The Cyclopropyl Group in Studies of Enzyme-Catalysed Reactions

  • C. J. Suckling
Part of the NATO ASI Series book series (ASIC, volume 273)

Abstract

The cyclopropylcarbinyl radical ring opening reaction has been applied to investigate the mechanism of many enzyme-catalysed reactions especially oxidation-reduction reactions. The advantages and limitations of this approach reflect a balance between accessibility of cyclopropane-containing substrates to enzymes and the intrinsic reactivity of substituted cyclopropylcarbinyl radicals. When both factors are taken into account, penetrating insights into the mechanisms of enzyme-catalysed reactions can be obtained by studies of the products of enzyme-catalysed reactions on cyclopropane- containing substrates.

Keywords

Ring Opening Probe Molecule Radical Mechanism Glyoxylic Acid Pyridinium Salt 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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REFERENCES

  1. 1.
    M.I. Page in ‘Enzyme Mechanisms’, eds. M.I. Page and A. Williams, Royal Society of Chemistry, London, 1987, p.l.Google Scholar
  2. 2.
    C.J. Suckling, Chem. Soc. Reviews, 1984, 13, 97.CrossRefGoogle Scholar
  3. 3.
    Y. Kanaoka, Angew. Chem. Int. Edn. Engl., 1977, 16, 137.CrossRefGoogle Scholar
  4. 4.
    H.M. McConnell and B.G. McFarland, Quart. Rev. Biophys., 1970, 3, 91.CrossRefGoogle Scholar
  5. 5.
    T.C. Liang and R.H. Abeles, Biochemistry, 1987, 26, 7603.CrossRefGoogle Scholar
  6. 6.
    K.F. Geoghan, A. Galdes, R.A. Martinelli, B. Holmquist, D.S. Auld, and B.L. Vallee, Biochemistry, 1983, 22, 2255; J.P.G. Malthouse, M.P. Gamscik, A.S.F. Boyd, N.E. Mackenzie, and A.I. Scott, J. Am. Chem. Soc., 1982, 104, 6811.Google Scholar
  7. 7.
    C.J. Suckling, Angew. Chem. Int. Edn. Engl., 1988, 27, 537.CrossRefGoogle Scholar
  8. 8.
    B. Maillard, D. Forrest, and K.V. Ingold, J. Am. Chem. Soc., 1976, 98, 7024.CrossRefGoogle Scholar
  9. 9.
    V.C. Emery and M. Akhtar in ‘Enzyme Mechanisms’, eds. M.I. Page and A. Williams, Royal Society of Chemistry, London, 1987, p.345; P. Haake, ibid., p.390.Google Scholar
  10. 10.
    W.G. Dauben, L. Schutte, R.E. Wolf, and E.J. Deviny, J. Org. Chem., 1969, 34, 2512; W.G. Dauben and R.E. Wolf, ibid., 1970, 35, 374.CrossRefGoogle Scholar
  11. 11 a.
    D.C. Nonhebel, C.J. Suckling, and J.C. Walton, Tetrahedron Lett., 1982, 23, 4477CrossRefGoogle Scholar
  12. 11 b.
    X.-Z. Quin and F. Williams, J. Am. Chem. Soc., 1987, 109, 595CrossRefGoogle Scholar
  13. 11 c.
    D. Laurie, E. Lucas, D.C. Nonhebel, C.J. Suckling, and J.C. Walton, Tetrahedron, 1986, 42, 1035CrossRefGoogle Scholar
  14. 11 d.
    C. Jamieson, J.C. Walton, and K.U. Ingold, J. Chem. Soc., Perkin Trans. 2, 1980, 1366Google Scholar
  15. 11 e.
    A.J. Castellino and T.C. Bruice, J. Am. Chem. Soc., 1988, 110, 1313.CrossRefGoogle Scholar
  16. 12.
    D.C. Nonhebel, S.T. Orszulik, and C.J. Suckling, J. Chem. Soc., Chem. Commun., 1982, 1146.Google Scholar
  17. 13.
    A. Effio, D. Griller, K.U. Ingold, A.L.J. Beckwith, and A.K. Serelis, J. Am. Chem. Soc., 1980, 102, 1734.CrossRefGoogle Scholar
  18. 14.
    S.K. Chung and S.U. Park, J. Org. Chem., 1982, 47, 3197.CrossRefGoogle Scholar
  19. 15.
    A.L.J. Beckwith, C.J. Easton, T. Lawrence, and A.K. Serelis, Aust. J. Chem., 1983, 36, 545; C. Chatgilialoglu, K.U. Ingold, and J.C. Scaiano, J. Am. Chem. Soc., 1981, 103, 7739.Google Scholar
  20. 16.
    J.T. Groves, W.J. Kruper Jr., and R.C. Haushalter, J. Am. Chem., Soc., 1980, 102, 6375.CrossRefGoogle Scholar
  21. 17.
    D.A. Tanner and A.R. Stein, J. Org. Chem., 1988, 53, 1642.CrossRefGoogle Scholar
  22. 18.
    R.P. Hanzlik and R.H. Tullman, J. Am. Chem. Soc., 1982, 104, 2048; T.L. MacDonald, K. Zirvi, L.T. Burka, P. Peyman, and F.P. Guengerich, ibid., 2050.Google Scholar
  23. 19.
    J.T. Groves and D.V. Subramanian, J. Am. Chem. Soc., 1984, 106, 2177.CrossRefGoogle Scholar
  24. 20.
    F.P.Guengerich and T.L. MacDonald, Accts. Chem. Res., 1984, 17, 9.CrossRefGoogle Scholar
  25. 21.
    L. Brown, W.J.S. Lyall, C.J. Suckling, and K.E. Suckling, J. Chem. Soc., Perkin Trans. 1., 1987, 595; D.J. Houghton, S.E. Beddows, K.E. Suckling, L. Brown, and C.J. Suckling, Tetrahedron Lett., 1986, 27, 4655.Google Scholar
  26. 22.
    P.R. Ortiz de Monellano and R.A. Stearns, J. Am. Chem. Soc., 1987, 109, 3415.CrossRefGoogle Scholar
  27. 23.
    K.E. Suckling, C.G. Smellie, I.E. Ibrahim, D.C. Nonhebel, and C.J. Suckling, FEBS Letters, 1982, 145, 179; C.J. Suckling, D.C. Nonhebel, L. Brown, K.E. Suckling, S. Seilman, and C.R. Wolf, Biochem. J., 1985, 232, 199.Google Scholar
  28. 24.
    R.A. Stearns and P.R. Ortiz de Montellano, J. Am. Chem. Soc., 1985, 107, 4081.CrossRefGoogle Scholar
  29. 25.
    H. Dalton, B.T. Golding, B.W. Waters, R. Higgins, and J.A. Taylor, J. Chem. Soc., Chem. Commun., 1981, 482.Google Scholar
  30. 26.
    P.F. Fitzpatrick and J.J. Villafranca, J. Am. Chem. Soc., 107, 5022.Google Scholar
  31. 27.
    J.W. Frost, S. Low, M.L. Cordeiro, and D. Li, J. Am. Chem. Soc., 1987, 109, 2166.CrossRefGoogle Scholar
  32. 28 a.
    E.J. Corey and R. Nagata, Tetrahedron Lett., 1987, 28, 5391CrossRefGoogle Scholar
  33. 28. b.
    E.J. Corey and R. Nagata, J. Am. Chem. Soc., 1988 submitted.Google Scholar
  34. 29.
    G.A. Hamilton, Prog. Bioorg. Chem., 1971, 1, 113.Google Scholar
  35. 30.
    S. Shinkai, H. Era, T. Tsuno, and O. Manabe, Bull. Chem. Soc. Jpn., 1984, 57, 1435; A. Shirra and C.J. Suckling, Tetrahedron Lett., 1975, 3323.Google Scholar
  36. 31.
    S. Shinkai in ‘Enzyme Chemistry, Impact and Applications’, ed. C.J. Suckling, Chapman & Hall, London, 1984, p.46.Google Scholar
  37. 32.
    L.H.P. Meyer, J.C.G. van Niel, and U.K. Pandit, Tetrahedron, 1984, 40, 5185.CrossRefGoogle Scholar
  38. 33.
    I. Maclnnes, D.C. Nonhebel, S.T. Orszulik, and C.J. Suckling, J. Chem. Soc., Perkin Trans. 1, 1982, 1146.Google Scholar
  39. 34.
    R.J. Breckenridge and C.J. Suckling, Tetrahedron, 1986, 42, 5665.CrossRefGoogle Scholar
  40. 35.
    D.A. Tanner and A. Kharrat, J. Org. Chem., 1988, 53, 1646.CrossRefGoogle Scholar
  41. 36.
    S. Fukuzumi, N.Nishizawa, and T. Tanaka, J. Org. Chem., 1984, 49, 3571; M.F. Powell and T.C. Bruice, J. Am. Chem. Soc., 1983, 105, 1014; A. Sinha and T.C. Bruice, ibid., 1984, 106, 7291; J.W. Bunting and N.P. Fitzgerald, Canad. J. Chem., 1985, 65, 655.Google Scholar
  42. 37.
    D.J. Livingston, S.L. Shanes, R. Gerris, and C.T. Walsh, Bioorg. Chem., 1987, 15, 358.CrossRefGoogle Scholar
  43. 38.
    L. Kerscher and D. Osterhelt, Eur. J. Biochem., 1981, 116, 595, TIBS, 1982, 7, 374.CrossRefGoogle Scholar
  44. 39.
    R.B. Silverman in ‘Topics in Medicinal Chemistry’, ed. P.J. Leeming, Royal Society of Chemistry, London, 1988, p.73.Google Scholar
  45. 40.
    R.B. Silverman and R.B. Yamasaki, Biochemistry, 1984, 23, 1822.Google Scholar
  46. 41.
    R.B. Silverman and P.A. Zieske, Biochemistry, 1985, 24, 2128.CrossRefGoogle Scholar
  47. 42.
    R.B. Silverman and P.A. Zieske, Biochem. Biophys. Res. Commun., 1986, 135, 154.CrossRefGoogle Scholar
  48. 43.
    M. Dijkstra, J. Frank Jzn., J.A. Jongenjan, and J.A. Duine, Eur. J. Biochem., 1984, 140, 369.CrossRefGoogle Scholar
  49. 44.
    T. Mincey, J.A. Bell, A.S. Mildvan, and R.H. Abeles, Biochemistry, 1981, 20, 7502; C. Parkes and R.H. Abeles, ibid., 1984, 23, 6355.Google Scholar
  50. 45.
    J.A. Duine personal communication.Google Scholar
  51. 46.
    B. Sherry and R.H. Abeles, Biochemistry, 1985, 24, 2595.CrossRefGoogle Scholar
  52. 47.
    A. Thibblin and W.P. Jencks, J. Am. Chem. Soc., 1979, 101, 4963.CrossRefGoogle Scholar
  53. 48.
    J.S. Wiseman, J.S. Nichols, and M. Kolpak, J. Biol. Chem., 1982, 257, 6328.Google Scholar
  54. 49.
    R.M. Adlington, J.E. Baldwin, and B.J. Rawlings, J. Chem. Soc., Chem. Commun., 1983, 290; G.D. Reiser, F.-J. Wang, N.E. Hoffmann, S.F. Yang, H.W. Liu, and C.J. Walsh, Proc. Natl. Acad. Sci. USA., 1984, 81, 3059.Google Scholar
  55. 50.
    M.C. Pirrung and G.M. McGeechan, J. Org. Chem.. 1983, 48, 5143.CrossRefGoogle Scholar
  56. 51.
    M.C. Pirrung, J. Am. Chem. Soc., 1983, 105, 7207; M.C. Pirrung and G.M. McGeechan, Angew. Chem. Int. Edn. Engl.. 1985, 24, 1044.Google Scholar
  57. 52.
    B.C. Gilbert, J.P. Larkin, and R.O.C. Norman, J. Chem. Soc., Per kin Trans. 1, 1972, 794.CrossRefGoogle Scholar
  58. 53.
    R.M. Dixon, B.T. Golding, S. Mwesigyne-Kibende, and D.C. Ramakrishna Rao, Phil. Trans. Roy. Soc. London Ser. B, 1985, 311, 531.CrossRefGoogle Scholar
  59. 54.
    J.E. Baldwin, R.M. Adlington, M.J.C. Crabbe, T. Homoto, and C.J. Schofield, Tetrahedron, 1987, 43, 4217.CrossRefGoogle Scholar
  60. 55.
    J.E. Baldwin, R.M. Adlington, B.P. Domayne-Hayman, G. Knight, and H.-H. Ting, J. Chem. Soc., Chem. Commun., 1987, 1161.Google Scholar
  61. 56.
    ‘Molecular actions and targets for cancer chemotherapeutic agents’, eds. A.C. Sartorelli, E. Lazo, J.R. Bertino, Bristol Meyers Cancer Symposium Series, Academic Press, New York, 1981.Google Scholar
  62. 57.
    D.E. Hathaway, ‘Molecular Aspects of Toxicology’, Royal Society of Chemistry, London, 1984, p.204.Google Scholar
  63. 58.
    D. Reichert, Angew. Chem. Int. Edn. Engl., 1981, 20, 135.CrossRefGoogle Scholar
  64. 59.
    for example, R.M. Pollack, R.H. Kayser, and C.L. Bevins, Biochem. Biophys. Res. Commun., 1979, 91, 783; J.M. Penning, Biochem. J., 1985, 226, 469.Google Scholar
  65. 60.
    R.A. Stearns and P.R. Ortiz de Montellano, J. Am. Chem. Soc., 1985, 107, 234.CrossRefGoogle Scholar
  66. 61.
    R.B. Silverman and P.A. Zieske, Biochemistry. 1985, 25, 341.CrossRefGoogle Scholar
  67. 62.
    H. Nakamura, S. Hasegawa, N. Shimada, A. Fujii, T. Takita, and Y. Iitaka, J. Antibiot., 1986, 39, 1626; S. Omura, M. Murata, N. Imamura, Y. Iwai, and H. Tanaka, J. Antibiot., 1984, 37, 1324.Google Scholar
  68. 63.
    C.J. Suckling, Proceedings of 10th International Symposium on Medicinal Chemistry, Budapest, 1988, in press.Google Scholar

Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • C. J. Suckling
    • 1
  1. 1.Department of Pure and Applied ChemistryUniversity of StrathclydeGlasgowScotland, UK

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