Derek A Pratt

Summary

Affiliation: University of Illinois
Country: USA

Publications

  1. ncbi request reprint O-H bond dissociation enthalpies in oximes: order restored
    Derek A Pratt
    Department of Chemistry, University of Illinois at Urbana Champaign, Urbana, Illinois 61801, USA
    J Am Chem Soc 126:10667-75. 2004
  2. ncbi request reprint Theoretical investigations into the intermediacy of chlorinated vinylcobalamins in the reductive dehalogenation of chlorinated ethylenes
    Derek A Pratt
    Department of Chemistry, University of Illinois at Urbana Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Am Chem Soc 127:384-96. 2005
  3. pmc Molecular dynamics simulations of arachidonic acid-derived pentadienyl radical intermediate complexes with COX-1 and COX-2: insights into oxygenation regio- and stereoselectivity
    Kristina E Furse
    Department of Chemistry, Center for Structural Biology, Vanderbilt University, Nashville, Tennessee 37232, USA
    Biochemistry 45:3206-18. 2006
  4. doi request reprint Preparation and investigation of vitamin B6-derived aminopyridinol antioxidants
    Remigiusz Serwa
    Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA
    Chemistry 16:14106-14. 2010
  5. pmc Pyridine and pyrimidine analogs of acetaminophen as inhibitors of lipid peroxidation and cyclooxygenase and lipoxygenase catalysis
    Tae Gyu Nam
    Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA
    Org Biomol Chem 7:5103-12. 2009
  6. ncbi request reprint Properties and reactivity of chlorovinylcobalamin and vinylcobalamin and their implications for vitamin B12-catalyzed reductive dechlorination of chlorinated alkenes
    Kevin M McCauley
    Department of Chemistry, University of Illinois at Urbana Champaign, 600 South Mathews Avenue, Urbana, Illinois, USA
    J Am Chem Soc 127:1126-36. 2005
  7. pmc Model studies of the histidine-tyrosine cross-link in cytochrome C oxidase reveal the flexible substituent effect of the imidazole moiety
    Derek A Pratt
    Department of Chemistry, University of Illinois at Urbana Champaign, Urbana, Illinois 61801, USA
    Org Lett 7:2735-8. 2005
  8. ncbi request reprint Tetrahydro-1,8-naphthyridinol analogues of alpha-tocopherol as antioxidants in lipid membranes and low-density lipoproteins
    Tae Gyu Nam
    Center in Molecular Toxicology and Vanderbilt Institute of Chemical Biology, Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA
    J Am Chem Soc 129:10211-9. 2007
  9. pmc Molecular dynamics simulations of arachidonic acid complexes with COX-1 and COX-2: insights into equilibrium behavior
    Kristina E Furse
    Department of Chemistry, Center for Structural Biology, Vanderbilt University, 5142 Biosciences MRB III, Nashville, Tennessee 37232 8725, USA
    Biochemistry 45:3189-205. 2006
  10. ncbi request reprint Lewis acid-promoted Kharasch-Curran additions: a competition kinetics study of bromine atom transfer addition of N-alpha-bromoacetyl-oxazolidinone to 1-hexene
    Hao Feng
    Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA
    J Org Chem 67:6050-4. 2002

Collaborators

Detail Information

Publications16

  1. ncbi request reprint O-H bond dissociation enthalpies in oximes: order restored
    Derek A Pratt
    Department of Chemistry, University of Illinois at Urbana Champaign, Urbana, Illinois 61801, USA
    J Am Chem Soc 126:10667-75. 2004
    ..The present results confirm the 1973 conclusion that simple steric effects, not electron delocalization or dramatic geometric changes, are responsible for the rather small differences in oxime O-H BDEs...
  2. ncbi request reprint Theoretical investigations into the intermediacy of chlorinated vinylcobalamins in the reductive dehalogenation of chlorinated ethylenes
    Derek A Pratt
    Department of Chemistry, University of Illinois at Urbana Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Am Chem Soc 127:384-96. 2005
    ..Thus, cob(I)alamin is expected to reduce these base-off vinyl-Cbls. Heterolytic cleavage of the Co-C bonds is much more favorable than homolysis (>21 kcal/mol) and is significantly more exergonic when coupled to chloride elimination...
  3. pmc Molecular dynamics simulations of arachidonic acid-derived pentadienyl radical intermediate complexes with COX-1 and COX-2: insights into oxygenation regio- and stereoselectivity
    Kristina E Furse
    Department of Chemistry, Center for Structural Biology, Vanderbilt University, Nashville, Tennessee 37232, USA
    Biochemistry 45:3206-18. 2006
    ..Instead, a combination of oxygen channeling, steric shielding, and selective radical trapping appears to be responsible. This work adds a dynamic perspective to the strong foundation of static structural data available for these enzymes...
  4. doi request reprint Preparation and investigation of vitamin B6-derived aminopyridinol antioxidants
    Remigiusz Serwa
    Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA
    Chemistry 16:14106-14. 2010
    ..These molecular aggregates mimic cell membranes that are the targets of oxidative damage in vivo...
  5. pmc Pyridine and pyrimidine analogs of acetaminophen as inhibitors of lipid peroxidation and cyclooxygenase and lipoxygenase catalysis
    Tae Gyu Nam
    Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA
    Org Biomol Chem 7:5103-12. 2009
    ..The pyrimidinols, however, were up to 17-fold more reactive to peroxyl radicals and up to 25-fold better inhibitors of prostaglandin biosynthesis than ApAP, with similar cytotoxicities to HepG2 cells at high levels of exposure...
  6. ncbi request reprint Properties and reactivity of chlorovinylcobalamin and vinylcobalamin and their implications for vitamin B12-catalyzed reductive dechlorination of chlorinated alkenes
    Kevin M McCauley
    Department of Chemistry, University of Illinois at Urbana Champaign, 600 South Mathews Avenue, Urbana, Illinois, USA
    J Am Chem Soc 127:1126-36. 2005
    ..These and other findings are discussed in the context of environmental studies on B12-catalyzed dechlorination of PCE and TCE and investigations of the haloalkene reductive dehalogenases that catalyze similar reactions...
  7. pmc Model studies of the histidine-tyrosine cross-link in cytochrome C oxidase reveal the flexible substituent effect of the imidazole moiety
    Derek A Pratt
    Department of Chemistry, University of Illinois at Urbana Champaign, Urbana, Illinois 61801, USA
    Org Lett 7:2735-8. 2005
    ..21, sigma(m)(-) = +0.45) but decreases the O-H BDE and E degrees of phenol due to its pi-electron-donating ability (sigma(p)(+) = -0.45)...
  8. ncbi request reprint Tetrahydro-1,8-naphthyridinol analogues of alpha-tocopherol as antioxidants in lipid membranes and low-density lipoproteins
    Tae Gyu Nam
    Center in Molecular Toxicology and Vanderbilt Institute of Chemical Biology, Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA
    J Am Chem Soc 129:10211-9. 2007
    ....
  9. pmc Molecular dynamics simulations of arachidonic acid complexes with COX-1 and COX-2: insights into equilibrium behavior
    Kristina E Furse
    Department of Chemistry, Center for Structural Biology, Vanderbilt University, 5142 Biosciences MRB III, Nashville, Tennessee 37232 8725, USA
    Biochemistry 45:3189-205. 2006
    ..The detailed comparisons for COX-1 versus COX-2 active site structural fluctuations may also provide useful information for design of new isozyme-selective inhibitors...
  10. ncbi request reprint Lewis acid-promoted Kharasch-Curran additions: a competition kinetics study of bromine atom transfer addition of N-alpha-bromoacetyl-oxazolidinone to 1-hexene
    Hao Feng
    Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA
    J Org Chem 67:6050-4. 2002
    ..Computation of C-Br bond dissociation energies (BDE) of the complexed and uncomplexed oxazolidinone bromide suggest that complexation lowers the BDE due to the effect of the strong electron-withdrawing group on the C-Br bond dipole...
  11. ncbi request reprint Kinetics and mechanism of the general-acid-catalyzed ring-closure of the malondialdehyde-DNA adduct, N2-(3-oxo-1-propenyl)deoxyguanosine (N2OPdG-), to 3-(2'-Deoxy-beta-D-erythro-pentofuranosyl)pyrimido[1,2-alpha]purin- 10(3H)-one (M1dG)
    James N Riggins
    Department of Biochemistry, Vanderbilt Institute of Chemical Biology, Center in Molecular Toxicology, Vanderbilt Ingram Cancer Center, Vanderbilt University School of Medicine, Nashville, Tennessee 37232, USA
    J Am Chem Soc 126:10571-81. 2004
    ..This work details the complexity of ring-closure in the nucleoside and oligonucleotides and provides new insight into the role of duplex DNA in catalyzing ring-opening and ring-closing of M1dG and N2OPdG...
  12. ncbi request reprint Peroxyl radical clocks
    Bill Roschek
    Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235, USA
    J Org Chem 71:3527-32. 2006
    ..5 x 10(6) M(-1) s(-1), k(H-linoleate) = 62 M(-1) s(-1)). This peroxyl radical clock methodology has been successfully applied to determine inhibition and propagation rate constants ranging from 10(0) to 10(7) M(-1) s(-1)...
  13. ncbi request reprint Theoretical calculations of carbon-oxygen bond dissociation enthalpies of peroxyl radicals formed in the autoxidation of lipids
    Derek A Pratt
    Department of Chemistry and the Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235, USA
    J Am Chem Soc 125:5801-10. 2003
    ....
  14. doi request reprint The unusual reaction of semiquinone radicals with molecular oxygen
    Luca Valgimigli
    Dipartimento di Chimica Organica A Mangini via San Giacomo 11, Universita di Bologna, 40126 Bologna, Italy
    J Org Chem 73:1830-41. 2008
    ..This reaction appears to be much more facile for 1,4-semiquinones than for their 1,2-isomers...
  15. doi request reprint Hock cleavage of cholesterol 5alpha-hydroperoxide: an ozone-free pathway to the cholesterol ozonolysis products identified in arterial plaque and brain tissue
    Johan Brinkhorst
    Department of Chemistry, Queen s University, 90 Bader Lane, Ontario, Canada K7L 3N6
    J Am Chem Soc 130:12224-5. 2008
    ....
  16. ncbi request reprint Role of hyperconjugation in determining carbon-oxygen bond dissociation enthalpies in alkylperoxyl radicals
    Derek A Pratt
    Department of Chemistry and Center for Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235, USA
    Org Lett 5:387-90. 2003
    ..In many cases, this hyperconjugative effect is greater than stabilization of the methyl radical by Y. All electron-withdrawing Y exert small destabilizing effects via inductive withdrawal of electrons from the polarized C-OO* bond...