Some influences of fluorine in bioorganic chemistry

(Note: The full text of this document is currently only available in the PDF Version )

David O’Hagan and Henry S. Rzepa


Abstract

The stereochemical outcome on processing fluorinated substrate analogues by enzymes can often be controlled by electronic and stereoelectronic factors associated with the fluorine atom.


References

  1. A. Bondi, J. Phys. Chem., 1964, 68, 441 CrossRef CAS .
  2. A. Stabel, L. Dasaradhi, D. O'Hagan and J. P. Rabe, Langmuir, 1995, 11, 1427 CrossRef CAS .
  3. H. Booth, T. B. Grindley and K. A. Khedhair, J. Chem. Soc., Chem. Commun., 1982, 1047 RSC .
  4. A. Warshel and J. Aqvist, Annu. Rev. Biophys. Biophys. Chem., 1991, 20, 267 Search PubMed ; A. Warshel and M. Levitt, J. Mol. Biol., 1976, 103, 227 CAS .
  5. J. P. Guthrie and R. Kluger, J. Am. Chem. Soc., 1993, 115, 11 569 CrossRef CAS .
  6. T. C. Bruice, Annu. Rev. Biochem., 1976, 45, 331 CrossRef CAS .
  7. F. M. Menger, Acc. Chem. Res., 1993, 26, 206 CrossRef CAS .
  8. M. J. S. Dewar, Enzyme, 1986, 36, 8 Search PubMed .
  9. J. Mann, Chem. Soc. Rev., 1987, 16, 318 Search PubMed .
  10. C. Walsh, Tetrahedron, 1982, 38, 871 CrossRef CAS .
  11. C. Walsh, Adv. Enzymol., 1982, 55, 197 Search PubMed .
  12. S. E. Chambers, E. Y. Lau and J. T. Gerig, J. Am. Chem. Soc., 1994, 116, 3603 CrossRef CAS ; D. H. Gregory and J. T. Gerig, Biopolymers, 1991, 31, 845 CrossRef CAS .
  13. E. A. Wang and C. Walsh, Biochemistry, 1981, 20, 7539 CrossRef CAS .
  14. L. Dasaradhi, D. O'Hagan, M. C. Petty and C. Pearson, J. Chem. Soc., Perkin Trans. 2, 1995, 221 RSC .
  15. B. McDonough, P. M. Macdonald, B. D. Sykes and R. N. McElhaney, Biochemistry, 1983, 22, 5097 CrossRef CAS ; K. J. Longmuir, R. A. Capaldi and F. W. Dahlquist, Biochemistry, 1977, 16, 5746 CrossRef CAS .
  16. R. D. Chambers, D. O'Hagan, B. Lamont and S. C. Jain, J. Chem. Soc., Chem. Commun., 1990, 1053 RSC .
  17. B. E. SmartMolecular Structure and Energetics, VCH, 1986, vol. 3, p. 141 Search PubMed ; N. C. Baird, Can. J. Chem., 1983, 61, 1567 Search PubMed ; L. Radom and P. J. Styles, Tetrahedron Lett., 1975, 789 CAS .
  18. J. E. Mark and P. J. Florey, J. Am. Chem. Soc., 1965, 87, 1415 CrossRef CAS .
  19. R. E. Wolf, J. R. Hartmann, J. M. E. Storey, B. M. Foxman and S. R. Cooper, J. Am. Chem. Soc., 1987, 109, 4328 CrossRef CAS .
  20. G. Bott, L. D. Field and S. Sternhill, J. Am. Chem. Soc., 1980, 102, 5618 CrossRef CAS .
  21. D. Seebach, Angew Chem., Int. Ed. Engl., 1990, 29, 1320 CrossRef .
  22. H. S. Mosher, J. E. Stevenot and D. O. Kimble, J. Am. Chem. Soc., 1956, 78, 4374 CrossRef CAS .
  23. For an excellent overview see: P. V. Ramachandran, A. V. Teodorovic and H. C. Brown, Tetrahedron, 1993, 49, 1725 Search PubMed .
  24. B. E. Smart, Characteristics of C–F Systems, in Organofluorine Chemistry: Principals and Commercial Applications, ed. R. E. Banks, Plenum, New York, 1994 Search PubMed .
  25. D. A. Dixon and B. E. Smart, J. Phys. Chem., 1991, 95, 1609 CrossRef CAS ; D. A. Dixon and B. E. Smart, The Effect of Fluorination on Polyacetylene and the Role of Internal Hydrogen Bonds to Fluorine, in Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series, 456, ed. J. T. Welch, Washington DC, 1991 Search PubMed ; L. A. Curtiss, D. J. Frurip and M. Blander, J. Am. Chem., Soc., 1978, 100, 79 Search PubMed .
  26. J. A. K. Howard, V. J. Hoy, D. O'Hagan and G. T. Smith, Tetrahedron, 1996, 53, 12 613 CrossRef .
  27. A. Fersht, Enzyme Structure and Mechanism, W. H. Freeman and Co, New York, 2nd edn., 1984, p. 298 Search PubMed .
  28. H. Adams, K. D. M. Harris, G. A. Hembury, C. A. Hunter, D. Livingstone and J. F. McCabe, Chem. Commun., 1996, 2531 RSC .
  29. H. S. Rzepa, M. H. Smith and M. L. Webb, J. Chem. Soc., Perkin Trans 2, 1994, 703 RSC .
  30. C. S. Page and H. S. Rzepa, to be published .
  31. W. Cleland and M. Kreevoy, Science, 1994, 264, 1887 CrossRef CAS ; P. A. Frey, S. A. Whitt and J. B. Tobin, Science, 1994, 264, 1927 CrossRef CAS .
  32. A. Warshel, A. Papazyan and P. A. Kollman, Science, 1995, 269, 102 CrossRef CAS ; W. W. Cleland and M. Kreevoy, Science, 1995, 269, 104 ; P. A. Frey, Science, 1995, 269, 104 .
  33. J. P. Guthrie, Chem. Biol., 1996, 3, 163 CrossRef CAS .
  34. L. Shimoni and J. P. Glusker, Struct. Chem., 1994, 5, 383 CAS ; P. Murray-Rust, W. C. Stallings, C. T. Monti, K. R. Preston and J. P. Glusker, J. Am. Chem. Soc., 1983, 105, 3206 CrossRef CAS .
  35. J. D. McCarter, M. J. Adam and S. G. Withers, Biochem. J., 1992, 286, 721 CAS .
  36. R. Engel, Chem. Rev., 1977, 77, 349 CrossRef CAS .
  37. G. M. Blackburn, D. L. Jakeman, A. J. Ivory and M. P. Williamson, Bioorg. Med. Chem. Lett., 1994, 4, 2573 CrossRef CAS ; G. M. Blackburn, D. E. Kent and F. Kolkmann, J. Chem. Soc., Perkin Trans. 1, 1984, 1119 RSC ; G. M. Blackburn, Chem. Ind. (London), 1981, 134 CAS .
  38. J. Nieschalk, A. S. Batsanov, D. O'Hagan and J. A. K. Howard, Tetrahedron, 1996, 52, 165 CrossRef CAS .
  39. G. R. J. Thatcher and A. S. Campbell, J. Org. Chem., 1993, 58, 2272 CrossRef CAS .
  40. P. Camilleri, A. J. Edwards, H. S. Rzepa and S. M. Green, J. Chem. Soc., Chem. Commun., 1992, 1122 RSC .
  41. J. Nieschalk and C. O'Hagan, J. Chem. Soc., Chem. Commun., 1995, 719 RSC .
  42. P. R. Adams and R. Harrison, Biochem. J., 1974, 141, 729 CAS ; P.-J. Cheng, R. Hickey, R. Engel and B. E. Tropp, Biochem. Biophys. Acta, 1974, 341, 85 Search PubMed .
  43. T. R. Burke, M. S. Smith, A. Otaka, M. Nomizu, P. R. Roller, G. Wolf, R. Case and S. E. Shoelson, Biochemistry, 1994, 33, 6490 CrossRef CAS .
  44. K. Faber, Biotransformations in Organic Chemistry, Springer, 2nd edn., 1995 Search PubMed ; Preparative Biotransformations; Whole Cell and Isolated Enzymes in Organic Synthesis, ed. S. M. Roberts, Wiley, Chichester, 1993 Search PubMed .
  45. L. Provencher, H. Wynn, J. B. Jones and A. R. Krawczyk, Tetrahedron: Asymmetry, 1993, 4, 2025 CrossRef CAS .
  46. C.-S. Chen and C. J. Sih, Angew. Chem., Int. Ed. Engl., 1989, 28, 695 CrossRef .
  47. J. T. Lin, T. Yamazaki and T. Kitazume, J. Org. Chem., 1987, 52, 3211 CrossRef CAS .
  48. H. S. Rzepa, M. L. Webb, A. M. Z. Slawin and D. J. Williams, J. Chem. Soc., Chem. Commun., 1991, 766 Search PubMed .
  49. O. Casher, D. O'Hagan, C. A. Rosenkranz, H. S. Rzepa and N. A. Zaidi, J. Chem. Soc., Chem. Commun., 1993, 1337 RSC .
  50. A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer Verlag, Berlin, 1983 Search PubMed .
  51. H. Senderowitz, P. Aped and B. Fuchs, Tetrahedron, 1993, 49, 3879 CrossRef CAS .
  52. G. A. Geffrey and J. H. Yates, J. Am. Chem. Soc., 1979, 101, 820 CrossRef .
  53. M. Hayashi and H. Kato, Bull. Chem. Soc. Jpn., 1980, 53, 2701 CAS .
  54. J. J. Irwin, T.-K. Ha and J. Dunitz, Helv. Chim. Acta., 1990, 73, 1805 CrossRef CAS .
  55. N. T. Anh and O. Eisenstein, Nouv. J. Chim., 1977, 1, 61 .
  56. S. S. Wong and M. N. Paddon-Row, J. Chem. Soc., Chem. Commun., 1990, 456 RSC .
  57. P. Kalaritis, R. W. Regenye, J. J. Partridge and D. L. Coffin, J. Org. Chem., 1990, 55, 812 CrossRef CAS .
  58. T. Kitazume, K. Murata and T. Ikeya, J. Fluorine Chem., 1986, 31, 143 CrossRef CAS .
  59. D. O'Hagan and H. S. Rzepa, J. Chem. Soc., Perkin Trans. 2, 1994, 3 RSC .
  60. C. F. Bridge, D. O'Hagan, K. A. Reynolds and K. K. Wallace, J. Chem. Soc., Chem. Commun., 1995, 2329 RSC .
  61. K. A. Reynolds, P. Wang, K. M. Fox, M. K. Speedie, Y. Lam and H. G. Floss, J. Bacteriol., 1992, 14, 3850 .
  62. S. Wolfe, Acc. Chem. Res., 1972, 5, 102 CrossRef CAS .
  63. R. D. Amos, N. C. Handy, P. G. Jones, A. J. Kirby, J. K. Parker, J. M. Percy and M. D. Su, J. Chem. Soc., Perkin Trans. 2, 1992, 549 RSC .
  64. N. C. Craig, L. G. Piper and V. L. Wheeler, J. Phys. Chem., 1971, 75, 1453 CrossRef CAS ; N. C. Craig and E. A. Entemann, J. Am. Chem. Soc., 1961, 83, 3047 CrossRef CAS .
  65. N. D. Epiotis, W. R. Cherry, S. Shaik, R. L. Yates and F. Bernardi, Top. Curr. Chem., 1977, 70, 1 Search PubMed .
  66. R. C. Bingham, J. Am. Chem. Soc., 1976, 98, 535 CrossRef CAS .
  67. For a good discussion, see: E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, 1994 Search PubMed .
  68. D. W. Fanshier, L. K. Gottwald and E. Kun, J. Biol. Chem., 1964, 239, 425 CAS .
  69. D. B. Harper and D. O'Hagan, Nat. Prod. Rep., 1994, 11, 123 RSC .
  70. R. Keck, H. Haas and J. Retey, FEBS Lett., 1980, 114, 287 CrossRef CAS .
  71. M. A. Marletta, P. A. Srere and C. Walsh, Biochemistry, 1981, 20, 3719 CrossRef CAS .
  72. D. O'Hagan and H. S. Rzepa, J. Chem. Soc., Chem. Commun., 1994, 2029 RSC .
  73. M. Karpusas, D. Holland and S. J. Remington, Biochemistry, 1991, 30, 6024 CrossRef CAS .
  74. M. Karpusas, B. Branchaud and S. J. Remington, Biochemistry, 1990, 29, 2213 CrossRef CAS .
  75. K. C. Usher, S. J. Remington, D. P. Martin and D. G. Drueckhammer, Biochemistry, 1994, 33, 7753 CrossRef CAS ; D. P. Martin, R. T. Bibart and D. G. Drueckhammer, J. Am. Chem. Soc., 1994, 116, 4660 CrossRef CAS .
  76. M. Gautschi and D. Seebach, Angew. Chem., Int. Ed. Engl., 1992, 31, 1083 CrossRef .
Click here to see how this site uses Cookies. View our privacy policy here.