The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants†

Abstract

References

1. J. D. Connolly and R. A. Hill, in Dictionary of Terpenoids, Chapman and Hall, New York, 1992.
2. S. L. Spurgeon and J. W. Porter, in Biosynthesis of Isoprenoid Compounds, ed. J. W. Porter and S. L. Spurgeon, John Wiley and Sons, New York, 1981, vol. 1, p. 1, and references cited therein.
3. N. Qureshi and J. W. Porter, in Biosynthesis of Isoprenoid Compounds, ed. J. W. Porter and S. L. Spurgeon, John Wiley and Sons, New York, 1981, vol. 1, p. 47, and references cited therein.
4. H. Kleinig, Annu. Rev. Plant Physiol., 1989, 40, 39.
5. J. Chappel, Annu. Rev. Plant Physiol., 1995, 46, 521.
6. T. J. Bach, Lipids, 1995, 30, 191.
7. H. K. Lichtenthaler, M. Rohmer and J. Schwender, Plant Physiol., 1998, 101, 643.
8. K. J. Treharne, E. I. Mercer and T. W. Goodwin, Biochem. J, 1966, 99, 239.
9. D. V. Banthorpe, B. V. Charlwood and M. J. O. Francis, Chem. Rev., 1972, 72, 115.
10. T. J. Bach and H. K. Lichtenthaler, in Ecology and Metabolism of Plant Lipids, ed. G. Fuller and W. D. Nes, Am. Chem. Soc. Symp. Series, 1987, 325, American Chemical Society, Washington DC, p. 109.
11. T. J. Bach, A. Motel and T. Weber, Rec. Adv. Phytochem., 1990, 24, 1.
12. K. Kreuz and H. Kleinig, Planta, 1981, 153, 578.
13. K. Kreuz and H. Kleinig, Eur. J. Biochem., 1984, 141, 531.
14. F. Lütke-Brinkhaus and H. Kleinig, Planta, 1987, 171, 406.
15. M. Rohmer, P. Bouvier-Navé and G. Ourisson, J. Gen. Microbiol., 1984, 130, 1137.
16. M. Rohmer, Pure Appl. Chem., 1993, 65, 1293.
17. G. Ourisson and M. Rohmer, Acc. Chem. Res., 1992, 25, 403 and references cited therein.
18. K. Poralla, T. Härtner and E. Kannenberg, FEMS Microbiol. Lett., 1984, 23, 253.
19. M. A. F. Hermans, B. Neuss and H. Sahm, J. Bacteriol., 1991, 173, 5592.
20. G. Kleemann, G. Alskog, A. M. Berry and K. Huss-Danell, Protoplasma, 1994, 183, 107.
21. E. L. Kannenberg, M. Perzl and T. Härtner, FEMS Microbiol. Lett., 1995, 127, 255.
22. G. Flesch and M. Rohmer, Eur. J. Biochem., 1988, 175, 405.
23. M. Rohmer, B. Sutter and H. Sahm, J. Chem. Soc., Chem. Commun., 1989, 1471.
24. M. Rohmer, M. Knani, P. Simonin, B. Sutter and H. Sahm, Biochem. J., 1993, 295, 517.
25. M. Rohmer, in Comprehensive Natural Product Chemistry, ed. D. E. Cane, Pergamon, Oxford, UK, 1999, vol. 2, ch. 3, p. 45, and references cited therein.
26. G. A. Sprenger, FEMS Microbiol. Lett., 1996, 145, 301.
27. S. Horbach, H. Sahm and R. Welle, FEMS Microbiol. Lett., 1993, 111, 135.
28. M. Rohmer, M. Seemann, S. Horbach, S. Bringer-Meyer and H. Sahm, J. Am. Chem. Soc., 1996, 118, 2564.
29. M. K. Schwarz, Ph D Thesis, Nb ETH 10951, Eidgenössische Technische Hochschule, Zürich, Switzerland, 1994, and references cited therein.
30. S. T. J. Broers, Ph D Thesis Nb 10978, Eidgenössische Technische Hochschule, Zürich, Switzerland, 1994.
31. D. Zhou and R. H. White, Biochem. J., 1991, 273, 627.
32. A. Yokota and K. I. Sasajima, Agric. Biol. Chem., 1984, 48, 149.
33. A. Yokota and K. I. Sasajima, Agric. Biol. Chem., 1986, 50, 2517.
34. S. David, B. Estramareix, J.-C. Fischer and M. C. Thérisod, J. Am. Chem. Soc., 1981, 103, 7351.
35. K. Himmeldirk, B. G. Sayer and I. D. Spenser, J. Am. Chem. Soc., 1998, 120, 3581 and references cited therein.
36. K. Himmeldirk, I. A. Kennedy, R. E. Hill, B. G. Sayer and I. A. Spenser, Chem. Commun., 1996, 1187.
37. S. Rosa Putra, L.-M. Lois, N. Campos, A. Boronat and M. Rohmer, Tetrahedron Lett., 1998, 39, 23.
38. D. Arigoni, S. Sagner, C. Latzel, W. Eisenreich, A. Bacher and M. H. Zenk, Proc. Natl. Acad. Sci. USA, 1997, 94, 10600.
39. G. A. Sprenger, U. Schörken, T. Wiegert, S. Grolle, A. A. de Graaf, S. V. Taylor, T. P. Begley, S. Bringer-Meyer and H. Sahm, Proc. Natl. Acad. Sci. USA, 1997, 94, 12857.
40. L.-M. Lois, N. Campos, S. Rosa Putra, K. Danielsen, M. Rohmer and A. Boronat, Proc. Natl. Acad. Sci. USA, 1998, 95, 2105.
41. B. M. Lange, M. R. Wildung, D. McCaskill and R. Croteau, Proc. Natl. Acad. Sci. USA, 1998, 95, 2100.
42. D. L. Turner, H. Santos, P. Fareleira, I. Pacheco, J. Le Gall and A. V. Xavier, Biochem. J., 1992, 285, 387.
43. D. Ostrovsky, A. Shashkov and A. Sviridov, Biochem. J., 1993, 295, 901.
44. D. Ostrovsky, E. Kharatian, T. Dubrovsky, O. Ogrel, I. Shipanova and L. Sibeldina, BioFactors, 1992, 4, 63.
45. D. Ostrovsky, E. Kharatian, I. Malarova, I. Shipanova, L. Sibeldina, A. Sashkov and G. Tantsirev, BioFactors, 1992, 3, 261.
46. S. W. Shah, S. Brandänge, D. Behr, J. Damén, S. Hagen and T. Anthonsen, Acta Chem. Scand., 1976, B30, 903.
47. R. W. Schramm, B. Tomaszewska and G. Peterson, Phytochemistry, 1979, 18, 1393.
48. R. Kringstad, A. Olsvik Singsaas, G. Rusten, G. Baekkemoen, B. Smestad Paulsen and A. Nordal, Phytochemistry, 1980, 19, 543.
49. J. de Pascual Terresa, J. C. Hernandez Aubanell, A. San Feliciano and J. M. Miguel del Corral, Tetrahedron Lett., 1980, 21, 1359.
50. C. W. Ford, Phytochemistry, 1981, 20, 2019.
51. P. Dittrich and S. J. Angyal, Phytochemistry, 1988, 27, 935.
52. J. Kitajima and Y. Tanaka, Chem. Pharm. Bull., 1993, 41, 1667.
53. A. A. Ahmed, M. H. Abd El-Razek, E. Abu Mostafa, H. J. Williams, A. I. Scott, J. H. Reibenspies and T. J. Mabry, J. Nat. Prod., 1996, 59, 1171.
54. T. Duvold, J.-M. Bravo, C. Pale-Grosdemange and M. Rohmer, Tetrahedron Lett., 1997, 38, 4769.
55. T. Duvold, P. Calì, J.-M. Bravo and M. Rohmer, Tetrahedron Lett., 1997, 38, 6181.
56. S. Sagner, W. Eisenreich, M. Fellermeier, C. Latzel, A. Bacher and M. H. Zenk, Tetrahedron Lett., 1998, 39, 2091.
57. T. Kuzuyama, S. Takahashi, W. Watanabe and H. Seto, Tetrahedron Lett., 1998, 39, 4509.
58. S. Takahashi, T. Kuzuyama, H. Watanabe and H. Seto, Proc. Natl. Acad. Sci. USA, 1998, 95, 9879.
59. Y. Shigi, J. Antimicrob. Chemother., 1989, 24, 131 and references cited therein.
60. T. Kuzuyama, T. Shimizu, S. Takahashi and H. Seto, 1998, Tetrahedron Lett., 1998, 39, 7913.
61. J. Zeidler, J. Schwender, C. Müller, J. Wiesner, C. Weidemeyer, E. Beck, H. Jomaa and H. K. Lichtenthaler, Z. Naturforsch., 1998, 53c, 980.
62. S. Pandian, S. Saengchan and T. S. Raman, Biochem. J., 1981, 196, 675.
63. S. Rosa Putra, A. Disch, J.-M. Bravo and M. Rohmer, FEMS Microbiol. Lett., 1998, 164, 169.
64. A. Disch, J. Schwender, C. Müller, H. K. Lichtenthaler and M. Rohmer, Biochem. J., 1998, 333, 381.
65. P. J. Proteau, J. Nat. Prod., 1998, 61, 841.
66. D. E. Cane, T. Rossi, A. M. Tillman and J. P. Pachtlako, J. Am. Chem. Soc., 1981, 103, 1838.
67. N. Orihara, K. Furihata and H. Seto, J. Antibiot., 1997, 50, 979.
68. N. Orihara, T. Kuzuyama, S. Takahashi, K. Furihata and H. Seto, J. Antibiot., 1998, 51, 676.
69. S. M. Li, S. Hennig and L. Heide, Tetrahedron Lett., 1998, 39, 2717.
70. K. Endler, U. Schuricht, L. Hennig, P. Wetzel, U. Holst, W. Aretz, D. Böttger and G. Huber, Tetrahedron Lett., 1998, 39, 13.
71. K. Irie, Y. Nakagawa, S. Tomimatsu and H. Ohigashi, Tetrahedron Lett., 1998, 39, 7929.
72. H. Seto, H. Watanabe and K. Furihata, Tetrahedron Lett., 1996, 37, 7979.
73. H. Seto, N. Orihara and K. Furihata, Tetrahedron Lett., 1998, 39, 9497.
74. G. Britton, T. W. Goodwin, W. J. S. Lockley, A. P. Mundy and N. J. Patel, J. Chem. Soc., Chem. Commun., 1979, 27.
75. C. Rieder, G. Strauβ, G. Fuchs, D. Arigoni, A. Bacher and W. Eisenreich, J. Biol. Chem., 1998, 273, 18099.
76. M. de Rosa, A. Gambacorta and B. Nicolaus, Phytochemistry, 1980, 19, 791.
77. N. Moldoveanu and M. Kates, Biochim. Biophys. Acta, 1988, 960, 164.
78. K. Kakinuma, M. Yamagishi, H. Fijimoto, N. Ikekawa and T. Oshima, J. Am. Chem. Soc., 1988, 110, 4861.
79. T. Eguchi, M. Morita and K. Kakinuma, J. Am. Chem. Soc., 1998, 120, 5247.
80. M. Rohmer, Progr. Drug Res., 1998, 50, 136.
81. T. W. Goodwin, Biochem. J., 1958, 68, 26.
82. T. W. Goodwin, Biochem. J., 1958, 70, 612.
83. D. Schulze-Siebert and G. Schultz, Plant Physiol., 1987, 84, 1233.
84. A. Heintze, J. Görlach, C. Leuschner, P. Hoppe, P. Hagestein, D. Schulze-Siebert and G. Schultz, Plant Physiol., 1990, 93, 1121.
85. J. Schwender, M. Seemann, H. K. Lichtenthaler and M. Rohmer, Biochem. J., 1996, 316, 73.
86. H. K. Lichtenthaler, J. Schwender, A. Disch and M. Rohmer, FEBS Lett., 1997, 400, 271.
87. A. Disch, A. Hemmerlin, T. J. Bach and M. Rohmer, Biochem. J., 1998, 331, 615.
88. M. Schwarz and D. Arigoni, in Comprehensive Natural Product Chemistry, ed. D. E. Cane, Pergamon, Oxford, 1999, vol. 2, ch. 14, p. 367.
89. J. G. Zeidler, H. K. Lichtenthaler, H. U. May and F. W. Lichtenthaler, Z. Naturforsch., Teil. G, 1997, 52, 15.
90. J. Piel, J. Donath, K. Bandemer and W. Boland, Angew. Chem., Int. Ed., 1998, 37, 2478.
91. W. Eisenreich, S. Sagner, M. H. Zenk and A. Bacher, Tetrahedron Lett., 1997, 38, 3889.
92. A. Contin, R. van der Heijden, A. W. M. Lefeber and R. Verpoorte, FEBS Lett., 1998, 434, 413.
93. K.-P. Adam, R. Thiel, J. Zapp and H. Becker, Arch. Biochem. Biophys., 1998, 354, 181.
94. W. Maier, B. Schneider and D. Strack, Tetrahedron Lett., 1998, 39, 521.
95. K.-P. Adam and J. Zapp, Phytochemistry, 1998, 48, 953.
96. K. Nabeta, T. Saitoh, K. Adachi and K. Komura, Chem. Commun., 1998, 671.
97. W. Eisenreich, B. Menhard, P. J. Hylands, M. H. Zenk and A. Bachert, Proc. Natl. Acad. Sci. USA, 1996, 93, 6431.
98. W. Knöss, B. Reuter and J. Zapp, Biochem. J., 1997, 326, 449.
99. K. Nabeta, T. Kawae, T. Kikuchi, T. Saitoh and H. Okuyama, J. Chem Soc., Chem. Commun, 1995, 2529.
100. K. Nabeta, T. Ishikawa, T. Kawae and H. Okuyama, J. Chem. Soc., Chem. Commun., 1995, 681.
101. K. Nabeta, T. Kawae, T. Saitoh and T. Kikuchi, J. Chem. Soc., Perkin Trans. 1, 1997, 261.
102. T. Duvold, Ph D Thesis, Université Louis Pasteur, Strasbourg, France, 1997.
103. J.-L. Giner and B. Jaun, Tetrahedron Lett., 1998, 39, 8021.
104. J.-L. Giner, B. Jaun and D. Arigoni, Chem. Commun., 1998, 1857.
105. P. J. Proteau, Tetrahedron Lett., 1998, 39, 9373.
106. M. McCaskill and R. Croteau, Tetrahedron Lett., 1999, 40, 653.