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Applications of soluble polymeric supports

  • Kurt Geckeler
  • V. N. Rajasekharan Pillai
  • Manfred Mutter
Conference paper
Part of the Advances in Polymer Science book series (POLYMER, volume 39)

Keywords

Acrylic Acid Peptide Synthesis Vinyl Alcohol Soluble Polymer Ethylene Oxide Unit 
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.

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References

  1. 1.
    For recent reviews on solid-phase synthesis, see: Erickson, B. W., Merrified, R. B.: Proteins, 3rd Ed. 2 (1976); Blossey, E. C., Neckers, D. C., (Editors): Benchmarks in chemistry — solid phase synthesis, Dowden, Hutchinson & Ross, Penn., 1975; Birr, Ch.: Aspects of the Merrifield Peptide Synthesis, Springer-Verlag, Heidelberg 1979Google Scholar
  2. 2.
    Neckers, D. C.: J. Chem. Educ., 52, 695 (1975)CrossRefGoogle Scholar
  3. 3.
    Overberger, C. G., Sannes, K. N.: Angew. Chem. 86, 139 (1974); Leznof, C. C., Chem. Soc. Rev. 3, 65 (1974); Patchornik, A., Kraus, M. A., in: Encyclopedia of Polymer Science and Technology (Bikales, N. M. (Editor)), Wiley, New York, 1976. Suppl. 1, p. 468CrossRefGoogle Scholar
  4. 4.
    Manecke, G., Storck, W.: Angew. Chem., 90, 691 (1978)CrossRefGoogle Scholar
  5. 5.
    Goldman, R., Goldstein, L., Katchalski, E., in: Biochemical Aspects of Reactions on Solid Supports, (G. R. Stark, (Ed.)), Academic Press, New York, 1974; Goldstein, L., Manecke, G., in: Applied Biochemistry, (L. B. Wingard Jr., Katchalski-Katzir, E., Goldstein, L., (Editors)), Academic Press, New York, 1976, Vol. 1. p. 23Google Scholar
  6. 6.
    Batz, H. G.: Adv. Polym. Sci., Vol. 23 (H. J. Cantow et al., (Ed.)), Springer-Verlag, Heidelberg, Berlin (1977), p. 25Google Scholar
  7. 7.
    Leznof, C. C.: Acc. Chem. Res. 11, 327 (1978)CrossRefGoogle Scholar
  8. 8.
    Crowley, J. I., Rapoport, H.: Acc. Chem. Res. 9, 135 (1976)CrossRefGoogle Scholar
  9. 9.
    Heitz, W.: Adv. Polym. Sci., Vol. 23 (H. J. Cantow et al., (Ed.)), Springer Verlag, Berlin (1977), p. 1Google Scholar
  10. 10.
    Frechet, J. M. J., Farrall, M. J., in: Chemistry and Properties of Cross-linked Polymers (Labana, S. S. (Ed.)), Academic Press (1977)Google Scholar
  11. 11.
    Flory, P. J.: J. Am. Chem. Soc. 61, 3334 (1939)CrossRefGoogle Scholar
  12. 12.
    Bayer, E. et al.: J. Am. Chem. Soc. 96, 7333 (1974)CrossRefGoogle Scholar
  13. 13.
    Andreatta, R. H., Rink, H.: Helv. Chim. Acta 56, 1205 (1973)CrossRefGoogle Scholar
  14. 14.
    Shemyakin, M. M. et al.: Tetrahedron Lett. 2323 (1965)Google Scholar
  15. 15.
    Green, B., Garson, L. R.: J. Chem. Soc. (C), 401 (1969)Google Scholar
  16. 16.
    Morawetz, H., in: Peptides: Chemistry, Structure and Biology (Walter, R., Meienhofer, J. (Eds.)), Ann Arbor Sci. Publ., Michigan (1975), p. 385–394Google Scholar
  17. 17.
    Blecher, H., Pfaender, P.: Liebigs Ann. Chem., 1263 (1973)Google Scholar
  18. 18.
    Geckeler, K., Bayer, E.: Liebigs Ann. Chem. 1671 (1975); Geckeler, K., Bayer, E.: Makromol. Chem. 175, 1995 (1974)Google Scholar
  19. 19.
    Bayer, E., Mutter, M.: Nature 237, 512 (1972)CrossRefGoogle Scholar
  20. 20.
    Mutter, M., Hagenmeier, H., Bayer, E.: Angew. Chem. Int. Ed. Engl. 10, 811 (1972)CrossRefGoogle Scholar
  21. 21.
    Mutter, M., Bayer, E.: Angew. Chem. Int. Ed. Engl. 13, 88 (1974)CrossRefGoogle Scholar
  22. 22.
    Mutter, M. Uhmann, R., Bayer, E.: Liebigs Ann. Chem. 901 (1975)Google Scholar
  23. 23.
    Bayer, E. et al.: Tetrahedron 34, 1829 (1978)CrossRefGoogle Scholar
  24. 24.
    Mutter, M.: Habilitationsschrift, Univers. Tübingen (1976)Google Scholar
  25. 25.
    Neidlinger, H., Dissertation, Univers. Mainz, Germany (1975)Google Scholar
  26. 26.
    Rahman, S. A., Anzinger, H., Mutter, M.: Biopolymers, (in press)Google Scholar
  27. 27.
    Toniolo, G., Bonoro, G. M., Palumbo, M., Pysh, E. S., in: Peptides 1976 (Loffet, A., Ed.) pp. 597–600, Univ. de Bruxelles, Brussels (1976)Google Scholar
  28. 28.
    Mutter, M.: Macromolecules 10, 1413 (1977)CrossRefGoogle Scholar
  29. 29.
    Imae, T., Ikeda, S.: Biopolymers 11, 509 (1972)CrossRefGoogle Scholar
  30. 30.
    Anzinger, H., Mutter, M., Bayer, E., Angew. Chem. 91, 747 (1979)CrossRefGoogle Scholar
  31. 31.
    Bayer, E., Mutter, M.: Chem. Ber. 107, 1344 (1974); Frank, H., Hagenmeier, H.: Tetrahedron 30, 2523 (1974); Mutter, M. et al.: Biopolymers 15, 917 (1976); Mutter, H., Mutter, M., Bayer, E.: Z. Naturforsch., 34b, 874 (1979); Goehring, W., Jung, G.: Liebigs Ann. Chem. 1965 (1975); Weber, U., Hoppe-Seyler's Z. Physiol. Chem. 356, 701 (1975); Frank, H., Hagenmeier, H., Beckmann Rep. 12–17 (1974); Hagenmeier, H.: Hoppe-Seyler's Z. Physiol. Chem. 356, 777 (1975); Stein, W., Dissertation Univers. Tübingen, Germany (1975)CrossRefGoogle Scholar
  32. 32.
    Künzi, H.: Ger. Off. 2435642, Appl. P. 2435642. 1, 24 pp.Google Scholar
  33. 33.
    Tjoeng, F. S. et al.: Biochim. Biophys. Acta 490, 489 (1977)Google Scholar
  34. 34.
    Tjoeng, F. S., Tong, E. K., Hodges, R. S.: J. Org. Chem. 43, 4190 (1978)CrossRefGoogle Scholar
  35. 35.
    Tjoeng, F. S. Hodges, R. S.: Tetrahedron Lett. 1273 (1979)Google Scholar
  36. 36.
    Pillai, V. N. R., Mutter, M., Bayer, E.: ibid. 3409 (1979)Google Scholar
  37. 37.
    Pillai, V. N. R.: Synthesis 23 (1980)Google Scholar
  38. 38.
    Mutter, M.: Tetrahedron Lett. 2839 (1978); Geckeler, K.: Polym. Bull. 1, 427 (1979)Google Scholar
  39. 39.
    Frank, H., Hagenmaier, H.: Experientia 31, 131 (1975)CrossRefGoogle Scholar
  40. 40.
    Frank, H., Meyer, H., Hagenmaier, H., in: Peptides: Chemistry, Structure and Biology (Walter R., Meienhofer, J. (Eds.)), Ann. Arbor Sci. Publ. Michigan (1975), p. 439Google Scholar
  41. 41.
    Jung, G. et al., in: Peptides: Chemistry, Structure and Biology (Walter, R., Meienhofer, J. (Eds.)), Ann. Arbor Sci. Publ. Michigan (1975), p. 433Google Scholar
  42. 42.
    Heusel, G. et al.: Angew. Chem. Int. Ed. Engl. 16, 142 (1977)CrossRefGoogle Scholar
  43. 43.
    Schott, H., Brandstetter, F., Bayer, E.: Makromol. Chem. 173, 247 (1973)CrossRefGoogle Scholar
  44. 44.
    Brandstetter, F., Schott, H., Bayer, E.: Tetrahedron Lett. 2997 (1973)Google Scholar
  45. 45.
    Köster, H.: ibid. 1535 (1972)Google Scholar
  46. 46.
    Hayatsu, H., Khorana, H. G.: J. Am. Chem. Soc. 88, 3182 (1966)CrossRefGoogle Scholar
  47. 47.
    Cramer, F. et al.: Angew. Chem. 78, 640 (1966)CrossRefGoogle Scholar
  48. 48.
    Schott, H.: Angew. Chem. Int. Ed. Engl. 12, 246 (1973)CrossRefGoogle Scholar
  49. 49.
    Ohtsuka, E. et al.: J. Am. Chem. Soc. 92, 3441 (1970)CrossRefGoogle Scholar
  50. 50.
    Cook, A. F.: J. Am. Chem. Soc. 92, 190 (1970)CrossRefGoogle Scholar
  51. 51.
    Seliger, H., Aumann, G.: Makromol. Chem. 176, 609 (1975)CrossRefGoogle Scholar
  52. 52.
    Collman, J. P., Reed, C. A.: J. Am. Chem. Soc. 95, 2048 (1973)CrossRefGoogle Scholar
  53. 53.
    Beyerman, H. C., de Leer, E. W. B., van Vossen, W.: J. Chem. Soc., Chem. Common., 929 (1972)Google Scholar
  54. 54.
    Crowley, J. I., Harvey, T. B., Rapoport, H.: J. Makromol. Sci. Chem. 7, 1118 (1973)CrossRefGoogle Scholar
  55. 55.
    Crowley, J. I., Rapoport, H.: J. Amer. Chem. Soc. 92, 6363 (1970)CrossRefGoogle Scholar
  56. 56.
    Scott, L. T. et al.: J. Am. Chem. Soc. 99, 625 (1977)CrossRefGoogle Scholar
  57. 57.
    Bayer, E. Schurig, V.: Angew. Chem. 87, 484 (1975)CrossRefGoogle Scholar
  58. 58.
    Brandstetter, F., Schott, H., Bayer, E.: Makromol. Chem. 176, 2163 (1975)CrossRefGoogle Scholar
  59. 59.
    Hallensleben, M. L.: Angew. Makromol. Chem. 31, 143 (1973)CrossRefGoogle Scholar
  60. 60.
    Hallensleben, M. L.: ibid. 31, 147 (1973)CrossRefGoogle Scholar
  61. 61.
    Hallensleben, M. L.: Z. Naturforsch. 28b, 540 (1973)Google Scholar
  62. 62.
    Kriech, W.: Dissertation, Univers. Tübingen, Germany (1977)Google Scholar
  63. 63.
    Appel, R., Willms, L.: J. Chem. Res. (S) 84 (1977); Appel, R., Willms, L.: ibid (M) 901 (1977)Google Scholar
  64. 64.
    Appel, R., Wihler, H. D.: Chem. Ber. 109, 3446 (1976)CrossRefGoogle Scholar
  65. 65.
    Schuttenberg, H., Schulz, R. C.: Angew. Chem. Int. Ed. Engl. 10, 856 (1971)Google Scholar
  66. 66.
    Schuttenberg, H. et al.: J. Makromol. Sci. Chem. 7, 1085 (1973)Google Scholar
  67. 67.
    Hahn, K., Schulz, R. C.: Angew. Makromol. Chem., 50, 53 (1976)CrossRefGoogle Scholar
  68. 68.
    Yamaguchi, H., Schulz, R. C.: Makromol. Chem. 177, 3441 (1976)CrossRefGoogle Scholar
  69. 69.
    Sato, Y., Kunieda, N., Kinoshita, M.: Chem. Lett., 1023 (1972)Google Scholar
  70. 70.
    Sato, R., Schulz, R. C.: Makromol. Chem. 180, 299 (1979)CrossRefGoogle Scholar
  71. 71.
    Günster, E., Schulz, R. C.: Makromol. Chem. 179, 2583 (1978)CrossRefGoogle Scholar
  72. 72.
    Schuttenberg, H., Schulz, R. C.: Angew. Chem. 88, 848 (1976)CrossRefGoogle Scholar
  73. 73.
    Günster, E. J., Schulz, R. C.: Makromol. Chem. 180, 1891 (1979)CrossRefGoogle Scholar
  74. 74.
    Mutter, M.: Tetrahedron Lett. 2843 (1978)Google Scholar
  75. 75.
    Kalir, R. et al.: Eur. J. Biochem. 59, 55 (1975)CrossRefGoogle Scholar
  76. 76.
    Bayer, E., Schurig, V.: Angew. Chem. Int. Ed. Engl. 14, 493 (1973)CrossRefGoogle Scholar
  77. 77.
    Bayer, E., Schurig, V.: Ger. Pat. Appl. DOS 2, 326, 489 (1973)Google Scholar
  78. 78.
    Bayer, E., Schurig, V.: Chem. Technol. 6, 212 (1976)Google Scholar
  79. 79.
    Pittman, C. U. Jr., Evans, G. O.: ibid. 3, 560 (1973)Google Scholar
  80. 80.
    Dumont, W. et al.: J. Am. Chem. Soc. 95, 8295 (1973)CrossRefGoogle Scholar
  81. 81.
    Tsuchida, E., Nishide, H.: Adv. Polym. Sci. 24, 1 (1977)Google Scholar
  82. 82.
    Geckeler, K. et al.: Pure Appl. Chem. 52, 1883 (1980)Google Scholar
  83. 83.
    Geckeler, K., Weingärtner, K., Bayer, E.: Makromol. Chem. 181, 585 (1980); Bayer, E., Geckeler, K., Weingärtner, K., in: Polymeric Amines and Ammonium Salts, (E. Goethals, Ed.), Pergamon Press, Oxford 1980, in pressCrossRefGoogle Scholar
  84. 84.
    Welzmann, N.: J. Polym. Sci. 33, 377 (1958)CrossRefGoogle Scholar
  85. 85.
    Mutter, M., Bayer, E.: Chem. Technol., in press; Bayer, E., Weingärtner, K., Geckeler, K.: Makromol. Chem., in pressGoogle Scholar
  86. 86.
    Geckeler, K., Mutter, M.: unpublished resultsGoogle Scholar
  87. 87.
    Katon, J. E.: Organic Semiconducting Polymers, Marcel Dekker, New York, 1976Google Scholar
  88. 88.
    Kakinoki, H. et al.: J. Polym. Sci. Polym. Lett. Ed. 14, 407 (1976)CrossRefGoogle Scholar
  89. 89.
    Higashi, F. et al.: ibid. 15, 2303 (1977)Google Scholar
  90. 90.
    Higashi, F., Cho, C. S., Kakinoki, H.: J. Polym. Sci. Polym. Chem. Ed. 17, 313 (1979)CrossRefGoogle Scholar
  91. 91.
    Staudinger, H., Frey, K., Stark, W.: Ber. dtsch. chem. Ges. 60, 1782 (1927)CrossRefGoogle Scholar
  92. 92.
    Hermann, W. O., Hochnel, W.: ibid. 60, 1658 (1927)CrossRefGoogle Scholar
  93. 93.
    Kikukowa, K., Nozakura, S., Murahashi, N.: Polym. J. 3, 52 (1972)CrossRefGoogle Scholar
  94. 94.
    Inagaki, F. et al.: Bull. Chem. Soc. Japan 45, 3384 (1972)CrossRefGoogle Scholar
  95. 95.
    Heyde, M. et al.: J. Amer. Chem. Soc. 94, 5222 (1972)CrossRefGoogle Scholar
  96. 96.
    Commercial name: Polyvidon, Melsungen, Germany, PVP-Jod, Alsdorf/GermanyGoogle Scholar
  97. 97.
    Hermann, A. M., Rembaum, A.: J. Polym. Sci. C 17, 107 (1967)Google Scholar
  98. 98.
    Matsubara, I., Magill, J. H.: Polymer, 7, 199 (1966)CrossRefGoogle Scholar
  99. 99.
    Schulz, R. C.: Pure Appl. Chem. 38, 227 (1974)Google Scholar
  100. 100.
    Lymann, D. J.: Rev. Macromol. Chem. 1, 355 (1966)Google Scholar
  101. 101.
    Mark, H. F.: Pure Appl. Chem. 16, 201 (1968)CrossRefGoogle Scholar
  102. 102.
    Kovanov, V. V.: Usp. Khim. Technol. Polim. 176 (1970)Google Scholar
  103. 103.
    Merigan, T. C.: Nature 214, 416 (1967)CrossRefGoogle Scholar
  104. 104.
    Ferruti, P.: Pharmacol. Res. Comm. 7, 1 (1975)CrossRefGoogle Scholar
  105. 105.
    Ringsdorf, H., in: Polymeric Delivery Systems (Kostelnik, R. J. (Ed.)), Midland Macromolecular Monographs, Vol. 5, p. 197, Gordon & Beach, New York, 1978Google Scholar
  106. 106.
    Panarin, E. F., Solovski, M. V., Ekzenphylarov, O. N.: Khim. Pharm. Zh. 5, 24 (1971); Chem. Abstr. 75, 152274d (1971)Google Scholar
  107. 107.
    Legator, M., C. A.: US Pat. 3,567,420 (1971)Google Scholar
  108. 108.
    Lane, E. W.: US Pat. 2,806,019 (1957)Google Scholar
  109. 109.
    Samour, C. M., Richards, M. C.: US Pat. 3,778,693 (1973); 3,879,447 (1975); 3,936,492 (1976)Google Scholar
  110. 110.
    Hoover, M. F.: US Pat. 3,539,684 (1970)Google Scholar
  111. 111.
    Rembaum, A.: Appl. Polym. Symp. 22, 299 (1973)Google Scholar
  112. 112.
    Conforth, J. W., D'Arcy Hart, P., Stock, J. A.: Nature 168, 150 (1951)CrossRefGoogle Scholar
  113. 113.
    Conforth, J. W., Morgan, E. D., Potts, K. T.: Tetrahedron 29, 1659 (1973)CrossRefGoogle Scholar
  114. 114.
    Abuchowski, A. et al.: J. Biol. Chem. 252, 3578 (1977)Google Scholar
  115. 115.
    Liu, K. J., Parsons, J. L.: Macromolecules 2, 529 (1969)CrossRefGoogle Scholar
  116. 116.
    Maxfield, J., Shepherd, I. W.: Polymer 16, 505 (1975)CrossRefGoogle Scholar
  117. 117.
    Geckeler, K., Mutter, M.: Z. Naturforsch. 34b, 23 (1979)Google Scholar
  118. 118.
    Weiner, B. Z., Zilkha, A.: J. Med. Chem. 16, 573 (1973)CrossRefGoogle Scholar
  119. 119.
    Smith, H., Marshall, A. C.: Nature, 232, 45 (1971)CrossRefGoogle Scholar
  120. 120.
    Butcher, B. T. et al.: Mol. Cryst. Liqu. Cryst. 12, 321 (1971)CrossRefGoogle Scholar
  121. 121.
    Ushakov, B. N., Panarin, E. F.: Dokl. Akad. Nauk. USSR 149, 334 (1963)Google Scholar
  122. 122.
    Ushakov, B. N., Panarin, E. F.: ibid. 147, 5 (1962)Google Scholar
  123. 123.
    Takesue, E., Hlavka, J. J., Boothe, J. H.: US Pat., 3,356,571 (1967)Google Scholar
  124. 124.
    Hofmann, V., Ringsdorf, H.: Makromol. Chem. 180, 595 (1979)CrossRefGoogle Scholar
  125. 125.
    Hirano, T., Klesse, W., Ringsdorf, H.: Makromol. Chem. 180, 1125 (1979)CrossRefGoogle Scholar
  126. 126.
    Batz, H. G., Ringsdorf, H., Ritter, H.: Makromol. Chem. 175, 2229 (1974)CrossRefGoogle Scholar
  127. 127.
    Ringsdorf, H., Forschungsbericht, BMFT FBT 76, 36-86-98 (1976)Google Scholar
  128. 128.
    Furhan, M., Moroson, H., in: Radiation, Protection and Sensitization (Moroson, H., Quintiliani (Eds.)), Taylor and Francis, p. 233 (1975)Google Scholar
  129. 129.
    Moroson, H., in: Chemotherapy of Cancer Dissemination and Metastasis (Garattini, S., Franchi, G., (Eds.)), Raven Press, New York p. 245, 1973Google Scholar
  130. 130.
    Ferruti, P. et al.: J. Med. Chem. 16, 496 (1973)CrossRefGoogle Scholar
  131. 131.
    Ferruti, P. et al.: J. Med. Chem., (in press)Google Scholar
  132. 132.
    Ringsdorf, H.: Strahlentherapie 132, 627 (1967)Google Scholar
  133. 133.
    Barnes, J. H. et al.: Eur. J. Med. Chem. 12, 467 (1977)Google Scholar
  134. 134.
    Overberger, C. G., Ringsdorf, H., Avchen, B.: J. Org. Chem. 30, 3088Google Scholar
  135. 135.
    Overberger, C. G., Ringsdorf, H.: J. Med. Chem. 8, 862 (1965)CrossRefGoogle Scholar
  136. 136.
    Montoya, R. et al.: Makromol. Chem. 178, 1221 (1977)CrossRefGoogle Scholar
  137. 137.
    Heet, G., Wesse, H.: Münch. Med. Wochenschr. 85, 11 (1943)Google Scholar
  138. 138.
    Wyandotte Chem. Corp., S. African Pat. 6,805,978; Chem. Abstr. 72, 39088 (1970)Google Scholar
  139. 139.
    Shehukovskaya, L., Kapustayanskaya, A. M., Kropachev, V. A.: USSR Pat. 3,281,10 (1970); Chem. Abstr. 77, 20349 (1972)Google Scholar
  140. 140.
    Das, P. K. et al.: J. Amer. Chem. Soc. 101, 239 (1979)CrossRefGoogle Scholar
  141. 141.
    Manecke, G.: Naturwissenschaften 51, 25 (1964)CrossRefGoogle Scholar
  142. 142.
    Zabovsky, O.: Immobilized enzymes, CRC Press, Cleveland, 1974Google Scholar
  143. 143.
    Silman, I. H., Katchalski, E.: Ann. Rev. Biochem. 35, 873 (1966)CrossRefGoogle Scholar
  144. 144.
    Smirnov, B. P., Manoilov, S. E.: Biokhimiya 31, 387 (1966)Google Scholar
  145. 145.
    Axen, R., Panath, J., Ernbach, S.: Nature 214, 1302 (1967)CrossRefGoogle Scholar
  146. 146.
    Mosbach, K.: Acta. Chem. Scand. 24, 2093 (1970)Google Scholar
  147. 147.
    Weetall, H.: Science 166, 615 (1969)CrossRefGoogle Scholar
  148. 148.
    O'Neill, S. P. et al.: Biotech. Bio Eng. 13, 319 (1971)CrossRefGoogle Scholar
  149. 149.
    Wykes, J. R., Dunnill, P., Lilly, M. D.: Biochim. Biophys. Acta 250, 522 (1971)Google Scholar
  150. 150.
    Manecke, G.: Pure Appl. Chem. 4, 507 (1962)Google Scholar
  151. 151.
    Barker, S. A., Somers, P. J., Eptom, R. E.: Carbohydr. Res. 8, 491 (1968)CrossRefGoogle Scholar
  152. 152.
    Barker, S. A., McLaren, J. V.: ibid. 14, 287 (1970)CrossRefGoogle Scholar
  153. 153.
    Ledingham, W. M., Hornby, W. E.: FEBS Letters 5, 118 (1969)CrossRefGoogle Scholar
  154. 154.
    Patel, R. P. et al.: Biopolymers 5, 577 (1967)CrossRefGoogle Scholar
  155. 155.
    Mitz, M. A., Sumania, L. J.: Nature 189, 576 (1961)CrossRefGoogle Scholar
  156. 156.
    Conte, A., Lehmann, K.: Hoppe-Seyler's Z. Physiol. Chem. 352, 533 (1971)Google Scholar
  157. 157.
    Levin, Y. et al.: Biochemistry 3, 1905 (1964)CrossRefGoogle Scholar
  158. 158.
    Abuchowski, A. et al.: J. Biol. Chem. 252, 3582 (1977)Google Scholar
  159. 159.
    Von Specht, B. U., Seinfeld, H., Brendel, W.: Hoppe-Seyler's Z. Physiol. Chem. 354, 1659 (1973)Google Scholar
  160. 160.
    Von Specht, B. U. et al.: Arch. Inst. Pharm. 213, 242 (1975)Google Scholar
  161. 161.
    Kopecek, J., Bozilova, H.: Eur. Polym. J. 9, 7 (1973)CrossRefGoogle Scholar
  162. 162.
    Drobnik, J. et al.: Makromol. Chem. 177, 2833 (1976)CrossRefGoogle Scholar
  163. 163.
    Katchalski, E. et al.: Arch. Biochim. Biophys. 88, 361 (1960)CrossRefGoogle Scholar
  164. 164.
    Letsinger, R. L., Savereide, T. J.: J. Am. Chem. Soc. 84, 3122 (1962)CrossRefGoogle Scholar
  165. 165.
    Sheehan, J. C., Bennet, G. B., Schneider, J. A.: J. Am. Chem. Soc. 88, 3455 (1966)CrossRefGoogle Scholar
  166. 166.
    Sakurada, I. et al.: Makromol. Chem. 91, 243 (1966)CrossRefGoogle Scholar
  167. 167.
    Morawetz, H. et al.: J. Am. Chem. Soc. 90, 651 (1968)CrossRefGoogle Scholar
  168. 168.
    Okubo, T., Ise, N.: Adv. Polym. Sci. 25, 136 (1977)Google Scholar
  169. 169.
    Arai, K., Ise, N.: Makromol. Chem. 176, 37 (1975)CrossRefGoogle Scholar
  170. 170.
    Arai, K., Hagiwara, N., Ise, N.: Nippon Kagoku Kaishi, 201 (1975)Google Scholar
  171. 171.
    Suzuki, K. et al.: Prepr. 21st Polym. Symp. 1045 (1972)Google Scholar
  172. 172.
    Kern, W., Herold, W., Scherhag, B.: Makromol. Chem. 17, 231 (1955)CrossRefGoogle Scholar
  173. 173.
    Kern, W., Scherhag, B.: ibid. 28, 209 (1958)CrossRefGoogle Scholar
  174. 174.
    Arcus, C. L., Gonzalez, C. G., Linnecar, D. F. C.: Chem. Comm. 1377 (1969)Google Scholar

Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • Kurt Geckeler
    • 1
  • V. N. Rajasekharan Pillai
    • 2
  • Manfred Mutter
    • 2
  1. 1.Institut für Organische ChemieUniversität TübingenTübingen
  2. 2.Institut für Organische ChemieUniversität MainzMainz

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