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Research on the correlation between the Pummerer reaction and penicillin biosynthesis (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Research on the correlation between the Pummerer reaction mechanism and β-lactam formation during penicillin biosynthesis is discussed based on our silicon-induced asymmetric Pummerer type reaction.

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References

  1. P. L. Roach, I. J. Clifton, C. M. H. Hensgens, N. Shibata, C. J. Schofield, J. Hajdu, and J. E. Baldwin, Nature (London),387 (June), 827 (1997).

    Google Scholar 

  2. P. L. Roach, I. J. Clifton, C. M. H. Hensgens, N. Shibata, A. J. Long, R. W. Strange, S. S. Hasnain, C. J. Schofield, J. E. Baldwin, and J. Hajdu, Eur. J. Biochem.,242, 736 (1996).

    Google Scholar 

  3. P. L. Roach, I. J. Clifton, V. Fulop, K. Harlos, G. J. Barton, J. Hajdu, I. Andersson, C. J. Schofield, and J. E. Baldwin, Nature (London),375 (June), 700 (1995).

    Google Scholar 

  4. N. Shibata, Chemistry Today (Gendai Kagaku), No. 324, 23 (1998).

    Google Scholar 

  5. Y. Kita and N. Shibata, Synlett., 289 (1996).

  6. Y. Kita, and N. Shibata, Yuki Gosei Kagaku Kyokai-Shi,52, 746 (1994).

    Google Scholar 

  7. Y. Kita, Phosphorus, Sulfur, Silicon,120 &121 145 (1997).

    Google Scholar 

  8. S. W. Queener and N. Neuss, in: Chemistry and Biology of β-Lactam Antibiotics, R. B. Morin and M. Gorman (eds.), Academic Press, New York (1982), pp. 22–81.

    Google Scholar 

  9. D. J. Aberhart, Tetrahedron,33, 1545 (1977).

    Google Scholar 

  10. O. K. Behrens, J. Corse, J. P. Edwards L. Garrison, R. G. Jones, Q. P. Soper, F. R. van Abeele, and C. W. Whotehead, J. Biol. Chem.,175, 793 (1948).

    Google Scholar 

  11. J. E. Baldwin, J. Heterocyclic Chem.,27, 71 (1990).

    Google Scholar 

  12. J. E. Baldwin and M. Bradley, Chem. Rev.,90, 1079 (1990).

    Google Scholar 

  13. J. E. Baldwin and Sir E. Abraham, Natural Product Reports, 129 (1988).

  14. J. E. Baldwin, R. M. Adlington, S. E. Moroney, L. D. Field, and J.-H. Ting, J. Chem. Soc. Chem. Commun., 984 (1984).

  15. J. E. Baldwin, R. M. Adlington, and R. Bohlmann, J. Chem. Soc. Chem. Commun., 357 (1985).

  16. S. Wolfe, R. J. Bowers, S. K. Hasan, and P. M. Kazmaier, Can. J. Chem.,59, 406 (1981).

    Google Scholar 

  17. G. Bahadur, J. E. Baldwin, T. Wan, and M. J. Jung, Chem. Soc. Chem. Commun., 1146 (1981).

  18. A. J. Birch and H. Smith, in: Amino Acids and Peptides with Antimetabolic Activity (Chiba Foundation Symposium), G. E. W. Wolstenholme and C. M. O'Conner (eds.), Churchill, London (1958), pp. 243–263.

    Google Scholar 

  19. A. I. Scott, S. E. Yoo, S.-K. Chung, and J. A. Lacadie, Tetrahedron Lett., 1137 (1976).

  20. R. L. Baxter, G. A. Thomson, and A. I. Scott, J. Chem. Soc., Chem. Commun., 32 (1984).

  21. H. R. V. Arnstein and J. C. Crawhall, Biochem. J.,67, 180 (1957).

    Google Scholar 

  22. T. Numata and S. Oae, Yuki Gosei, Kagaku Kyokai-Shi.,35, 726 (1977).

    Google Scholar 

  23. T. Numata, Yuki Gosei Kagaku Kyokai-Shi.,36, 845 (1978).

    Google Scholar 

  24. S. Oae and T. Numata, Isot. Org. Chem.,5, 45 (1980).

    Google Scholar 

  25. S. Oae, T. Numata, and T. Yoshimura, in: The Chemistry of the Sulphonium Group, C. J. M. Stirling and S. Patai (eds.), John Wiley, New York (1981), p. 571.

    Google Scholar 

  26. O. D. Lucchi, U. Miotti, and G. Modena, Organic Reactions,40, 157 (1991).

    Google Scholar 

  27. D. S. Grierson and H.-P. Husson, in: Comprehensive Organic Synthesis, Vol. 6, B. M. Trost and I. Fleming (eds), Pergamon Press, Oxford (1991), p. 910.

    Google Scholar 

  28. R. Pummerer, Chem. Ber.,42, 2282 (1909).

    Google Scholar 

  29. idem,43, 1401 (1910).

    Google Scholar 

  30. Y. Kita, H. Yasuda, O. Tamura, F. Itoh, and Y. Tamura, Tetrahedron Lett.,25, 4681 (1984).

    Google Scholar 

  31. idem,35, 562 (1987).

    Google Scholar 

  32. N. J. Leonard and R. Y. J. Ning, Org. Chem.,32, 677 (1967).

    Google Scholar 

  33. R. D. G. Cooper, J. Am. Chem. Soc.,94, 1018 (1972).

    Google Scholar 

  34. R. B. Morin, E. M. Gordon, T. McGrath, and R. Shuman, Tetrahedron Lett., 2159 (1973).

  35. R. B. Morin, E. M. Gordon, and J. R. Lake, Tetrahedron Lett., 5213 (1973).

  36. J. E. Baldwin, S. B. Haber, and J. J. Kitchin, Chem. Soc. Chem. Commun., 790 (1973).

  37. J. Cheney, C. J. Moores, J. A. Raleigh, A. I. Scott, and D. W. Young, J. Chem. Soc. Chem. Commun., 47 (1974).

  38. J. Cheney, C. J. Moores, J. A. Raleigh, A. I. Scott, and D. W. Young, J. Chem. Soc. Perkin Trans. I, 986 (1974).

  39. S. Nakatsuka, H. Tanio, and Y. Kishi, J. Am. Chem. Soc.,97, 5008, 5010 (1975).

    Google Scholar 

  40. J. E. Baldwin, A. Au, M. Christie, S. B. Haber, and D. Hesson, J. Am. Chem. Soc.,97, 5957 (1975).

    Google Scholar 

  41. J. E. Baldwin, M. Christie, S. B. Haber, and L. I. Kruse, J. Am. Chem. Soc.,98, 3045 (1976).

    Google Scholar 

  42. J. E. Baldwin and M. Jung, J. Chem. Soc. Chem. Commun., 609 (1978).

  43. A. L. J. Beckwith and C. J. Easton, Tetrahedron,39, 3995 (1983).

    Google Scholar 

  44. N. Shibata, J. E. Baldwin, and M. E. Wood, Bioorgan. & Med. Chem. Lett.,7, 413 (1997).

    Google Scholar 

  45. N. Shibata, J. E. Baldwin, A. Jacobs, and M. E. Wood, Tetrahedron,52, 12839 (1996).

    Google Scholar 

  46. N. Shibata, J. E. Baldwin, A. Jacobs, and M. E. Wood, Synlett., 519 (1996).

  47. S. Wolfe, P. M. Kazmaier, and H. Auksi, Can. J. Chem.,57, 2417 (1979).

    Google Scholar 

  48. S. Wolfe, R. J. Bowers, S. K. Hasan, and P. M. Kazmaier, ibid.,59, 406 (1981).

    Google Scholar 

  49. T. Kaneko, J. Am. Chem. Soc.,107, 5409 (1985).

    Google Scholar 

  50. T. Kaneko, Y. Okamoto, and K. Hatada, J. Chem. Soc. Chem., Commun., 1511 (1987).

  51. Y. Kita, O. Tamura, and Y. Tamura, Yuki Gosei Kagaku Kyokai-Shi,44, 1118 (1986).

    Google Scholar 

  52. Y. Kita, Yakugaku Zasshi.,106, 269 (1986).

    Google Scholar 

  53. Y. Kita, J. Haruta, T. Fujii, J. Segawa, and Y. Tamura, Synthesis, 451 (1981).

  54. Y. Kita, J. Haruta, J. Segawa, and Y. Tamura, Tetrahedron Lett., 4311 (1979).

  55. Y. Kita, O. Tamura, T. Miki, and Y. Tamura, Tetrahedron Lett.,28, 6479 (1987).

    Google Scholar 

  56. Y. Kita, O. Tamura, N. Shibata, and T. Miki, chem. Pharm. Bull.,38, 1473 (1990).

    Google Scholar 

  57. Y. Kita, O. Tamura, N. Shibata, and T. Miki, J. Chem. Soc. Perkin Trans. I, 1862 (1989).

    Google Scholar 

  58. Y. Kita, N. Shibata, O. Tamura, and T. Miki, Chem. Pharm. Bull.,39, 2225 (1991).

    Google Scholar 

  59. Y. Kita, N. Shibata, T. Miki, Y. Takemura, and O. Tamura, J. Chem. Soc. Chem. Commun., 727 (1990).

  60. idem, Chem. Pharm. Bull.,40, 12 (1992).

    Google Scholar 

  61. Y. Kita, O. Tamura, T. Miki, H. Tono, N. Shibata, and Y. Tamura, Tetrahedron Lett.,30, 729 (1989).

    Google Scholar 

  62. Y. Kita, N. Shibata, N. Kawano, T. Tohjo, C. Fujimori, and H. Ohishi, J. Am. Chem. Soc.,116, 5116 (1994).

    Google Scholar 

  63. Y. Kita, N. Shibata, N. Kawano, T. Tohjo, and K. Matsumoto, Tetrahedron Lett.,36, 115 (1995).

    Google Scholar 

  64. J. E. Baldwin, A. L. J. Becwith, A. P. Davis, G. Procter, and K. A. Singleton, Tetrahedron,37, 2181 (1981).

    Google Scholar 

  65. C. J. Easton, J. Chem. Soc. Chem. Commun., 1349 (1983).

  66. S. Wolfe and P. M. Kazmaier, Can. J. Chem.,57, 2388 2397 (1979).

    Google Scholar 

  67. Y. Kita, N. Shibata, N. Yoshida, S. Fukui, and C. Fujimori, Tetrahedron Lett.,35, 2569 (1994).

    Google Scholar 

  68. Y. Kita, N. Shibata, N. Yoshida, S. Fukui, N. Kawano, C. Fujimori, N. Yoshikawa, and S. Fujita, J. Chem. Soc. Perkin Trans. I, 3335 (1994).

    Google Scholar 

  69. Y. Kita, N. Shibata, and N. Yoshida, Tetrahedron Lett.,34, 4063 (1993).

    Google Scholar 

  70. Y. Kita, N. Shibata, S. Fukui, and S. Fujita, Tetrahedron Lett.,35, 9733 (1994).

    Google Scholar 

  71. Y. Kita, N. Shibata, N. Yoshida, and S. Fujita, J. Chem. Soc. Perkin Trans. I, 3335 (1994).

    Google Scholar 

  72. Y. Kita, N. Shibata, N. Kawano, S. Fukui, and C. Fujimori, Tetrahedron Lett.,35, 3575 (1994).

    Google Scholar 

  73. C. J. Rowe, C. P. Shorrock, T. DW. Claridge, and J. D. Sutherland, Chemistry & Biology,5, 229 (1998).

    Google Scholar 

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Authors
  1. Norio Shibata
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  2. Yasuyuki Kita
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Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, Toyama 930-0194, Japan. Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871, Japan. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1463–1474, November, 1998.

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Shibata, N., Kita, Y. Research on the correlation between the Pummerer reaction and penicillin biosynthesis (review). Chem Heterocycl Compd 34, 1237–1248 (1998). https://doi.org/10.1007/BF02256804

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  • DOI: https://doi.org/10.1007/BF02256804

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