Target Sites for Herbicide Action pp 29-56

Part of the Topics in Applied Chemistry book series (TAPP)

Amino Acid Synthesis

  • David M. Mousdale
  • John R. Coggins

Abstract

Green plants share with most microbial species the capacity to synthesize all the major amino acids; the few exceptions are parasitic and depend on the nitrogen metabolism of the host plant. In addition, many nonprotein “uncommon” amino acids are produced, and frequently accumulated, in large amounts in a range of species; these are important in plant/plant, plant/insect, and plant/animal relationships.1 The amino acids essential for mammalian diets are phenylalanine, tryptophan, lysine, leucine, isoleucine, valine, threonine, and methionine for adults, with the addition of arginine and histidine for immature animals (the third aromatic amino acid required for protein synthesis, tyrosine, can be formed metabolically, given an adequate dietary intake of phenylalanine). The biosynthetic routes for these 10 amino acids are particularly attractive targets for toxicologically safe herbicides and for pesticides aimed at plant pathogens; the potential for antibiotics may be more limited because medicinally important microorganisms tend to inhabit nutritionally rich habitats.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    E. A. Bell, FEBS Lett. 64, 29 (1976).PubMedCrossRefGoogle Scholar
  2. 2.
    B. J. Miflin (ed.), The Biochemistry of Plants: Volume 5, Amino Acids and Derivatives, Academic Press, New York (1980).Google Scholar
  3. 3.
    A. H. Fitter and R. K. M. Hay, Environmental Physiology of Plants, Academic Press, London (1983).Google Scholar
  4. 4.
    J. S. Titus and S. M. Kang, Hort. Rev. 4, 204 (1982).Google Scholar
  5. 5.
    B. J. Miflin and P. L. Lea, Annu. Rev. Plant Physiol 28, 299 (1977).CrossRefGoogle Scholar
  6. 6.
    E. Haslam, The Shikimate Pathway, Butterworths, London (1974).Google Scholar
  7. 7.
    U. Weiss and J. M. Edwards, The Biosynthesis of Aromatic Compounds, John Wiley and Sons, New York (1980).Google Scholar
  8. 8.
    T. N. Tateoka, Bot. Mag. (Tokyo) 81, 103 (1968).Google Scholar
  9. 9.
    P. M. Dewick and E. Haslam, Biochem. J. 113, 537 (1969).PubMedGoogle Scholar
  10. 10.
    R. Saijo, Agric. Biol. Chem. 47, 455 (1983).CrossRefGoogle Scholar
  11. 11.
    V. I. Osipov and L. P. Aleksandrova, Zh. Obshch. Biol 47, 79 (1986).Google Scholar
  12. 12.
    A. M. Boudet, A. Graziana, and R. Ranjeva, in: The Biochemistry of Plant Phenolics ( C. F. Van Sumere and P. J. Lea, eds.), p. 135, Clarendon Press, Oxford (1985).Google Scholar
  13. 13.
    A. Lewendon and J. R. Coggins, Biochem. J. 213, 187 (1983).PubMedGoogle Scholar
  14. 14.
    K. D. Duncan, A. Lewendon, and J. R. Coggins, FEBS Leu. 165, 121 (1984).CrossRefGoogle Scholar
  15. 15.
    H. C. Steinrucken and N. Amrhein, Eur. J. Biochem. 143, 341 (1984).PubMedCrossRefGoogle Scholar
  16. 16.
    D. M. Mousdale and J. R. Coggins, Planta 160, 78 (1984).CrossRefGoogle Scholar
  17. 17.
    D. M. Mousdale and J. R. Coggins, J. Chromatogr. 367, 217 (1986).PubMedCrossRefGoogle Scholar
  18. 18.
    J. E. Ream, H. C. Steinrucken, C. A. Porter, and J. A. Sikorski, Plant Physiol. 87, 232 (1988).PubMedCrossRefGoogle Scholar
  19. 19.
    M. B. Berlyn and N. H. Giles, J. Bacteriol. 99, 222 (1969).PubMedGoogle Scholar
  20. 20.
    J. Lumsden and J. R. Coggins, Biochem. J. 161, 599 (1977).PubMedGoogle Scholar
  21. 21.
    V. B. Patel and N. H. Giles, Biochim. Biophys. Acta 567, 24 (1979).PubMedCrossRefGoogle Scholar
  22. 22.
    H. C. Steinrucken and N. Amrhein, Eur. J. Biochem. 143, 351 (1984).PubMedCrossRefGoogle Scholar
  23. 23.
    J. L. Rubin, C. G. Gaines, and R. A. Jensen, Plant Physiol. 75, 839 (1984).PubMedCrossRefGoogle Scholar
  24. 24.
    N. Amrhein, in: The Shikimic Acid Pathway ( E. E. Conn, ed.), p. 83, Plenum Press, New York (1986).CrossRefGoogle Scholar
  25. 25.
    N. Amrhein, J. Schab, and H. C. Steinrucken, Naturwissenschaften 67, 356 (1980).CrossRefGoogle Scholar
  26. 26.
    H. C. Steinrucken and N. Amrhein, Biochem. Biophys. Res. Commun. 94, 1207 (1980).PubMedCrossRefGoogle Scholar
  27. 27.
    M. R. Boocock and J. R. Coggins, FEBS Lett. 154, 127 (1983).PubMedCrossRefGoogle Scholar
  28. 28.
    D. L. Anton, L. Hestrom, S. M. Fish, and R. H. Abeles, Biochemistry 22, 5903 (1983).CrossRefGoogle Scholar
  29. 29.
    R. Bode, C. Melo, and D. Birnbaum, Arch. Microbiol. 140, 83 (1984).PubMedCrossRefGoogle Scholar
  30. 30.
    E. S. Sharps, Anal. Biochem. 140, 183 (1984).PubMedCrossRefGoogle Scholar
  31. 31.
    C. S. Smith, D. Pratt and G. A. Thompson, Plant Cell Rep. 5, 298 (1986).CrossRefGoogle Scholar
  32. 32.
    G. Parr, S. R. Padgette, L. Brundage, and G. M. Kishore, Fed. Proc. 46, 1977 (1987).Google Scholar
  33. 33.
    G. M. Kishore and D. M. Shah, Annu. Rev. Biochem. 57, 627 (1988).PubMedCrossRefGoogle Scholar
  34. 34.
    K. S. Anderson, K. A. Johnson, A. J. Benesi, and J. A. Sikorski, Biochemistry 28, 1936 (1989).Google Scholar
  35. 35.
    P. J. Cassidy and F. M. Kahan, Biochemistry 12, 1364 (1973).PubMedCrossRefGoogle Scholar
  36. 36.
    F. M. Kahan, J. S. Kahan, P. J. Cassidy, and H. Kropp, Ann. N.Y. Acad. Sci. 235, 364 (1974).PubMedCrossRefGoogle Scholar
  37. 37.
    R. I. Zemell and R. A. Anwar, J. Biol. Chem. 250, 4959 (1975).PubMedGoogle Scholar
  38. 38.
    M. R. Boocock, Ph.D. thesis, University of Glasgow (1983).Google Scholar
  39. 39.
    K. L. Carlson and O. C. Burnside, Weed Sci. 32, 841 (1984).Google Scholar
  40. 40.
    S. S. Abdel-Meguid, W. W. Smith, and G. S. Bild, J. Mol. Biol. 186, 673 (1985).PubMedCrossRefGoogle Scholar
  41. 41.
    Q. K. Huynh, G. M. Kishore, and G. S. Bild, J. Biol. Chem. 263, 735 (1988).PubMedGoogle Scholar
  42. 42.
    S. R. Padgette and G. M. Kishore, Fed. Proc. 46, 216 (1987).Google Scholar
  43. 43.
    Q. K. Huynh, Arch. Biochem. Biophys. 258, 233 (1987).PubMedCrossRefGoogle Scholar
  44. 44.
    S. R. Padgette, Q. K. Huynh, S. Aykent, R. D. Sammons, J. A. Sikorksi, and G. M. Kishore, J. Biol. Chem. 263, 1798 (1988).PubMedGoogle Scholar
  45. 45.
    Q. K. Huynh, S. C. Bauer, G. S. Bild, G. M. Kishore, and J. R. Borgmeyer, J. Biol. Chem. 263, 11636 (1988).PubMedGoogle Scholar
  46. 46.
    P. Sprankle, W. F. Meggitt, and D. Penner, Weed Sci. 23, 229 (1975).Google Scholar
  47. 47.
    Q. K. Huynh, J. Biol. Chem. 263, 11631 (1988).PubMedGoogle Scholar
  48. 48.
    D. M. Stalker, W. R. Hiatt, and L. Cornai, J. Biol. Chem. 260, 4724 (1985).PubMedGoogle Scholar
  49. 49.
    A. Schulz, D. Sost, and N. Amrhein, Arch. Microbiol. 137, 121 (1984).CrossRefGoogle Scholar
  50. 50.
    D. Sost, A. Schulz, and N. Amrhein, FEBS Lett. 173, 238 (1984).CrossRefGoogle Scholar
  51. 51.
    G. M. Kishore, L. Brundage, K. Kolk, S. R. Padgette, D. Rochester, Q. K. Huynh, and G. della-Cioppa, Fed. Proc. 45, 1506 (1986).Google Scholar
  52. 52.
    G. M. Kishore, D. M. Shah, S. R. Padgette, G. della-Cioppa, C. Gasser, D. Re, C. Hironake, M. Taylor, J. Wibbenmeyer, D. Eichholtz, N. Hoffmann, X. Delannay, R. Horsch, H. Klee, S. Rogers, D. Rochester, L. Brundage, P. Sanders, and R. T. Fraley, In: Biotechnology for Crop Protection (P. A. Hedin, J. J. Menn, and R. M. Hollingworth, eds.), ACS Symposium Series, No. 379, p. 37, American Chemical Society, Washington, D.C. (1985).Google Scholar
  53. 53.
    S. G. Rogers, L. A. Brand, S. B. Holder, E. S. Sharps, and M. J. Brackin, Appl. Environ. Microbiol. 46, 37 (1983).PubMedGoogle Scholar
  54. 54.
    G. Kunze, R. Bode, H. Rintala, and J. Hofmeister, Curr. Genet. 15, 91 (1989).PubMedCrossRefGoogle Scholar
  55. 55.
    D. M. Shah, R. B. Horsch, H. J. Klee, G. M. Kishore, J. A. Winter, N. E. Turner, C. M. Hironaka, P. R. Sanders, C. S. Gasser, S. Aykent, N. R. Siegel, S. G. Rogers, and R. T. Fraley, Science 233, 478 (1986).PubMedCrossRefGoogle Scholar
  56. 56.
    G. S. Gasser, J. A. Winter, C. M. Hironaka, and D. M. Shah, J. Biol. Chem. 263, 4280 (1988).PubMedGoogle Scholar
  57. 57.
    G. della-Cioppa, S. C. Bauer, B. K. Klein, D. M. Shah, R. T. Fraley, and G. M. Kishore, Proc. Natl. Acad. Sci. U.S.A. 83, 6873 (1986).PubMedCrossRefGoogle Scholar
  58. 58.
    L. Cornai, D. Facciotti, W. R. Hiatt, G. Thompson, R. E. Rose, and D. M. Stalker, Nature 317, 741 (1985).CrossRefGoogle Scholar
  59. 59.
    J. J. Fillatti, J. Kiser, R. Rose, and L. Cornai, Bio/ Technology 5, 726 (1987).CrossRefGoogle Scholar
  60. 60.
    G. della-Cioppa, S. C. Bauer, M. L. Taylor, D. E. Rochester, and B. K. Klein, Biol Technology 5, 579 (1987).CrossRefGoogle Scholar
  61. 61.
    R. A. Jensen, Physiol. Plant. 66, 164 (1985).CrossRefGoogle Scholar
  62. 62.
    H. J. Klee, Y. M. Muskopf, and C. S. Gasser, Mol. Gen. Genet. 210, 437 (1987).PubMedCrossRefGoogle Scholar
  63. 63.
    R. M. Hauptmann, G. della-Cioppa, A. G. Smith, G. M. Kishore, and J. M. Widholm, Mol. Gen. Genet. 211, 357 (1988).CrossRefGoogle Scholar
  64. 64.
    E. D. Nazfiger, J. M. Widholm, H. C. Steinrucken, and J. L. Killmer, Plant Physiol. 76, 571 (1984).CrossRefGoogle Scholar
  65. 65.
    C. M. Smith, D. Pratt, and G. A. Thompson, Plant Cell Rep. 5, 298 (1986).CrossRefGoogle Scholar
  66. 66.
    C. C. Smart, D. Johanning, G. Muller, and N. Amrhein, J. BioL Chem. 260, 16338 (1985).PubMedGoogle Scholar
  67. 67.
    W. E. Dyer, S. C. Weller, R. A. Bressan, and K. M. Hermann, Plant Physiol. 88, 661 (1988).PubMedCrossRefGoogle Scholar
  68. 68.
    A. Schulz, A. Kruper, and N. Amrhein, FEMS MicrobioL Leu. 28, 297 (1985).CrossRefGoogle Scholar
  69. 69.
    A. K. Singh, M. V. Sailaja, and H. N. Singh, FEMS MicrobioL. Lett. 60, 187 (1989).Google Scholar
  70. 70.
    O. Gottrup, P. A. O’Sullivan, R. J. Schraa, and W. H. Vanden Born, Weed Res. 16, 197 (1976).CrossRefGoogle Scholar
  71. 71.
    M. A. Waldecker and D. L. Wyse, Weed Sci. 33, 299 (1985).Google Scholar
  72. 72.
    P. Sprankle, C. L. Sandberg, W. F. Meggitt, and D. Penner, Weed Sci. 26, 673 (1978).Google Scholar
  73. 73.
    K. Lund-Hoie, Meld. Norges Landbrukshogskole 55, 2 (1976).Google Scholar
  74. 74.
    J. K. Moore, H. D. Braymer, and A. D. Larson, Appl Environ. Microbiol. 46, 316 (1983).PubMedGoogle Scholar
  75. 75.
    T. H. Balthazor and L. E. Hallas, Appl. Environ. Microbiol. 51, 432 (1986).PubMedGoogle Scholar
  76. 76.
    U. Roisch and F. Lingens, Hoppe-Seyler’s Z. Physiol. Chem. 361, 1049 (1980).PubMedCrossRefGoogle Scholar
  77. 77.
    J. L. Rubin, C. G. Gaines, and R. A. Jensen, Plant Physiol. 70, 833 (1982).PubMedCrossRefGoogle Scholar
  78. 78.
    R. Bode, C. Melo Ramos, and D. Birnbaum, FEMS MicrobioL Lett. 23, 7 (1984).Google Scholar
  79. 79.
    R. S. Fischer, A. Berry, C. G. Gaines, and R. A. Jensen, J. BacterioL 168, 1147 (1986).PubMedGoogle Scholar
  80. 80.
    R. J. Ganson and R. A. Jensen, Arch. Biochem. Biophys. 260, 85 (1988).PubMedCrossRefGoogle Scholar
  81. 81.
    G. S. Byng, R. J. Whitaker, and R. A. Jensen, Can. J. Bot. 63, 1021 (1985).CrossRefGoogle Scholar
  82. 82.
    N. Amrhein, B. Deus, P. Gehrke, and H. C. Steinrucken, Plant Physiol. 66, 830 (1980).PubMedCrossRefGoogle Scholar
  83. 83.
    J. Berlin and L. Witte, Z. Naturforsch., C36, 210 (1981).Google Scholar
  84. 84.
    H. Hollander-Czytko and N. Amrhein, Plant Sci. Lett. 29, 89 (1983).CrossRefGoogle Scholar
  85. 85.
    N. Ishikura, S. Teramoto, Y. Takeshima, and S. Mitsui, Plant Cell Physiol. 27, 677 (1986).Google Scholar
  86. 86.
    J. M. Becerril, S. O. Duke, and J. Lydon, Phytochemistry 28, 695 (1989).CrossRefGoogle Scholar
  87. 87.
    B. A. Bohm, Chem. Rev. 65, 435 (1965).CrossRefGoogle Scholar
  88. 88.
    J. A. Gougler and D. R. Geiger, Plant Physiol. 68, 668 (1981).PubMedCrossRefGoogle Scholar
  89. 89.
    P. Sprankle, W. F. Meggitt, and D. Penner, Weed Sci. 23, 235 (1975).Google Scholar
  90. 90.
    L. C. Haderlie, F. W. Slife, and H. S. Butler, Weed Res. 18, 269 (1978).CrossRefGoogle Scholar
  91. 91.
    M. E. Foley, E. D. Nazfiger, F. W. Slife, and L. M. Wax, Weed Sci. 31, 76 (1983).Google Scholar
  92. 92.
    R. E. Hoagland, S. O. Duke, and C. D. Elmore, Plant Sci. Lett. 13, 291 (1978).CrossRefGoogle Scholar
  93. 93.
    R. E. Hoagland, S. O. Duke, and C. D. Elmore, Physiol Plant. 46, 357 (1979).CrossRefGoogle Scholar
  94. 94.
    S. O. Duke, R. E. Hoagland, and C. D. Elmore, Plant Physiol. 65, 17 (1980).PubMedCrossRefGoogle Scholar
  95. 95.
    S. Margit, C. Jolan, and K. Erzsebet, Bot. Kozlem. 70, 151 (1983).Google Scholar
  96. 96.
    L. M. Kitchen, W. W. Witt, and C. E. Rieck, Weed Sci. 29, 513 (1981).Google Scholar
  97. 97.
    L. M. Kitchen, W. W. Witt, and C. E. Rieck, Weed Sci. 29, 571 (1981).Google Scholar
  98. 98.
    D. J. Cole, J. C. Caseley, and A. D. Dodge, Weed Res. 23, 173 (1983).CrossRefGoogle Scholar
  99. 99.
    A. Munoz-Reuda, C. Gonzalez-Murua, J. M. Becerril, and M. F. Sanchez-Diaz, Physiol. Plant. 66, 63 (1986).CrossRefGoogle Scholar
  100. 100.
    T. T. Lee, Physiol. Plant. 54, 289 (1982).CrossRefGoogle Scholar
  101. 101.
    T. T. Lee and T. Dumas, Plant Physiol. 72, 855 (1983).PubMedCrossRefGoogle Scholar
  102. 102.
    T. T. Lee and T. Dumas, J. Plant Growth Regul. 4, 29 (1985).CrossRefGoogle Scholar
  103. 103.
    H. E. Umbarger, in: Amino Acids: Biosynthesis and Genetic Regulation ( K. M. Hermann and R. L. Somerville, eds.), p. 245, Addison-Wesley, Reading, Massachusetts (1983).Google Scholar
  104. 104.
    J. V. Schloss, D. E. Van Dyck, J. F. Vasta, and R. M. Kutny, Biochemistry 24, 4952 (1985).PubMedCrossRefGoogle Scholar
  105. 105.
    L. M. Ciskanik and J. V. Schloss, Biochemistry 24, 3357 (1985).Google Scholar
  106. 106.
    L. M. Ciskanik and J. V. Schloss, Fed. Proc. 45, 1607 (1985).Google Scholar
  107. 107.
    J. V. Schloss, In: Flavins and Flavoproteins (R. C. Bray, P. C. Engel, and S. G. Mayhew, eds.), p. 737, de Gruyter, Berlin (1984).Google Scholar
  108. 108.
    B. K. Singh and G. K. Schmitt, Plant PhysioL 89 (Supplement), 175 (1989).Google Scholar
  109. 109.
    L. Eoyang and P. M. Silverman, Methods EnzymoL 166, 435 (1988).PubMedCrossRefGoogle Scholar
  110. 110.
    J. V. Schloss and D. E. Van Dyk, Methods EnzymoL 166, 445 (1988).PubMedCrossRefGoogle Scholar
  111. 111.
    Z. Barak, J. M. Calvo, and J. V. Schloss, Methods EnzymoL 166, 455 (1988).PubMedCrossRefGoogle Scholar
  112. 112.
    D. Schulze-Siebert, D. Heineke, H. Scharf, and G. Schultz, Plant Physiol. 76, 465 (1984).PubMedCrossRefGoogle Scholar
  113. 113.
    B. K. Singh and G. K. Schmitt, Plant Physiol. 89, 54 (1989).Google Scholar
  114. 114.
    A. V. Jones, R. M. Young, and K. Leto, Plant Physiol. 77, S293 (1985).Google Scholar
  115. 115.
    B. J. Mazur, C.-F. Chui, and J. K. Smith, Plant Physiol. 85, 1110 (1987).PubMedCrossRefGoogle Scholar
  116. 116.
    J. Durner and P. Boger, Z. Naturforsch., 43, 850 (1988).Google Scholar
  117. 117.
    B. J. Miflin, Phytochemistry 8, 2271 (1969).CrossRefGoogle Scholar
  118. 118.
    B. J. Miflin, Arch. Biochem. Biophys. 146, 542 (1971).PubMedCrossRefGoogle Scholar
  119. 119.
    J. K. Bryan, In: The Biochemistry of Plants (B. J. Miflin, ed.), Vol. 5, p. 403, Academic Press, New York (1980).Google Scholar
  120. 120.
    M. J. Muhitch, Plant Physiol. 86, 23 (1988).PubMedCrossRefGoogle Scholar
  121. 121.
    J. K. Smith, J. V. Schloss, and B. J. Mazur, Proc. NatL Acad. Sci. U.S.A. 86, 4179 (1989).PubMedCrossRefGoogle Scholar
  122. 122.
    R. A. LaRossa and J. V. Schloss, J. Biol. Chem. 259, 8753 (1984).PubMedGoogle Scholar
  123. 123.
    S. C. Falco and K. S. Dumas, Genetics 109, 21 (1985).PubMedGoogle Scholar
  124. 124.
    R. S. Chaleff and C. J. Mauvais, Science 224, 1443 (1984).PubMedCrossRefGoogle Scholar
  125. 125.
    T. B. Ray, Plant Physiol. 75, 827 (1984).PubMedCrossRefGoogle Scholar
  126. 126.
    D. L. Shaner, P. C. Anderson, and M. A. Stidham, Plant Physiol. 76, 545 (1984).PubMedCrossRefGoogle Scholar
  127. 127.
    M. J. Muhitch, D. L. Shaner, and M. A. Stidham, Plant Physiol. 83, 451 (1987).PubMedCrossRefGoogle Scholar
  128. 128.
    W. A. Kleschick, M. J. Costales, J. E. Dunbar, R. W. Meikle, W. T. Monte, N. R. Pearson, S. W. Snider, and A. P. Vinogradoff, Abstracts of the 194th ACS National Meeting, New Orleans, No. AGRO162 (1987).Google Scholar
  129. 129.
    B. C. Gerwick and V. Loney, Abstracts of the 194th ACS National Meeting, New Orleans, No. AGRO163 (1987).Google Scholar
  130. 130.
    Y. Nezu, F. Ojima, S. Kusano, Y. Tokokawa, T. Miyazawa, and I. Kajiwara, European Patent Application 223406 (1987).Google Scholar
  131. 131.
    R. Y. Xing and W. B. Whitman, J. Bacteriol. 169, 4486 (1987).PubMedGoogle Scholar
  132. 132.
    W. A. Kleschick and B. C. Gerwick, In: Prospects for Amino Acid Biosynthesis Inhibitors in Crop Protection and Pharmaceutical Chemistry (L. G. Copping, J. Dalziel, and A. D. Dodge, eds.), British Crop Protection Council Monograph No. 42, p. 139 (1989).Google Scholar
  133. 133.
    M. V. Subramanian, V. Loney, and L. Pao, In: Prospects for Amino Acid Biosynthesis Inhibitors in Crop Protection and Pharmaceutical Chemistry (L. G. Copping, J. Dalziel, and A. D. Dodge, eds.), British Crop Protection Council Monograph No. 42, p. 97 (1989).Google Scholar
  134. 134.
    T. R. Hawkes, In: Prospects for Amino Acid Biosynthesis Inhibitors in Crop Protection and Pharmaceutical Chemistry (L. G. Copping, J. Dalziel, and A. D. Dodge, eds.), British Crop Protection Council Monograph No. 42, p. 131 (1989).Google Scholar
  135. 135.
    C. C. Hodges, J. Avalos, P. J. McCall, L. E. Stafford, and P. R. Yackovitch, Abstracts of the 194th ACS National Meeting, New Orleans, No. AGRO164 (1987).Google Scholar
  136. 136.
    M. V. Subramanian and M. Kozuch, Plant Physiol. 89, 176 (1989).Google Scholar
  137. 137.
    J. V. Schloss, L. M. Ciskanik, and D. E. Van Dyk, Nature 331, 360 (1988).CrossRefGoogle Scholar
  138. 138.
    D. Shaner, B. Singh, K. Newhouse, M. Stidham, and G. Schmitt, Biochemistry 28, 1935 (1989).Google Scholar
  139. 139.
    G. K. Schmitt and B. K. Singh, Plant Physiol. 89 (Supplement), 53 (1989).Google Scholar
  140. 140.
    N. Yadav, R. E. McDevitt, S. Benard, and S. C. Falco, Proc. Natl. Acad. Sci. U.S.A. 83, 4418 (1986).PubMedCrossRefGoogle Scholar
  141. 141.
    S. N. Maiti, M. W. Zink, and G. H. Rank, Can. J. Microbiol. 34, 680 (1988).PubMedCrossRefGoogle Scholar
  142. 142.
    B. Rathinasabapathi, D. Williams, and J. King, Plant Physiol. 89, 190 (1989).Google Scholar
  143. 143.
    J. K. Smith, C. J. Mauvais, S. Knowlton, and B. J. Mazur, Biotechnology for Crop Protection (P. A. Hedin, J. J. Menn, and R. M. Hollingworth, eds.), ACS Symposium Series, No. 379, p. 25, American Chemical Society, Washington, D.C. (1985).Google Scholar
  144. 144.
    G. W. Haughn, J. Smith, B. Mazur, and C. Somerville, Mol. Gen. Genet. 211, 266 (1988).CrossRefGoogle Scholar
  145. 145.
    D. Friedberg and J. Seijffers, Arch. Microbiol. 150, 278 (1988).CrossRefGoogle Scholar
  146. 146.
    P. C. Anderson and M. Georgeson, in: The Biochemical Basis of Herbicide Action, 27th Harden Conference Abstracts, Wye College, Ashford, U.K. (1986).Google Scholar
  147. 147.
    J. M. Gabard, P. J. Charest, V. N. Iyer, and B. L. Miki, Plant Physiol. 91, 574 (1989).PubMedCrossRefGoogle Scholar
  148. 148.
    R. A. LaRossa, T. K. Van Dyk, and D. R. Smulski, J. Bacteriol. 169, 1372 (1987).PubMedGoogle Scholar
  149. 149.
    D. Scheel and J. E. Casida, Pestic. Biochem. Physiol. 23, 398 (1985).CrossRefGoogle Scholar
  150. 150.
    A. Schulz, P. Sponemann, H. Kocher, and F. Wengenmayer, FEBS Lett. 238, 375 (1988).PubMedCrossRefGoogle Scholar
  151. 151.
    J. V. Schloss and A. Aulabaugh, Biochemistry 28, 1936 (1989).Google Scholar
  152. 152.
    J. L. Hilton, P. C. Kearney, and B. N. Ames, Arch. Biochem. Biophys. 112, 544 (1965).PubMedCrossRefGoogle Scholar
  153. 153.
    T. Klopotowski and D. Hulanicka, Acta Biochim. Polon. 10, 209 (1963).PubMedGoogle Scholar
  154. 154.
    A. Wiater, T. Klopotowski, and G. Bagdasarian, Acta Biochim. Polon. 18, 309 (1971).PubMedGoogle Scholar
  155. 155.
    P. J. Casselton, Nature 204, 93 (1964).CrossRefGoogle Scholar
  156. 156.
    P. J. Casselton, Physiol. Plant. 19, 411 (1966).CrossRefGoogle Scholar
  157. 157.
    J. N. Siegel and A. C. Gentile, Plant Physiol. 41, 670 (1966).PubMedCrossRefGoogle Scholar
  158. 158.
    M. E. Davies, Phytochemistry 10, 783 (1971).CrossRefGoogle Scholar
  159. 159.
    K. A. Sund, E. C. Putala, and H. N. Little, J. Agric. Food Chem. 8, 210 (1960).CrossRefGoogle Scholar
  160. 160.
    F. T. Wolf, Nature 193, 901 (1962).PubMedCrossRefGoogle Scholar
  161. 161.
    J. L. Hilton, J. Agric. Food Chem. 17, 182 (1969).CrossRefGoogle Scholar
  162. 162.
    D. R. Heim and I. M. Larrinua, Plant Physiol. 89 (Supplement), 175 (1989).Google Scholar
  163. 163.
    D. Hulanicka, T. Klopotowski, and D. A. Smith, J. Gen. Microbiol. 72, 291 (1972).PubMedCrossRefGoogle Scholar
  164. 164.
    S. R. Singer and C. N. McDaniel, Plant Physiol. 78, 411 (1985).PubMedCrossRefGoogle Scholar
  165. 165.
    R. Bode, P. Casper, and G. Kunze, Biochem. Physiol. Pflanzen 178, 457 (1983).Google Scholar
  166. 166.
    K. Duncan, R. M. Edwards, and J. R. Coggins, FEBS Lett. 241, 83 (1988).PubMedCrossRefGoogle Scholar
  167. 167.
    B. J. Miflin and P. J. Lea, in: The Biochemistry of Plants, Vol. 5, Amino Acids and Derivatives ( B. J. Miflin, ed.), p. 169, Academic Press, New York (1980).Google Scholar
  168. 168.
    E. R. Stadtman, A. Ginsburg, J. E. Ciardi, J. Yeh, S. B. Hennig, and B. M. Shapiro, Adv. Enzyme Regul. 8, 99 (1970).PubMedCrossRefGoogle Scholar
  169. 169.
    G. R. Stewart, A. F. Mann, and P. A. Fentem, in: The Biochemistry of Plants, Vol. 5, Amino Acids and Derivatives ( B. J. Miflin, ed.), p. 271, Academic Press, New York (1980).Google Scholar
  170. 170.
    S. F. McNally, B. Hirel, P. Gadal, A. F. Mann, and G. R. Stewart, Plant Physiol. 72, 23 (1983).CrossRefGoogle Scholar
  171. 171.
    M. Lara, H. Porta, J. Padilla, J. Folch, and F. Sanchez, Plant Physiol. 76, 1019 (1984).PubMedCrossRefGoogle Scholar
  172. 172.
    J. R. Botella, J. P. Verbelen, and V. Valpuesta, Plant Physiol. 88, 943 (1988).PubMedCrossRefGoogle Scholar
  173. 173.
    A. K. Tobin, S. M. Ridley, and G. R. Stewart, Planta 163, 544 (1985).CrossRefGoogle Scholar
  174. 174.
    A. C. Kendall, S. W. J. Bright, N. P. Hall, A. J. Keys, P. J. Lea, J. C. Turner, and R. M. Wallsgrove, in: Progress in Photosynthesis Research (J. Biggens, ed.), Vol. 3, p. 629, Martinus Nijhoff, Dordrecht (1987).Google Scholar
  175. 175.
    R. H. McParland, J. G. Guevara, R. R. Becker, and H. J. Evans, Biochem. J. 153, 597 (1976).Google Scholar
  176. 176.
    A. Meister, in: The Enzymes (P. D. Boyer, ed.), Vol. 10, p. 699, Academic Press, New York (1974).Google Scholar
  177. 177.
    T. D. Meek, K. A. Johnson, and J. J. Villafranca, Biochemistry 21, 2158 (1982).PubMedCrossRefGoogle Scholar
  178. 178.
    T. D. Meek and J. J. Villafranca, Biochemistry 19, 5513 (1980).PubMedCrossRefGoogle Scholar
  179. 179.
    E. Bayer, K. H. Gugel, H. Hagele, M. Hagenmaier, S. Jessipow, W. A. Konig, and H. Zahner, Heiv. Chim. Acta 55, 224 (1972).CrossRefGoogle Scholar
  180. 180.
    K. Tachibana, T. Watanabe, Y. Sekizawa, and T. Takematsu, J. Pestic. Sci. 11, 33 (1986).CrossRefGoogle Scholar
  181. 181.
    A. Wild and C. Ziegler, Z. Naturforsch., C 44, 97 (1989).Google Scholar
  182. 182.
    J. A. Colanduoni and J. J. Villafranca, Bioorg. Chem. 14, 163 (1986).CrossRefGoogle Scholar
  183. 183.
    E. W. Logusch, D. M. Walker, J. F. McDonald, and J. E. Franz, Biochemistry 28, 3043 (1989).PubMedCrossRefGoogle Scholar
  184. 184.
    J. D. Gass and A. Meister, Biochemistry 9, 1380 (1970).PubMedCrossRefGoogle Scholar
  185. 185.
    F. C. Wedler, Y. Sugiyama, and K. E. Fisher, Biochemistry 21, 2168 (1982).PubMedCrossRefGoogle Scholar
  186. 186.
    J. J. Villafranca, D. E. Ash, and F. C. Wedler, Biochemistry 15, 544 (1976).PubMedCrossRefGoogle Scholar
  187. 187.
    R. Manderscheid and A. Wild, J. Plant Physiol. 123, 135 (1986).CrossRefGoogle Scholar
  188. 188.
    M. Hopfner, G. Reifferscheid, and A. Wild, Z. Naturforsch., C 43, 194 (1988).Google Scholar
  189. 189.
    M. Leason, D. Cunliffe, D. Parkin, P. J. Lea, and B. J. Miflin, Phytochemistry 21, 855 (1982).CrossRefGoogle Scholar
  190. 190.
    M. A. Acaster and P. D. J. Weitzman, FEBS Lett. 189, 241 (1985).CrossRefGoogle Scholar
  191. 191.
    A Wild and R. Manderscheid, Z. Naturforsch., C 39, 500 (1984).Google Scholar
  192. 192.
    S. Imai, H. Seto, T. Sasaki, T. Tsuruoka, H. Ogawa, A. Satoh, S. Inouye, T. Niida, and N. Otake, J. Antibiot. 38, 687 (1985).PubMedCrossRefGoogle Scholar
  193. 193.
    T. J. Knight, R. D. Durbin, and P. J. Langston-Unkefer, J. Bacteriol. 169, 1954 (1987).PubMedGoogle Scholar
  194. 194.
    P. J. Langston-Unkefer, A. C. Robinson, T. J. Knight, and R. D. Durbin, J. Biol. Chem. 262, 1608 (1987).PubMedGoogle Scholar
  195. 195.
    P. J. Lea, K. W. Joy, J. L. Ramos, and M. G. Guerrero, Phytochemistry 23, 1 (1984).CrossRefGoogle Scholar
  196. 196.
    A. Wild, H. Sauer, and W. Ruhle, Z. Naturforsch., C 42, 263 (1987).Google Scholar
  197. 197.
    H. Sauer, A. Wild, and W. Ruhle, Z. Naturforsch., C 42, 270 (1987).Google Scholar
  198. 198.
    M. Lacuesta, B. Gonzalez-Moro, C. Gonzalez-Murua, P. Aparicio-Tejo, and A. MunozRueda, J. Plant Physiol. 134, 304 (1989).CrossRefGoogle Scholar
  199. 199.
    H. Kocher, Aspects Appl. Biol. 4, 227 (1983).Google Scholar
  200. 200.
    G. D. Trogisch, H. Kocher, and W. R. Ullrich, Z. Naturforsch., C 44, 33 (1989).Google Scholar
  201. 201.
    C. Ziegler and A. Wild, Z. Naturforsch., C 44, 103 (1989).Google Scholar
  202. 202.
    G. Donn, E. Tischer, J. A. Smith, and H. M. Goodman, J. Mol. Appl. Genet. 2, 621 (1984).PubMedGoogle Scholar
  203. 203.
    M. Deak, G. Donn, A. Feher, and D. Dudits, Plant Cell Rep. 7, 158 (1988).CrossRefGoogle Scholar
  204. 204.
    P. Eckes, P. Schmitt, W. Daub, and F. Wengenmayer, Mol. Gen. Genet. 217, 263 (1989).PubMedCrossRefGoogle Scholar
  205. 205.
    Y. Ishida, T. Hiyoshi, M. Sano, and T. Kumashiro, Plant Sci. 63, 227 (1989).CrossRefGoogle Scholar
  206. 206.
    S. M. Ridley and S. F. McNally, Plant Sci. 39, 31 (1985).CrossRefGoogle Scholar
  207. 207.
    K. Bartsch and C. C. Tebbe, Appl. Environ. Microbiol. 55, 711 (1989).PubMedGoogle Scholar
  208. 208.
    M. De Block, J. Botterman, M. Vandewiele, J. Dockx, C. Thoen, V. Gossele, N. R. Movva, L. Tompson, M. Van Montagu, and J. Leemans, EMBO J. 6, 2513 (1987).PubMedGoogle Scholar
  209. 209.
    C. J. Thompson, N. R. Movva, R. Tizard, R. Crameri, J. E. Davies, M. Lauwereys, and J. Botterman, EMBO J. 6, 2519 (1987).PubMedGoogle Scholar
  210. 210.
    G. S. Hartley and T. F. West, Chemicals for Pest Control, Pergamon Press, Oxford (1969).Google Scholar
  211. 211.
    M. F. Balandrin, J. A. Klocke, E. S. Wurtele, and W. M. Bollinger, Science 228, 1154 (1985).PubMedCrossRefGoogle Scholar
  212. 212.
    J. M. Widholm, Physiol. Plant. 25, 75 (1971).CrossRefGoogle Scholar
  213. 213.
    J. M. Widholm, Biochim. Biophys. Acta 320, 217 (1973).PubMedCrossRefGoogle Scholar
  214. 214.
    C. N. Hankins, M. T. Largen, and S. E. Mills, Plant Physiol. 57, 101 (1976).PubMedCrossRefGoogle Scholar
  215. 215.
    W. Grosse, Z. Pflanzenphysiol. 80, 463 (1976).Google Scholar
  216. 216.
    D. M. Mousdale and J. R. Coggins, FEBS Lett. 205, 328 (1986).CrossRefGoogle Scholar
  217. 217.
    P. A. Bartlett, in: The Shikimic Acid Pathway ( E. E. Conn, ed.), p. 119, Plenum Press, New York (1986).CrossRefGoogle Scholar
  218. 218.
    H. Bickel and G. Schultz, Phytochemistry 18, 498 (1979).CrossRefGoogle Scholar
  219. 219.
    P. A. Bartlett, U. Maitra, and P. M. Chouinard, J. Am. Chem. Soc. 108, 8068 (1986).CrossRefGoogle Scholar
  220. 220.
    D. L. Pompliano, L. M. Reimer, S. Myrvold, and J. W. Frost, J. Am. Chem. Soc. 111, 1866 (1989).CrossRefGoogle Scholar
  221. 221.
    E. W. Logusch, Tetrahedron Lett. 29, 6055 (1988).CrossRefGoogle Scholar
  222. 222.
    S. Fushiya, K. Maeda, T. Funayama, and S. Nozoe, J. Med. Chem. 31, 480 (1988).PubMedCrossRefGoogle Scholar
  223. 223.
    A. Cornish-Bowden, FEBS Lett. 203, 3 (1986).PubMedCrossRefGoogle Scholar
  224. 224.
    J. R. Coggins, in: Biotechnology and Crop Improvement and Protection (P. R. Day, ed.), British Crop Protection Council Monograph No. 34, p. 101 (1986).Google Scholar
  225. 225.
    A. C. Baillie, J. R. Corbett, J. R. Dowsett, and P. McCloskey, Pestic. Sci. 3, 113 (1972).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1991

Authors and Affiliations

  • David M. Mousdale
    • 1
  • John R. Coggins
    • 1
  1. 1.Department of BiochemistryUniversity of GlasgowGlasgowUK

Personalised recommendations