Robert Coates

Summary

Affiliation: University of Illinois
Country: USA

Publications

  1. ncbi request reprint Syn- and anti-selective Prins cyclizations of delta,epsilon-unsaturated ketones to 1,3-halohydrins with Lewis acids
    R Brandon Miles
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 71:1493-501. 2006
  2. ncbi request reprint Stereoselective prins cyclizations of delta, epsilon-unsaturated ketones to cis-3-chlorocyclohexanols with TiCl(4)
    Chad E Davis
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana 61801, USA
    Angew Chem Int Ed Engl 41:491-3. 2002
  3. ncbi request reprint Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates
    Matthew M Ravn
    Department of Chemistry, University of Illinois, 600 S Mathews Avenue, Urbana, Illinois 61801, USA
    J Am Chem Soc 124:6998-7006. 2002
  4. pmc Interception of the enzymatic conversion of farnesyl diphosphate to 5-epi-aristolochene by using a fluoro substrate analogue: 1-fluorogermacrene A from (2E,6Z)-6-fluorofarnesyl diphosphate
    Juan A Faraldos
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801, USA
    Chembiochem 8:1826-33. 2007
  5. ncbi request reprint Probing the role of the DXDD motif in Class II diterpene cyclases
    Sladjana Prisic
    Department of Biochemistry, Biophysics, and Molecular Biology, Iowa State University, Molecular Biology Building, Ames, IA 50011, USA
    Chembiochem 8:869-74. 2007
  6. pmc Stereochemistry and deuterium isotope effects associated with the cyclization-rearrangements catalyzed by tobacco epiaristolochene and hyoscyamus premnaspirodiene synthases, and the chimeric CH4 hybrid cyclase
    David J Schenk
    Department of Chemistry, University of Illinois, 600 South Mathews Ave, Urbana, IL 61801, USA
    Arch Biochem Biophys 448:31-44. 2006
  7. ncbi request reprint Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling
    Qingwu Jin
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 70:4667-75. 2005
  8. ncbi request reprint Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes
    Yinghua Jin
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Am Chem Soc 127:7834-42. 2005
  9. ncbi request reprint Eremophilane sesquiterpenes from capsidiol
    Yuxin Zhao
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 69:7428-35. 2004
  10. ncbi request reprint Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol
    Marek Urbansky
    Department of Chemistry, University of Illinois at Urbana Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    Org Lett 6:135-8. 2004

Research Grants

  1. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 2001
  2. STRUCTURES OF ANTIBIOTICS AND RELATED COMPOUNDS
    Robert Coates; Fiscal Year: 2003
  3. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 1980
  4. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 1992
  5. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 1993
  6. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 2006

Collaborators

  • Chad E Davis
  • Marek Urbansky
  • Rodney Croteau
  • David J Schenk
  • Yuxin Zhao
  • Juan A Faraldos
  • Sladjana Prisic
  • Chandraiah Lagisetti
  • Joseph P Noel
  • R Brandon Miles
  • Qingwu Jin
  • Yinghua Jin
  • David C Williams
  • Joe Chappell
  • Reuben J Peters
  • Matthew M Ravn
  • Jennifer A Digits
  • Mitchell L Wise
  • Jianjun Xu
  • Kathleen Rising Manna
  • Courtney M Starks
  • Mehri Hezari
  • Shunji Takahashi
  • Jacob D Surjan
  • Jessica L Bailey
  • Bryan C Duffy
  • Jonathan W Lockner
  • Gregory L Helms
  • Patrick J Casey
  • Hyung Jung Pyun

Detail Information

Publications15

  1. ncbi request reprint Syn- and anti-selective Prins cyclizations of delta,epsilon-unsaturated ketones to 1,3-halohydrins with Lewis acids
    R Brandon Miles
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 71:1493-501. 2006
    ....
  2. ncbi request reprint Stereoselective prins cyclizations of delta, epsilon-unsaturated ketones to cis-3-chlorocyclohexanols with TiCl(4)
    Chad E Davis
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana 61801, USA
    Angew Chem Int Ed Engl 41:491-3. 2002
  3. ncbi request reprint Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates
    Matthew M Ravn
    Department of Chemistry, University of Illinois, 600 S Mathews Avenue, Urbana, Illinois 61801, USA
    J Am Chem Soc 124:6998-7006. 2002
    ....
  4. pmc Interception of the enzymatic conversion of farnesyl diphosphate to 5-epi-aristolochene by using a fluoro substrate analogue: 1-fluorogermacrene A from (2E,6Z)-6-fluorofarnesyl diphosphate
    Juan A Faraldos
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801, USA
    Chembiochem 8:1826-33. 2007
    ....
  5. ncbi request reprint Probing the role of the DXDD motif in Class II diterpene cyclases
    Sladjana Prisic
    Department of Biochemistry, Biophysics, and Molecular Biology, Iowa State University, Molecular Biology Building, Ames, IA 50011, USA
    Chembiochem 8:869-74. 2007
  6. pmc Stereochemistry and deuterium isotope effects associated with the cyclization-rearrangements catalyzed by tobacco epiaristolochene and hyoscyamus premnaspirodiene synthases, and the chimeric CH4 hybrid cyclase
    David J Schenk
    Department of Chemistry, University of Illinois, 600 South Mathews Ave, Urbana, IL 61801, USA
    Arch Biochem Biophys 448:31-44. 2006
    ..The results are explained by consideration of the conformations of individual intermediates, and by imposing the requirement of stereoelectronically favorable proton additions and eliminations...
  7. ncbi request reprint Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling
    Qingwu Jin
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 70:4667-75. 2005
    ..e., overall anti electrophilic addition. The implications of these findings for the mechanism of the cyclization and rearrangement are discussed...
  8. ncbi request reprint Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes
    Yinghua Jin
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Am Chem Soc 127:7834-42. 2005
    ....
  9. ncbi request reprint Eremophilane sesquiterpenes from capsidiol
    Yuxin Zhao
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 69:7428-35. 2004
    ..The minimum inhibitory concentration for capsidiol (3-10 ng) was at least 1 order of magnitude lower than that of any of the derivatives and considerably lower than those previously reported for ketoconazole, nystatin, and propiconazole...
  10. ncbi request reprint Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol
    Marek Urbansky
    Department of Chemistry, University of Illinois at Urbana Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    Org Lett 6:135-8. 2004
    ..The new scheme offers a straightforward route to analogues and labeled forms...
  11. ncbi request reprint Total synthesis of (+/-)-cameroonan-7alpha-ol and biomimetic rearrangements to related nopsane sesquiterpenes
    Chad E Davis
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 68:6935-43. 2003
    ..The rearrangements observed afford chemical precedent for the biogenetic pathways in the literature for these silphinane sesquiterpenes...
  12. ncbi request reprint Regio- and stereoselectivity of diethylaluminum azide opening of trisubstituted epoxides and conversion of the 3 degrees azidohydrin adducts to isoprenoid aziridines
    Chad E Davis
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 68:75-82. 2003
    ..Six of the 3 degrees,2 degrees azidohydrins were converted to the corresponding aziridines by primary-selective silylations of four azido diols, mesylations, and reductive cyclizations with LiAlH(4)...
  13. ncbi request reprint Stereospecificity and kinetic mechanism of human prenylcysteine lyase, an unusual thioether oxidase
    Jennifer A Digits
    Department of Pharmacology and Cancer Biology, Duke University Medical Center, Durham, NC 27710, USA
    J Biol Chem 277:41086-93. 2002
    ..These results provide substantial new information on the catalytic mechanism of prenylcysteine lyase...
  14. ncbi request reprint Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis
    Mitchell L Wise
    Institute of Biological Chemistry, Washington State University, Pullman, Washington 99164, USA
    J Am Chem Soc 124:8546-7. 2002
    ....
  15. ncbi request reprint The dioxanone approach to (2S,3R)-2-C-methylerythritol 4-phosphate and 2,4-cyclodiphosphate, and various MEP analogues
    Chandraiah Lagisetti
    Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
    J Org Chem 72:9886-95. 2007
    ....

Research Grants29

  1. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 2001
    ..Specific prenyl transferase inhibitors would have significant biochemical applications in the study of regulatory and signal-transducing proteins, as well as potential in cancer chemotherapy. ..
  2. STRUCTURES OF ANTIBIOTICS AND RELATED COMPOUNDS
    Robert Coates; Fiscal Year: 2003
    ....
  3. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 1980
    ..A similar investigation is proposed for studying the stereochemistry of the methyl group oxidations in sterol biosynthesis...
  4. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 1992
    ..6. Determination of the stereochemistry and isotope effects of eliminations that terminate enzymatic cyclizations producing enantiomeric monoterpenes...
  5. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 1993
    ..The fundamental knowledge gained from this research will enhance our understanding of the specificities and catalytic mechanisms of important enzymes associated with the isoprenoid biosynthetic pathway...
  6. SPECIFICITY IN TERPENE AND STEROL BIOSYNTHESIS
    Robert Coates; Fiscal Year: 2006
    ..A new synthesis of deoxyxylulose pathway intermediates and inhibitors will afford access to useful mechanistic tools and compounds having significant potential for treatment of malaria and other parasitic diseases. ..