* Hock Cleavage of Cholesterol 5α-Hydroperoxide: An
     Ozone-Free Pathway to the Cholesterol Ozonolysis Products Identified in Arterial Plaque and Brain Tissue.
     Journal of the American Chemical Society 2008, 130, 12224-12225. (highlighted in ACS’s C & E News).
(38) Mukund Jha & Derek A. Pratt* Kinetic Solvents Effects on Peroxyl Radical Reactions. Chemical
     Communications 2008, 1252-1254.
(37) Luca Valgimigli, Riccardo Amorati, Maria Grazia Fumo, Gino A. DiLabio, Gian Franco Pedulli, Keith U.
     Ingold & Derek A. Pratt* The Unusual Reaction of Semiquinone Radicals with Molecular Oxygen. Journal
     of Organic Chemistry 2008, 73, 1830-1841.
(36) Tae-Gyu Nam, Christopher L. Rector, Hye-Young Kim, A. F.-P. Sonnen, R. Meyer, Werner M. Nau,
     Jeffrey Atkinson, Julia Rintoul, Derek A. Pratt* & Ned A. Porter Tetrahydro-1,8-Naphthyridinol
     Analogues of α-Tocopherol as Antioxidants in Lipid Membranes and Low Density Lipoproteins. Journal of
     the American Chemical Society 2007, 129, 10211-10219.
(35) Claus Schneider, Derek A. Pratt, Ned A. Porter & Alan R. Brash* Control of Oxygenation Specificity in
     Cyclooxygenase and Lipoxygenase Catalysis. Chemistry & Biology 2007, 14, 473-488.
(34) Derek A. Pratt* & Wilfred A. van der Donk On the Role of Alkylcobalamins in the Vitamin B12-
     Catalyzed Reductive Dehalogenation of Perchloroethylene and Trichloroethylene. Chemical Communications
     2006, 558-560.
Post-Doctoral/Graduate/Undergraduate Studies
(33) Russell P. Pesevanto, Derek A. Pratt, Jerry Jeffers & Wilfred A.van der Donk* Model Studies of the CuB
     Site of Cytochrome c Oxidase Utilizing a Zn(II) Complex Containing an Imidazole-Phenol Cross-Linked
     Ligand. Dalton Transactions 2006, 3326-3337.
(32) William P. Roschek, Jr., Keri A. Tallman, Jason G. Gillmore, Derek A. Pratt, Carlo Punta & Ned A.
     Porter* Peroxyl Radical Clocks. Journal of Organic Chemistry 2006, 71, 3527-3532.




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(31) Kristina E. Furse, Derek A. Pratt, Claus Schneider, Alan Brash, Ned A. Porter & Terry P. Lybrand*
     Molecular Dynamics Simulations of Arachidonic Acid-Derived Pentadienyl Radical Intermediate
     Complexes with COX-1 and COX-2: Insights into Oxygenation Regio- and Stereoselectivity. Biochemistry
     2006, 45, 3206-3218.
(30) Kristina E. Furse, Derek A. Pratt, Ned A. Porter & Terry P. Lybrand* Molecular Dynamics Simulations of
     Arachidonic Acid Complexes with COX-1 and COX-2: Insights into Equilibrium Behavior. Biochemistry
     2006, 45, 3189-3205.
(29) Hye-Young Kim, Derek A. Pratt*, Jennifer Seal, Maikel Wijtmans & Ned A. Porter* Lipid-Soluble 3-
     Pyridinol Antioxidants Spare α-Tocopherol and Do Not Efficiently Mediate Peroxidation of Cholesterol
     Esters in Human Low-Density Lipoprotein. Journal of Medicinal Chemistry 2005, 48, 6787-6789.
(28) Derek A. Pratt, Russell P. Pesevanto & Wilfred A. van der Donk* Model Studies of the Histidine-Tyrosine
     Cross-Link in Cytochrome c Oxidase Reveal the Flexible Substituent Effect of the Imidazole Moiety.
     Organic Letters 2005, 7, 2735-2738.
(27) Tae-gyu Nam, Maikel Wijtmans, Derek A. Pratt* & Ned A. Porter* Regioselective Addition of n-
     Alkyllithium to α,α’-Disubstituted-1,8-Naphthyridines: Synthesis of 6-Amino-3-Pyridinol Analogs of α-
     Tocopherol. Synthesis 2005, 9, 1397-1404 (special issue dedicated to Prof. Bernd Giese).
(26) Peter Mulder,* Hans-Gert Korth, Derek A. Pratt, Gino DiLabio, Luca Valgimigli, Gian Franco Pedulli &
     K. U. Ingold A Critical Re-Evaluation of the O-H Bond Dissociation Enthalpy of Phenol. Journal of Physical
     Chemistry A 2005, 109, 2647-2655.
(25) Kevin M. McCauley, Derek A. Pratt, Scott R. Wilson, Justin Shey, Theodore J. Burkey & Wilfred A. van
     der Donk* Properties and Reactivity of Chlorovinylcobalamin and Vinylcobalamin and their Implications
     for Vitamin B12-Catalyzed Reductive Dechlorination of Chlorinated Alkenes. Journal of the American Chemical
     Society 2005, 127, 1126-1136.
(24) Derek A. Pratt* & Wilfred A. van der Donk* Theoretical Investigations into the Intermediacy of
     Chlorinated Vinylcobalamins in the Reductive Dechlorination of Chlorinated Ethylenes. Journal of the
     American Chemical Society 2005, 127, 384-396.
(23) Maikel Wijtmans, Derek A. Pratt,* Luca Valgimigli, Remigiusz Serwa, Johan Brinkhorst, Gian Franco
     Pedulli & Ned A. Porter* Synthesis and Reactivity of Some 6-Substituted-2,4-Dimethyl-3-Pyridinols, A
     Novel Class of Chain-Breaking Antioxidants. Journal of Organic Chemistry 2004, 69, 9215-9223.
(22) Derek A. Pratt,* Jessie A. Blake, Peter Mulder, John Walton, Hans-Gert Korth & K. U. Ingold O-H Bond
     Dissociation Enthalpies in Oximes: Order Restored. Journal of the American Chemical Society 2004, 126, 10667-
     10675.
(21) James N. Riggins, Derek A. Pratt, Markus Voehler, J. Scott Daniels & Lawrence J. Marnett* Kinetic and
     Structural Evaluation of the General Acid Catalyzed Ring-Closure of the Malondialdehyde-DNA adduct,
     N2-(3-oxo-1-propenyl)-guanine (N2OPG-) to Pyrimido[1,2-a]purin-10(3H)-one (M1G). Journal of the American
     Chemical Society 2004, 126, 10571-10581.
(20) Derek A. Pratt,* Gino A. DiLabio,* Peter Mulder* & K. U. Ingold* Bond Strengths in Toluenes, Anilines
     and Phenols: To Hammett or Not? Accounts of Chemical Research 2004, 37, 334-340.
(19) Jessie A. Blake, Derek A. Pratt, Shuqiong Lin, John C. Walton, Peter Mulder* & K. U. Ingold Thermolyses
     of O-Phenyl Oxime Ethers. A New Source of Iminyl Radicals and a New Source of Aryloxyl Radicals.
     Journal of Organic Chemistry 2004, 69, 3112-3120.
(18) Jessie A. Blake, Keith U. Ingold, Shuqiong Lin, Peter Mulder,* Derek A. Pratt, Brad Sheeller & John C.
     Walton* Thermal Decomposition of O-Benzyl Ketoximes; Role of Reverse Radical Disproportionation.
     Organic and Biomolecular Chemistry 2004, 2, 415-420.

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(17) Luca Valgimigli,* Giovanni Brigati, Gian Franco Pedulli, Gino A. DiLabio, Marina Mastragostino, Catia
     Arbizzani & Derek A. Pratt* The Effect of Ring Nitrogens on the Homolytic Reactivity of Phenolic
     Compounds: Understanding the Radical-Scavenging Ability of Pyrimidinols. Chemistry: A European Journal
     2003, 9, 4997-5010.
(16) Maikel Wijtmans, Derek A. Pratt,* Luca Valgimigli,* Gino A. DiLabio, Gian Franco Pedulli* & Ned A.
     Porter* 6-Amino-3-Pyridinols: Towards Diffusion-Controlled Chain-Breaking Antioxidants. Angewandte
     Chemie Intl. Ed. 2003, 42, 4370-4373, (corrigendum, 4847).
(15) Derek A. Pratt, Jeremy H. Mills & Ned A. Porter* Theoretical Calculations of Carbon-Oxygen Bond
     Dissociation Enthalpies of Peroxyl Radicals Formed in the Autoxidation of Lipids. Journal of the American
     Chemical Society 2003, 125, 5801-5810.
(14) Derek A. Pratt & Ned A. Porter* The Role of Hyperconjugation in Determining the Carbon-Oxygen
     Bond Dissociation Enthalpies of Alkylperoxyl Radicals. Organic Letters 2003, 5, 387-390.
(13) Gino A. DiLabio,* Grzegorz Litwinienko,* Shuquiong Lin, Derek A. Pratt & K. U. Ingold Revised
     Structure for the Diphenylaminyl Radical: The Importance of Theory in the Assignment of Electronic
     Transitions in Ph2X • (X = CH, N) and PhY • (Y = CH2, NH, O) Journal of Physical Chemistry A 2002, 106,
     11719-11725.
(12) Derek A. Pratt,* Luca Valgimigli, Gino A. DiLabio, Gian Franco Pedulli & K. U. Ingold Substituent
     Effects on the Bond Dissociation Enthalpies of Aromatic Amines. Journal of the American Chemical Society
     2002, 124, 11085-11092.
(11) Hao Feng, Ivanka Kavrakova, Derek A. Pratt, Joel Tellinghuisen & Ned A. Porter* Lewis Acids Catalyzed
     Karasch-Curran Additions from 2-Bromoacetyl-2-oxazolidinone Amide to 1-Hexene: A Competition
     Kinetic Study. Journal of Organic Chemistry 2002, 67, 6050-6054.
(10) Keri A. Tallman, Derek A. Pratt & Ned A. Porter* Kinetic Products of Linoleate Peroxidation: Rapid β-
     Fragmentation of Non-Conjugated Peroxyls. Journal of the American Chemical Society 2001, 123, 11827-11828.
(9)   Derek A. Pratt,* Martine I. deHeer, Peter Mulder & K. U. Ingold Oxygen-Carbon Bond Dissociation
      Enthalpies of Benzyl Phenyl Ethers and Anisoles. An Example of Temperature Dependent Substituent
      Effects. Journal of the American Chemical Society 2001, 123, 5518-5526.
(8)   Derek A. Pratt,* Gino A. DiLabio, Gian Franco Pedulli, Giovanni Brigati & Luca Valgimigli* 5-
      Pyrimidinols: Novel Chain-Breaking Antioxidants More Effective Than Phenols. Journal of the American
      Chemical Society 2001, 123, 4625-4626.
(7)   Ned A. Porter,* Huiyong Yin & Derek A. Pratt The Peroxy Acid-Hydroxy Dioxirane Equilibrium: Base
      Promoted Exchange of Peroxy Acid Oxygens. Journal of the American Chemical Society 2000, 122, 11272-11273.
(6)   Walter Reints, Derek A. Pratt, Hans-Gert Korth & Peter Mulder* The O-O Bond Dissociation Enthalpy
      in Di-Trifluoromethyl Peroxide (CF3OOCF3). Very Low Pressure Pyrolysis and DFT Computations. Journal
      of Physical Chemistry A 2000, 104, 10713-10720.
(5)   Gino A. DiLabio,* Derek A. Pratt & James S. Wright Theoretical Calculation of Ionization Potentials for
      Disubstituted Benzene: Additivity Versus Non-Additivity of Substituent Effects. Journal of Organic Chemistry
      2000, 65, 2195-2203.
(4)   G. A. DiLabio* & D. A. Pratt Density Functional Theory-Based Model Calculations for Accurate Bond
      Dissociation Enthalpies. 2. Studies of X-X and X-Y (X,Y=C,N,O,S,Halogen) Bonds. Journal of Physical
      Chemistry A 2000, 104, 1938-1943.
(3)   G. A. DiLabio,* D. A. Pratt & J. S. Wright Theoretical Calculation of Gas-Phase Ionization Potentials for
      Mono- and Poly-Substituted Benzenes. Chemical Physics Letters 1999, 311, 215-220.


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(2)    Derek A. Pratt, J. S. Wright & K. U. Ingold* A Theoretical Study of Carbon-Halogen Bond Dissociation
       Enthalpies of Substituted Benzyl Halides. How Important are Polar Effects? Journal of the American Chemical
       Society 1999, 121, 4877-4882.
(1)    G. A. DiLabio, D. A. Pratt, A. D. LoFaro & J. S. Wright* Theoretical Study of X-H Bond Energetics
       (X=C,N,O,S): Application to Substituent Effects, Gas Phase Acidities and Redox Potentials. Journal of
       Physical Chemistry A 1999, 103, 1653-1661.
Submitted Manuscripts
       Di Hu & Derek A. Pratt* Secondary Orbital Interactions in the Propagation Steps of Lipid Peroxidation.
       Chemical Communications.
       Riccardo Amorati, Gian Franco Pedulli, Derek A. Pratt* & Luca Valgimigli Protonated Persistent
       Nitroxides: “Radical” Radical-Trapping Antioxidants. Angewandte Chemie International Edition.
       Sean Malmberg, J. Scott Parent, Derek A. Pratt & Ralph A. Whitney* Isomerization and Elimination
       Reactions of Brominated Poly(isobutylene-co-isoprene). Macromolecules.
Manuscripts in Preparation
       Krista Butts, Philip Lynett, Vipraja Vaidya & Derek A. Pratt* The Mechanism of Radical-Trapping
       Antioxidant Activity of Plant-Derived Thiosulfinates.
       Alaina McGrath, Riccardo Amorati, Luca Valgimigli & Derek A. Pratt* The Amazing Redox Behaviour of
       Sulfenic Acids.
       Riccardo Amorati, Derek A. Pratt, Carmelo Daquino, Mario C. Foti & Keith U. Ingold Influence of
       Remote Intramolecular Hydrogen Bonds on the Stabilities of Phenoxyl Radicals and Benzyl Cations.

PATENTS
  • “Novel Chain-Breaking Antioxidants” Derek A. Pratt, Gino A. DiLabio & Luca Valgimigli, U.S. Patent No.
     6,835,216 (2004)
  • “Chain-Breaking Antioxidants” Derek A. Pratt, Gino A. DiLabio & Luca Valgimigli, U.S. Patent No.
     7,547,709 (2009)

INVITED LECTURES
2010
  • Pacifichem Symposium on Reactive Intermediates and Unusual Molecules (December)
  • Vanderbilt Institute for Chemical Biology, Vanderbilt University, Nashville, TN (December)
  • EUCHEM Conference on Organic Free Radicals, Bologna, Italy (June)
  • Department of Chemistry, Duquesne University, Pittsburgh, PA (March)
  • Department of Chemistry, Johns Hopkins University, Baltimore, MD (March)
2009
  • 4th Pacific Symposium on Radical Chemistry, Shanghai Institute of Organic Chemistry, China
  • Département de Chimie, Université de Provence, Marseille, France
  • Infineum LP, Linden, NJ
  • Division of Organic Chemistry Young Investigators Symposium, ACS National Meeting, Washington, D.C.

                                                         -5-
 • Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France
 • Department of Chemistry, McGill University, Montreal, PQ
2008
 • 10th International Symposium on Organic Free Radicals, Heron Island, Australia
 • Department of Biochemistry, Queen’s University, Kingston, ON
2007
 • Department of Pharmacology & Toxicology, Queen’s University, Kingston, ON
 • Department of Chemistry, University of Ottawa, Ottawa, ON
 • 90th Canadian Chemistry Conference and Exhibition. Winnipeg, MB
 • Department of Chemistry, Brock University, St. Catherines, ON
2005
 • Department of Chemistry, University of British Columbia, Vancouver, BC
 • Department of Chemistry, University of Victoria, Victoria, BC
 • 36th Great Lakes Regional Meeting of the American Chemical Society, Peoria, IL
 • Department of Chemistry, Queen’s University, Kingston, ON
2003
 • 55th Southeast Regional Meeting of the American Chemical Society, Atlanta, GA (November, 2003)
2002
 • Department of Organic Chemistry “A. Mangini”, University of Bologna, Bologna, Italy (July, 2002)
 • Eastman Chemical Co., Kingsport, TN (January, 2002)
2001
 • Pacific Northwest National Laboratory, Richland, WA (April, 2001)

TEACHING
Undergraduate
CHEM 245: Applied Organic Chemistry (2005-2006; 2006-2007)
CHEM 311: Mechanistic Organic Chemistry (2007-2008; 2008-2009; 2009-2010)
Graduate
CHEM 882: Mechanistic Organic Chemistry (2005-2006; 2006-2007; 2007-2008; 2008-2009; 2009-2010)
CHEM 983: Solving Reaction Mechanisms (2006-2007)

TRAINING
Post-Doctoral Researchers
Name                   Tenure                                          Position Following Departure
Daria Trofimova        August 2008 – January 2010                      Post-Doctoral Researcher, Queen’s
Vipraja Vaidya         January 2008 – September 2008                   Assoc. Scientific Manager, Biocon Ltd.
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Mukund Jha            March 2006 – June 2008                      Assistant Professor, Nippissing Univ.
Susheel Nara          November 2005 – September 2008              Assoc. Scientific Manager, Biocon Ltd.

Graduate Students
Name                  Degree/Years                                Position Following Departure
Phil Lynett           2009 – current                              in progress
Jianxing Yang         2009 – current                              in progress
Graham Garrett        2009 – current (co-supervised, S. Parent)   in progress
Alaina McGrath        2008 – current                              in progress
Dong Yan              2008 – current (co-supervised, C. Funk)     in progress
Rami Dhanoa           2007 – current                              in progress
Di Hu                 M.Sc. / 2007-2009                           R.A., Kingston General Hospital
Jason Hanthorn        Ph.D. / 2006 – current                      in progress
Matthew Morrison      M.Sc. / 2006-2008                           D.D.S., McGill Univ.
Johan Brinkhorst      M.Sc. / 2006-2008                           R.A., Univ. of Provence, France

Undergraduate Students
Name                   Degree/Year Completed (Expected)           Position Following Departure
Evan Haidusz           B.Sc. / 2010                               in progress
Stephanie Hofley       B.Sc. / 2010                               in progress
Paul Ricketts          B.Sc. / 2010                               in progress
Krista Butts           B.Sc. / 2009                               M.D., Dalhousie Univ.
Mark Rattle            B.Sc. / 2009                               M.Sc., McMaster Univ.
Andrea Greschner       B.Sc. / 2008                               M.Sc., McGill Univ.
Chris Witiw            B.Sc. / 2008                               M.D., Univ. of Manitoba
Gabrielle Bouchard     B.Sc. / 2007                               M.Sc., Queen’s Univ.
Amelie Menard          B.Sc. / 2007                               Ph.D., McGill Univ.
Mayuran Srikantha      B.Sc. / 2007                               M.Sc., Univ. of Toronto
Heather Stefanison     B.Sc. / 2006                               M.D., McGill Univ.
Michael Tam            B.Sc. / 2006                               M.Sc., Univ. of Toronto
Tony Zemanek           B.Sc./ 2006                                Engineer, Hatch Ltd.




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