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Recent developments in the field of biologically active peptides

  • Gunter Schmidt
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 136)

Abstract

The abbreviations and symbols for amino acids and peptides used in this article comply with the rules published by the IUPAC Commission for Biochemical Nomenclature; see: J. Biol. Chem. 245, 6489 (1970); ibid. 247, 977 (1972); ibid. 250, 3215 (1975); Biochem. J. 126, 773 (1972). The amino acids are in the L-configuration; in the case of D-amino acids the abbreviations are prefixed by the letter D.

Keywords

Atrial Natriuretic Peptide Peptide Synthesis Active Peptide Gastric Inhibitory Polypeptide Peptide Protein 
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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16 References

  1. 1.
    Wünsch, E.: Synthese von Peptiden, Houben-Weyl, Bd. 15/1 und 2, Georg Thieme Verlag, Stuttgart 1974Google Scholar
  2. 2. a)
    Schröder, E., Lübke, K.: The Peptides I, Academic Press, New York 1965Google Scholar
  3. 2. b)
    Schröder, E., Lübke, K., Kloss, G.: Chemie und Biochemie der Aminosäuren, Peptide und Proteine I und II, Georg Thieme Verlag, Stuttgart 1975Google Scholar
  4. 3.
    Gross, E., Meienhofer, J.: The Peptides, Vol. 1, 2, 3, Academic Press, New York 1979, 1980, 1981Google Scholar
  5. 4.
    Finn, F. M., Hofmann, K.: The Synthesis of Peptides by Solution Methods with Emphasis on Peptide Hormones, in: The Proteins, Vol. II (ed. Neurath, H., Hill, R. L.), p. 105, Academic Press, New York 1976Google Scholar
  6. 5.
    Jakubke, H.-D., Jeschkeit, H.: Aminosäuren, Peptide, Proteine, Verlag Chemie, Weinheim 1982Google Scholar
  7. 6.
    Bláha, K.: Linear Peptides: Synthetic Methods; Wade, R.: Linear Peptides: Synthesis and Structure — Activity Relationships; Wieland, T., Birr, C.: Homodetic Cyclic Peptides, in: Amino Acids, Peptides and Related Compounds, International Review of Science, Vol. 6 (ed. Rydon, H. N.), p. 73, 97, 183, Butterworths, London 1976Google Scholar
  8. 7.
    Stammer, C. H.: Procedures for Peptide Synthesis; Wade, R.: New Syntheses of Naturally Occurring Peptides and Analogues, in: Amino Acids, Peptides and Related Compounds, MTP International Review of Science, Vol. 6 (ed. Hey, D. H., John, D. I.) p. 135, 161, Butterworths, London 1976Google Scholar
  9. 8. a)
    Bodanszky, M.: Principles of Peptide Synthesis, Springer Verlag, Berlin 1984Google Scholar
  10. 8. b)
    Bodanzsky, M., Bodanzsky, A.: The Practice of Peptide Synthesis, Springer Verlag, Berlin 1982Google Scholar
  11. 9. a)
    Erickson, B. W., Merrifield, R. B.: Solid-Phase Peptide Synthesis, in The Proteins, Vol. II (ed. Neurath, H., Hill, R. L.), p. 255, Academic Press, New York 1976Google Scholar
  12. 9. b)
    Barany, G., Merrifield, R. B.: Solid-Phase Peptide Synthesis, in: The Peptides, Vol. 2 (ed. Gross, E., Meienhofer, J.) p. 1, Academic Press, New York 1980Google Scholar
  13. 10.
    Birr, C.: Aspects of the Merrifield Peptide Synthesis, Springer Verlag, Berlin 1978Google Scholar
  14. 11. a)
    Pillai, V. N. R., Mutter, M.: New Perspectives in Polymer-Supported Peptide Synthesis, in: Topics in Current Chemistry (ed. Boschke, F. L.), p. 119, Springer Verlag, Berlin 1982Google Scholar
  15. 11. b)
    Atherton, E., Logan, C. J., Sheppard, R. C.: J. Chem. Soc. Perkin Trans. I 1981, 538Google Scholar
  16. 11. c)
    Sheppard, R. C.: Chemistry in Britain 19, 402 (1983)Google Scholar
  17. 12. a)
    Mutter, M., Hagenmaier, H., Bayer, E.: Angew. Chemie 83, 883 (1971)Google Scholar
  18. 12. b)
    Mutter, M., Bayer, E.: The Liquid-Phase Method for Peptide Synthesis, in: The Peptides, Vol. 2 (ed. Gross, E., Meienhofer, J.), p. 285, Academic Press, New York 1980Google Scholar
  19. 13.
    Jakubke, H.-D., Kuhl, P., Könnecke, A.: Angew. Chem. 97, 79 (1985)Google Scholar
  20. 14.
    Kuhl, P., Zapevalova, N. P., Könnecke, A., Jakubke, H.-D.: Monatsh. Chem. 114, 343 (1983)Google Scholar
  21. 15.
    Kullmann, W.: J. Org. Chem. 47, 5300 (1982)Google Scholar
  22. 16.
    Chaiken, I. M., Komoriya, A., Ohno, M., Widmer, F.: Appl. Biochem. Biotechnol. 7, 385 (1982)Google Scholar
  23. 17.
    Davies, J. E., Gassen, H. G.: Angew. Chem. 95, 26 (1983)Google Scholar
  24. 18.
    Wengenmayer, F.: Angew. Chem. 95, 874 (1983)Google Scholar
  25. 19.
    Spatola, A. F.: Peptide Backbone Modifications, in: Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, vol. 7 (ed. Weinstein, B.), p. 267, Dekker, New York 1983Google Scholar
  26. 20.
    Goodmann, M., Chorev, M.: The Synthesis and Conformational Analysis of Retro-Inverso-Analogues of Biologically Active Molecules, in: Perspectives in Peptide Chemistry (ed. Eberle, A., Geiger, R., Wieland, T.), p. 283, S. Karger, Basel 1981Google Scholar
  27. 21.
    Schröder, E., Rufer, C., Schmiechen, R.: Aminosäure-, Peptid-und Proteohormone, in: Pharmazeutische Chemie, p. 468, Georg Thieme Verlag, Stuttgart 1982Google Scholar
  28. 22.
    Greven, H. M., de Wied, D.: Neuropeptides and Behaviour, in: Perspectives in Peptide Chemistry (ed. Eberle, A., Geiger, R., Wieland, T.), p. 356, S. Karger, Basel 1981Google Scholar
  29. 23.
    Tregear, G. W., Niall, H. D., Potts, J. T., Leemann, S. E., Chang, M. M.: Nature, New Biol. 232, 87 (1971)Google Scholar
  30. 24.
    Niedrich, H., Oehme, P., Mehlis, B., Bienert, M., Bergmann, J., Berger, H.: Substance P-Structural Features and Regulatory Functions, in: Perspectives in Peptide Chemistry (ed. Eberle, A., Geiger, R., Wieland, T.), p. 344, S. Karger, Basel 1981Google Scholar
  31. 25.
    Caranikas, S., Mizrahi, J., Escher, E., Regoli, D.: J. Med. Chem. 25, 1313 (1982)Google Scholar
  32. 26.
    Chorev, M., Rubini, E., Gilon, C., Wormser, U., Selinger, Z.: J. Med. Chem. 26, 129 (1983)Google Scholar
  33. 27.
    Pessi, A., Pinori, M., Verdini, A. S., Viscomi, G. C.: J. Chem. Soc. Commun. 1983, 195Google Scholar
  34. 28.
    Munekata, E., Okada, M., Kimura, S., Sugita, Y., Kanazawa, I., Matsudo, T., Otsuka, M.: Chem. Lett. 1984, 1013Google Scholar
  35. 29. a)
    Carraway, R., Leeman, S. E.: J. Biol. Chem. 248, 6854 (1973)Google Scholar
  36. 29. b)
    Carraway, R., Leeman, S. E.: ibid. 250, 1907 (1975)Google Scholar
  37. 30.
    St-Pierre, S., Lalonde, J.-M., Gendreau, M., Quirion, R., Regoli, D., Rioux, F.: J. Med. Chem. 24, 370 (1981)Google Scholar
  38. 31.
    Hughes, J., Smith, T. W., Kosterlitz, H. W., Fothergill, L. A., Morgan, B. A., Morris, H. R.: Natur 258, 577 (1975)Google Scholar
  39. 32.
    Blake, J., Tseng, L.-F., Chang, W.-C., Li, C. H.: Int. J. Peptide Protein Res. 11, 323 (1978)Google Scholar
  40. 33.
    Yamashiro, D., Westphal, M., Holy, K., Li, C. H.: Int. J. Peptide Protein Res. 21, 389 (1983)Google Scholar
  41. 34.
    Shimohiagashi, Y., Stammer, C. H.: J. Chem. Soc. Perkin Trans. I 1983, 803Google Scholar
  42. 35.
    Deeks, T., Crooks, P. A., Waigh, R. D.: J. Med. Chem. 26, 762 (1983)Google Scholar
  43. 36.
    Fauchère, J.-L., Pfenninger, S., Do, K. Q., Lemieux, C., Schiller, P. W.: Helv. Chim. Acta 66, 1053 (1983)Google Scholar
  44. 37.
    Shimohiagashi, Y., Dunning, jr. J. W., Kolar, A. J., Stammer, C. H.: Int. J. Peptide Protein Res. 21, 202 (1983)Google Scholar
  45. 38.
    Pless, J., Bauer, W., Cardinaux, F., Closse, A., Hauser, D., Huguenin, R., Roemer, D., Buescher, H.-H., Hill, R. C.: Helv. Chim. Acta 62, 398 (1979)Google Scholar
  46. 39.
    Peterman, C., Fauchère, J.-L.: Helv. Chim. Acta 66, 1513 (1983)Google Scholar
  47. 40.
    Richman, S. J., Goodman, M., Naguyen, T. M.-D., Schiller, P. W.: Int. J. Peptide Protein Res. 25, 648 (1985)Google Scholar
  48. 41.
    Gesellchen, P. D., Shuman, R. T.: Brit.-Pat. 2065 132 (1980), E. LillyGoogle Scholar
  49. 42.
    Shuman, R. T.: Brit.-Pat. 2065 135 (1981), E. LillyGoogle Scholar
  50. 43.
    Mazur, R. H., Tyner, D. A., Hallinan, E. A.: EP 0 081 838 (1982), G. D. Searle & Co.Google Scholar
  51. 44.
    Morley, J. S.: EP 0 083 849 (1982), ICI Ltd.Google Scholar
  52. 45. a)
    Wilkinson, S., Wrigglesworth, R., Hardy, G. W.: EP 0 075 334 (1982), The Wellcome Foundation Ltd.Google Scholar
  53. 45. b)
    Schwartz, J.-C., Costentin, J., Lecomte, J.-M.: Trends in Pharmacological Sciences 6 (12), 472 (1985)Google Scholar
  54. 46. a)
    Llorens, C., Gilles, G., Swerts, J.-P., Perdrisot, R., Fournie-Zaluski, M.-C., Schwartz, J.-C., Roques, B. P.: Biochem. Biophys. Res. Commun. 96, 1710 (1980)Google Scholar
  55. 46. b)
    Evans, D. A., Mathre, D. J.: J. Org. Chem. 50, 1830 (1985)Google Scholar
  56. 47.
    Benovitz, D. E., Spatola, A. F.: Peptides 6, 648 (1985)Google Scholar
  57. 48.
    Drugs of the Future 7, 803 (1982)Google Scholar
  58. 49.
    Chang, K.-J., Killian, A., Hazum, E., Cuatrecasas, P.: Science 212, 75 (1981)Google Scholar
  59. 50.
    Goldstein, A., Tachibana, S., Lowney, L. I., Hunkapiller, M., Hood, L.: Proc. Natl. Acad. Sci. USA 76, 6666 (1979)Google Scholar
  60. 51.
    Li, C. H., Yamashiro, D., Ferrara, P., Tseng, L.-F., Way, E. L.: Int. J. Peptide Protein Res. 21, 331 (1983)Google Scholar
  61. 52.
    Montecucchi, P. C., DeCastiglione, R., Erspamer, V.: Int. J. Peptide Protein Res. 17, 316 (1981)Google Scholar
  62. 53.
    Yamashiro, D., Nicolas, P., Li, C. H.: Int. J. Peptide Protein Res. 21, 219 (1983)Google Scholar
  63. 54.
    Salvadori, S., Marastoni, M., Balboni, G., Sarto, G. P., Tomatis, R.: J. Med. Chem. 28, 769 (1985)Google Scholar
  64. 55.
    Takagi, H., Shiomi, H., Ueda, H., Amano, H.: Nature 282, 410 (1979)Google Scholar
  65. 56.
    Takagi, H., Shiomi, H., Fukui, K., Hayashi, K., Kiso, Y., Kitagawa, K.: Life Sci. 31, 1733 (1982)Google Scholar
  66. 57. a)
    Kitagawa, K., Kawai, N., Kiso, Y., Akita, T., Fukui, K., Amano, H., Takagi, H.: Chem. Pharm. Bull. 31, 2349 (1983)Google Scholar
  67. 57. b)
    Kitagawa, K., Kawai, N., Kiyama, S., Akita, T., Kiso, Y., Ueda, H., Ming, G., Takagi, H.: Chem. Pharm. Bull. 33, 377 (1985)Google Scholar
  68. 58.
    Schonenberger, G. A., Monnier, M.: Proc. Natl. Acad. Sci. USA 74, 1282 (1977)Google Scholar
  69. 59.
    Mikhaleva, I., Sargsyan, A., Ivanov, V.: Proc. of the 17th Eur. Peptide Symp., p. 563, Prague 1982Google Scholar
  70. 60.
    Schmidt, G.: Pharmazie in unserer Zeit 1, 181 (1972)Google Scholar
  71. 61.
    Bøler, J., Enzmann, F., Folkers, K., Bowers, C. Y., Schally, A. V.: Biochem. Biophys. Res. Commun. 37, 705 (1969)Google Scholar
  72. 62.
    Burgus, R., Dunn, T. F., Desiderio, D., Ward, D., Vale, W., Guillemin, R.: Nature 226, 321 (1970)Google Scholar
  73. 63.
    Rivier, J., Vale, W., Monahan, M., Ling, N., Burgus, R.: J. Med. Chem. 15, 479 (1972)Google Scholar
  74. 64. a)
    Wissmann, H., König, W., Geiger, R.: DE 2 033 600 (1972), Hoechst AGGoogle Scholar
  75. 64. b)
    Folkers, K., Enzmann, F. H.: US-Pat. 3 746 697 (1973) Austin, USAGoogle Scholar
  76. 65.
    Fujino, M., Nishimura, O., Nagawa, Y., Fukuda, N.: DOS 2 712 086 (1977), TakedaGoogle Scholar
  77. 66.
    Drugs of the Future 7, 167 (1982)Google Scholar
  78. 67.
    Schally, A. W., Arimura, A., Baba, Y., Nair, R. M. G., Matsuo, H., Redding, T. W., Debeljuk, L., White, W. F.: Biochem. Biophys. Res. Commun. 43, 393 (1971)Google Scholar
  79. 68. a)
    König, W., Geiger, R., Sandow, J. K.: EP 0 041 243 (1980), Hoechst AGGoogle Scholar
  80. 68. b)
    König, W., Teetz, V., Jäger, G., Geiger, R.: DE 2 905 502 (1980), Hoechst AGGoogle Scholar
  81. 69.
    König, W., Geiger, R., Sandow, J.: DOS 2 438 350 (1974), Hoechst AGGoogle Scholar
  82. 70. a)
    Karcher, H. L.: Selecta 43, 3548 (1984)Google Scholar
  83. 70. b)
    Drugs of the Future 7, 565 (1982) ibid. 4, 173 (1979)Google Scholar
  84. 71. a)
    Coy, D. H., Vilchez-Martinez, J. A., Coy, E. J., Schally, A. V.: J. Med. Chem. 19, 423 (1976)Google Scholar
  85. 71. b)
    Gendrich, R. L., Rippel, R. H., Seely, J. H.: US-Pat. 4 005 063 (1977), Abbott Lab., USAGoogle Scholar
  86. 71. c)
    Drugs of Today, Vol. 21, 393 (1985)Google Scholar
  87. 72.
    Nestor, J. J., Jones, G. H., Vickery, B. H.: DE 3 021 736 (1980), Syntex, USAGoogle Scholar
  88. 73.
    Nutt, R. F.: EP 0 070 021 (1982), Merck, USAGoogle Scholar
  89. 74.
    Nutt, R. F., Veber, D. F., Curley, P. E., Saperstein, R., Hirschmann, R.: Int. J. Peptide Protein Res. 21, 66 (1983)Google Scholar
  90. 75. a)
    Veber, D. F., Holly, F. W., Strachan, R. G., Paleveda, W. J., Nutt, R. F., Hirschmann, R.: US-Pat. 4 161 521 (1979), Merck, USAGoogle Scholar
  91. 75. b)
    Sarantakis, D.: US-Pat. 4 093 609 (1978), American HomeGoogle Scholar
  92. 76.
    Kamber, B.: EP 0 083 305 (1982), Ciba-GeigyGoogle Scholar
  93. 77.
    Drugs of the Future 9, 342 (1984)Google Scholar
  94. 78.
    Drugs of the Future 6, 491 (1981)Google Scholar
  95. 79. a)
    Veber, D. F., Nutt, R. F.: US-Pat. 4 191 754 (1980), Merck, USAGoogle Scholar
  96. 79. b)
    Freidinger, R. M., Veber, D. F.: J. Am. Chem. Soc. 101, 6129 (1979)Google Scholar
  97. 79. c)
    Freidinger, R. M., Colton, C. D., Perlow, D. S., Whitter, W. L., Paleveda, W. J., Veber, D. F.: Proc. of the 8th Am. Peptide Symp., p. 349, Tucson 1983Google Scholar
  98. 80. a)
    Wynants, C., van Binst, G., Loosli, H. R.: Int. J. Peptide Protein Res. 25, 608 (1985)Google Scholar
  99. 80. b)
    Lamberts, S. W. J., Uitterlinden, P., Verschoor, L., van Dongen, K. J., del Pozo, E.: New Engl. J. Med. 313, 1576 (1985)Google Scholar
  100. 81.
    Vale, W., Spies, J., Rivier, C., Rivier, J.: Science 213, 1394 (1981)Google Scholar
  101. 82.
    Morell, J. L., Brown, J. H.: Int. J. Peptide Protein Res. 26, 49 (1985)Google Scholar
  102. 83.
    Schally, A. V., Redding, T. W., Chang, R. C. C., Arimura, A., Huang, W. Y., Coy, D. H., Meyers, C. A., Pedroza, E., Kastin, A. J., Turkelson, C., in: Polypeptide Hormones (ed. Beers, R. F., Bassett, E. G.), p. 169, Ravens Press, New York 1980Google Scholar
  103. 84.
    Guillemin, R., Brazeau, P., Böhlen, P., Esch, F., Ling, N., Wehrenberg, W. B.: Science 218, 585 (1982)Google Scholar
  104. 85.
    Rivier, J., Spiess, J., Thorner, M., Vale, W.: Nature 300, 276 (1982)Google Scholar
  105. 86. a)
    Fujii, N., Shimokura, M., Nomizu, M., Yajima, H., Shono, F., Tsuda, M., Yoshitake, A.: Chem. Pharm. Bull. 32, 520 (1984)Google Scholar
  106. 86. b)
    Fujii, N., Lee, W., Shimoruka, M., Yajima, H.: ibid. 32, 739 (1984)Google Scholar
  107. 87. a)
    Li, C. H., Yamashiro, D.: J. Am. Chem. Soc. 92, 7608 (1970)Google Scholar
  108. 87. b)
    Blake, J., Li, C. H.: Int. J. Peptide Protein Res. 7, 495 (1975)Google Scholar
  109. 87. c)
    Blake, J., Li, C. H.: ibid. 11, 323 (1978)Google Scholar
  110. 88.
    Kappeler, H., Schwyzer, R.: Helv. Chim. Acta 44, 1136 (1961)Google Scholar
  111. 89.
    Schröder, E., Lübke, K.: The Peptides II, Academic Press, New York 1966Google Scholar
  112. 90.
    Schwyzer, R., Sieber, P.: Helv. Chim. Acta 49, 134 (1963)Google Scholar
  113. 91. a)
    du Vigneaud, V., Ressler, C., Swan, J. M., Roberts, C. W., Katsoyannis, P. G., Gordon, S.: J. Am. Chem. Soc. 75, 4879 (1953)Google Scholar
  114. 91. b)
    Katsoyannis, P. G., Gish, D. T., du Vigneaud, V.: ibid. 79, 4516 (1957)Google Scholar
  115. 92.
    Zaoral, M., Vávra, I., Machova, A., Sorm, F.: DOS 1 643 273 (1967), Czeskoslovenská akademie PragGoogle Scholar
  116. 93.
    Vinick, F. J., Jung, S.: J. Org. Chem. 48, 392 (1983)Google Scholar
  117. 94.
    Josefsson, L.: Int. J. Peptide Protein Res. 21, 459 (1983)Google Scholar
  118. 95.
    Ferrero, P., Guidotti, A., Conti-Tronconi, B., Costa, E., Neuropharmacology 23, 1359 (1984)Google Scholar
  119. 96.
    Jorpes, J. E., Mutt, V.: Acta Chem. Scand. 15, 1790 (1961)Google Scholar
  120. 97.
    Bodanszky, M., Ondetti, M. A., Levine, S. D., Williams, N. J.: J. Am. Chem. Soc. 89, 6753 (1967)Google Scholar
  121. 98.
    Ondetti, M. A., Narayanan, V. L., von Saltza, M., Sheehan, J. T., Sabo, E. F., Bodanszky, M.: J. Am. Chem. Soc. 90, 4711 (1968)Google Scholar
  122. 99.
    Wünsch, E., Wendlberger, G.: Chem. Ber. 105, 2508 (1972)Google Scholar
  123. 100.
    Uchiyama, M., Sato, T., Yoshino, H., Tsuchiya, Y., Tsuda, T., Konishi, M., Tsujii, M., Hisatake, Y., Koiwa, A.: Chem. Pharm. Bull. 33, 1990 (1985)Google Scholar
  124. 101.
    Staub, A., Sinn, L. G., Behrens, O. K.: Science 117, 628 (1953)Google Scholar
  125. 102.
    Bromer, W. W., Sinn, L. G., Staub, A., Behrens, O. K.: J. Am. Chem. Soc. 79, 2798 (1957)Google Scholar
  126. 103. a)
    Wünsch, E.: Z. Naturforschg. 22b, 1269 (1967)Google Scholar
  127. 103. b)
    Wünsch, E., Zwick, A., Fontana, A.: Chem. Ber. 101, 326 (1968)Google Scholar
  128. 104.
    Merrifield, R. B., Mojsov, S.: The Chemical Synthesis of Glucagon, in: Glucagon I, Handbook of Experimental Pharmacology, Vol. 66/I (ed. Lefèbvre, P. J.), p. 23, Springer Verlag, Berlin 1983Google Scholar
  129. 105.
    Bodanszky, M., Klausner, Y. S., Said, S. I.: Proc. Natl. Acad. Sci. USA 70, 382 (1973)Google Scholar
  130. 106. a)
    Tatemoto, K.: Peptides 5, 151 (1984)Google Scholar
  131. 106. b)
    Nokihara, K., Yanaihara, C., Iguchi, K., Fukuta, S., Tanaka, M., Mochizuki, T., Tatemoto, K., Lundberg, J. M., Mutt, V., Yanaihara, N.: J. Am. Chem. Soc. 106, 7909 (1984)Google Scholar
  132. 107.
    Moroder, L., Göhring, W., Thamm, P., Wünsch, E., Tatemoto, K., Mutt, V., Bataille, D.: Z. Naturforschg. 37b, 772 (1982)Google Scholar
  133. 108.
    Brown, J. C., Dryburgh, J. R.: Can. J. Biochem. 49, 867 (1971)Google Scholar
  134. 109.
    Gregory, H., Hardy, P. M., Jones, D. S., Kenner, G. W., Sheppard, R. C.: Nature 204, 931 (1964)Google Scholar
  135. 110. a)
    Gregory, H., Laird, A. H., Morley, J. S., Smith, J. M.: J. Chem. Soc. (C) 1968, 552Google Scholar
  136. 110. b)
    Gregory, H., Morley, J. S.: ibid. 1968, 910Google Scholar
  137. 110. c)
    Morley, J. S.: ibid. 1969, 809Google Scholar
  138. 110 d).
    Briggs, M. T., Morley, J. S.: J. Chem. Soc. Perkin Trans. I 1979, 2138Google Scholar
  139. 111. a)
    Brown, E., Sheppard, R. C., Williams, B. J.: J. Chem. Soc. Perkin Trans. I 1983, 1161Google Scholar
  140. 111. b)
    ibid. 1983, 75Google Scholar
  141. 112.
    Tam, J. P., Merrifield, R. B.: Int. J. Peptide Protein Res. 26, 262 (1985)Google Scholar
  142. 113.
    Mutt, V., Jorpes, J. E.: Eur. J. Biochem. 6, 156 (1968)Google Scholar
  143. 114.
    Wünsch, E., Moroder, L., Wilschowitz, L., Göhring, W., Scharf, R., Gardner, J. D.: Hoppe-Seyler's Z. Physiol. Chem. 362, 143 (1981)Google Scholar
  144. 115.
    Moroder, L., Wilschowitz, L., Gemeiner, M., Göhring, W., Knof, S., Scharf, R., Thamm, P., Gardner, J. D., Solomon, T. E., Wünsch, E.: Hoppe-Seyler's Z. Physiol. Chem. 362, 929 (1981)Google Scholar
  145. 116.
    Bodanszky, M., Natarajan, S., Hahne, W., Gardner, J. D.: J. Med. Chem. 20, 1047 (1977)Google Scholar
  146. 117. a)
    Martinez, J., Bali, J.-P., Magous, R., Laur, J., Lignon, M.-F., Briet, C., Nisato, D., Castro, B.: J. Med. Chem. 28, 273 (1985)Google Scholar
  147. 117. b)
    Martinez, J., Bali, J.-P., Rodriguez, M., Castro, B., Magous, R., Laur, J., Lignon, M.-F.: J. Med. Chem. 28, 1874 (1985)Google Scholar
  148. 118.
    Yajima, H., Futaki, S., Fujii, N., Akaji, K., Funakoshi, S., Sakurai, M., Katakura, S., Inoue, K., Hosotani, R., Tobe, T., Segawa, T., Inoue, A., Tatemoto, K., Mutt, V.: J. Chem. Soc. Chem. Commun. 1985, 877Google Scholar
  149. 119. a)
    Märki, W., Spiess, J., Tach'e, Y., Brown, M., Rivier, J. E.: J. Am. Chem. Soc. 103, 3178 (1981)Google Scholar
  150. 119. b)
    Minamino, N., Kangawa, K., Hisayuki, M.: Biochem. Biophys. Res. Commun. 119, 14 (1984)Google Scholar
  151. 119. c)
    Fujii, N., Futaki, S., Akaji, K., Yajima, H., Inoue, A., Segawa, T.: Chem. Pharm. Bull. 33, 3731 (1985)Google Scholar
  152. 120.
    Rivier, J. E., Brown, M. R.: Biochemistry 17, 1766 (1978)Google Scholar
  153. 121.
    Bernardi, L., Bosisio, G., DeCastiglione, R., Goffredo, O.: Experientia 23, 700 (1967)Google Scholar
  154. 122.
    Cuttitta, F., Carney, D. N., Mulshine, J., Moody, T. W., Fedorko, J., Fischler, A., Minna, J. D.: Nature 316, 823 (1985)Google Scholar
  155. 123.
    Brown, J. C., Cook, M. A., Dryburgh, J. R.: Can. J. Biochem. 51, 533 (1973)Google Scholar
  156. 124.
    Wünsch, E., Wendelberger, G., Deimer, K.-H.: Hoppe-Seyler's Z. Physiol. Chem. 357, 447 (1976)Google Scholar
  157. 125.
    Geiger, R.: Chemiker-Ztg. 100, 111 (1976)Google Scholar
  158. 126.
    Meienhofer, J., Schnabel, E., Bremer, H., Brinkhoff, O., Zabel, R., Sroka, W., Klostermeyer, H., Brandenburg, D., Okuda, T., Zahn, H.: Z. Naturforschg. 18b, 1120 (1963)Google Scholar
  159. 127.
    Ullrich, A., Bell, J. R., Chen, E. Y., Herrera, R., Petruzzelli, L. M., Dull, T. J., Gray, A., Coussens, L., Liao, Y.-C., Tsubokawa, M., Mason, A., Seeburg, P. H., Grunfeld, C., Rosen, O. M., Ramachandran, J.: Nature 313, 756 (1985)Google Scholar
  160. 128.
    Sieber, P., Kamber, B., Hartmann, A., Jöhl, A., Riniker, B., Rittel, W.: Helv. Chim. Acta 57, 2617 (1974)Google Scholar
  161. 129. a)
    Kovacevic, S., Fayerman, J. T., Miller, J. R., Richardson, M. A.: Brit. Pat. 2 133 798 (1983), E. LillyGoogle Scholar
  162. 129. b)
    Kovacevic, S., Miller, J. R., Hsiung, H. M.: Brit. Pat. 2 133 797 (1983), E. LillyGoogle Scholar
  163. 130. a)
    Markussen, J.: BE 887.780 (1981), Novo IndustriGoogle Scholar
  164. 130. b)
    Markussen, J.: DE 3 229.674 (1982), Novo IndustriGoogle Scholar
  165. 131.
    Tischio, J. P., Patrick, J. E., Weintraub, H. S., Chasin, M., Goldstein, G.: Int. J. Peptide Protein Res. 14, 479 (1979)Google Scholar
  166. 132.
    Audhya, T., Goldstein, G.: Int. J. Peptide Protein Res. 22, 187 (1983)Google Scholar
  167. 133.
    König, W., Geiger, R., Obermeier, R., Müllner, H.: DE 3 146 598 (1981), Hoechst AGGoogle Scholar
  168. 134.
    Goldstein, A. L., Low, T. L. K., McAdoo, M., McClure, J., Thurman, G. B., Rossio, J., Lai, C.-Y., Chang, D., Wang, S.-S., Harvey, C., Ramel, A. H., Meienhofer, J.: Proc. Natl. Acad. Sci. USA 74, 725 (1977)Google Scholar
  169. 135.
    Wang, S. S., Makofske, R., Bach, A., Merrifield, R. B.: Int. J. Peptide Protein Res. 15, 1 (1980)Google Scholar
  170. 136.
    Mokotoff, M., Patchornik, A.: Int. J. Peptide Protein Res. 21, 145 (1983)Google Scholar
  171. 137.
    Wang, S. S., Kulesha, I. D., Winter, D. P.: J. Am. Chem. Soc. 101, 253 (1979)Google Scholar
  172. 138.
    Felix, A. M., Heimer, E. P., Wang, C.-T., Lambros, T. J., Swistok, J., Roszkowski, M., Ahmad, M., Confalone, D., Scott, J. W., Parker, D., Meienhofer, J., Trzeciak, A., Gillessen, D.: Int. J. Peptide Protein Res. 26, 130 (1985)Google Scholar
  173. 139.
    Bach, J. F., Dardenne, M., Pleau, J.-M., Rosa, J.: Nature 266, 55 (1977)Google Scholar
  174. 140. a)
    Abiko, T., Kumikawa, M., Dazai, S., Sekino, H., Higuchi, H.: Chem. Pharm. Bull. 27, 2207 (1979)Google Scholar
  175. 140. b)
    Blanot, D., Martinez, J., Anger, G., Bricas, E.: Int. J. Peptide Protein Res. 14, 41 (1979)Google Scholar
  176. 140. c)
    Gyotoku, J., Imaizumi, A., Terada, S., Kimoto, E.: Int. J. Peptide Protein Res. 21, 135 (1983)Google Scholar
  177. 141.
    Najjar, V. A., Nishioka, K.: Nature 228, 672 (1970)Google Scholar
  178. 142.
    Nishioka, K., Amoscato, A. A., Babcock, G. F., Banks, R. A., Phillips, J. H.: Cancer Investigation 2, 39 (1984)Google Scholar
  179. 143.
    Wenger, R. M.: Angew. Chem. 97, 88 (1985)Google Scholar
  180. 144.
    Traber, R., Loosli, H.-R., Hofmann, H., Kuhn, M., von Wartburg, A.: Helv. Chim. Acta 65, 1655 (1982)Google Scholar
  181. 145.
    Petcher, T. J., Weber, H. P., Rüegger, A.: Helv. Chim. Acta 59, 1480 (1976)Google Scholar
  182. 146.
    Wenger, R. M.: Helv. Chim. Acta 66, 2672 (1983)Google Scholar
  183. 147.
    Wenger, R. M.: Helv. Chim. Acta 67, 502 (1984)Google Scholar
  184. 148.
    Baschang, G., Tarcsay, L., Hartmann, A., Stanek, J.: EP 0 027 258 (1980), Ciba-GeigyGoogle Scholar
  185. 149.
    Wiesmüller, K.-H., Bessler, W., Jung, G.: Hoppe-Seyler's Z. Physiol. Chem. 364, 593 (1983)Google Scholar
  186. 150.
    Královec, J.: Drugs of the Future 8, 615 (1983)Google Scholar
  187. 151.
    Kunz, H., Kauth, H.: Liebigs Ann. Chem. 1983, 337; ibid. 1983, 360Google Scholar
  188. 152.
    Krueger, J. M., Pappenheimer, J. R., Karnovsky, M. L.: J. Biol. Chem. 257, 1664 (1982)Google Scholar
  189. 153.
    Krueger, J. M., Walter, J., Karnovsky, M. L., Chedid, L., Choay, J. P., Lefrancier, P., Lederer, E.: J. Exp. Med. 159, 68 (1984)Google Scholar
  190. 154.
    Krueger, J. M., Kornovsky, M. L., Martin, S. A., Pappenheimer, J. R., Walter, J., Biemann, K.: J. Biol. Chem. 259, 12659 (1984)Google Scholar
  191. 155.
    Lerner, R. A., Green, N., Alexander, H., Liu, F.-T., Sutcliffe, J. G., Shinnick, T. M.: Proc. Natl. Acad. Sci. USA 78, 3403 (1981)Google Scholar
  192. 156.
    Audibert, F., Jolivet, M., Chedid, L., Alouf, J. E., Boquet, P., Rivaille, P., Siffert, O.: Nature 289, 593 (1981)Google Scholar
  193. 157.
    Emini, E. A., Jameson, B. A., Wimmer, E.: Nature 304, 699 (1983)Google Scholar
  194. 158.
    Hemmi, K., Aratani, M., Takeno, H., Okada, S., Miyazaki, Y., Nakaguchi, O., Kitaura, Y., Hashimoto, M.: J. Antibiot. 35, 1300 (1982)Google Scholar
  195. 159. a)
    Kitaura, Y., Nakaguchi, O., Hemmi, K., Aratani, M., Takeno, H., Okada, S., Tanaka, H., Hashimoto, M.: EP 0 027 260 (1980), Fujisawa PharmaceuticalGoogle Scholar
  196. 159. b)
    Kitaura, Y., Nakaguchi, O., Hemmi, K., Yonishi, S., Takeno, H., Okada, S., Hashimoto, M.: EP 0 057 419 (1982), Fujisawa PharmaceuticalGoogle Scholar
  197. 160.
    Izumi, S., Nakahara, K., Gotoh, T., Hashimoto, S., Kino, T., Okuhara, M., Aoki, H., Imanaka, H.: J. Antibiot. 36, 566 (1983)Google Scholar
  198. 161.
    Mine, Y., Yokota, Y., Wakai, Y., Fukuda, S., Nishida, M., Goto, S., Kuwahara, S.: J. Antibiot. 36, 1045 (1983)Google Scholar
  199. 162.
    Mine, Y., Watanabe, Y., Tawara, S., Yokota, Y., Nishida, M., Goto, S., Kuwahara, S.: J. Antibiot. 36, 1059 (1983)Google Scholar
  200. 163.
    Closse, A., Huguenin, R.: Helv. Chim. Acta 57, 553 (1974)Google Scholar
  201. 164. a)
    Rich, D. H., Jasensky, R. D.: J. Am. Chem. Soc. 101, 5413 (1979)Google Scholar
  202. 164. b)
    Pastuszak, J., Gardner, J. H., Singh, J., Rich, D. H.: J. Org. Chem. 47, 2982 (1982)Google Scholar
  203. 164. c)
    Kawai, M., Jasensky, R. D., Rich, D. H.: J. Am. Chem. Soc. 105, 4456 (1983)Google Scholar
  204. 165.
    Schmidt, U., Beuttler, T., Lieberknecht, A., Griesser, H., Tetrahedron Lett. 24, 3573 (1983)Google Scholar
  205. 166.
    Chakravarty, P. K., Carl, P. L., Weber, M. J., Katzenellenbogen, J. A.: J. Med. Chem. 26, 633 (1983)Google Scholar
  206. 167.
    Umezawa, H., Aoyagi, T., Shirai, T., Nishizawa, R., Suzuki, M., Saino, T.: DOS 2 947 140 (1979), Nippon KayakuGoogle Scholar
  207. 168.
    Drugs of the Future 6, 604 (1981)Google Scholar
  208. 169.
    Cushman, D. W., Ondetti, M. A.: Prog. Med. Chem. 17, 41 (1980)Google Scholar
  209. 170.
    Ondetti, M. A., Cushman, D. W.: J. Med. Chem. 24, 355 (1981)Google Scholar
  210. 171.
    Khosla, M. C., Hall, M. M., Smeby, R. R., Bumpus, F. M.: J. Med. Chem. 17, 431 (1974)Google Scholar
  211. 172.
    Drugs of the Future 6, 542 (1981)Google Scholar
  212. 173.
    Bumpus, F. M., Khosla, M. C., Smeby, R. R.: DOS 2 520 106 (1975), Abbott LaboratoriesGoogle Scholar
  213. 174.
    Drugs of the Future 6, 634 (1981)Google Scholar
  214. 175.
    Drugs of the Future 6, 527 (1981)Google Scholar
  215. 176.
    Geiger, R.: Arzneim.-Forsch./Drug Res. 34(II), 1386 (1984)Google Scholar
  216. 177.
    Patchett, A. A., Harris, E., Tristam, E. W., Wyvratt, M. J., Wu, M. T., Taub, D., Peterson, E. R., Ikeler, T. J., ten Broeke, J., Payne, L. G., Ondeyka, D. L., Thorsett, E. D., Greenlee, W. J., Lohr, N. S., Hoffsommer, R. D., Joshua, H., Ruyle, W. V., Rothrock, J. W., Aster, S. D., Maycock, A. L., Robinson, F. M., Hirschmann, R., Sweet, C. S., Ulm, E. H., Gross, D. M., Vassil, T. C., Stone, C. A.: Nature 288, 280 (1980)Google Scholar
  217. 178.
    Teetz, V., Geiger, R., Henning, R., Urbach, H.: Arzneim.-Forsch./Drug Res. 34 (II) 1399 (1984)Google Scholar
  218. 179.
    Greenlee, W. J., Allibone, P. L., Perlow, D. S., Patchett, A. A., Ulm, E. H., Vassil, T. C.: J. Med. Chem. 28, 434 (1985)Google Scholar
  219. 180.
    Gruenfeld, N., Stanton, J. L., Yuan, A. M., Ebetino, F. H., Browne, L. J., Gude, C., Huebner, C. F.: J. Med. Chem. 26, 1277 (1983)Google Scholar
  220. 181.
    Ksander, G. M., Yan, A. M., Diefenbacher, C. G., Stanton, J. L.: J. Med. Chem. 28, 1606 (1985)Google Scholar
  221. 182.
    Attwood, M. R., Hassall, C. H., Lambert, R. W., Lawton, G. R.: DOS 3 317 290 (1983), Hoffmann-La Roche, SchweizGoogle Scholar
  222. 183.
    Skeggs, L. T., Lentz, K. E., Kahn, J. R., Hochstrasser, H.: J. Exp. Med. 128, 13 (1968)Google Scholar
  223. 184. a)
    Szelke, M., Leckie, B., Hallett, A., Jones, D. M., Sueiras, J., Atrash, B., Lever, A. F.: Nature 299, 555 (1982)Google Scholar
  224. 184. b)
    Leckie, B., Szelke, M., Hallet, A., Hughes, M., Lever, A. F., McIntyre, G., Morton, J. J., Tree, M.: Clin. Exp. Hypertens. A 5, 1221 (1983)Google Scholar
  225. 184. c)
    Haber, E.: Clin. Exp. Hypertens. A 5, 1193 (1983)Google Scholar
  226. 185.
    Boger, J., Lohr, N. S., Ulm, E. H., Poe, M., Blaine, E. H., Fanelli, G. M., Lin, T.-Y., Payne, L. S., Schorn, T. W., La Mont, B. I., Vassil, T. C., Stabilito, I. I., Veber, D. F., Rich, D. H., Bopari, A. S.: Nature 303, 81 (1983)Google Scholar
  227. 186.
    Rittle, K. E., Homnick, C. F., Ponticello, G. S., Evans, B. E.: J. Org. Chem. 47, 3016 (1982)Google Scholar
  228. 187. a)
    Veber, D. F., Boger, J.: EP 0 077 028 (1982), Merck, USAGoogle Scholar
  229. 187. b)
    Veber, D. F., Rich, D. H.: EP 0 077 029 (1982), Merck, USAGoogle Scholar
  230. 188.
    Boger, J.: Proc. of the 8th Am. Peptide Symp., p. 569, Tucson 1983Google Scholar
  231. 189. a)
    Rich, D. H., Salituro, F. G., Holladay, M. W.: Proc. of the 8th Am. Peptide Symp., p. 139, 511, Tucson 1983Google Scholar
  232. 189. b)
    Rich, D. H., Sun, E. T. O.: J. Med. Chem. 23, 27 (1980)Google Scholar
  233. 189. c)
    Rich, D. H.: ibid. 28, 263 (1985)Google Scholar
  234. 190. a)
    Bock, M. G., Boger, J. S., Brady, S. F. Veber, D. F.: EP 0 157 409 (1985), Merck, USAGoogle Scholar
  235. 190. b)
    Boger, J. S.: EP 0 156 318 (1985), EP 0 156 319 (1985) and EP 0 156 320 (1985), Merck, USAGoogle Scholar
  236. 190. c)
    Bock, M. G., Dipardo, R. M., Boger, J. S.: EP 0 156 321 (1985), Merck, USAGoogle Scholar
  237. 190. d)
    Boger, J. S., Bock, M. G.: EP 0 156 322 (1985), Merck, USAGoogle Scholar
  238. 190. e)
    Boger, J., Payne, L. S., Perlow, D. S., Lohr, N. S., Poe, M., Blaine, E. H., Ulm, E. H., Schorn, T. W., LaMont, B. I., Lin, T.-Y., Kawai, M., Rich, D. H., Veber, D. F.: J. Med. Chem. 28, 1779 (1985)Google Scholar
  239. 191.
    Boissonas, R. A., Guttmann, St., Jaquenoud, P.-A.: Helv. Chim. Acta 43, 1349 (1960); ibid. 43, 1481 (1960)Google Scholar
  240. 192. a)
    Bertaccini, G.: Pharmacol. Rev. 28, 127 (1976)Google Scholar
  241. 192. b)
    Miller, R. J.: J. Med. Chem. 27, 1239 (1984)Google Scholar
  242. 193.
    Sandrin, E., Boissonas, R. A.: Experientia 18, 59 (1962)Google Scholar
  243. 194.
    Lübke, K., Schröder, E., Schmiechen, R., Gibian, H.: Liebigs Ann. Chem. 679, 195 (1964)Google Scholar
  244. 195. a)
    Chillemi, F., Bernardi, L., Bosisio, G.: Gazz. Chim. Ital. 94, 891 (1964)Google Scholar
  245. 195. b)
    Bernardi, L., Bosisio, G., Chillemi, F., DeCaro, G., DeCastiglione, R., Erspamer, V., Glaesser, A., Goffredo, O.: Experientia 20, 306 (1964)Google Scholar
  246. 195. c)
    Buck, S. H., Burcher, E.: Trends in Pharmacological Sciences 7, 65 (1986)Google Scholar
  247. 196.
    Voelter, W., Zech, K., Jung, G., Sewing, K.-F.: Tetrahedron 28, 2649 (1972)Google Scholar
  248. 197.
    Chillemi, F.: Gazz. Chim. Ital. 95, 402 (1965)Google Scholar
  249. 198.
    Voelter, W., Zech, K., Jung, G., Sewing, K.-F.: Tetrahedron 28, 5963 (1972)Google Scholar
  250. 199.
    Anastasi, A.: Experientia 33, 857 (1977)Google Scholar
  251. 200.
    Bernardi, L., Bosisio, G., DeCastiglione, R.: Experientia 23, 700 (1967)Google Scholar
  252. 201.
    Zetler, G.: DE 3 138 233 (1981), Farmitalia-Carlo ErbaGoogle Scholar
  253. 202.
    Flynn, T. G., de Bold, M. L., de Bold, A. J.: Biochem. Biophys. Res. Commun. 117, 859 (1983)Google Scholar
  254. 203. a)
    Kangawa, K., Matsuo H., Biochem. Biophys. Res. Commun. 118, 131 (1984)Google Scholar
  255. 203. b)
    Kangawa, K., Fukada, A., Matsuo, H.: Nature 313, 397 (1985)Google Scholar
  256. 204.
    Kangawa, K., Tawaragi, Y., Oikawa, S., Mizuno, A., Sakuragawa, Y., Nakazato, H., Fukuda, A., Minamino, N., Matsuo, H.: Nature 312, 152 (1984)Google Scholar
  257. 205. a)
    Seidah, N. G., Lazure, C., Chrétien, M., Thibault, G., Gracia, R., Cantin, M., Genest, J., Nutt, R. F., Brady, S. F., Lyle, T. A., Paleveda, W. J., Colton, C. D., Ciccarone, T. M., Veber, D. F.: Proc. Natl. Acad. Sci. USA 81, 2640 (1984)Google Scholar
  258. 205. b)
    Nutt, R. F., Brady, S. F., Lyle, T. A., Dylion-Colton, C., Paleveda, W. J., Ciccarone, T. M., Blaine, E. H., Winquist, R. J., Bennet, C. D., Hirschmann, R., Veber, D. F.: Proc. of 18th Eur. Peptide Symp., p. 513, Djurönäset 1984, SwedenGoogle Scholar
  259. 206. a)
    Currie, M. G., Geller, D. M., Cole, B. R., Siegel, N. R., Fok, K. F., Adams, S. P., Eubanks, S. R., Galluppi, G. R., Needleman, P.: Science 1983, 67Google Scholar
  260. 206. b)
    Needleman, P.: US-Pat. 4 496 544 and 4 508 712 (1985), Washington University, St. LouisGoogle Scholar
  261. 207.
    Fok, K. F., Tjoeng, F. S., Houbion, J. A., Spear, K. L., Nugent, S. T., Eubanks, S. R., Zupec, M. E., Olins, G., Blehm, D. J., Adams, S. P., Wakitani, K., Needleman, P.: Proc, of the 9th Am. Peptide Symp., p. 953, Toronto 1985Google Scholar
  262. 208.
    Riniker, B., Brugger, M., Kamber, B., Sieber, P., Rittel, W.: Helv. Chim. Acta 52, 1073 (1969)Google Scholar
  263. 209.
    Sakakibara, S., Noda, T., Morikawa, T., Munekata, E., Kimura, T., Nakagawa, Y.: DOS 2 616 399 (1976), Toyo Jozo K. K.Google Scholar
  264. 210.
    Orlowski, R. C., Stahl, G. L., Colescott, R. L.: US-Pat. 4 528 132 (1984), Armour Pharmaceutical Co., USAGoogle Scholar
  265. 211.
    Izumiya, N., Kato, T., Aoyagi, H., Waki, M., Kondo, M.: Synthetic Aspects of Biologically Active Cyclic Peptides, J. Wiley & Sons, New York 1979Google Scholar
  266. 212.
    Hassall, C. H., Johnson, W. H., Theobald, C. J.: J. Chem. Soc. Perkin Trans. I. 1979, 1451Google Scholar
  267. 213.
    Kupryszewski, G.: Synthetic Oligopeptide Derivatives with Antibacterial Activity, in: Perspectives in Peptide Chemistry (ed. Eberle, A., Geiger, R., Wieland, T.), p. 307, S. Karger, Basel 1981Google Scholar
  268. 214.
    Alewood, P. F., Perich, J. W., Johns, R. B.: Synthetic Commun. 12, 821 (1982)Google Scholar
  269. 215.
    Maier, L.: Phosphorus and Sulfur, Vol. 14, 295 (1983)Google Scholar
  270. 216. a)
    Atherton, R. F., Hall, J. M., Hassall, C. H., Lambert, R. W., Ringrose, P. S.: DOS 2 730 524 (1977); DOS 2 730 549 (1977), Hoffmann-La Roche, SwitzerlandGoogle Scholar
  271. 216. b)
    Atherton, F. R., Hassall, C. H., Lambert, R. W.: J. Med. Chem. 29, 29 (1986)Google Scholar
  272. 217.
    Meienhofer, J., Patel, R. P.: Int. J. Peptide Protein Res. 3, 347 (1971)Google Scholar
  273. 218. a)
    Benz, G.: Liebigs Ann. Chem. 1984, 1399Google Scholar
  274. 218. b)
    Metzger, K. G., Pfitzner, J., Schmidt, D., Weyland, H., Benz, G., Schröder, T.: DOS 3 102 137 (1981); DOS 3 102 136 (1981), BAYER AGGoogle Scholar
  275. 219.
    Gross, E., Morell, J. L.: J. Am. Chem. Soc. 92, 2919 (1970), ibid. 93, 4634 (1971)Google Scholar
  276. 220.
    Wakamiya, T., Shimbo, K., Sano, A., Fukase, K., Shiba, T.: Bull. Chem. Soc. Jpn. 56, 2044 (1983)Google Scholar
  277. 221.
    Hagenmaier, H., Keckeisen, A., Zähner, H., König, W. A.: Liebigs Ann. Chem. 1979, 1494Google Scholar
  278. 222. a)
    Hass, W., König, W. A.: Liebigs Ann. Chem. 1982, 1615Google Scholar
  279. 222. b)
    Rathmann, R., König, W. A., Schmalle, H., Carlsson, G., Bosch, R., Hagenmaier, H., Winter, W.: Liebigs Ann. Chem. 1984, 1216Google Scholar
  280. 223. a)
    König, W. A., Hass, W., Dehler, W., Fiedler, H.-P., Zähner, H.: Liebigs Ann. Chem. 1980, 622Google Scholar
  281. 223. b)
    Zimmermann, G., Hass, W., Faasch, H., Schmalle, H., König, W. A.: Liebigs Ann. Chem. 1985, 2165.Google Scholar
  282. 224.
    Merrifield, R. B., Vizoli, L. D., Boman, H. G.: Biochemistry 21, 5020 (1982)Google Scholar
  283. 225.
    Andreau, D., Merrifield, R. B., Steiner, H., Boman, H. G.: Proc. of the 18th Eur. Peptide Symp., p. 541, Djurönäset 1984, SwedenGoogle Scholar
  284. 226.
    Payne, J. W., Jakes, R., Hartley, B. S.: Biochem. J. 117, 757 (1970)Google Scholar
  285. 227. a)
    Schmitt, H., Jung, G.: Liebigs Ann. Chem. 1985, 321Google Scholar
  286. 227. b)
    Jung, G., Brückner, H., Schmitt, H.: Properties of the Membrane Modifying Polypeptide Antibiotics Alamethicin and Trichotoxin A-40, in: Structure and Activity of Natural Peptides, (ed. Voelter, W., Weitzel, G.), p. 75, Walter de Gruyter, Berlin 1981Google Scholar
  287. 228. a)
    Bartmann, W., Beck, G., Angew. Chem. 94, 767 (1982)Google Scholar
  288. 228. b)
    Samuelsson, B.: Science 220, 568 (1983)Google Scholar
  289. 229.
    Corey, E. J., Clark, D. A., Goto, G., Marfat, A., Mioskowski, C.: J. Am. Chem. Soc. 102, 1436 (1980)Google Scholar
  290. 230. a)
    Gleason, J. G.: Abstracts of the 2nd SCI-RSC Medicinal Chemistry Symposium, Cambridge 1983Google Scholar
  291. 230. b)
    Saksena, A. K., Green, M. J., Mangiaracina, P., Wong, J. K., Kreutner, W., Gulbenkian, A. R.: Tetrahedron Lett. 26, 6423 (1985)Google Scholar
  292. 231.
    Shiba, T.: Peptide Chemistry 1977, Proc. of the 15th Symp. on Pept. Chem., Osaka 1977Google Scholar
  293. 232.
    Bayer, E., Gugel, K. H., Hägele, K., Hagenmaier, H., Jessipow, S., König, W. A., Zähner, H.: Helv. Chim. Acta 55, 224 (1972)Google Scholar
  294. 233. a)
    Wieland, T.: Chemie in unserer Zeit 13, 56 (1979)Google Scholar
  295. 233. b)
    Witkop, B.: Naturwissenschaftliche Rundschau 36, 261 (1983)Google Scholar
  296. 234.
    Wieland, T., Faesel, J., Konz, W.: Liebigs Ann. Chem. 722, 197Google Scholar
  297. 235. a)
    Bodanszky, M., Stahl, G. L.: Proc. Natl. Acad. Sci. USA 71, 2791 (1974)Google Scholar
  298. 235. b)
    Bodanszky, M., Bednarek, M. A., Yiotakis, A. E., Curtis, R. W.: Int. J. Peptide Protein Res. 20, 16 (1982)Google Scholar
  299. 236.
    Williams, D. H., Santikarn, S., DeAngelis, F., Smith, R. J., Reid, D. G., Oelrichs, P. B., McLeod, J. K.: J. Chem. Soc. Perkin Trans. I, 1983, 1869Google Scholar
  300. 237. a)
    Mazur, R. H., Schlatter, J. M., Goldcamp, A. H.: J. Am. Chem. Soc. 91, 2684 (1969)Google Scholar
  301. 237. b)
    Mazur, R. H., Reuter, J. A., Swiatek, K. A., Schlatter, J. M.: J. Med. Chem. 16, 1284 (1973)Google Scholar
  302. 238. a)
    Otagiri, K., Miyake, I., Ishibashi, N., Fukui, H., Kanehisa, H., Okai, H.: Bull. Chem. Soc. Jpn. 56, 1116 (1983)Google Scholar
  303. 238. b)
    Otagiri, K., Shigenaga, T., Kanehisa, H., Okai, H.: ibid. 57, 90 (1984)Google Scholar
  304. 239.
    Fuller, W. D., Goodman, M., Verlander, M. S.: J. Am. Chem. Soc. 107, 5821 (1985)Google Scholar

Copyright information

© Springer-Verlag 1986

Authors and Affiliations

  • Gunter Schmidt
    • 1
  1. 1.EP-FE Chemisch wissenschaftliches Labor, BAYER AGWuppertal 1Germany

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