Skip to main content
SpringerLink
Log in

Activation and Coupling

  • Chapter
Principles of Peptide Synthesis

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 16))

Abstract

Formation of an amide bond between two amino acids is an energy-requiring reaction. Carboxylic acids do react with amines at elevated temperatures and amides can be produced this way. For instance, ammonium acetate can be converted to acetamide by heating. The temperatures, however, at which such transformations occur far exceed the limits considered safe for complex peptides. In fact, peptide synthesis is usually performed at or below room temperature and coupling methods which involve heating of the reaction mixture are regarded as not generally useful. Therefore, in order to form a peptide bond, one of the groups that will produce the desired amide, either the carboxyl or the amino group, must be activated.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 74.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Rzeszotarska, B., Taschner, E.: Proc. Sixth European Peptide Symposium, Athens, 1963 (Zervas, L. ed.) p. 135, Oxford: Pergamon Press 1966

    Google Scholar 

  2. Curtius, Th.: Ber. dtsch. Chem. Ges. 35, 3226 (1902)

    CAS  Google Scholar 

  3. Fischer, E.: Ber. dtsch. Chem. Ges. 36, 2094 (1903)

    CAS  Google Scholar 

  4. Brenner, M.: in Peptides, Proceedings of the Eighth European Peptide Symposium, Nordwijk, 1966 (Beyerman, H. C., van de Linde, A., Maasen van den Brink, eds.) p. 1, Amsterdam: North Holland Publishing 1967

    Google Scholar 

  5. Taschner, E., Rzeszotarska, B., Lubiewska, L.: Chem. Ind. 402 (1967)

    Google Scholar 

  6. Heikens, D., Hermans, P. H., van Velden, P. F.: Nature 174, 1187 (1954)

    CAS  Google Scholar 

  7. Schwyzer, R., Iselin, B., Feurer, M.: Helv. Chim. Acta 38, 69 (1955)

    CAS  Google Scholar 

  8. Taschner, E., Rzeszotarska, B., Kuziel, A.: Acta Chim. Hung. 44, 67 (1965)

    CAS  Google Scholar 

  9. Chapman, T. M., Freedman, E. A.: J. Org. Chem. 38, 3908 (1973)

    CAS  Google Scholar 

  10. Brenner, M., Zimmermann, J. P., Wehrmüller, Quitt, P., Photaki, I.: Experientia 11, 397 (1955)

    CAS  Google Scholar 

  11. Brenner, M., Zimmermann, J. P., Wehrmüller, J., Quitt, P., Hartmann, A., Schneider, W., Beglinger, U.: Helv. Chim. Acta 40, 1497 (1957)

    CAS  Google Scholar 

  12. Brenner, M., Hofer, W.: Helv. Chim. Acta 44, 1794; 1798 (1961)

    CAS  Google Scholar 

  13. Ugi, L: Angew. Chem. (Int. Ed. English) 1, 8 (1962)

    Google Scholar 

  14. Ugi, I.: in “The Peptides”, Vol. 2, p. 365 (Gross, E., Meienhofer, J., eds.) New York: Academic Press 1980

    Google Scholar 

  15. Waki, M., Meienhofer, J.: J. Amer. Chem. Soc. 99, 6075 (1977)

    CAS  Google Scholar 

  16. Marquarding, D., Burghard, H., Ugi, I., Urban, R., Klusacek, H.: J. Chem. Res. (M) 0915; (S) p. 82 (1977)

    Google Scholar 

  17. Pettit, G. R.: „Synthetic Peptides“, Vol. 4, p. 22, Amsterdam: Elsevier 1976

    Google Scholar 

  18. Bodanszky, M.: in “Prebiotic and Biochemical Evolution” (Kimball, A. R., Oro, J., eds.) p. 217, Amsterdam: North Holland Publ. 1971

    Google Scholar 

  19. Bodanszky, M.: Ann. N.Y. Acad. Sci. 88, 655 (1960)

    CAS  Google Scholar 

  20. Merrifield, R. B.: J. Amer. Chem. Soc. 85, 2149 (1963)

    CAS  Google Scholar 

  21. Fujii, N., Yajima, H.: J. Chem. Soc. Perkin I, 789; 797; 804; 811; 819; 831 (1981)

    Google Scholar 

  22. Sieber, P., Riniker, B., Brugger, M., Kamber, B., Rittel, W.: Helv. Chim. Acta 53, 2135 (1970)

    CAS  Google Scholar 

  23. Medzihradszky-Schweiger, H.: Acta Chim. Acad. Sci. Hung. 34, 213 (1962)

    CAS  Google Scholar 

  24. Kaufmann, K. D., Raddatz, F., Bauschke, S.: Z. Chem. 15, 449 (1975)

    CAS  Google Scholar 

  25. Höfmann, K., Magee, M. Z., Lindenmann, A.: J. Amer. Chem. Soc. 72, 2814 (1950)

    Google Scholar 

  26. Curtius, T., Levy, L.: J. prakt. Chem. 70, 89 (1904)

    CAS  Google Scholar 

  27. Cheung, H. T., Blout, E. R.: J. Org. Chem. 30, 315 (1965)

    CAS  Google Scholar 

  28. Zahn, H., Schnabel, E.: Liebigs Ann. Chem. 605, 212 (1957)

    CAS  Google Scholar 

  29. Guttmann, S., Boissonnas, R. A.: Helv. Chim. Acta 41, 1852 (1958)

    CAS  Google Scholar 

  30. Medzihradszky, K., Bruckner, V., Kajtár, M., Löw, M., Bajusz, S., Kisfaludy, L.: Acta Chim. Acad. Sci. Hung. 30, 105 (1962)

    CAS  Google Scholar 

  31. Honzl, J., Rudinger, J.: Collect. Czech. Chem. Commun. 26, 2333 (1961)

    CAS  Google Scholar 

  32. Shiori, T., Ninomiya, K., Yamada, S.: J. Amer. Chem. Soc. 94, 6203 (1972)

    Google Scholar 

  33. Curtius, T.: Ber. dtsch. Chem. Ges. 23, 3023 (1890)

    Google Scholar 

  34. Inouye, K., Watanabe, K.: J. Chem. Soc. Perkin I, 1911 (1977)

    Google Scholar 

  35. Schnabel, E.: Liebigs Ann. Chem. 659, 168 (1962)

    CAS  Google Scholar 

  36. Meienhofer, J.: The Peptides, Vol. I, p. 197, New York: Academic Press 1979

    Google Scholar 

  37. Klausner, Y., Bodanszky, M.: Synthesis 8, 549 (1974)

    Google Scholar 

  38. Curtius, T.: J. prakt. Chem. 24, 239 (1881)

    Google Scholar 

  39. Chantrenne, H.: Nature 160, 603 (1947)

    CAS  Google Scholar 

  40. Chantrenne, H.: Biochim. Biophys. Acta 2, 286 (1948)

    CAS  Google Scholar 

  41. Chantrenne, H.: Nature 164, 576 (1949)

    CAS  Google Scholar 

  42. Chantrenne, H.: Biochim. Biophys. Acta 4, 484 (1950)

    CAS  Google Scholar 

  43. Sheehan, J. C., Frank, V. S.: J. Amer. Chem. Soc. 72, 1312 (1950)

    CAS  Google Scholar 

  44. Wieland, T., Kern, W., Sehring, R.: Liebigs Ann. Chem. 569, 117 (1950); cf. also Wieland, T., Sehring, R.: ibid. 569, 122 (1950)

    CAS  Google Scholar 

  45. Vaughan, J. R., Jr., Osato, R. L.: J. Amer. Chem. Soc. 73, 5553 (1951)

    CAS  Google Scholar 

  46. Zaoral, M.: Coll. Czech. Chem. Commun. 27, 1273 (1962)

    CAS  Google Scholar 

  47. du Vigneaud, V., Ressler, C., Swan, J. M., Roberts, C. W., Katsoyannis, P. G., Gordon, S.: J. Amer. Chem. Soc. 75, 4879 (1953).

    Google Scholar 

  48. Galpin, I. J., Handa, B. K., Hudson, D., Jackson, A. G., Kenner, G. W., Ohlsen, S. R., Ramage, R., Singh, B., Tyson, R. G.: Peptides 1976 (Loffet, A., ed.) p. 247. Editions de l’Université de Bruxelles, Belgium (1976)

    Google Scholar 

  49. Boissonnas, R. A.: Helv. Chem. Acta 34, 874 (1951)

    CAS  Google Scholar 

  50. Vaughan, J. R., Jr.: J. Amer. Chem. Soc. 73, 3547 (1951); Vaughan, J. R., Jr., Osato, R. L.: ibid. 74, 676 (1952)

    CAS  Google Scholar 

  51. Wieland, T., Bernhard, H.: Liebigs Ann. Chem. 572, 190 (1951)

    CAS  Google Scholar 

  52. Bodanszky, M., Tolle, J. C.: Int. J. Peptide Protein Research 10, 380 (1977)

    CAS  Google Scholar 

  53. Sarges, R., Witkop, B.: J. Amer. Chem. Soe. 87, 2020 (1965)

    CAS  Google Scholar 

  54. Tilak, M.: Tetrahedron Lett. 849 (1970)

    Google Scholar 

  55. van Zon, A., Beyerman, H. C.: Helv. Chim. Acta 56, 1729 (1973); ibid., 59, 1112(1976)

    Google Scholar 

  56. Anderson, G. W., Biodinger, J., Young, R. W., Welcher, A. D.: J. Amer. Chem. Soc. 74, 5304 (1952)

    CAS  Google Scholar 

  57. Anderson, G. W., Young, R. W.: J. Amer. Chem. Soc. 74, 5307 (1952)

    CAS  Google Scholar 

  58. Anderson, G. W., Biodinger, J., Welcher, A. D.: J. Amer. Chem. Soc. 74, 5309 (1952)

    CAS  Google Scholar 

  59. Albertson, N. F.: Org. Reactions, Vol. 12, p. 157. New York: Wiley 1962

    Google Scholar 

  60. Tarbell, D. S.: Acct. Chem. Res. 2, 296 (1969)

    CAS  Google Scholar 

  61. Meienhofer, J.: The Peptides (Gross, E., Meienhofer, J., eds.) Vol. 1, p. 263. New York: Academic Press 1979

    Google Scholar 

  62. E. Wünsch: Synthese von Peptiden. Methoden der Organischen Chemie. Vol. XV2, Houben-Weyl). Stuttgart: Thieme 1974

    Google Scholar 

  63. Süs, O.: Liebigs Ann. Chem. 572, 96 (1951)

    Google Scholar 

  64. Young, R. W., Wood, K. H., Joyce, R. J., Anderson, G. W.: J. Amer. Chem. Soc. 78, 2126 (1956)

    CAS  Google Scholar 

  65. Goldschmidt, S., Obermeier, F.: Liebigs Ann. Chem. 588, 24 (1954)

    CAS  Google Scholar 

  66. Anderson, G. W., Welcher, A. D., Young, R. W.: J. Amer. Chem. Soc. 73, 501 (1951)

    CAS  Google Scholar 

  67. Crofts, P. C., Markes, J. H. H., Rydon, H. N.: J. Chem. Soc, 4250 (1958)

    Google Scholar 

  68. Crofts, P.C., Markes, J. H. H., Rydon, H. N.: J. Chem. Soc, 3610 (1959)

    Google Scholar 

  69. Vaughan, J. R., Jr.: J. Amer. Chem. Soc. 73, 1389 (1951)

    CAS  Google Scholar 

  70. Wieland, T., Heinke, B.: Liebigs Ann. Chem. 599, 70 (1956)

    CAS  Google Scholar 

  71. Wieland, T., Heinke, B.: Liebigs Ann. Chem. 615, 184 (1958)

    CAS  Google Scholar 

  72. Martinez, J., Winternitz, F.: Bull. Soc. Chim. France, 4707 (1972); cf. also Das, K. C., Lin, Y., Weinstein, B.: Experientia 25, 1238 (1969)

    Google Scholar 

  73. Bates, A. J., Galpin, I. J., Hallett, A., Hudson, D., Kenner, G. W., Ramage, R.: Helv. Chim. Acta 58, 688 (1975)

    CAS  Google Scholar 

  74. Gawne, G., Kenner, G. W., Sheppard, R. C.: J. Amer. Chem. Soc. 91, 5669 (1969)

    CAS  Google Scholar 

  75. Bates, A. J., Kenner, G. W., Ramage, R., Sheppard, R. C.: in “Peptides 1972”, p. 124 (Hanson, H., Jakubke, D. eds.). Amsterdam: North Holland Publ. 1973

    Google Scholar 

  76. Castro, B., Dormoy, J. R.: Bull. Soc. Chim. France, 3034 (1971)

    Google Scholar 

  77. Castro, B., Dormoy, J. R.: Tetrahedron Lett., 3243 (1973)

    Google Scholar 

  78. Barstow, L. E., Hruby, V. J.: J. Org. Chem. 36, 1305 (1971)

    CAS  Google Scholar 

  79. Wieland, T., Seelinger, A.: Chem. Ber. 104, 3992 (1971)

    CAS  Google Scholar 

  80. Yamada, S., Takeuchi, Y.: Tetrahedron Lett., 3595 (1971)

    Google Scholar 

  81. Castro, B., Dormoy, J. R.: Tetrahedron Lett., 4747 (1972)

    Google Scholar 

  82. Castro, B., Dormoy, J. R.: Bull. Soc. Chim. France, 3359 (1973)

    Google Scholar 

  83. Appel, R., Willms, L.: Chem. Ber. 112, 1057, 1064 (1979)

    Google Scholar 

  84. Mitin, Y. V., Glinskaya, O. V.: Tetrahedron Lett., 5267 (1969)

    Google Scholar 

  85. Yamazaki, N., Higashi, F.: Tetrahedron Lett., 5047 (1972)

    Google Scholar 

  86. Kenner, G. W.: Chem. Ind., 15 (1951)

    Google Scholar 

  87. Kenner, G. W., Stedman, R. J.: J. Chem. Soc, 2069 (1952)

    Google Scholar 

  88. Clayton, D. W., Farrington, J. A., Kenner, G. W., Turner, J. M.: J. Chem. Soc, 1398 (1957)

    Google Scholar 

  89. Theodoropoulos, D., Gazopoulos, J.: J. Org. Chem. 27, 2091 (1962)

    CAS  Google Scholar 

  90. Cronyn, M. W., Jiu, J.: J. Amer. Chem. Soc. 74, 4726 (1952)

    CAS  Google Scholar 

  91. Sheehan, J. C., Johnson, D. A.: J. Am. Chem. Soc. 74, 4726 (1952)

    CAS  Google Scholar 

  92. Leuchs, H.: Ber. dtsch. Chem. Ges. 39, 857 (1906); Leuchs, H., Geiger, W.: ibid. 41, 1721 (1908)

    CAS  Google Scholar 

  93. Hunt, M., du Vigneaud, V.: J. Biol. Chem. 124, 699 (1938)

    CAS  Google Scholar 

  94. Bailey, J. L.: Nature 164, 889; J. Chem. Soc, 3461 (1950)

    Google Scholar 

  95. Langebeck, W., Kresse, P.: J. prakt. Chem. 2, 261 (1955)

    Google Scholar 

  96. Bartlett, P. D., Jones, R. H.: J. Amer. Chem. Soc. 79, 2153 (1957); Bartlett, P. D., Dittmer, D. C.: ibid. 79, 2159 (1957)

    CAS  Google Scholar 

  97. Denkewalter, R. G., Schwam, H., Strachan, R. G., Beesley, T. E., Veber, D. F., Schoenewaldt, E. F., Barkemeyer, H., Paleveda, W. J., Jr., Jacob, T. A., Hirschmann, R.: J. Amer. Chem. Soc. 88, 3163 (1966)

    CAS  Google Scholar 

  98. Le Quesne, W. J., Young, G. T.: J. Chem. Soc, 1954, 1959 (1950); 594 (1952)

    Google Scholar 

  99. Schröder, E., Klieger, E.: Liebigs Ann. Chem. 673, 208 (1964)

    Google Scholar 

  100. King, F. E., Kidd, D. A. A.: J. Chem. Soc, 3315 (1949); ibid.2976 (1951)

    Google Scholar 

  101. Klieger, E., Gibian, H.: Liebigs Ann. Chem. 655, 195 (1962)

    CAS  Google Scholar 

  102. Weygand, F., Huber, P., Weiss, K.: Z. Naturf. 22b, 1084 (1967)

    Google Scholar 

  103. Weygand, F., di Bello, C.: Z. Naturf. 24b, 314 (1969)

    Google Scholar 

  104. Buyle, R., Viehe, H. G.: Angew. Chem. 76, 572 (1964)

    CAS  Google Scholar 

  105. Wieland, T., Birr, C., Flor, F.: Angew. Chem. 83, 333 (1971)

    Google Scholar 

  106. Khorana, H. G.: Chem. Ind., 1087 (1955)

    Google Scholar 

  107. Sheehan, J. C., Hlavka, J. J.: J. Org. Chem. 21, 439 (1956)

    CAS  Google Scholar 

  108. Sheehan, J. C., Cruickshank, P. A., Boshart, G. L.: J. Org. Chem. 26, 2525 (1961)

    CAS  Google Scholar 

  109. Chen, F. M. F., Kukoda, K., Benoiton, N. L.: Synthesis, 928 (1978)

    Google Scholar 

  110. Schüssler, H., Zahn, H.: Chem. Ber. 95, 1076 (1962)

    Google Scholar 

  111. Schwyzer, R., Feurer, M., Iselin, B., Kägi, H.: Helv. Chim. Acta 38, 80 (1955)

    CAS  Google Scholar 

  112. Iselin, B., Feurer, M., Schwyzer, R.: Helv. Chim. Acta 38, 1508 (1955)

    CAS  Google Scholar 

  113. Gordon, M., Miller, J. G., Day, A. R.: J. Amer. Chem. Soc. 70, 1946 (1948)

    CAS  Google Scholar 

  114. Gordon, M., Miller, J. G., Day, A. R.: J. Amer. Chem. Soc 71, 1245 (1949)

    CAS  Google Scholar 

  115. Wieland, T., Schäfer, W., Bokelmann, E.: Liebigs Ann. Chem. 573, 99 (1951)

    CAS  Google Scholar 

  116. Lynen, F., Reichert, E.: Angew. Chem. 63, 47 (1951)

    CAS  Google Scholar 

  117. Bodanszky, M.: Nature 175, 685 (1955)

    CAS  Google Scholar 

  118. Bodanszky, M., Bath, R. J.: Chem. Commun., 1259 (1969)

    Google Scholar 

  119. Bodanszky, M., Bath, R. J., Chang, A., Fink, M. L., Funk, K. W., Greenwald, S. M., Klausner, Y. S.: Chemistry and Biology of Peptides (Meienhofer, J., ed.) p. 203. Ann Arbor, Mich.: Ann Arbor Sci. Publ. 1972

    Google Scholar 

  120. Bodanszky, M., Funk, K. W., Fink, M. L.: J. Org. Chem. 38, 3565 (1973)

    CAS  Google Scholar 

  121. Bodanszky, M., Kondo, M., Yang-Lin, C., Sigler, G. F.: J. Org. Chem. 39, 444 (1974)

    CAS  Google Scholar 

  122. Bodanszky, M., Szelke, M., Tömörkény, E., Weisz, E.: Chem. Ind., 1517 (1955); Acta Chim. Acad. Sci. Hung. 11, 179 (1957)

    CAS  Google Scholar 

  123. Bodanszky, M.: Acta Chim. Acad. Sci. Hung. 10, 335 (1957)

    CAS  Google Scholar 

  124. Bodanszky, M., du Vigneaud, V.: Nature 183, 1324 (1959)

    CAS  Google Scholar 

  125. Bodanszky, M., du Vigneaud, V.: J. Amer. Chem. Soc. 81, 5688 (1959)

    CAS  Google Scholar 

  126. Farrington, J. A., Kenner, G. W., Turner, J. M.: Chem. Ind., 601 (1955); J. Chem. Soc, 1407 (1957)

    Google Scholar 

  127. Kupryszewski, G.: Rocz. Chem. 35, 595 (1961); Chem. Abstr. 55, 27121 (1961)

    CAS  Google Scholar 

  128. Kupryszewski, G., Kaczmarek, M.: Rocz. Chem. 35, 931 (1961); Chem. Abstr. 56, 6081 (1962)

    CAS  Google Scholar 

  129. Kovacs, J., Kisfaludy, L., Ceprini, M. Q.: J. Amer. Chem. Soc. 89, 183 (1967)

    CAS  Google Scholar 

  130. Kisfaludy, L., Löw, M., Nyéki, O., Szirtes, R., Schön, L: Liebigs Ann. Chem., 1421 (1973)

    Google Scholar 

  131. Kisfaludy, L., Roberts, J. E., Johnson, R. H., Mayers, G. L., Kovács, J.: J. Org. Chem. 35, 3563 (1970)

    CAS  Google Scholar 

  132. Pless, J., Boissonnas, R. A.: Helv. Chim. Acta 46, 1609 (1963)

    Google Scholar 

  133. König, W., Geiger, R.: Chem. Ber. 106, 3626 (1973)

    Google Scholar 

  134. Mazur, R. H.: J. Org. Chem. 28, 2498 (1963)

    CAS  Google Scholar 

  135. Wieland, T., Vogeler, K.: Liebigs Ann. Chem. 680, 125 (1964)

    CAS  Google Scholar 

  136. Wieland, T., Determann, H., Kahle, W.: Angew. Chem. (Int. Ed.) 2, 154 (1903)

    Google Scholar 

  137. Beyerman, H. C., Maassen van den Brink, W.: Proc. Chem. Soc. (London), 266 (1963)

    Google Scholar 

  138. Jones, J. H., Young, G. T.: J. Chem. Soc. C., 436 (1968)

    Google Scholar 

  139. Trudelle, Y.: Chem. Commun., 639 (1971)

    Google Scholar 

  140. Johnson, B. J., Jacobs, P. M.: Chem. Commun., 73 (1968)

    Google Scholar 

  141. Johnson, B. J., Jacobs, P. M.: J. Org. Chem. 33, 4524 (1968)

    CAS  Google Scholar 

  142. Johnson, B. J., Ruettinger, T. A.: J. Org. Chem. 35, 255 (1970)

    CAS  Google Scholar 

  143. Iselin, B., Rittel, W., Sieber, P., Schwyzer, R.: Helv. Chim. Acta 40, 373 (1957)

    CAS  Google Scholar 

  144. Wieland, T., Lewalter, J., Birr, C.: Liebigs Ann. Chem. 740, 31 (1970)

    CAS  Google Scholar 

  145. Wieland, T., Birr, C., Fleckenstein, P.: Liebigs Ann. Chem. 756, 14 (1972)

    CAS  Google Scholar 

  146. Sheehan, J. C., Daves, G. D.: J. Org. Chem. 29, 2006 (1964)

    CAS  Google Scholar 

  147. Treiber, R. L.: Experientia 29, 1335 (1973)

    CAS  Google Scholar 

  148. Kenner, G. W., Seely, J. H.: J. Amer. Chem. Soc. 94, 3259 (1972)

    CAS  Google Scholar 

  149. Martynov, F. V., Samarcev, M. A.: Z. Obsc. Chim. 39, 940 (1964); C. A. 71, 405-16(1969)

    Google Scholar 

  150. Bankowski, K., Drabarek, S.: Roczniki Chem. 45, 1205 (1971)

    CAS  Google Scholar 

  151. Bankowski, K., Drabarek, S.: Roczniki Chem. 46, 607 (1972)

    CAS  Google Scholar 

  152. Stewart, F. H. C.: Austral. J. Chem. 21, 411;1639 (1968)

    Google Scholar 

  153. Kazmierczak, R., Kupryszewski, G.: Roczniki Chem. 37, 659 (1963)

    CAS  Google Scholar 

  154. Jakubke, H. D.: Z. Naturforsch. 20b, 273 (1965)

    CAS  Google Scholar 

  155. Taschner, E., Rzeszotarska, B., Lubiewska, L.: Liebigs Ann. Chem. 690, 177 (1965)

    CAS  Google Scholar 

  156. Dutta, A. S., Morley, J. S.: J. Chem. Soc. C., 2896 (1971)

    Google Scholar 

  157. Mitin, Y. V., Nadezhdina, L. B.: Zh. Org. Khim. 4, 1181 (1968); Chem. Abstr. 69, 87227 (1968)

    CAS  Google Scholar 

  158. Jakubke, H. D.: Z. Chem. 5, 453 (1965)

    Google Scholar 

  159. Lloyd, K., Young, G. T.: Chem. Commun., 1400 (1968; J. Chem. Soc. C., 2890 (1971)

    Google Scholar 

  160. Jakubke, H. D.: Z. Chem. 3, 65 (1963)

    CAS  Google Scholar 

  161. Jakubke, H. D.: Chem. Ber. 97, 2816 (1964); Liebigs Ann. Chem. 682, 244 (1965)

    CAS  Google Scholar 

  162. Klausner, Y. S., Neiri, T. H., Schneider, E.: in “Peptides. Proc. Fifth Amer. Peptide Symp.” (Goodman, M., Meienhofer, J., eds.), p. 536. New York: Wiley 1977

    Google Scholar 

  163. Losse, G., Hoffmann, K. H., Hetzer; G.: Liebigs Ann. Chem. 684, 236 (1965)

    Google Scholar 

  164. Weygand, F., Steglich, W.: Angew. Chem. 73, 757 (1961)

    CAS  Google Scholar 

  165. Nefkens, G. H. L., Tesser, G. L: J. Amer. Chem. Soc. 83, 1263 (1961)

    CAS  Google Scholar 

  166. Anderson, G. W., Zimmermann, J. E., Callahan, F. M.: J. Amer. Chem. Soc. 85, 3039 (1963); ibid. 86, 1839 (1964)

    CAS  Google Scholar 

  167. Bittner, S., Knobler, Y., Frankel, M.: Tetrahedron Lett., 95 (1965)

    Google Scholar 

  168. Beaumont, S. M., Hanford, B. O., Jones, J. H., Young, G. T., Chem. Commun., 53 (1965); cf. also Hanford, B. O., Jones, J. H., Young, G. T., Johnson, T. N. F.: J. Chem. Soc, 6814 (1965)

    Google Scholar 

  169. König, W., Geiger, R.: Chem. Ber. 103, 788, 2024 (1970)

    Google Scholar 

  170. Sheehan, J. C., Hess, G. P.: J. Amer. Chem. Soc. 77, 1067 (1955)

    CAS  Google Scholar 

  171. Savrda, J.: J. Org. Chem. 42, 3199 (1977)

    CAS  Google Scholar 

  172. Jeschkeit, H.: Z. Chem. 8, 20 (1968)

    CAS  Google Scholar 

  173. Jeschkeit, H.: Z. Chem. 9, 266 (1969)

    Google Scholar 

  174. Lubiewska-Nakonieczna, L., Rzeszotarska, B., Taschner, E.: Justus Liebigs Ann. Chem., 157(1970)

    Google Scholar 

  175. Govindachari, T. R., Nagarajan, K., Rajappa, S.: Tetrahedron 22, 3367 (1966)

    CAS  Google Scholar 

  176. Rajappa, S., Nagarajan, K., Iyer, V. S.: Tetrahedron 22, 4805 (1967)

    Google Scholar 

  177. Paquette, L. A.: J. Amer. Chem. Soc. 87, 5186 (1965)

    CAS  Google Scholar 

  178. Sarantakis, D., Sutherland, J. K., Tortorella, C., Tortorella, V.: J. Chem. Soc. C., 72 (1968)

    Google Scholar 

  179. Taylor, E. C., Kinzle, F., McKillop, A.: J. Org. Chem. 35, 1672 (1970)

    CAS  Google Scholar 

  180. Rothe, M., Kunitz, F. W.: Liebigs Ann. Chem. 609, 88 (1957)

    CAS  Google Scholar 

  181. Elliott, D. F., Russell, D. W.: Biochem. J. 66, 49P (1957)

    Google Scholar 

  182. Arens, J. F.: Rec. Trav. Chim. Pay-Bas 74, 769 (1955)

    CAS  Google Scholar 

  183. Bodanszky, M., Birkhimer, C. A.: Chem. Ind. (London), 1620 (1962)

    Google Scholar 

  184. Iselin, B., Schwyzer, R.: Helv. Chim. Acta 43, 1760 (1960)

    Google Scholar 

  185. Sakakibara, S., Inukai, N.: Bull. Chem. Soc. Jpn. 37, 1231 (1964); ibid. 38, 1979 (1965)

    CAS  Google Scholar 

  186. Fletcher, G. A., Löw, M., Young, G. T.: J. Chem. Soc. Perkin Trans. I, 1162 (1973)

    Google Scholar 

  187. Yamazaki, N., Higashi, F., Niwano, M.: Tetrahedron 30, 1319 (1974)

    CAS  Google Scholar 

  188. Martinez, J., Winternitz, F.: Tetrahedron Lett., 2631 (1975)

    Google Scholar 

  189. Appel, R., Gläsel, U.: Chem. Ber. 113, 3511 (1980)

    CAS  Google Scholar 

  190. Muramatsu, I., Hirabayashi, T., Hagitani, A.: Nippon Kagaku Zasshi 84, 855 (1963); Chem. Abstr. 60, 12100c (1964)

    CAS  Google Scholar 

  191. Gais, H. F.: Angew. Chem. 17, 597 (1978)

    Google Scholar 

  192. Neuenschwander, M., Lienhard, U., Fahrni, H. P., Jurni, B.: Helv. Chim. Acta 61, 2428 (1978); Neuenschwander, M., Fahrni, H. P., Lienhard, U.: ibid. 61, 2437 (1978)

    CAS  Google Scholar 

  193. Benoiton, N. L., Chen, F. M. F.: Can. J. Chem. 59, 384 (1981)

    CAS  Google Scholar 

  194. Bates, H. S., Jones, J. H., Ramage, W. L, Witty, M. J.: in “Peptides 1980” (Brunfeldt, K., ed.), p. 185. Copenhagen: Sriptor 1981

    Google Scholar 

  195. Belleau, B., Malek, G.: J. Amer. Chem. Soc. 90, 1651 (1968)

    CAS  Google Scholar 

  196. Bodanszky, M., Tolle, J. C., Gardner, J. D., Walker, M. D., Mutt, V.: Int. J. Peptide Protein Res. 16, 402 (1980)

    CAS  Google Scholar 

  197. Kiso, Y., Kai, Y., Yajima, H.: Chem. Pharm. Bull. 21, 2507 (1973)

    CAS  Google Scholar 

  198. Bodanszky, M., Conklin, L. E.: J. Chem. Soc. Chem. Commun., 773 (1967)

    Google Scholar 

  199. Losse, G., Demuth, E.: Chem. Ber. 94, 1762 (1961)

    CAS  Google Scholar 

  200. Stevens, C. L., Munk, M. E.: J. Amer. Chem. Soc. 80, 4065, 4069 (1958)

    Google Scholar 

  201. Woodward, R. B., Olofson, R. A.: J. Amer. Chem. Soc. 83, 1007 (1961)

    CAS  Google Scholar 

  202. Woodward, R. B., Olofson, R. A., Mayer, H.: J. Amer. Chem. Soc. 83, 1010 (1961)

    CAS  Google Scholar 

  203. Weygand, F., Hoffmann, D., Wünsch, E.: Z. Naturforsch. 21b, 426 (1966)

    Google Scholar 

  204. Wünsch, E., Drees, F.: Chem. Ber. 99, 110 (1966)

    Google Scholar 

  205. Staab, H. A.: Liebigs Ann. Chem. 609, 75 (1957); cf. also Staab, H. A., Wendel, K.: Chem. Ber. 96, 3374 (1963)

    CAS  Google Scholar 

  206. Anderson, G. W., Paul, R.: J. Amer. Chem. Soc. 80, 4423 (1958); ibid. 82, 4596 (1960)

    CAS  Google Scholar 

  207. Bodanszky, M., Sheehan, J. T.: Chem. Ind., 1597 (1966)

    Google Scholar 

  208. Mukaiyama, T., Ueki, M., Maruyama, H., Matsueda, R.: J. Amer. Chem. Soc. 90, 4490 (1968); ibid. 91, 1554 (1969)

    CAS  Google Scholar 

  209. Klausner, Y. S., Bodanszky, M.: Synthesis, 453 (1972)

    Google Scholar 

  210. Panneman, H. J., Marx, A. F., Arens, J. F.: Rec. Trav. Chim. Pays-Bas 78, 487 (1959)

    CAS  Google Scholar 

  211. Heslinga, L., Arens, J. F.: Rec. Trav. Chim. Pays-Bas 76, 982 (1957)

    CAS  Google Scholar 

  212. Kemp, D. S., Chien, S. W.: J. Amer. Chem. Soc. 89, 2743 (1967)

    CAS  Google Scholar 

  213. Olofson, R. A., Marino, Y. L.: Tetrahedron 26, 1779 (1970)

    CAS  Google Scholar 

  214. Anderson, G. W.: Ann. N.Y. Acad. Sci. 88, 676 (1960)

    CAS  Google Scholar 

  215. Staab, H. A., Wendel, K.: Chem. Ber. 93, 2902 (1960); cf. also Staab, H. A.: Angew. Chem. 74, 407 (1962)

    CAS  Google Scholar 

  216. Hollitzer, O., Seewald, A., Steglich, W.: Angew. Chem. 15, 444 (1976)

    CAS  Google Scholar 

  217. Kinoshita, H., Inomata, K., Miyano, O., Kotake, H.: Bull. Chem. Soc. Jpn. 52, 2619 (1979)

    CAS  Google Scholar 

  218. Grieco, P. A., Yokoyama, Y., Williams, E.: J. Org. Chem. 43, 1283 (1978).

    CAS  Google Scholar 

  219. Grieco, P. A., Clark, D. S., Withers, G. P.: J. Org. Chem. 44, 2945 (1979)

    CAS  Google Scholar 

  220. Yajima, EL, Akaji, K., Hirota, Y., Fujii, N.: Chem. Pharm. Bull. 28, 3140 (1980)

    CAS  Google Scholar 

  221. Jackson, A. G., Kenner, G. W., Moore, G. A., Ramage, R., Thorpe, W. D.: Tetrahedron Lett., 3627 (1976)

    Google Scholar 

  222. Hegarty, A. F., McCarthy, D. G.: J. Amer. Chem. Soc. 102, 4537 (1980)

    CAS  Google Scholar 

  223. Itoh, M., Nojima, H., Notani, J., Hagiwara, D., Takai, K.: Tetrahedron Lett., 3089 (1974)

    Google Scholar 

  224. Kiso, Y., Miyazaki, T., Satomi, M., Hiraiwa, H., Akita, T.: J. Chem. Soc. Chem. Commun., 1029 (1980)

    Google Scholar 

  225. Mukaiyama, T., Matsueda, R., Suzuki, M.: Tetrahedron Lett., 1901 (1970)

    Google Scholar 

  226. Mukaiyama, T., Matsueda, R., Maruyama, H.: Bull. Chem. Soc. Jpn. 43, 1271 (1970)

    CAS  Google Scholar 

  227. Bergmann, M., Fraenkel-Conrat, H.: J. Biol. Chem. 119, 707 (1937)

    CAS  Google Scholar 

  228. Bergmann, M., Fruton, J. S.: J. Biol. Chem. 124, 321 (1938)

    CAS  Google Scholar 

  229. Homandberg, G. A., Mattis, J. A., Laskowski, M., Jr.: Biochemistry 17, 5220 (1978)

    CAS  Google Scholar 

  230. Isowa, Y., Ohmori, M., Ichikawa, T., Kurita, H., Sato, M., Mori, K.: Bull. Chem. Soc. Jpn. 50, 2762 (1977)

    CAS  Google Scholar 

  231. Oka, T., Morihara, K.: J. Biochem. 84, 1277 (1978)

    CAS  Google Scholar 

  232. Morihara, K., Oka, T.: Biochem. J. 163, 531 (1977)

    CAS  Google Scholar 

  233. Bodanszky, M., Fried, J.: U.S. Pat. 3, 276,961 (1966)

    Google Scholar 

  234. Inouye, K., Watanabe, K., Morihara, K., Tochino, Y., Kanaka, T., Emura, J., Sakakibara, S.: J. Amer. Chem. Soc. 101, 751 (1979)

    CAS  Google Scholar 

  235. Morihara, K., Oka, T., Tsuzuki, H.: Nature 280, 412 (1979)

    CAS  Google Scholar 

  236. Breddam, K., Widmer, F., Johansen, J. T.: Carlsberg Res. Commun. 45, 237 (1980)

    CAS  Google Scholar 

  237. Takai, H., Sakato, K., Nakamizo, N., Isowa, Y.: in “Peptide Chemistry 1980” (Okawa, K., ed.), p. 213. Protein Research Foundation, Osaka (1981)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Case Western Reserve University, Cleveland, OH, 44106, USA

    Miklos Bodanszky

Authors
  1. Miklos Bodanszky
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1984 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Bodanszky, M. (1984). Activation and Coupling. In: Principles of Peptide Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 16. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-96763-4_2

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-96763-4_2

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-96765-8

  • Online ISBN: 978-3-642-96763-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation