Advertisement

Chemische Modifikationen von Proteinen

  • Felix Haurowitz
Part of the Handbuch der Physiologisch- und Pathologisch-Chemischen Analyse book series (HOPPE-SEYLER, volume 4)

Zusammenfassung

Unter den Aminosäuren, welche das Proteinmolekül bilden, sind einige mit reaktionsf ähigen Seitenketten. Durch Oxydation, Reduktion, Acylierung, Alkylierung und durch andere Reaktionen dieser Seitenketten erhält man chemisch modifizierte Proteine. Die. meisten der in solchen Reaktionen angewandten Reagentien greifen an mehreren Typen von Seitenketten an. Es gibt derzeit keine Reagentien, welche nur mit freien Aminogruppen oder nur mit Hydroxylgruppen reagieren. Es ist daher nicht möglich, die modifizierten Proteine auf Grund der reagierenden Atomgruppen einzuteilen.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. 1.
    Yang, J. T., and J. F. Foster: Am. Soc. 76, 1588 (1954).Google Scholar
  2. 2.
    Scheraga, H. A., and L. Mandelkern: Am. Soc. 75, 179 (1953).Google Scholar
  3. 3.
    Katz, S.,: Diss. phil. Harvard University 1950. [Neurath-Bailey, Proteins, Bd IB, S. 846].Google Scholar
  4. 4.
    Barbu, E., and M. Joly: Discuss. Faraday Soc. 13, 77 (1953).Google Scholar
  5. 5.
    Mizushima, S.: Nature 164, 918 (1949).PubMedGoogle Scholar
  6. 6.
    Steinhardt, J.: Kgl. danske Vid. Selsk. mat.-fysiske Medd. 14, no. 11 (1937).Google Scholar
  7. 7.
    Levy, M., and A. E. Benaglia: J. biol. Ch. 186, 829 (1950).Google Scholar
  8. 8.
    Kuhn, W., u. H. Kuhn: Heiv. 28, 1539 (1945).Google Scholar
  9. 9.
    Lumry, R., and H. Eyring: J. physic. Chem. 58, 110 (1954).Google Scholar
  10. 1.
    Stary, Z.: H. 144, 147 (1925); 186, 137 (1930).Google Scholar
  11. 2.
    MirsxY, A. E., and M. L. Anson: J. gen. Physiol. 19, 439 (1936).Google Scholar
  12. 3.
    Kuhn, R., u. P. Desnuelle: H. 251, 14 (1938).Google Scholar
  13. 4.
    Brand, E., and B. Kassel: J. biol. Ch. 133, 437 (1949).Google Scholar
  14. 5.
    Hellerman, L., F. P. Chinard and V. R. Dietz: J. biol. Ch. 147, 443 (1943).Google Scholar
  15. 6.
    Hess, W. C., and M. X. Sullivan: J. biol. Ch. 151, 635 (1943).Google Scholar
  16. 7.
    Herriott, R. M.: Adv. Protein Chem. 3, 170 (1947).Google Scholar
  17. 8.
    Bettelheim, F. R.: J. biol. Ch. 212, 235 (1955).Google Scholar
  18. 9.
    Bentley, H. R., E. E. Mcdermott, T. Moran, J. Pace and J. K. Whitehead: Ptoc. R. Soc. London (B) 137, 402 (1950).Google Scholar
  19. 1.
    Sizer, I. W.: J. biol. Ch. 169, 303 (1947).Google Scholar
  20. 2.
    Edman, P.: J. biol. Ch. 168, 367 (1947).Google Scholar
  21. 3.
    Boissonas, R. A.: Nature 171, 304 (1953).Google Scholar
  22. 4.
    Thompson, A. R.: Biochim. biophysica Acta, N. Y. 15, 299 (1953).Google Scholar
  23. 5.
    Fruton, J. S., and H. Clarke: J. biol. Ch. 106, 667 (1934).Google Scholar
  24. 6.
    Goddard, D. R., and L. MicxAelis: J. biol. Ch. 112, 361 (1935).Google Scholar
  25. 7.
    Ward, W. H., L. M. High and H. P. Lundgren: J. polymer Sci. 1, 22 (1946).Google Scholar
  26. 8.
    Mautaner, J.: H. 78, 28 (1912).Google Scholar
  27. 9.
    Walker, E.: Biochem. J. 19, 1082 (1925).PubMedGoogle Scholar
  28. 10.
    Clarke, H. T.: J. biol. Ch. 97, 235 (1932).Google Scholar
  29. 11.
    Blackburn, S., R. Consden and H. Phillipps: Biochem. J. 38, 23 (1944).Google Scholar
  30. 12.
    Fromageot, C., M. JuTisz, D. Meyer et L. Penasse: Biochim. biophysica Acta, N. Y. 6, 283 (1950/51).Google Scholar
  31. 13.
    Karrer, P., u. B. J. R. Nicolaus: Hely. 35, 1581 (1952).Google Scholar
  32. 14.
    Jutisz, M., D. Meyer et L. Penasse: Bull. Soc. chim. France 1954, 1087.Google Scholar
  33. 15.
    Chibnall, A. C., and M. W. Rees: Biochem. J. 48, Xlvii (1951).Google Scholar
  34. 16.
    Grassmann, W., H. HÖRmann U. H. Endres: H. 296, 208 (1954).Google Scholar
  35. 1.
    Crawiiall, J. C., and D. E. Elliot: Nature 175, 299 (1955).Google Scholar
  36. 2.
    Chibnall, A. C., and M. W. Rees: Biochem. J. 48, Xlvii (1951).Google Scholar
  37. 3.
    Hauroitz, F.: H. 256, 28 (1938).Google Scholar
  38. 4.
    Herriott, R. M., and J. H. Northrop: J. gen. Physiol. 18, 35 (1934); 19, 383 (1936).Google Scholar
  39. 5.
    Neuberger, A.: Biochem. J. 32, 1452 (1938).PubMedGoogle Scholar
  40. 6.
    Olcott, H. S., and H. Fraenkel-Conrat: Chem. Reviews 41, 151 (1947).Google Scholar
  41. 7.
    Baddiley, J., R. A. Kekwick and E. M. Train: Nature 170, 968 (1952).PubMedGoogle Scholar
  42. 8.
    Goldschmidt, S.: H. 183, 244 (1929).Google Scholar
  43. Goldschmidt, S., U. W. SchÖN: H. 165, 279 (1927).Google Scholar
  44. 9.
    Felix, K., u. A. Lang: H. 188, 96 (1930).Google Scholar
  45. 10.
    Abderhalden, E., u. H. Brockmann: B. Z. 226, 209 (1930).Google Scholar
  46. 11.
    Mellon, E. F., A. H. Korn and S. R. HoovER: Am. Soc. 69, 827 (1947).Google Scholar
  47. 12.
    GuRin, S., and H. T. Clarke: J. biol. Ch. 107, 395 (1934).Google Scholar
  48. 13.
    Christensen, H. N.: J. biol. Ch. 160, 75 (1945).Google Scholar
  49. 14.
    Edlbacher, S., u. B. Fuchs: H. 144, 133 (1921).Google Scholar
  50. 15.
    Udenfriend, S., and S. F. Velick: J. biol. Ch. 190, 733 (1951).Google Scholar
  51. 16.
    Weber, G.: Biochem. J. 51, 145, 155 (1952).PubMedGoogle Scholar
  52. 17.
    Steiner, R. F.: Arch. Biochem. 46, 291 (1953).PubMedGoogle Scholar
  53. 1.
    Stahmann, M. A., and R. B. Becker: Am. Soc. 74, 2698 (1952).Google Scholar
  54. 2.
    Fraenkel-Conrat, H.: Biochim. biophysica Acta, N. Y. 10, 180 (1953).Google Scholar
  55. 3.
    LettrÉ, H., u. R. Haas: H. 266, 31, 267, 108 (1940).Google Scholar
  56. 4.
    Timasheff, S. N., and F. F. Nord: Arch. Biochem. 31, 320 (1951).PubMedGoogle Scholar
  57. 5.
    SchÖBerl, A.: Angew. Chem. (A) 60, 7 (1948).Google Scholar
  58. 6.
    Clutton, R. F., C. R. Harington and M. E. YuIll: Biochem. J. 32, 1111 (1938).Google Scholar
  59. 7.
    Micheel, F., u. K. Schmidt: Makromol. Chem. 3, 210, 217, 247 (1949).Google Scholar
  60. 8.
    Tracy, A. H., and W. F. Ross: J. biol. Ch. 146, 63 (1942).Google Scholar
  61. 9.
    Olcott, H. S., and H. Fraenkel-Conrat: Chem. Reviews 41, 151, s. bes. S. 177 (1947).Google Scholar
  62. 10.
    Hopkins, S. J., and A. Wormall: Biochem. J. 28, 2125 (1934).PubMedGoogle Scholar
  63. 11.
    Fraenkel-Conrat, H.: J. biol. Ch. 152, 385 (1944).Google Scholar
  64. 12.
    Fieser, L. F., and H. J. Creech: Amer. J. Cancer 30, 555 (1937).Google Scholar
  65. 12.
    Creech, H. J., H. F. H.Vas and J. Andre: Cancer Res. 13, 335 (1953).Google Scholar
  66. 13.
    Creech, H. J., and R. M. Peck: Am. Soc. 74, 463, 468 (1952); 75, 2364 (1953).Google Scholar
  67. 14.
    Coons, A. H., and M. H. Kaplan: J. exp. Med. 91, 1 (1950).PubMedGoogle Scholar
  68. 15.
    Roche, J., R. Michel et J. Schiller: Cr. 219, 38 (1944).Google Scholar
  69. 18.
    Edman, P.: Acta chem. stand. 4, 277, 283 (1950).Google Scholar
  70. 1.
    Edman, P.: Acta chem. scand. 4, 277, 283 (1950).Google Scholar
  71. 2.
    Dautrevaux, M., et G. Biserte: Cr. 240, 1153 (1955).Google Scholar
  72. 3.
    Landmann, N.: Am. Soc. 75, 3638 (1953).Google Scholar
  73. 4.
    Reith, W. S., and N. M. Waldron: Biochem. J. 56, 111, 116 (1954).PubMedGoogle Scholar
  74. 5.
    Schramm, G., u. G. W. Schneider: Z. Naturforsch. 9b, 209 (1954).Google Scholar
  75. 6.
    Reitz, H. C., R. E. Ferrel, H. Fraenkel-Conrat and H. S. Olcott: Am. Soc. 68, 1024 (1946).Google Scholar
  76. Elliott, D. F.: Biochem. J. 50, 542 (1952).PubMedGoogle Scholar
  77. 8.
    Mayer, M., and M. Heidelberger: Am. Soc. 68, 17 (1946).Google Scholar
  78. 9.
    Rimington, C.: Biochem. J. 21, 272 (1927).PubMedGoogle Scholar
  79. 10.
    Ferrel, R. E., H. S. Olcott and H. Fraenkel-Conrat: Am. Soc. 70, 2101 (1948).Google Scholar
  80. 11.
    Grabar, P., M. Pacht et E. Bourland: Bull. Soc. Chim. biol. 33, 690 (1951).Google Scholar
  81. 12.
    Balls, A. K., and E. F. Jansen: Adv. Enzymol. 13, 321 (1952).Google Scholar
  82. 13.
    Jansen, E. F., A. L. Curl and A. K. Balls: J biol. Ch. 190, 557 (1951).Google Scholar
  83. 1.
    Boursnell, J. C., and E. C. Webb: Nature 164, 875 (1949).PubMedGoogle Scholar
  84. 2.
    Michel, H. O., and S. Krop: J. biol. Ch. 190, 119 (1951).Google Scholar
  85. 3.
    Jansen, E. F., M. D. F. Nutting, R. Jang and A. K. Balls: J. biol. Ch. 179, 189 (1949).Google Scholar
  86. 4.
    Jansen, E. F., A. L. Curl and A. K. Balls: J. biol. Ch. 190, 557 (1951).Google Scholar
  87. 5.
    Roche, J., et M. Mourgue: Cr. 226, 1848 (1948).Google Scholar
  88. 6.
    Wormall, A.: J. exp. Med. 51, 295 (1930).PubMedGoogle Scholar
  89. 7.
    Leonis, J., et A. Levy: Bull. Soc. Chim. biol. 33, 779 (1951).Google Scholar
  90. 8.
    Philpot, J. S. L., and P. A. Small: Biochem. J. 32, 542 (1938).PubMedGoogle Scholar
  91. 9.
    Maurer, P. H., and M. Heidelberger: Am. Soc. 73, 2070, 2072, 2076 (1951).Google Scholar
  92. 10.
    Eagle, H.: Proc. Soc. exp. Biol. Med. 34, 39 (1936).Google Scholar
  93. 11.
    Herriott, R. M.: Adv. Protein Chem. 3, 212 (1947).Google Scholar
  94. 12.
    Weill, C. E., and M. L. Caldwell: Am. Soc. 67, 212 (1945).Google Scholar
  95. 13.
    Edlbacher, S.: H. 112, 80 (1921).Google Scholar
  96. 14.
    Haurowitz, F.: H. 256, 28 (1938).Google Scholar
  97. 15.
    Saroff, H. A., N. R. Rosenthal, E. R. Adamik, N. Hages and H. A. Scheraga: J. biol. Ch. 205, 255 (1953).Google Scholar
  98. 16.
    Charles, A. F., and D. A. Scott: Trans. R. Soc. Canada (V) 26, 335 (1932).Google Scholar
  99. 17.
    Herriott, R. M.: Adv. Protein Chem. 3, 1 (1947).Google Scholar
  100. 18.
    Kuhn, R., u. H. W. RÜLins: B. 85, 38 (1952).Google Scholar
  101. 19.
    Bowman, R. E.: Soc. 1950, 1350.Google Scholar
  102. 20.
    Ingram, V. M.: J. biol. Ch. 202, 201 (1953).Google Scholar
  103. 1.
    Charles, A. F., and D. A. Scott: Trans. R. Soc. Canada (V) 26, 335 (1932).Google Scholar
  104. 2.
    Fraenkel-Conrat, H., and H. S. Olcott: J. biol. Ch. 161, 259 (1945).Google Scholar
  105. 3.
    Mommaerts, W. F. H. M., and H. Neurath: J. biol. Ch. 185, 909 (1950).Google Scholar
  106. 4.
    Bowman, R. E.: Soc. 1950, 1350.Google Scholar
  107. 5.
    Ingram, V. M.: J. biol. Ch. 202, 201 (1953).Google Scholar
  108. 6.
    Herriott, R. M.: Adv. Protein Chem. 3, 1 (1947).Google Scholar
  109. 7.
    Kuhn, R., u. H. W. RüLins: B. 85, 38 (1952).Google Scholar
  110. 8.
    Rapkine, L.: C. R. Soc. Biol. 112, 790 (1933).Google Scholar
  111. 9.
    Smythe, C. V.: J. biol. Ch. 114, 60 (1936).Google Scholar
  112. 10.
    Barron, E. S. G., and T. P. Singer: Science, N. Y. 97, 356 (1943).Google Scholar
  113. 11.
    Michaelis, L., and M. Schubert: J. biol. Ch. 106, 331 (1934).Google Scholar
  114. 12.
    Olcott, H. S., and H. Fraenkel-Conrat: Chem. Reviews 41, 151 (1947).Google Scholar
  115. 13.
    Sanger, F.: Biochem. J. 39, 507 (1946).Google Scholar
  116. 14.
    Fraenkel-Conrat, H.: J. biol. Ch. 154, 227 (1944).Google Scholar
  117. 15.
    Gaunt, W. E., and A. Wormall: Biochem. J. 33, 908 (1939).PubMedGoogle Scholar
  118. 16.
    Desreux, V., E. Fredericq et P. Fischer: Bull. Soc. Chim. biol. 28, 7 (1946).Google Scholar
  119. 17.
    Olcott, H. S., and H. Fraenkel-Conrat: Chem. Reviews 41, 186 (1947).Google Scholar
  120. 18.
    Banks, T. E., S. C. Boursnell, C. E. Francis, F. L. Hopwood and A. Wormall: Biochem. J. 40, 745 (1946).Google Scholar
  121. 18.
    Berenblum, I., and A. Wormall: Biochem. J. 33, 908 (1939).Google Scholar
  122. 20.
    Fruton, J. S., W. H. Stein and S. Moore: J. org. Chem. 11, 559, 691 (1946).Google Scholar
  123. 21.
    Carpenter, F. H., J. L. WooD, C. M. Stevens and V. DU Vigneaud: Am. Soc. 70, 2551 (1948).Google Scholar
  124. 1.
    Herriott, R. M., M. L. Anson and J. H. Northrop: J. gen. Physiol. 30, 185 (1946).PubMedGoogle Scholar
  125. 2.
    Fruton, J. S., W. H. Stein and S. Moore: J. org. Chem. 11, 559, 691 (1946).Google Scholar
  126. 3.
    Banks, T. E., S. C. Boursnell, C. E. Francis, F. L. HopwooD and A. Wormall: Biochem. J. 40, 745 (1946).Google Scholar
  127. 4.
    Francis, G. E., W. Mulligan and A. Wormall: Biochem. J. 60, 363 (1955).PubMedGoogle Scholar
  128. 5.
    Watkins, W. M., and A. Wormall: Biochem. J. 51, 577 (1951).Google Scholar
  129. 5.
    Auerbach, C., and J. M. RoBson: Nature 157, 302 (1946).Google Scholar
  130. 6.
    Stocken, L. A., and R. H. S. Thompson: Physiol. Rev. 29, 168 (1949).PubMedGoogle Scholar
  131. 7.
    Desreux, V., E. Fredericq et P. Fischer: Bull. Soc. Chim. biol. 28, 7 (1946).Google Scholar
  132. 9.
    Greenstein, J. P.: J. biol. Ch. 109, 529, 541 (1935).Google Scholar
  133. 10.
    Hughes, W. L., H. A. Saroff and A. L. Carney: Am. Soc. 71, 2476 (1949).Google Scholar
  134. 11.
    SchÜTte, E.: H. 279, 52, 59 (1943).Google Scholar
  135. 12.
    Christensen, H. N.: J. biol. Ch. 160, 75 (1945).Google Scholar
  136. 13.
    Hughes, W. L.; in: Neurath-Bailey, Proteins Bd. II, S. 693.Google Scholar
  137. 14.
    Roche, J., and R. Michel: Adv. Protein Chem. 6, 253 (1951).PubMedGoogle Scholar
  138. 15.
    Wormall, A.: J. exp. Med. 51, 295 (1930).PubMedGoogle Scholar
  139. 16.
    Haurowitz, F., M. Vardar and P. Schwerin: J. Immunol. 43, 327, 331 (1942).Google Scholar
  140. 17.
    Oswald, A.: H. 70, 310 (1910).Google Scholar
  141. 18.
    Pauly, H.: B. 43, 2243 (1910).Google Scholar
  142. 19.
    Shahrokh, B. K.: J. biol. Ch. 151, 659 (1943).Google Scholar
  143. 20.
    Herriott, R. M.: J. gen. Physiol. 25, 185 (1941).PubMedGoogle Scholar
  144. 21.
    Herriott, R. M.: Adv. Protein Chem. 3, 208 (1947).Google Scholar
  145. 1.
    Ludwig, W., H. P. MÜTzenbecher: H. 258, 195 (1939).Google Scholar
  146. z Harrington, C.: Soc. 1944, 193.Google Scholar
  147. 3.
    Blum, F., u. E. Strauss: H. 112, 164 (1921).Google Scholar
  148. Anson, M. L.: J. gen. Physiol. 23, 321 (1940)7.Google Scholar
  149. 5.
    Fraenkel-Conrat, H.: J. biol. Ch. 217, 373 (1955).Google Scholar
  150. 6.
    Cannan, R. K.: Fed. Proc. 11, 194 (1952). Wormall, A.: J. exp. Med. 51, 295 (1930).Google Scholar
  151. 8.
    Haurowitz, F., M. Vardar and P. Schwerin: J. Immunol. 43, 327, 331 (1942).Google Scholar
  152. 9.
    French, D., and J. T. Ensall: Adv. Protein Chem. 2, 277 (1945).Google Scholar
  153. 10.
    Levy, M.: J. biol. Ch. 109, 365 (1935).Google Scholar
  154. 11.
    Gustavson, K. H.: Adv. Protein Chem. 5, 354 (1949).Google Scholar
  155. 12.
    Fraenkel-Conrat, H., M. Cooper and H. S. Olcott: Am. Soc. 67, 950 (1945).Google Scholar
  156. 13.
    Alexander, P., D. Carter and K. G. Johnson: Biochero. J. 48, 435 (1951).Google Scholar
  157. 14.
    Fraenkel-Conrat, H., and H. S. Olcott: J. biol. Ch. 174, 827 (1948). Am. Soc. 70, 2673 (1948).Google Scholar
  158. 15.
    Micheel, F., u. B. Herold: H. 293, 187 (1953).Google Scholar
  159. 16.
    Micheel, F., E. Istel u. E. Schnacke: B. 82, 131 (1949).Google Scholar
  160. 1.
    Schlack, P., u. W. Kumpf: H. 154, 125 (1926).Google Scholar
  161. 2.
    Johnson, T. B., and B. H. Nicolet: Am. Soc. 33, 1973 (1911).Google Scholar
  162. 3.
    Tibbs, J.: Nature 168, 910 (1951).PubMedGoogle Scholar
  163. 4.
    Edwards, J. T., and S. Nielson: Chem. & Industr. 1953, 197Google Scholar
  164. 5.
    Baptist, V. H., and H. B. Bull: Am. Soc. 75, 1727 (1953).Google Scholar
  165. 6.
    Fox, S. `V., T. L. Hurst, J. F. Griffith and O. L. Underwoon: Am. Soc. 77, 3119 (1955).Google Scholar
  166. 7.
    Haurowitz, F., R. L. Hardin and M. Zimmerman: Fed. Proc. 13, 225 (1954) sowie unveröffentlichte Versuche.Google Scholar
  167. 8.
    Pauly, H.: H. 94, 284 (1915).Google Scholar
  168. 9.
    Landsteiner, K.: The Specificity of Serological Reactions. Cambridge, Mass. 1946.Google Scholar
  169. 10.
    Haurowitz, F.: Biol. Reviews 27, 247 (1952). Fortschr. d. Allergielehre (Hrsg. Kallos, P.) S. 19. Basel 1939.Google Scholar
  170. 11.
    Boyd, W. C., and S. B. Hooker: J. biol. Ch. 104, 329 (1934); 110, 457 (1935).Google Scholar
  171. 12.
    Pauling, L., D. Pressman and A. L. Grossberg: Am. Soc. 66, 784 (1944).Google Scholar
  172. 1.
    Haurowitz, F., and H. Walter: Proc. Soc. exp. Biol. Med. 88, 67 (1944).Google Scholar
  173. Crampton, C. F., H. Reller and F. HAuxowrrz: Proc. Soc. exp. Biol. Med. 80, 488 (1952).Google Scholar
  174. 2.
    Kapeller-Adler, R., u. G. Boxer: B Z 285, 55 (1936).Google Scholar
  175. 3.
    Eagle, H., and P. Vickers: J. biol. Ch. 114, 193 (1936).Google Scholar
  176. 4.
    Higgins, H. G., and D. Frazer: Austral. J. sci. Res. (A) 5, 736 (1954).Google Scholar
  177. 5.
    Gelewitz, E. W., W. L. Riedeman and I. M. Klotz: Arch. Biochem. 53, 411 (1954).PubMedGoogle Scholar
  178. 6.
    Hellermarr, L.: Physiol. Rev. 17, 454 (1937)Google Scholar
  179. L. Hellerman, F. P. Chinard and V. R. Dietz: J. biol. Ch. 147, 443 (1943).Google Scholar
  180. 7.
    Singer, T. P., and E. S. G. Barron: J. biol. Ch. 157, 241 (1945).Google Scholar
  181. 8.
    Kolthoff, I. M., W. Stricks and L. Morren: Analyt. Chem., Washington 26, 366 (1954).Google Scholar
  182. 9.
    Pihar, O.: Chem. Listy 47, 1647, 1652 (1953).Google Scholar
  183. 10.
    Hughes, W. L. jr.: Am. Soc. 69, 1836 (1947).Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1960

Authors and Affiliations

  • Felix Haurowitz
    • 1
  1. 1.BloomingtonUSA

Personalised recommendations