Advertisement

Complexation of iron by siderophores a review of their solution and structural chemistry and biological function

  • Kenneth N. Raymond
  • Gertraud Müller
  • Berthold F. Matzanke
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 123)

Keywords

Hydroxamic Acid Protonation Constant M6ssbauer Spectrum Iron Removal Mugineic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

X References

  1. 1.
    Twort, F. W., Ingram, G. L. Y.: Proc. Roy. Soc. Ser. B. Biol. Sci. 84, 517 (1912)Google Scholar
  2. 2.
    Francis, J., Madinaveitia, J., Macturk, H. M., Snow, G. A.: Nature 163, 365 (1949)Google Scholar
  3. 3.
    Francis, J., Macturk, H. M., Madinaveitia, J., Snow, G. A.: Biochem. J. 55, 596 (1953)Google Scholar
  4. 4.
    Snow, G. A.: J. Chem. Soc., 4080 (1954)Google Scholar
  5. 5.
    For a complete chronicle of the mycobactins see: Snow, G. A.: Bacteriol. Rev. 34, 99 (1970)Google Scholar
  6. 6.
    Horowitz, N. H., Charlang, G., Horn, G., Williams, N. P.: J. Bacteriol. 127, 135 (1976)Google Scholar
  7. 7.
    See, for example, Glynn, A. A.: Sym. Soc. Gen. Microbiol. 22 75 (1972); Rogers, H. J.: Infect. Immun. 7, 445 (1973)Google Scholar
  8. 8.
    Schroth, M. N., Hancock, J. G.: Science 216, 1376 (1982)Google Scholar
  9. 9.
    Olsen, R. A., Clark, R. B., Bennett, J. H.: Am. Scientist 69, 378 (1981)Google Scholar
  10. 10.
    Anderson, W. F., Hiller, M. C. (Ed.): Development of Iron Chelators for Clinical Use, Bethesda, Maryland 1975Google Scholar
  11. 11.
    Anderson, W. F.: ACS Symp. Series 140, 251, 1980Google Scholar
  12. 12.
    Raymond, K. N., Smith, W. L.: Structure and Bonding 43, 159, 1981Google Scholar
  13. 13.
    Development of Iron Chelators for Clinical Use. Martell, A. E., Anderson, W. F., Badman, D. G., Eds., Elsevier/North-Holland, New York, 1981Google Scholar
  14. 14.
    Raymond, K. N., Pecoraro, V. L., Harris, W. R., Carrano, C. J. in: Environmental Migration of Long-Lived Radionuclides, IAEA, Vienna 1982, p. 571Google Scholar
  15. 15.
    Bulman, R. A.: Structure and Bonding 34, 39, 1978Google Scholar
  16. 16.
    Raymond, K. N., Chung, T. D. Y., Pecoraro, V. L., Carrano, C. J. in: The Biochemistry and Physiology of Iron, Saltman, P., Hegenauer, J., Eds., Elsevier Biomedical, New York 1982, p. 649Google Scholar
  17. 17.
    Tidmarsh, G. F., Klebba, Ph. E., Rosenberg, L. L.: J. Inorg. Biochem. 18, 161 (1983)Google Scholar
  18. 18.
    Neilands, J. B.: Ann. Rev. Nutr. 1, 27 (1981)Google Scholar
  19. 19.
    Neilands, J. B. (Ed.): Microbial Iron Metabolism, Academic Press, New York 1974Google Scholar
  20. 20.
    Emery, T.: Metal Ions in Biological Systems 7, 77 (1977)Google Scholar
  21. 21.
    Byers, B. R., Arcenaux, J. E. L. in: Microorganisms and Minerals, Weinberg, E. D., Ed., Marcel Dekker, New York 1977, p. 215Google Scholar
  22. 22.
    Lankfort, C. E.: CRC Crit. Rev. Microbiol. 2, 273 (1973)Google Scholar
  23. 23.
    Weinberg, E. D.: Microbiol. Rev. 42, 45 (1978)Google Scholar
  24. 24.
    Raymond, K. N., Harris, W. R., Carrano, C. J., Weitl, F. L.: ACS Symp. Ser. 140, 313, 1980Google Scholar
  25. 25.
    Waid, J. S. in: Soil Biochemistry, Paul, E. A., McLaren, A. D., Eds., Marcel Dekker, New York 1974, p. 65Google Scholar
  26. 26.
    Neilands, J. B.: Structure and Bonding 1, 59, 1966Google Scholar
  27. 27.
    Neilands, J. B. in: Inorganic Biochemistry, Eichhorn, G. L., Ed., Elsevier Sci. Publ. Co., Amsterdam 1973, p. 167Google Scholar
  28. 28.
    Neilands, J. B., Ratledge, C. in: Handbook of Microbiology, Vol. IV, Laskin, A. I., Lechevalier, H. A., Eds., CRC Press, Boca Raton, Florida 1982, p. 565Google Scholar
  29. 29.
    Neilands, J. B.: Ann. Rev. Biochem. 50, 715 (1981)Google Scholar
  30. 30.
    Harris, W. R., Carrano, C. J., Raymond, K. N.: J. Am. Chem. Soc. 101, 2722 (1979)Google Scholar
  31. 31.
    Adapa, S., Huber, P., Keller-Schierlein, W.: Helvetica Chimica Acta 65, 1818 (1982)Google Scholar
  32. 32.
    Hough, E., Rogers, D.: Biochem. Biophys. Res. Commun. 57, 73 (1974)Google Scholar
  33. 33.
    Neilands, J. B., Peterson, T., Leong, S. A.: ACS Symp. Ser. 140, 263, 1980Google Scholar
  34. 34.
    Teintze, M., Hossain, M. B., Barnes, C. I., Leong, J., van der Helm, D.: Biochemistry 20, 6446 (1981)Google Scholar
  35. 35.
    Teintze, M., Leong, J.: ibid. 20, 6457 (1981)Google Scholar
  36. 36.
    Carrano, C. J., Copper, S. R., Raymond, K. N.: J. Am. Chem. Soc. 101, 599 (1979)Google Scholar
  37. 37.
    Bell, S. J., Friedman, S. A., Leong, J.: Antimicrobial Agents and Chemotherapy 15, 384 (1979)Google Scholar
  38. 38.
    Latimer, W. M.: Oxidation Potentials, Prentice Hall, Englewood Cliffs, New Jersey 1952Google Scholar
  39. 39.
    Philson, S. B., Linás, M. J.: Biol. Chem. 257, 8086 (1982)Google Scholar
  40. 40.
    Philson, S. B., Llinás, M. J.: ibid. 257, 8081 (1982)Google Scholar
  41. 41.
    Hulcher, F. H.: Biochemistry 21, 4491 (1982)Google Scholar
  42. 42.
    Emery, T.: Biochim. Biophys. Acta 629, 382 (1980)Google Scholar
  43. 43.
    Frederick, C. B., Bentley, M. S., Shive, W.: Biochemistry 20, 2436 (1981)Google Scholar
  44. 44.
    Yancey, R. J., Finkelstein, R. A.: Infection Immunity 32, 600 (1981)Google Scholar
  45. 45.
    Cox, C. D., Graham, R.: J. Bacteriol. 137, 357 (1979)Google Scholar
  46. 46.
    McCullough, W. G., Merkal, R. S.: ibid. 137, 243 (1979)Google Scholar
  47. 47.
    Takemoto, T., Nomoto, K., Fushiya, S., Ouchi, R., Kusano, G., Hikino, H., Takagi, S., Matsuura, Y., Kakudo, M.: Proc. Japan. Acad. 54 Ser. B., 469, 1978Google Scholar
  48. 48.
    Sugiura, Y., Tanaka, H.: J. Am. Chem. Soc. 103, 6979 (1981)Google Scholar
  49. 49.
    Fushiya, S., Sato, Y., Nozoe, S.: Tetrahedron Lett. 21, 3071 (1980)Google Scholar
  50. 50.
    Nomoto, K., Yoshioka, H., Arima, M., Fushiya, S., Takagi, S., Takemoto, T.: Chimia 35, 249 (1981)Google Scholar
  51. 51.
    Budénínský, M., Budzikiewicz, H., Procházka, Ź., Ripperger, H., Roemer, A., Scholz, G., Schreiber K.: Phytochemistry 19, 2295 (1980)Google Scholar
  52. 52.
    Nienhuis, A. W., Anderson, W. F. in: Development of Iron Chelators for Clinical Use, Anderson, W. F., Hiller, M. C., Eds., Elsevier/North-Holland, New York 1981Google Scholar
  53. 53.
    Ellis, J. T., Schulman, I., Smith, C. H.: Am. J. Pathol. 30, 287 (1954)Google Scholar
  54. 54.
    Walker, R. J., Williams, R. in: Iron in Biochemistry and Medicine, Jacobs, A., Worwood, M., Eds., Academic Press, New York 1974, p. 596Google Scholar
  55. 55.
    Wohler, F.: Acta Haematol. 30, 65 (1963)Google Scholar
  56. 56.
    Barry, M., Flynn, D. M., Letsky, E. A., Risdon, R. A.: Br. Med. J. 1, 16 (1974)Google Scholar
  57. 57.
    Pippard, M. J., Callender, S. T., Letsky, E. A., Weatherall, D. J.: Lancet, 1178 (1978)Google Scholar
  58. 58.
    Hallberg, L., Hedenberg, L.: J. Haematol. 2, 67 (1965)Google Scholar
  59. 59.
    Morgan, E. H.: Biochim. Biophys. Acta 244, 103 (1971)Google Scholar
  60. 60.
    Waxman, H. S., Brown, E. B.: Progr. Hematol. 6, 338 (1969)Google Scholar
  61. 61.
    Maehr, H.: Pure Appl. Chem. 28, 603 (1971)Google Scholar
  62. 62.
    Emery, T.: Adv. Enzymol. Relat. Areas Mol. Biol. 35, 135 (1971)Google Scholar
  63. 63.
    Zähner, H., Diddens, H., Keller-Schierlein, W., Naegeli, H. U.: Jap. J. Antibiotics 30, 5 (1977)Google Scholar
  64. 64.
    Hartmann, A., Fiedler, H.-P., Braun, V.: Eur. J. Biochem. 99, 517 (1979)Google Scholar
  65. 65.
    Braun, V., Hantke, K. in: Organization of Procariotic Cell Membranes, Vol. II, Ghosh, B. K., Ed., CRC Press, Boca Ratan, Florida 1981, pp. 1–73Google Scholar
  66. 66.
    Fiss, E. H., Stanley-Samuelson, P., Neilands, J. B.: Biochemistry 21, 4517 (1982)Google Scholar
  67. 67.
    Bickel, H., Hall, E., Keller-Schierlein, W., Prelog, V., Vischet, E., Wettstein, A.: Helvet. Chimica Acta 43, 2129 (1960)Google Scholar
  68. 68.
    Atkins, C. L., Neilands, J. B.: Biochemistry 7, 3734 (1968)Google Scholar
  69. 69.
    Diekmann, H.: Arch. Mikrobiol. 73, 65 (1970)Google Scholar
  70. 70.
    Keller-Schierlein, W., Diekmann, H.: Helv. Chim. Acta 53, 2035 (1970)Google Scholar
  71. 71.
    Emery, T.: Biochemistry 4, 1410 (1965)Google Scholar
  72. 72.
    Sayer, J. M., Emergy, T.: ibid. 7, 184 (1968)Google Scholar
  73. 73.
    Diekmann, H.: Angew. Chem. 7, 551 (1968)Google Scholar
  74. 74.
    Widmer, J., Keller-Schierlein, W.: Helv. Chim. Acta 57, 1904 (1974)Google Scholar
  75. 75.
    Keller-Schierlein, W.: ibid. 52, 603 (1969)Google Scholar
  76. 76.
    Naegeli, H. U., Keller-Schierlein, W.: ibid. 61, 2088 (1978)Google Scholar
  77. 77.
    Isowa, Y., Takashima, T., Ohmori, M., Kurita, H., Sato, M., Mori, K.: Bull. Chem. Soc. Jap. 45, 1461 and 1464 (1972)Google Scholar
  78. 78.
    Isowa, Y., Takashima, T., Ohmori, M., Kurita, H., Sato, M., Mori, K.: ibid. 45, 1467 (1972)Google Scholar
  79. 79.
    Isowa, Y., Ohmori, M., Kurita, H.: ibid. 47, 215 (1974)Google Scholar
  80. 80.
    Maurer, P. J., Miller, M. J.: J. Am. Chem. Soc. 104, 3096 (1982)Google Scholar
  81. 81.
    Macham, L. P., Ratledge, C., Norton, J. C.: Infect. Immun. 12, 1242 (1975)Google Scholar
  82. 82.
    Macham, L. P., Ratledge, C.: J. Gen. Microbiol. 89, 379 (1975)Google Scholar
  83. 83.
    Lee, B. H., Miller, M. J.: J. Org. Chem. 48, 24 (1983)Google Scholar
  84. 84.
    Maurer, P. J., Miller, M. J.: J. Am. Chem. Soc. 105, 240 (1983)Google Scholar
  85. 85.
    Atkins, C. L.: Thesis, Univ. of California, Berkeley 1970Google Scholar
  86. 86.
    Smith, W. L., Raymond, K. N.: J. Am. Chem. Soc. 102, 1252 (1980)Google Scholar
  87. 87.
    Rodgers, S. J., Raymond, K. N.: J. Med. Chem. 26, 439 (1983)Google Scholar
  88. 88.
    Olson, R. K., Ramasamy, K., Emery, T.: J. Am. Chem. Soc. in pressGoogle Scholar
  89. 89.
    Carrano, C. J., Raymond, K. N.: ibid. 101, 5401 (1979)Google Scholar
  90. 90.
    Jacobs, A., White, G. P., Tait, G. P.: Biochem. Biophys. Res. Comm. 74, 1626 (1977)Google Scholar
  91. 91.
    Bergeron, R. J., Kline, S. G.: J. Am. Chem. Soc. 104, 4489 (1982)Google Scholar
  92. 92.
    Weitl, F. L., Raymond, K. N.: ibid. 101, 2728 (1979). Note in particular references for DCC mediated condensations of amino acids with unprotected catechols. According to this paper enterobactin synthesis (Ref. 98) was performed with protected catechols under the reaction conditions describedGoogle Scholar
  93. 93.
    Pollack, J. R., Neilands, J. B.: Biochem. Biophys. Res. Comm. 38, 989 (1971)Google Scholar
  94. 94.
    O'Brien, I. G., Gibson, F.: Biochem. Biophys. Acta 215, 393 (1970)Google Scholar
  95. 95.
    O'Brien, I. G., Cox, G. B., Gibson, F.: ibid. 237, 537 (1971)Google Scholar
  96. 96.
    Bryce, G. F., Weller, R., Brot, N.: Biochem. Biophys. Res. Comm. 42, 871 (1971)Google Scholar
  97. 97.
    Guterman, S. K., Morris, P. M., Tannenberg, W. J. K.: Gen. Pharmacol. 9, 123 (1978)Google Scholar
  98. 98.
    Corey, E. J., Battacharyya, S.: Tetrahedron Lett. 45, 3919 (1977)Google Scholar
  99. 99.
    Rastetter, W. H., Erickson, T. J., Venuti, M. C.: J. Org. Chem. 46, 3579 (1981)Google Scholar
  100. 100.
    Shanzer, A., Libman, J.: J. Chem. Soc., Chem. Commun., 846 (1983)Google Scholar
  101. 101.
    Harris, W. R., Weitl, F. L., Raymond, K. N.: ibid. 176 (1979)Google Scholar
  102. 102.
    Pecoraro, V. L., Weitl, F. L., Raymond, K. N.: J. Am. Chem. Soc. 103, 5133 (1981)Google Scholar
  103. 103.
    Weitl, F. L., Harris, W. R., Raymond, K. N.: J. Med. Chem. 22, 1281 (1979)Google Scholar
  104. 104.
    Venuti, M. C., Rastetter, W. H., Neilands, J. B.: ibid. 22, 123 (1979)Google Scholar
  105. 105.
    Lodge, G. S., Gaines, C. G., Arcenaux, J. E. L., Byers, B. R.: Biochem. Biophys. Res. Commun. 97, 1291 (1980)Google Scholar
  106. 106.
    Heidinger, S., Braun, V., Pecoraro, V. L., Raymond, K. N.: J. Bacteriol. 153, 109 (1983)Google Scholar
  107. 107.
    Collins, D. J., Lewis, C., Swan, J. M.: Aust. J. Chem. 27, 2593 (1974)Google Scholar
  108. 108.
    Corey, E. J., Hurt, S. D.: Tetrahedron Lett. 45, 3923 (1977)Google Scholar
  109. 109.
    Collins, D. J., Lewis, C., Swan, J. M.: Aust. J. Chem. 28, 673 (1975)Google Scholar
  110. 110.
    Hollifield, W. C., Jr., Neilands, J. B.: Biochemistry 17, 1922 (1978)Google Scholar
  111. 111.
    Tait, G. H.: Biochem. J. 146, 191 (1975)Google Scholar
  112. 112.
    Peterson, T., Falk, K.-E., Leong, S. A., Klein, M. P., Neilands, J. B.: J. Am. Chem. Soc. 102, 7715 (1980)Google Scholar
  113. 113.
    Harris, W. R., Raymond, K. N.: ibid. 101, 6534 (1979)Google Scholar
  114. 114.
    Grady, R. W., Graziano, J. H., Akers, K. A., Cerami, A. J.: Pharmacol. Exp. Ther. 196, 478 (1976)Google Scholar
  115. 115.
    Weitl, F. L., Raymond, K. N., Durbin, P. W.: J. Med. Chem. 24, 203 (1981)Google Scholar
  116. 116.
    Goldstein, A., Aronow, L., Kalman, S. K.: Principles of Drug Action, Wiley, New York, 1974Google Scholar
  117. 117.
    Weitl, F. L., Raymond, K. N.: J. Org. Chem. 46, 5234 (1981)Google Scholar
  118. 118.
    Raymond, K. N., Kappel, M. J., Pecoraro, V. L., Harris, W. R., Carrano, C. J., Weitl, F. L., Durbin, P. W. in: Actinides in Perspective, Edelstein, N. M., Ed., Pergamon Press, Oxford and New York 1982, pp. 491–507Google Scholar
  119. 119.
    Sofen, S. R., Cooper, S. R., Raymond, K. N.: Inorg. Chem. 18, 1611 (1979)Google Scholar
  120. 120.
    Weitl, F. L., Raymond, K. N.: J. Am. Chem. Soc. 102, 2289 (1980)Google Scholar
  121. 121.
    Kappel, M. J., Raymond, K. N.: submitted for publication in J. Am. Chem. Soc.Google Scholar
  122. 122.
    Harris, W. R., Carrano, C. J., Cooper, S. R., Sofen, S. R., Avdeef, A., McArdle, J. V., Raymond, K. N.: J. Am. Chem. Soc. 101, 6097 (1979)Google Scholar
  123. 123.
    Harris, W. R., Raymond, K. N., Weitl, F. L.: ibid. 103, 2667 (1981)Google Scholar
  124. 124.
    Harris, W. R., Carrano, C. J., Raymond, K. N.: ibid. 101, 2213 (1979)Google Scholar
  125. 125.
    Anderegg, G., L'Eplattenier, F., Schwarzenbach, G.: Helv. Chim. Acta 46, 1409 (1963)Google Scholar
  126. 126.
    Kappel, M. J., Raymond, K. N.: Inorg. Chem. 21, 3437 (1982)Google Scholar
  127. 127.
    Birus, M., Bradić, Z., Kugunžić, N., Pribanić, M.: Inorg. Chim. Acta 78, 87 (1983)Google Scholar
  128. 128.
    Monzyk, B., Crumbliss, A. L.: J. Am. Chem. Soc. 104, 4921 (1982)Google Scholar
  129. 129.
    Pecoraro, V. L., Wong, G. B., Kent, T. A., Huynh, B. H., Raymond, K. N.: ibid. 105, 4617 (1983)Google Scholar
  130. 130.
    Pecoraro, V. L., Harris, W. R., Wong, G. B., Carrano, C. J., Raymond, K. N.: ibid. 105, 4623 (1983)Google Scholar
  131. 131.
    Stover, B. J., Brunger, F. W.: Radiat. Res. 33, 381 (1968)Google Scholar
  132. 132.
    Welch, M. J., Welch, T. J. in: Radiopharmaceuticals, Supramanian, G., Roads, P. G., Copper, D. J., Sodd, R. C., Eds., Soc. of Nuclear Medicine, New York 1975, pp. 73–79Google Scholar
  133. 133.
    Clausen, J., Edeling, C. J., Fogh, J.: Cancer Res. 34, 1931 (1974)Google Scholar
  134. 134.
    Noujain, A. A., Lentle, B. C., Hill, J. R., Terner, U. K., Wong, H.: Int. J. Nucl. Med. Biol. 6, 193 (1979)Google Scholar
  135. 135.
    Shaiman, R. D.: Acta Crystallogr., Sect. H. H 32, 751 (1976)Google Scholar
  136. 136.
    Taylor, G. N., Williams, J. L., Roberts, L., Albertan, D. R., Shabestari, L.: Health Phys. 27, 285 (1974)Google Scholar
  137. 137.
    Edwards, G. L., Hayes, R. L.: J. Nucl. Med. 10, 103 (1969)Google Scholar
  138. 138.
    Harper, P. V.: Int. J. Appl. Rad. Isotopes 28, 5 (1977)Google Scholar
  139. 139.
    Gelb, M. H., Harris, D. C.: Arch. Biochem. Biophys. 200, 439 (1980)Google Scholar
  140. 140.
    Woodworth, R. C., Morallee, K. G., Williams, R. J. P.: Biochemistry 9, 839 (1970)Google Scholar
  141. 141.
    Pecoraro, V. L., Wong, G. B., Raymond, K. N.: Inorg. Chem. 21, 2209 (1982)Google Scholar
  142. 142.
    Lehninger, A. L.: Biochemie, Verlag Chemie Weinheim, 1979Google Scholar
  143. 143.
    Robinson, J. P., McArdle, J. V.: J. Inorg. Nucl. Chem. 43, 1951 (1981)Google Scholar
  144. 144.
    Rosenberg, H., Young, I. Y. in: Microbial Iron Metabolism, Neilands, J. B., Ed., Academic Press, New York 1974, pp. 67–82Google Scholar
  145. 145.
    Langman, L., Young, I. G., Trost, G., Rosenberg, H., Gibson, F.: J. Bacteriol. 112, 1142 (1972)Google Scholar
  146. 146.
    Bryce, G. F., Brot, N.: Biochemistry 11, 1708 (1972)Google Scholar
  147. 146. a)
    Ball, E. G., Chem, T. T.: J. Biol. Chem. 102, 691 (1933)Google Scholar
  148. 147.
    Mentasti, E., Pelizetti, E., Saini, G.: J. Chem. Soc. Dalton Trans., 2609 (1973); J. Inorg. Nucl. Chem. 38, 785 (1976)Google Scholar
  149. 148.
    Hider, R. C., Mohd-Nor, A. R., Silver, J., Morrison, I. E. G., Rees, L. V. C.: J. Chem. Soc. Dalton Trans., 609 (1981)Google Scholar
  150. 149.
    Howlin, B., Hider, R. C., Silver, J.: ibid. 1433 (1982)Google Scholar
  151. 150.
    Kipton, H., Powell, J., Taylor, M. C.: Aust. J. Chem. 35, 739 (1982)Google Scholar
  152. 151.
    Hider, R. C., Silver, J., Neilands, J. B., Morrison, I. E. G., Rees, L. V. G.: FEBS Lett. 102, 325 (1979)Google Scholar
  153. 152.
    Hamed, M. Y., Hider, R. C., Silver, J.: Inorg. Chim. Acta 66, 13 (1982)Google Scholar
  154. 153.
    Matzanke, B. F., Huynh, B. H., Raymond, K. N.: Paper in preparationGoogle Scholar
  155. 154.
    Harris, W. R., Pecoraro, V. L.: Biochemistry 22, 292 (1983)Google Scholar
  156. 155.
    Tufano, T. P., Pecoraro, V. L., Raymond, K. N.: Biochim. Biophys. Acta 668, 420 (1981)Google Scholar
  157. 156.
    Monzyk, K. B., Crumbliss, A. L.: Inorg. Chim. Acta 55, L 5 (1981)Google Scholar
  158. 157.
    Kazmi, S. A., McArdle, S. V.: Inorg. Biochem. 15, 153 (1981)Google Scholar
  159. 158.
    Monzyk, K. B., Crumbliss, A. L.: J. Am. Chem. Soc. 101, 6203 (1979)Google Scholar
  160. 159.
    Biruš, M., Kujundzić, N., Pribanić, M.: Inorg. Chim. Acta 55, 65 (1980)Google Scholar
  161. 160.
    Kazmi, S. A., McArdle, J. V.: J. Inorg. Nucl. Chem. 43, 3031 (1981)Google Scholar
  162. 161.
    Lovenberg, W., Buchanan, B. B., Rabinowtiz, J. C.: J. Biol. Chem. 236, 3899 (1963)Google Scholar
  163. 162.
    Basolo, F., Pearson, R. G. in: Mechanisms of Inorganic Reactions, 2nd Ed., John Wiley & Sons, Inc., New York 1967, p. 152Google Scholar
  164. 163.
    Emery, T., Hoffer, P. B.: J. Nucl. Med. 21, 935 (1980)Google Scholar
  165. 164.
    Tufano, T. P.: Ph. D. Dissertation, Univ. of California, Berkeley, California 1982Google Scholar
  166. 165.
    Tufano, T. P., Raymond, K. N.: J. Am. Chem. Soc. 103, 6617 (1981)Google Scholar
  167. 166.
    Raymond, K. N., Tufano, T. P. in: The Biological Chemistry of Iron, Dunford, H. B., Dolphin, D., Raymond, K. N., Seiker, L., Eds., D. Reidel Publishing, Boston, London 1982, pp. 85–105Google Scholar
  168. 167.
    Olson, D. C., Margerum, D. W.: J. Am. Chem. Soc. 85, 297 (1963)Google Scholar
  169. 168.
    Wickmann, H. H., Klein, M. P., Shirley, D. A.: J. Chem. Phys. 42, 2113 (1965)Google Scholar
  170. 169.
    Dowsing, R. D., Gibson, J. F.: ibid. 50, 294 (1968)Google Scholar
  171. 170.
    Wickmann, H. H., Klein, M. P., Shirley, D. A.: Phys. Rev. 152, 345 (1966)Google Scholar
  172. 171.
    Bock, J. L., Lang, G.: Biochim. Biophys. Acta 264, 245 (1972)Google Scholar
  173. 172.
    Spartalian, K., Osterhuis, W. T., Neilands, J. B.: J. Chem. Phys. 62, 3538 (1975)Google Scholar
  174. 173.
    Ehrenberg, A.: Nature 178, 379 (1956)Google Scholar
  175. 174.
    Raymond, K. N., Abu-Dari, K., Sofen, S. R.: ACS Symp. Ser. 119, 133, 1980Google Scholar
  176. 175.
    Leong, J., Raymond, K. N.: J. Am. Chem. Soc. 96, 6628 (1974)Google Scholar
  177. 176.
    Leong, J., Raymond, K. N.: ibid. 97, 293 (1975)Google Scholar
  178. 177.
    Müller, G., Barclay, S. J., Raymond, K. N.: Manuscript in preparationGoogle Scholar
  179. 178.
    Isied, S. S., Kuo, G., Raymond, K. N.: J. Am. Chem. Soc. 98, 1763 (1976)Google Scholar
  180. 179.
    Leong, J., Bell, S. J.: Inorg. Chem. 17, 1886 (1978)Google Scholar
  181. 180.
    Hossain, M. B., Eng-Wilmot, D. L., Loghry, R. A., van der Helm, D.: J. Am. Chem. Soc. 102, 5766 (1980)Google Scholar
  182. 181.
    van der Helm, D., Baker, J. R., Eng-Wilmot, D. L., Hossain, M. B., Loghry, R. A.: ibid. 102, 4224 (1980)Google Scholar
  183. 182.
    Raymond, K. N. in: Advances in Chemistry Series No. 162, Bioinorganic Chemistry-II, J. Am. Chem. Soc., 1977, p. 33Google Scholar
  184. 183.
    Abu-Dari, K., Ekstrand, J. D., Freyberg, D. P., Raymond, K. N.: Inorg. Chem. 18, 108 (1979)Google Scholar
  185. 184.
    Leong, J., Raymond, K. N.: J. Am. Chem. Soc. 96, 1757 (1974)Google Scholar
  186. 185.
    Zalkin, A., Forrester, J. D., Templeton, D. H.: ibid. 88, 1810 (1966)Google Scholar
  187. 186.
    Norrestam, R., Stensland, B., Brándén, C. J.: J. Mol. Biol. 99, 501 (1975)Google Scholar
  188. 187.
    van der Helm, D., Poling, M.: J. Am. Chem. Soc. 98, 82 (1976)Google Scholar
  189. 188.
    Carrano, C. J., Raymond, K. N.: ibid. 100, 5371 (1978)Google Scholar
  190. 189.
    Barclay, S. J., Huynh, B. H., Raymond, K. N.: Paper in preparationGoogle Scholar
  191. 190.
    Barclay, S. J., Riley, P. E., Raymond, K. N.: J. Am. Chem. Soc. 104, 6802 (1982)Google Scholar
  192. 191.
    White, D. L., Scarrow, R. C., Raymond, K. N.: Paper in preparationGoogle Scholar
  193. 192.
    Abu-Dari, K., Raymond, K. N.: J. Am. Chem. Soc. 99, 2003 (1977)Google Scholar
  194. 193.
    Klebba, P. E., McIntosh, M., Neilands, J. B.: J. Bacteriol. 149, 880 (1982)Google Scholar
  195. 194.
    Leong, J., Neilands, J. B., Raymond, K. N.: Biochem. Biophys. Res. Commun. 60, 1066 (1974)Google Scholar
  196. 195.
    Arcenaux, J. E. L., Davis, W. B., Downer, D. N., Haydon, A. H., Byers, B. R.: J. Bacteriol. 115, 919 (1973)Google Scholar
  197. 196.
    Leong, J., Neilands, J. B.: ibid. 126, 823 (1976)Google Scholar
  198. 197.
    Brown, K. A., Ratledge, C.: FEBS Lett. 53, 262 (1975)Google Scholar
  199. 198.
    Arcenaux, J. E. L., Byers, B. R.: J. Bacteriol. 141, 715 (1980)Google Scholar
  200. 199.
    Gaines, C. G., Lodge, J. S., Arcenaux, J. E. L., Byers, B. R.: ibid. 148, 527 (1981)Google Scholar
  201. 200.
    Straka, J. G., Emergy, T.: Biochim. Biophys. Acta 569, 277 (1979)Google Scholar
  202. 201.
    Lodge, J. S., Gaines, C. G., Arcenaux, J. E. L., Byers, B. R.: J. Bacteriol. 149, 771 (1982)Google Scholar
  203. 202.
    Bauminger, E. R., Cohen, S. G., Dickson, D. P. E., Levy, A., Ofer, S., Yariv, J.: Biochim. Biophys. Acta 623, 237 (1980)Google Scholar
  204. 203.
    McIntosh, M. A., Earhart, C. F.: Biochem. Biophys. Res. Commun. 70, 315 (1976)Google Scholar
  205. 204.
    Braun, V., Hancock, R. E. W., Hantke, K., Hartmann, A.: J. Supramol. Struct. 5, 37 (1976)Google Scholar
  206. 205.
    Coulton, W.: Biochim. Biophys. Acta 717, 154 (1982)Google Scholar
  207. 206.
    Ernst, J. F., Winkelmann, G.: ibid. 500, 27 (1977)Google Scholar
  208. 207.
    Müller, G., Winkelmann, G.: FEMS Microbiol. Lett. 10, 327 (1981)Google Scholar
  209. 208.
    Neilands, J. B., Erickson, J., Rastetter, W. H.: J. Biol. Chem. 256, 3831 (1981)Google Scholar
  210. 209.
    Schneider, R., Hartmann, A., Braun, V.: FEMS Microbiol. Lett. 11, 115 (1981)Google Scholar
  211. 210.
    Müller, G., Raymond, K. N.: Manuscript in preparationGoogle Scholar
  212. 211.
    Coulton, J. W., Naegeli, H.-U., Braun, V.: Eur. J. Biochem. 99, 39 (1979)Google Scholar
  213. 212.
    Wayne, R., Frick, K., Neilands, J. B.: J. Bacteriol. 126, 7 (1976)Google Scholar
  214. 213.
    Winkelmann, G., Braun, V.: FEMS Microbiol. Lett. 11, 237 (1981)Google Scholar
  215. 214.
    Wong, G. B., Kappel, M. J., Raymond, K. N., Matzanke, B., Winkelmann, G.: J. Am. Chem. Soc. 105, 810 (1983)Google Scholar
  216. 215.
    Schwarzenbach, G., Schwarzenbach, K.: Helv. Chim. Acta 46, 1390 (1963)Google Scholar
  217. 216.
    Martell, A. E., Smith, R. M.: Critical Stability Constants, Plenum Press, New York 1977Google Scholar
  218. 217.
    Cooper, S. R., McArdle, J. V., Raymond, K. N.: Proc. Natl. Acad. Sci. USA 75, 3551 (1978)Google Scholar
  219. 218.
    Anderson, B. F., Buckingham, D. A., Robertson, G. B., Webb, J., Murray, K. S., Clark, D. E.: Nature 262, 772 (1976)Google Scholar
  220. 219.
    Letkeman, P., Martell, A. E., Motekaitis, R. J.: Coord. Chem. 10, 47 (1980)Google Scholar
  221. 220.
    Harris, W. R., Martell, A. E.: Inorg. Chem. 15, 713 (1976)Google Scholar
  222. 221.
    Chasteen, N. D.: Coord. Chem. Rev. 22, 1 (1977)Google Scholar
  223. 222.
    Aasa, R., Malmström, B. G., Saltman, P., Vanngard, T.: Biochim. Biophys. Acta 75, 203 (1963)Google Scholar
  224. 223.
    Emery, T.: Biochemistry 5, 3694 (1966)Google Scholar
  225. 224.
    Ecker, D. J., Passavant, C. W., Emery, T.: Biochim. Biophys. Acta 720, 242 (1982)Google Scholar
  226. 225.
    Keller-Schierlein, W., Deér, A.: Helv. Chim. Acta 46, 1907 (1963)Google Scholar
  227. 226.
    Rastetter, W. H., Erickson, T. J., Venuti, M. C.: J. Org. Chem. 46, 3579 (1981)Google Scholar
  228. 227.
    Rogers, H. J., Synge, C., Kimber, B., Bayley, P. M.: Biochim. Biophys. Acta 497, 548 (1977)Google Scholar

Copyright information

© Springer-Verlag 1984

Authors and Affiliations

  • Kenneth N. Raymond
    • 1
  • Gertraud Müller
    • 1
  • Berthold F. Matzanke
    • 1
  1. 1.Department of ChemistryUniversity of CaliforniaBerkeleyUSA

Personalised recommendations