Applied Biochemistry and Microbiology

, Volume 43, Issue 2, pp 115–138

2-C-methylerythritol phosphate pathway of isoprenoid biosynthesis as a target in identifying new antibiotics, herbicides, and immunomodulators: A review

  • Yu. V. Ershov
Article

Abstract

Specific inhibitors of 2-C-methylerythritol phosphate pathway (MEP-pathway), including compounds obtained based on its metabolites, may compose a new class of antibiotics combining high efficiency and low toxicity. MEP-pathway of isoprenoid biosynthesis is a promising target in identifying new herbicides, immunomodulators, and other physiologically active compounds.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Biosynthesis of Isoprenoid Compounds, Porter, J.W. and Spurgeo, S.L., Eds., New York: Wiley, 1981.Google Scholar
  2. 2.
    Paseshnichenko, V.A., Biosintez i biologicheskaya aktivnost’rastitel’nykh terpenoidov i steroidov (Biosynthesis and Biological Activity of Plant Terpenoids and Steroids), Itogi Nauki Tekhn., Ser. Biol. Khim., Moscow: VINITI, 1987, vol. 25.Google Scholar
  3. 3.
    Rohmer, M., Pure Appl. Chem., 1993, vol. 65, no. 6, pp. 1293–1298.Google Scholar
  4. 4.
    Lichtenthaler, H.K., Annu. Rev. Plant Physiol. Plant Mol. Biol., 1999, vol. 50, pp. 47–65.PubMedCrossRefGoogle Scholar
  5. 5.
    Rohmer, M., Prog. Drug Res, 1998, vol. 50, pp. 135–154.PubMedGoogle Scholar
  6. 6.
    Eisenreich, W., Rohdich, F., and Bacher, A., Trends Plant Sci., 2001, vol. 6, no. 2, pp. 78–84.PubMedCrossRefGoogle Scholar
  7. 7.
    Rohdich, F., Kis, K., Bacher, A., and Eisenreich, W., Curr. Opin. Chem. Biol., 2001, vol. 5, no. 5, pp. 535–540.PubMedCrossRefGoogle Scholar
  8. 8.
    Kuzuyama, T., Biosci. Biotechnol. Biochem., 2002, vol. 66, no. 8, pp. 1619–1627.PubMedCrossRefGoogle Scholar
  9. 9.
    Rodriguez-Concepcion, M. and Boronat, A., Plant Physiol., 2002, vol. 130, no. 3, pp. 1079–1089.PubMedCrossRefGoogle Scholar
  10. 10.
    Rodriguez-Concepcion, M., Curr. Pharm. Design, 2004, vol. 10, no. 19, pp. 2391–2400.CrossRefGoogle Scholar
  11. 11.
    Ershov, Yu.V., Usp. Biol. Khim., 2005, vol. 45, pp. 307–354.Google Scholar
  12. 12.
    Rohmer, M., Bouvier-Nave, P., and Ourisson, G., J. Gen. Microbiol., 1984, vol. 130, no. 5, pp. 1137–1150.Google Scholar
  13. 13.
    Rohmer, M., Knani, M., Simonin, P., Sutter, B., and Sahm, H., Biochem. J., 1993, vol. 295, pp. 517–524.PubMedGoogle Scholar
  14. 14.
    Rohmer, M., Seemann, M., Horbach, S., Bringer-Meyer, S., and Sahm, H., J. Am. Chem. Soc., 1996, vol. 118, no. 11, pp. 2564–2566.CrossRefGoogle Scholar
  15. 15.
    Zhou, D. and White, R.H., Biochem. J., 1991, vol. 273, pp. 627–634.PubMedGoogle Scholar
  16. 16.
    Schwarz, M. and Arigoni, D., in Comprehensive Natural Product Chemistry, Cane, D., Ed., Oxford: Pergamon, 1999, pp. 367–369.Google Scholar
  17. 17.
    Lois, L.M., Campos, N., Putra, S.R., Danielsen, K., Rohmer, M., and Boronat, A., Proc. Natl. Acad. Sci. USA, 1998, vol. 95, no. 5, pp. 2105–2110.PubMedCrossRefGoogle Scholar
  18. 18.
    Sprenger, G.A., Schorken, U., Wiegert, T., Grolle, S., Graaf, A.A., Taylor, S.V., Begley, T.P., Bringer-Meyer, S., and Sahm, H., Proc. Natl. Acad. Sci. USA, 1997, vol. 94, no. 24, pp. 12857–12862.PubMedCrossRefGoogle Scholar
  19. 19.
    Kuzuyama, T., Takagi, M., Takahashi, S., and Seto, H., J. Bacteriol., 2000, vol. 182, no. 4, pp. 891–897.PubMedCrossRefGoogle Scholar
  20. 20.
    Harker, M. and Bramley, P.M., FEBS Lett., 1999, vol. 448, no. 1, pp. 115–119.PubMedCrossRefGoogle Scholar
  21. 21.
    Estevez, J.M., Cantero, A., Romero, C., Kawaide, H., Jimenez, L.F., Kuzuyama, T., Seto, H., Kamiya, Y., and Leon, P., Plant Physiol., 2000, vol. 124, no. 1, pp. 95–103.PubMedCrossRefGoogle Scholar
  22. 22.
    Therisod, M., Fischer, J.C., and Estramareix, B., Biochem. Biophys. Res. Commun., 1981, vol. 98, no. 2, pp. 374–379.PubMedCrossRefGoogle Scholar
  23. 23.
    Tazoe, M., Ichikawa, K., and Hoshino, T., Boisci. Biotechnol. Biochem., 2002, vol. 66, no. 4, pp. 934–936.CrossRefGoogle Scholar
  24. 24.
    Sauret-Gueto, S., Uros, E.M., Ibanez, E., Boronat, A., and Rodriguez-Concepcion, M., FEBS Lett., 2006, vol. 580, no. 3, pp. 736–740.PubMedCrossRefGoogle Scholar
  25. 25.
    Altincicek, B., Hintz, M., Sanderbrand, S., et al., FEMS Microbiol. Letts., 2000, vol. 190, no. 2, pp. 329–333.Google Scholar
  26. 26.
    Sandmann, G. and Boger, P., Z. Naturforsch., A: Phys. Sci., 1986, vol. 41c, no. 10, pp. 729–732.Google Scholar
  27. 27.
    Zeidler, J., Schwender, J., Muller, C., et al., Z. Naturforsch., A: Phys. Sci., 1998, vol. 53c, no. 12, pp. 980–986.Google Scholar
  28. 28.
    Lange, B.M., Ketchum, R.E.B., and Croteau, R.B., Plant Physiol., 2001, vol. 127, no. 1, pp. 305–314.PubMedCrossRefGoogle Scholar
  29. 29.
    Zeidler, J., Schwender, J., Muller, C., and Lichtenthaler, H.K., Biochem. Soc. Trans., 2000, vol. 28, no. 6, pp. 796–798.PubMedCrossRefGoogle Scholar
  30. 30.
    Baiguz, A. and Asami, T., Phytochemistry, 2005, vol. 66, no. 15, pp. 1787–1796.CrossRefGoogle Scholar
  31. 31.
    Muller, C., Schwender, J., Zeidler, J., and Lichtenthaler, H.K., Biochem. Soc. Trans., 2000, vol. 28, no. 6, pp. 792–793.CrossRefGoogle Scholar
  32. 32.
    Patent USA. 1983. No. 4405357.Google Scholar
  33. 33.
    Norman, M.A., Liebl, R.A., and Widholm, J.M., Plant Physiol., 1990, vol. 92, no. 3, pp. 777–784.PubMedGoogle Scholar
  34. 34.
    El Naggar, S.F., Creekmore, R.W., Schocken, M., et al., J. Agric. Food Chem., 1992, vol. 40, no. 5, pp. 880–883.CrossRefGoogle Scholar
  35. 35.
    Lichtenthaler, H.K., Zeidler, J., Schwender, J., and Muller, C., Z. Naturforsch. A: Phys. Sci., 2000, vol. 55c, nos. 5–6, pp. 305–313.Google Scholar
  36. 36.
    Burdett, A.S., Stevens, M.M., and Macmillan, D.L., Environ. Toxicol. Chem., 2001, vol. 20, no. 10, pp. 2229–2236.PubMedCrossRefGoogle Scholar
  37. 37.
    Crestani, M., Menezes, C., Glusczak, L., et al., Ecotoxicol. Environ. Saf., 2006, vol. 65, no. 1, pp. 48–55.PubMedCrossRefGoogle Scholar
  38. 38.
    Proteau, P.J., Bioorg. Chem., 2004, vol. 32, no. 6, pp. 483–493.PubMedCrossRefGoogle Scholar
  39. 39.
    Shigi, Y.J., J. Antimicrob. Chemother., 1989, vol. 24, no. 2, pp. 131–145.PubMedCrossRefGoogle Scholar
  40. 40.
    Kuzuyama, T., Takahashi, S., Watanabe, H., and Seto, H., Tetrahedron Lett., 1998, vol. 39, no. 18, pp. 4509–4512.CrossRefGoogle Scholar
  41. 41.
    Patent USA. 1989. No. 4846872.Google Scholar
  42. 42.
    Kuzuyama, T., Shimizu, T., Takahashi, S., and Seto, H., Tetrahedron Lett., 1998, vol. 39, no. 24, pp. 7913–7916.CrossRefGoogle Scholar
  43. 43.
    Koppisch, A.T., Fox, D.T., Blagg, B.S., and Poulter, C.D., Biochemistry, 2002, vol. 41, no. 1, pp. 236–243.PubMedCrossRefGoogle Scholar
  44. 44.
    Mac, Sweeney A., Lange, R., Fernandes, R.P., et al., J. Mol. Biol., 2005, vol. 345, no. 1, pp. 115–127.CrossRefGoogle Scholar
  45. 45.
    Testa, C.A., Cornish, R.M., and Poulter, C.D., J. Bacteriol., 2004, vol. 186, no. 2, pp. 473–480.PubMedCrossRefGoogle Scholar
  46. 46.
    Sakamoto, I., Ichimura, K., and Ohrui, H., Biosci. Biotechnol. Biochem., 2000, vol. 64, no. 9, pp. 1915–1922.PubMedCrossRefGoogle Scholar
  47. 47.
    Steinbacher, S., Kaiser, J., Eisenreich, W., et al., J. Biol. Chem., 2003, vol. 278, no. 20, pp. 18401–18407.PubMedCrossRefGoogle Scholar
  48. 48.
    Jomaa, H., Wiesner, J., Sanderbrand, S., et al., Science, 1999, vol. 285, no. 5433, pp. 1573–1576.PubMedCrossRefGoogle Scholar
  49. 49.
    Fernandes, R.P., Phaosiri, C., and Proteau, P.J., Arch. Biochem. Biophys., 2005, vol. 444, no. 2, pp. 159–164.PubMedGoogle Scholar
  50. 50.
    Reuter, K., Sanderbrand, S., Jomaa, H., et al., J. Biol. Chem., 2002, vol. 277, no. 7, pp. 5378–5384.PubMedCrossRefGoogle Scholar
  51. 51.
    Ricagno, S., Grolle, S., Bringer-Meyer, S., et al., Biochim. Biophys. Acta, 2004, vol. 1698, no. 1, pp. 37–44.PubMedGoogle Scholar
  52. 52.
    Dhiman, R.K., Schaeffer, M., L., Bailey A.M., et al., J. Bacteriol., 2005, vol. 187, no. 24, pp. 8395–8402.PubMedCrossRefGoogle Scholar
  53. 53.
    Silber, K., Heidler, P., Kurz, T., and Klebe, G., J. Med. Chem., 2005, vol. 48, no. 10, pp. 3547–3563.PubMedCrossRefGoogle Scholar
  54. 54.
    Katayama, N., Tsubotani, S., Nozaki, Y., et al., J. Antibiot. (Tokyo), 1990, vol. 43, no. 3, pp. 238–246.Google Scholar
  55. 55.
    Woo, Y.H., Fernandes, R.P., and Proteau, P.J., Bioorg. Med. Chem., 2006, vol. 14, no. 7, pp. 2375–2385.PubMedCrossRefGoogle Scholar
  56. 56.
    Kurz, T., Geffken, D., and Wackendorff, C., Z. Naturforsch., A: Phys. Sci., 2003, vol. 58b, no. 1, pp. 106–110.Google Scholar
  57. 57.
    Kurz, T., Geffken, D., and Wackendorff, C., Z. Naturforsch., A: Phys. Sci., 2003, vol. 58b, no. 6, pp. 457–461.Google Scholar
  58. 58.
    Kuntz, L., Tritsch, D., Grosdemange-Billiard, C., et al., Biochem. J., 2005, vol. 386, pp. 127–135.PubMedCrossRefGoogle Scholar
  59. 59.
    Reichenberg, A., Wiesner, J., Weidemeyer, C., et al., Bioorg. Med. Chem. Lett., 2001, vol. 11, no. 6, pp. 833–835.PubMedCrossRefGoogle Scholar
  60. 60.
    Ortmann, R., Wiesner, J., Reichenberg, A., et al., Bioorg. Med. Chem. Lett., 2003, vol. 13, no. 13, pp. 2163–2166.PubMedCrossRefGoogle Scholar
  61. 61.
    Ortmann, R., Wiesner, J., Reichenberg, A., et al., Arch. Pharm. (Weinheim), 2005, vol. 338, no. 7, pp. 305–314.CrossRefGoogle Scholar
  62. 62.
    Kurz, T., Schluter, K., Kaula, U., et al., Bioorg. Med. Chem., 2006, vol. 14, no. 15, pp. 5121–5135.PubMedCrossRefGoogle Scholar
  63. 63.
    Haemers, T., Wiesner, J., Van Poecke, S., et al., Bioorg. Med. Chem. Lett., 2006, vol. 16, no. 7, pp. 1888–1891.PubMedCrossRefGoogle Scholar
  64. 64.
    Courtois, M., Mincheva, Z., Andreu, F., et al., J. Enzyme Inhib. Med. Chem., 2004, vol. 19, no. 6, pp. 559–565.PubMedCrossRefGoogle Scholar
  65. 65.
    Mincheva, Z., Courtois, M., Andreu, F., et al., Phytochemistry, 2005, vol. 66, no. 15, pp. 1797–1803.PubMedCrossRefGoogle Scholar
  66. 66.
    Hemmi, K., Takeno, H., Hashimoto, M., and Kamiya, T., Chem. Pharm. Bull. (Tokyo), 1982, vol. 30, no. 1, pp. 111–118.Google Scholar
  67. 67.
    Kuroda, Y., Okuhara, M., Goto, T., et al., and Imanaka, H., J. Antibiot. (Tokyo), 1980, vol. 33, no. 1, pp. 29–35.Google Scholar
  68. 68.
    Walker, J.R. and Poulter, C.D., J. Org. Chem., 2005, vol. 70, no. 24, pp. 9955–9959.PubMedCrossRefGoogle Scholar
  69. 69.
    Hoeffler, J.F., Tritsch, D., Grosdemange-Billiard, C., and Rohmer, M., Eur. J. Biochem., 2002, vol. 269, no. 18, pp. 4446–4457.PubMedCrossRefGoogle Scholar
  70. 70.
    Wong, A., Munos, J.W., Devasthali, V., et al., Org. Lett., 2004, vol. 6, no. 20, pp. 3625–3628.PubMedCrossRefGoogle Scholar
  71. 71.
    Fox, D.T. and Poulter, C.D., J. Org. Chem., 2005, vol. 70, no. 6, pp. 1978–1985.PubMedCrossRefGoogle Scholar
  72. 72.
    Fox, D.T. and Poulter, C.D., Biochemistry, 2005, vol. 44, no. 23, pp. 8360–8368.PubMedCrossRefGoogle Scholar
  73. 73.
    Phaosiri, C. and Proteau, P., Bioorg. Med. Chem. Lett., 2004, vol. 2, no. 21, pp. 5309–5312.CrossRefGoogle Scholar
  74. 74.
    Takahashi, S., Kuzuyama, T., Watanabe, H., and Seto, H., Proc. Natl. Acad. Sci. USA, 1998, vol. 95, no. 17, pp. 9879–9884.PubMedCrossRefGoogle Scholar
  75. 75.
    Krall, L., Raschke, M., Zenk, M.H., and Baron, C., FEBS Lett., 2002, vol. 527, nos. 1–3, pp. 315–318.PubMedCrossRefGoogle Scholar
  76. 76.
    Herforth, C., Wiesner, J., Heidler, P., et al., Bioorg. Med. Chem., 2004, vol. 12, no. 4, pp. 755–762.PubMedCrossRefGoogle Scholar
  77. 77.
    Herforth, C., Wiesner, J., Franke, S., et al., J. Comb. Chem, 2002, vol. 4, no. 4, pp. 302–314.PubMedCrossRefGoogle Scholar
  78. 78.
    Gabrielsen, M., Rohdich, F., Eisenreich, W., et al., Eur. J. Biochem., 2004, vol. 271, no. 14, pp. 3028–3035.PubMedCrossRefGoogle Scholar
  79. 79.
    Testa, C.A., Lherbet, C., Pojer, F., et al., Biochim. Biophys. Acta, 2006, vol. 1764, no. 1, pp. 85–96.PubMedGoogle Scholar
  80. 80.
    Lherbet, C., Pojer, F., Richard, S.B., et al., Biochemistry, 2006, vol. 45, no. 11, pp. 3548–3553.PubMedCrossRefGoogle Scholar
  81. 81.
    Lillo, A.M., Tetzlaff, C.N., Sangari, F.J., and Cane, D.E., Bioorg. Med. Chem. Lett., 2003, vol. 13, no. 4, pp. 737–739.PubMedCrossRefGoogle Scholar
  82. 82.
    Yoshioka, T., Shimizu, H., and Ohrui, H., Boisci. Biotechnol. Biochem., 2004, vol. 68, no. 6, pp. 1259–1264.CrossRefGoogle Scholar
  83. 83.
    Kemp, L.E., Bond, C.S., and Hunter, W.N., Acta Crystallogr. D. Biol. Crystallogr, 2001, vol. 57, pp. 1189–1191.PubMedCrossRefGoogle Scholar
  84. 84.
    Kemp, L.E., Bond, C.S., and Hunter, W.N., Acta Crystallogr. D. Biol. Crystallogr, 2003, vol. 59, pp. 607–610.PubMedCrossRefGoogle Scholar
  85. 85.
    Richard, S.B., Bowman, M.E., Kwiatkowski, W., et al., Nat. Struct. Biol., 2001, vol. 8, no. 7, pp. 641–648.PubMedCrossRefGoogle Scholar
  86. 86.
    Richard, S.B., Lillo, A.M., Tetzlaff, C.N., et al., Biochemistry, 2004, vol. 43, no. 38, pp. 12189–12197.PubMedCrossRefGoogle Scholar
  87. 87.
    Gabrielsen, M., Kaiser, J., Rohdich, F., et al., FEBS J, 2006, vol. 273, no. 5, pp. 1065–1073.PubMedCrossRefGoogle Scholar
  88. 88.
    Miallau, L., Alphey, M.S., Kemp, L.E., et al., Proc. Natl. Acad. Sci. USA, 2003, vol. 100, no. 16, pp. 9173–9178.PubMedCrossRefGoogle Scholar
  89. 89.
    Wada, T., Kuzuyama, T., Satoh, S., et al., J. Biol. Chem., 2003, vol. 278, no. 32, pp. 30022–30027.PubMedCrossRefGoogle Scholar
  90. 90.
    Lange, B.M., Rujan, T., Martin, W., and Croteau, R., Proc. Natl. Acad. Sci. USA, 2000, vol. 97, no. 24, pp. 13172–13177.PubMedCrossRefGoogle Scholar
  91. 91.
    Steinbacher, S., Kaiser, J., Wungsintaweekul, J., et al., J. Mol. Biol., 2002, vol. 316, no. 1, pp. 79–88.PubMedCrossRefGoogle Scholar
  92. 92.
    Kemp, L.E., Bond, C.S., and Hunter, W.N., Proc. Natl. Acad. Sci. USA, 2002, vol. 99, no. 10, pp. 6591–6596.PubMedCrossRefGoogle Scholar
  93. 93.
    Richard, S.B., Ferrer, J.L., Bowman, M.E., et al., J. Biol. Chem., 2002, vol. 277, no. 10, pp. 8667–8672.PubMedCrossRefGoogle Scholar
  94. 94.
    Kishida, H., Wada, T., Unzai, S., et al., Acta Crystallogr. Sect. D. Biol. Crystallogr., 2003, vol. 59, pp. 23–31.CrossRefGoogle Scholar
  95. 95.
    Gabrielsen, M., Bond, C.S., Hallyburton, I., et al., J. Biol. Chem., 2004, vol. 279, no. 50, pp. 52753–52761.PubMedCrossRefGoogle Scholar
  96. 96.
    Hunter, W.N., Bond, C.S., Gabrielsen, M., and Kemp, L.E., Biochem. Soc. Trans., 2003, vol. 31, pp. 537–542.PubMedCrossRefGoogle Scholar
  97. 97.
    Sgraja, T., Kemp, L.E., Ramsden, N., and Hunter, W.N., Acta Crystallograph. Sect. F. Struct. Biol. Cryst. Commun, 2005, vol. 61, pp. 625–629.PubMedCrossRefGoogle Scholar
  98. 98.
    Kemp, L.E., Alphey, M.S., Bond, C.S., et al., Acta Crystallogr. Sect. D. Biol. Crystallogr., 2005, vol. 61, pp. 45–52.CrossRefGoogle Scholar
  99. 99.
    Rohdich, F., Wungsintaweekul, J., Fellermeier, M., et al., Proc. Natl. Acad. Sci. USA, 1999, vol. 96, no. 21, pp. 11758–11763.PubMedCrossRefGoogle Scholar
  100. 100.
    Kuzuyama, T., Takagi, M., Kaneda, K., et al., Tetrahedron Lett., 2000, vol. 41, no. 3, pp. 703–706.CrossRefGoogle Scholar
  101. 101.
    Rohdich, F., Wungsintaweekul, J., Eisenreich, W., et al., Proc. Natl. Acad. Sci. USA, 2000, vol. 97, no. 2, pp. 6451–6456.PubMedCrossRefGoogle Scholar
  102. 102.
    Lange, B.M. and Croteau, R., Proc. Natl. Acad. Sci. USA, 1999, vol. 96, no. 24, pp. 13714–13719.PubMedCrossRefGoogle Scholar
  103. 103.
    Kuzuyama, T., Takagi, M., Kaneda, K., et al., Tetrahedron Lett., 2000, vol. 41, no. 2, pp. 2925–2928.CrossRefGoogle Scholar
  104. 104.
    Luttgen, H., Rohdich, F., Herz, S., et al., Proc. Natl. Acad. Sci. USA, 2000, vol. 97, no. 3, pp. 1062–1067.PubMedCrossRefGoogle Scholar
  105. 105.
    Rohdich, F., Wungsintaweekul, J., Luttgen, H., et al., Proc. Natl. Acad. Sci. USA, 2000, vol. 97, no. 15, pp. 8251–8256.PubMedCrossRefGoogle Scholar
  106. 106.
    Grieshaber, N.A., Fischer, E.R., Mead, D.J., et al., Proc. Natl. Acad. Sci. USA, 2004, vol. 101, no. 19, pp. 7451–7456.PubMedCrossRefGoogle Scholar
  107. 107.
    Ostrovskii, D.N., Lysak, E.I., Demina, G.R., and Binyukov, V.I., Mikrobiologiya, 2000, vol. 69, no. 5, pp. 620–628.Google Scholar
  108. 108.
    Ostrovsky, D., Shipanova, I., Sibeldina, L., et al., FEBS Lett., 1992, vol. 298, nos. 2–3, pp. 159–161.PubMedCrossRefGoogle Scholar
  109. 109.
    Demina, G.R., Pleshakova, O.V., Sibel’dina, L.A., et al., Biokhimiya, 1995, vol. 60, vol. 3, pp. 481–487.Google Scholar
  110. 110.
    Ostrovskii, D.N., Dosanov, K.Sh., Kalyuk, A.N., et al., Mikrobiologiya, 1994, vol. 63, no. 3, pp. 431–438.Google Scholar
  111. 111.
    Ostrovskii, D.N., Lysak, E.I., Sibel’dina, L.A., et al., Dokl. Akad. Nauk, 1994, vol. 337, no. 5, pp. 687–689.Google Scholar
  112. 112.
    Shchipanova, I.N., Kharat’yan, E.F., Sibel’dina, L.A., et al., Biokhimiya, 1992, vol. 57, vol. 5, pp. 862–872.Google Scholar
  113. 113.
    Ostrovsky, D., Diomina, G., Shipanova, I., et al., Biofactors, 1994, vol. 4, nos. 3–4, pp. 155–159.PubMedGoogle Scholar
  114. 114.
    Ostrovsky, D., Kharatian, E., Dubrovsky, T., et al., Biofactors, 1992, vol. 4, no. 1, pp. 63–68.PubMedGoogle Scholar
  115. 115.
    Ostrovsky, D., Shashkov, A., and Sviridov, A., Biochem. J., 1993, vol. 295, pp. 901–902.PubMedGoogle Scholar
  116. 116.
    Lysak, E.I., Ogrel’, O.D., Kharat’yan, E.F., et al., Mikrobiologiya, 1995, vol. 64, no. 3–4, pp. 437–441.Google Scholar
  117. 117.
    Ogrel’, O.D., Fegeding, K.V., Kaprel’yants, A.S., and Lysak, E.I., Ngo Min’ Shon, Sudarikov A.B., Ostrovskii, D.N., Biokhimiya, 1996, vol. 61, no. 7, pp. 1294–1302.Google Scholar
  118. 118.
    Ogrel, O.D., Fegeding, K.V., Kharatian, E.F., et al., Curr. Microbiol., 1996, vol. 32, no. 4, pp. 225–228.PubMedCrossRefGoogle Scholar
  119. 119.
    Altincicek, B., Duin, E.C., Reichenberg, A., et al., FEBS Lett., 2002, vol. 532, no. 3, pp. 437–440.PubMedCrossRefGoogle Scholar
  120. 120.
    Kollas, A.K., Duin, E.C., Eberl, M., et al., FEBS Lett., 2002, vol. 532, no. 3, pp. 432–436.PubMedCrossRefGoogle Scholar
  121. 121.
    Seemann, M., Bui, B.T., Wolff, M., et al., Angew. Chem., Int. Ed. Engl., 2002, vol. 41, no. 22, pp. 4337–4339.CrossRefGoogle Scholar
  122. 122.
    Seemann, M., Wegner P., Schunemann V., et al., J. Biol. Inorg. Chem., 2005, vol. 10, no. 2, pp. 131–137.PubMedCrossRefGoogle Scholar
  123. 123.
    Seemann, M., Bui, B.T., Wolff, M., et al., FEBS Lett., 2006, vol. 580, no. 6, pp. 1547–1552.PubMedCrossRefGoogle Scholar
  124. 124.
    Zepeck, F., Grawert, T., Kaiser, J., et al., J. Org. Chem, 2005, vol. 70, no. 23, pp. 9168–9174.PubMedCrossRefGoogle Scholar
  125. 125.
    Puan, K.J., Wang, H., Dairi, T., Kuzuyama, T., and Morita, C.T., FEBS Lett., 2005, vol. 579, no. 17, pp. 3802–3806.PubMedCrossRefGoogle Scholar
  126. 126.
    Gil, M.J., Coego, A., Mauch-Mani, B., et al., Plant J., 2005, vol. 44, no. 1, pp. 155–166.PubMedCrossRefGoogle Scholar
  127. 127.
    Poquet, Y., Constant, P., Halary, F., et al., Eur. J. Immunol., 1996, vol. 212, no. 10, pp. 110–117.Google Scholar
  128. 128.
    Hintz, M., Reichenberg, A., Altincicek, B., et al., FEBS Lett., 2001, vol. 509, no. 2, pp. 317–322.PubMedCrossRefGoogle Scholar
  129. 129.
    Eberl, M., Hintz, M., Jamba, Z., et al., Infect. Immun., 2004, vol. 72, no. 8, pp. 4881–4883.PubMedCrossRefGoogle Scholar
  130. 130.
    Wolff, M., Seemann, M., Bui, T.S.B., et al., FEBS Lett., 2003, vol. 541, nos. 1–3, pp. 115–120.PubMedCrossRefGoogle Scholar
  131. 131.
    Grawert, T., Kaiser, J., Zepeck, F., et al., J. Am. Chem. Soc., 2004, vol. 126, no. 40, pp. 12847–12855.PubMedGoogle Scholar
  132. 132.
    Rohrich, R., C, Englert, N., Troschke, K., et al., FEBS Lett., 2005, vol. 579, no. 28, pp. 6433–6438.PubMedCrossRefGoogle Scholar
  133. 133.
    Adam, P., Hecht, S., Eisenreich, W., et al., Proc. Natl. Acad. Sci. USA, 2002, vol. 99, no. 19, pp. 12108–12113.PubMedCrossRefGoogle Scholar
  134. 134.
    Botella-Pavia, P., Besumbes, O., Phillips, M.A., et al., Plant J., 2004, vol. 40, no. 2, pp. 188–199.PubMedCrossRefGoogle Scholar
  135. 135.
    Cunningham, F.X., Lafond, T.P., and Gantt, E., J. Bacteriol., 2000, vol. 182, no. 20, pp. 5841–5848.PubMedCrossRefGoogle Scholar
  136. 136.
    McAteer, S., Coulson, A., McLennan, N., and Masters M, J. Bacteriol., 2001, vol. 183, no. 24, pp. 7403–7407.PubMedCrossRefGoogle Scholar
  137. 137.
    Rodriguez-Concepcion, M., Campos, N., Lois, L.M., et al., FEBS Lett., 2000, vol. 473, no. 3, pp. 328–332.PubMedCrossRefGoogle Scholar
  138. 138.
    Okada, K. and Hase, T., J. Biol. Chem., 2005, vol. 280, no. 21, pp. 20672–20679.PubMedCrossRefGoogle Scholar
  139. 139.
    Hahn, F.M., Hurlburt, A.P., and Poulter, C.D., J. Bacteriol., 1999, vol. 181, no. 15, pp. 4499–4504.PubMedGoogle Scholar
  140. 140.
    Ershov, Y., Gantt, R.R., Cunningham, F.X., and Gantt, E., FEBS Lett., 2000, vol. 473, no. 3, pp. 337–340.PubMedCrossRefGoogle Scholar
  141. 141.
    Kuzuyama, T. and Seto, H., Nat. Prod. Rep., 2003, vol. 20, no. 2, pp. 171–183.PubMedCrossRefGoogle Scholar
  142. 142.
    Laupitz, R., Hecht, S., Amslinger, S., et al., Eur. J. Biochem., 2004, vol. 271, no. 13, pp. 2658–2669.PubMedCrossRefGoogle Scholar
  143. 143.
    Lawrence, J.C., Curr. Opin. Microbiol., 1999, vol. 2, pp. 519–523.PubMedCrossRefGoogle Scholar
  144. 144.
    Doolittle, W.F., Trends Genet., 1998, vol. 14, no. 8, pp. 307–311.PubMedCrossRefGoogle Scholar
  145. 145.
    Summons, R.E., Jahnke, L.L., Hope, J.M., and Logan, G.A., Nature (London), 1999, vol. 400, no. 6744, pp. 554–557.CrossRefGoogle Scholar
  146. 146.
    Boucher, Y. and Doolittle, W.F., Mol. Microbiol., 2000, vol. 37, no. 4, pp. 703–716.PubMedCrossRefGoogle Scholar
  147. 147.
    Disch, A., Schwender, J., Muller, C., et al., Biochem. J., 1998, vol. 333, pp. 381–388.PubMedGoogle Scholar
  148. 148.
    Schwender, J., Gemunden, C., and Lichtenthaler, H.K., Planta, 2001, vol. 212, no. 3, pp. 416–423.PubMedCrossRefGoogle Scholar
  149. 149.
    Eberl, M., Hintz, M., Reichenberg, A., et al., FEBS Lett., 2003, vol. 544, nos. 1–3, pp. 4–10.PubMedCrossRefGoogle Scholar
  150. 150.
    Testa, C.A. and Brown, M.J., Curr. Pharm. Biotechnol., 2003, vol. 4, no. 4, pp. 248–259.PubMedCrossRefGoogle Scholar
  151. 151.
    Begley, M., Gahan, C.G., Kollas, A.K., et al., FEBS Lett., 2004, vol. 561, nos. 1–3, pp. 99–104.PubMedCrossRefGoogle Scholar
  152. 152.
    Seto, H., Watanabe, H., and Furihata, K., Tetrahedron Lett., 1996, vol. 37, no. 4, pp. 7979–7981.CrossRefGoogle Scholar
  153. 153.
    Hamano, Y., Dairi, T., Yamamoto, M., et al., Boisci. Biotechnol. Biochem., 2002, vol. 66, no. 4, pp. 808–819.CrossRefGoogle Scholar
  154. 154.
    White, A., Handler, P., Smith, E., et al., Principles of Biochemistry, New York: McGraw-Hill, 1978. Translated under the title Osnovy biokhimii, Moscow: Mir, 1981, pp. 429–454.Google Scholar
  155. 155.
    Rohdich, F., Zepeck, F., Adam, P., et al., Proc. Natl. Acad. Sci. USA, 2003, vol. 100, no. 4, pp. 1586–1591.PubMedCrossRefGoogle Scholar
  156. 156.
    Rohdich, F., Bacher, A., and Eisenreich, W., Biochem. Soc. Trans., 2005, vol. 33, pp. 785–791.PubMedCrossRefGoogle Scholar
  157. 157.
    Lell, B., Ruangweerayut, R., Wiesner, J., et al., Antimicrob. Agents Chemother., 2003, vol. 47, no. 2, pp. 735–738.PubMedCrossRefGoogle Scholar
  158. 158.
    Missinou, M.A., Borrmann, S., Schindler, A., et al., Lancet, 2002, vol. 360, no. 9349, pp. 1941–1942.PubMedCrossRefGoogle Scholar
  159. 159.
    Borrmann, S., Adegnika, A.A., Matsiegui, P.B., et al., J. Infect. Dis., 2004, vol. 189, no. 5, pp. 901–908.PubMedCrossRefGoogle Scholar
  160. 160.
    Sicard, H., Al Saati, T., Delsol, G., and Fournie, J.J., Mol. Med., 2001, vol. 7, no. 10, pp. 711–722.PubMedGoogle Scholar
  161. 161.
    Belmant, C., Espinosa, E., Poupot, R., et al., J. Biol. Chem., 1999, vol. 274, no. 45, pp. 32079–32084.PubMedCrossRefGoogle Scholar
  162. 162.
    Feurle, J., Espinosa, E., Eckstein, S., et al., J. Biol. Chem., 2002, vol. 277, no. 1, pp. 148–154.PubMedCrossRefGoogle Scholar
  163. 163.
    Slama, K. and Williams, C.M., Nature (London), 1966, vol. 210, no. 33, pp. 32079–32084.CrossRefGoogle Scholar
  164. 164.
    Slama, K. and Williams, C.M., Proc. Natl. Acad. Sci. USA, 1965, vol. 54, no. 2, pp. 411–414.PubMedCrossRefGoogle Scholar
  165. 165.
    Bede, J.C., Musser, R.O., Felton, G.W., and Korth, K.L., Plant Mol.Biol, 2006, vol. 60, no. 4, pp. 519–531.PubMedCrossRefGoogle Scholar
  166. 166.
    Soe, A., Bartram, S., Gatto, N., and Boland, W., Isotopes Environ. Health Stud., 2004, vol. 40, no. 3, pp. 175–180.PubMedCrossRefGoogle Scholar
  167. 167.
    Ginger, M.L., Chance, M.L., Sadler, I.H., and Goad, L.G., J. Biol. Chem., 2001, vol. 276, no. 15, pp. 11674–11682.PubMedCrossRefGoogle Scholar
  168. 168.
    Ershov, Y.V., Gantt, R.R., Cunningham, F.X., and Gantt, E., J. Bacteriol., 2002, vol. 184, no. 18, pp. 5045–5051.PubMedCrossRefGoogle Scholar
  169. 169.
    Poliquin, K., Ershov, Y.V., Cunningham, F.X., et al., J. Bacteriol., 2004, vol. 186, no. 14, pp. 4685–4693.PubMedCrossRefGoogle Scholar
  170. 170.
    Martin, G.J., Lavoine-Hanneguelle, S., Mabon, F., and Martin, M.L., Phytochemistry, 2004, vol. 65, no. 20, pp. 2815–2831.PubMedCrossRefGoogle Scholar
  171. 171.
    Wolfertz, M., Sharkey, T.D., Boland, W., and Kuhnemann, F., Plant Physiol., 2004, vol. 135, no. 4, pp. 1939–1945.PubMedCrossRefGoogle Scholar
  172. 172.
    Gottlin, E.B., Benson, R.E., Conary, S., et al., J. Biomol. Screen, 2003, vol. 8, no. 3, pp. 332–339.PubMedCrossRefGoogle Scholar
  173. 173.
    Meyer, O., Grosdemange-Billiard, C., Tritsch, D., and Rohmer, M., Org. Biomol. Chem., 2003, vol. 1, no. 24, pp. 4367–4372.PubMedCrossRefGoogle Scholar
  174. 174.
    Bouvier, F., d’Harlingue, A., Suire, C., et al., Plant Physiol., 1998, vol. 117, no. 4, pp. 1423–1431.PubMedCrossRefGoogle Scholar
  175. 175.
    Cane, D.E., Chow, C., Lillo, A., and Kang, I., Bioorg. Med. Chem., 2001, vol. 9, no. 6, pp. 1467–1477.PubMedCrossRefGoogle Scholar
  176. 176.
    Argyrou, A. and Blanchard, J.S., Biochemistry, 2004, vol. 43, no. 14, pp. 4375–4384.PubMedCrossRefGoogle Scholar
  177. 177.
    Richard, S.B., Lillo, A.M., Tetzlaff, C.N., et al., Biochemistry, 2004, vol. 43, no. 38, pp. 12189–12197.PubMedCrossRefGoogle Scholar
  178. 178.
    Herz, S., Wungsintaweekul, J., Schuhr, C.A., et al., Proc. Natl. Acad. Sci. USA, 2000, vol. 97, no. 6, pp. 2486–2490.PubMedCrossRefGoogle Scholar
  179. 179.
    Rohdich, F., Eisenreich, W., Wungsintaweekul, J., et al., Eur. J. Biochem., 2001, vol. 268, no. 11, pp. 3190–3197.PubMedCrossRefGoogle Scholar
  180. 180.
    Kaneda, K., Kuzuyama, T., Takagi, M., et al., Proc. Natl. Acad. Sci. USA, 2001, vol. 98, no. 3, pp. 932–937.PubMedCrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Inc. 2007

Authors and Affiliations

  • Yu. V. Ershov
    • 1
  1. 1.Bach Institute of BiochemistryRussian Academy of SciencesMoscowRussia

Personalised recommendations