Tactics and Strategy in Peptide Synthesis

  • Miklos Bodanszky
Part of the Springer Laboratory book series (SLM)

Abstract

Over and above the problems of activation, coupling, protection and removal of protecting groups there are some more general aspects of peptide synthesis which, in order to be treated in a systematic manner, need to be identified and defined. Thus, schemes for the combination of various protecting groups have to be developed for syntheses in which certain blocking groups, e.g. those applied for the masking of the α-amino function, must be removed after coupling, while others are expected to stay intact throughout the chain building process. Considerations which govern the selection of protecting groups and coupling methods can be designated tactics. A separate, although not independent, part of the plan of a synthesis of a large peptide is the general design of the synthetic scheme. Decisions such as the construction of a. long chain from larger segments or from single residues, form the strategy of synthesis. A further category, the techniques of peptide synthesis, encompasses methods of facilitation, the choice between synthesis carried out in solution and chain building in which the peptide is anchored to an insoluble support. Experimental devices which simplify the isolation of intermediates or dispense with their isolation will also be discussed among the varieties of techniques proposed for peptide synthesis. It seems to us that for the sake of exact communication between peptide chemists, these concepts [1–3] have to be clearly distinguished and consistently described with appropriate terms.

Keywords

Carboxyl Benzyl Vasopressin Sulfhydryl Weinstein 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Bodanszky M, Ondetti MA (1966) In: Peptide synthesis (2nd ed), WileyInterscience, New York, p 161Google Scholar
  2. 2.
    Bodanszky M, Klausner YS, Ondetti MA (1976) In: Peptide Synthesis (2nd ed), Wiley-Interscience, New York, p 177Google Scholar
  3. 3.
    Bodanszky M (1981) In: Eberle A, Geiger R, Wieland T (eds) Perspectives in Peptide Chemistry. Karger S, Basel, p 15Google Scholar
  4. 4.
    Bodanszky M, du Vigneaud V (1959) Nature 183: 1324PubMedGoogle Scholar
  5. 5.
    Barany G, Merrifield RB (1977) J Amer Chem Soc 99: 7363Google Scholar
  6. 6.
    Riniker B, Kamber B, Sieber P (1975) Helv Chim Acta 58: 1086PubMedGoogle Scholar
  7. 7.
    Sieber P, Kamber B, Hartmann A, Jöhl A, Riniker B, Rittel W (1974) Helv Chim Acta 57: 2617PubMedGoogle Scholar
  8. 8.
    Schwyzer R, Kappeler H (1963) Helv Chim Acta 46: 1550Google Scholar
  9. 9.
    Bodanszky M, Williams NJ (1967) J Amer Chem Soc 89: 685Google Scholar
  10. 10.
    Bodanszky M, Ondetti MA, Levine SD, Williams NJ (1967) J Amer Chem Soc 89: 6753Google Scholar
  11. 11.
    Carpino LA, Han GY (1972) J Org Chem 37: 3404Google Scholar
  12. 12.
    Bodanszky M, Tolle JC, Gardner JD, Walker MD, Mutt V (1980) Int J Peptide Protein Res 16: 402Google Scholar
  13. 13.
    Bodanszky M, Tolle JC, Bednarek MA, Schiller PW (1981) Int J Peptide Protein Res 17: 444Google Scholar
  14. 14.
    Bodanszky M, Bednarek MA, Bodanszky A, Tolle JC (1981) In: Brunfeldt K (ed) Peptides 1980. Scriptor, Copenhagen, p 93Google Scholar
  15. 15.
    Carpino LA, Tsao JH, Ringsdorf H, Fell E, Hettisch G (1978) J Chem Soc Chem Commun, p 358Google Scholar
  16. 16.
    Sieber P (1977) Helv Chim Acta 60: 2711Google Scholar
  17. 17.
    Kiso Y, Ukawa K, Akita T (1980) J Chem Soc Chem Commun, p 101Google Scholar
  18. 18.
    Kenner GW, Seely JH (1972) J Amer Chem Soc 94: 3259Google Scholar
  19. 19.
    du Vigneaud V, Gish DT, Katsoyannis PG, Hess GP (1958) J Amer Chem Soc 80: 3355Google Scholar
  20. 20.
    Bodanszky M, Bednarek MA (1982) Int J Peptide Protein Res 20: 434Google Scholar
  21. 21.
    Bednarek MA, Bodanszky M (1983) Int J Peptide Protein Res 21: 196Google Scholar
  22. Kessler H, Siegmeier R (1983) Tetrahedron Lett, p 281Google Scholar
  23. 22.
    Royer GP, Anantharamaiah GM (1979) J Amer Chem Soc 101: 3394Google Scholar
  24. 23.
    Pettit GR (1976) In: Synthetic Peptides, vol 4, Elsevier, Amsterdam, p 22Google Scholar
  25. 24.
    du Vigneaud V, Ressler C, Swan JM, Roberts CW, Katsoyannis PG, Gordon S (1953) J Amer Chem Soc 75: 4879Google Scholar
  26. 25.
    Rittel W, Iselin B, Kappeler H, Riniker B, Schwyzer R (1957) Helv Chim Acta 40: 614Google Scholar
  27. 26.
    Schwarz H, Bumpus FM, Page IH (1957) J Amer Chem Soc 79: 5697Google Scholar
  28. 27.
    Guttmann S, Boissonnas RA (1958) Helv Chim Acta 41:1852Google Scholar
  29. Guttmann S, Boissonnas RA (1959) Helv Chim Acta 42: 1257Google Scholar
  30. 28.
    Schwyzer R, Sieber P (1963) Nature 199: 172PubMedGoogle Scholar
  31. 29.
    Hirschmann R, Mutt RF, Veber DF, Vitali RA, Varga SL, Jacob TA, Holly FW, Denkewalter RC (1969) J Amer Chem Soc 91: 507Google Scholar
  32. 30.
    Romovacek H, Dowd SR, Kawasaki K, Nishi N, Hofmann K (1979) J Amer Chem Soc 101: 6081Google Scholar
  33. 31.
    Yajima H, Fujii N (1980) J Chem Soc Chem Commun, p 115Google Scholar
  34. 32.
    Bodanszky M (1971) In: Kimball AP, Oro J (eds) Prebiotic and Biochemical Evolution. North Holland, Amsterdam, p 217Google Scholar
  35. 33.
    Hardy PM, Samworth DJ (1977) J Chem Soc Perkin I, p 1954Google Scholar
  36. 34.
    Ugi I, Marquarding D, Urban R (1982) In: Weinstein B (ed) Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, vol 6. Dekker, New York, p 245Google Scholar
  37. 35.
    Urban R, Eberle G, Marquarding D, Rehn D, Rehn H, Ugi I (1976) (Int ed) Angew Chem, 627Google Scholar
  38. 36.
    Waki M, Meienhofer J (1977) J Amer Chem Soc 99: 6075Google Scholar
  39. 37.
    Bacher JM, Naider F (1978) Biopolymers 17: 2189Google Scholar
  40. 38.
    Letsinger RL, Komet MJ (1963) J Amer Chem Soc 85: 3045Google Scholar
  41. 39.
    Felix AM, Merrifield RB (1970) J Amer Chem Soc 92: 1385Google Scholar
  42. 40.
    Inouye K, Watanabe K (1977) J Chem Soc, Perkin I, p 1911Google Scholar
  43. 41.
    Deer A, Fried JH, Halpern B (1967) Austral J Chem 20: 797Google Scholar
  44. 42.
    Brenner M, Zimmermann JP, Wehrmüller J, Quitt P, Hartmann A, Schneider W, Beglinger U (1957) Helv Chim Acta 40: 1497Google Scholar
  45. 43.
    Brenner M, Hofer W (1961) Helv Chim Acta 44: 1794Google Scholar
  46. 44.
    Bodanszky M, Bodanszky A (1967) Chem Commun, p 591Google Scholar
  47. 45.
    Sarges R, Witkop B (1965) J Amer Chem Soc 89: 2020Google Scholar
  48. 46.
    Tilak MA (1970) Tetrahedron Lett, p 849Google Scholar
  49. 47.
    van Zon A, Beyerman HC (1973) Helv Chim Acta 56: 1729PubMedGoogle Scholar
  50. van Zon A, Beyerman HC (1976) ibid., 59:1112Google Scholar
  51. 48.
    Weygand F, Huber P, Weiss K (1967) Z Naturforsch 22b: 1084Google Scholar
  52. 49.
    Mehlis B, Apelt H, Bergmann J, Niedrich H (1972) J Pact Chem 314: 390Google Scholar
  53. 50.
    Kisfaludy L, Schön I, Szirtes T, Nyéki O, Löw M (1974) Tetrahedron Lett, p 1785Google Scholar
  54. 51.
    Hirschmann R, Schwam H, Strachan RG, Schoenewaldt EF, Barkemeyer H, Miller SM, Conn JB, Garsky V, Veber DF, Denkewalter RB (1971) J Amer Chem Soc 93: 2746Google Scholar
  55. 52.
    Dewey RS, Schoenewaldt EF, Joshua H, Paleveda WJ Jr, Schwam H, Barkemeyer H, Arison BH, Veber DR, Strachan RG, Milkowski J, Denkewalter RG, Hirschmann R (1971) J Org Chem 36: 49PubMedGoogle Scholar
  56. 53.
    Gutte B, Merrifield RB (1969) J Amer Chem Soc 91: 501Google Scholar
  57. 54.
    Bodanszky M (1960) Ann NY Acad Sci 88: 655Google Scholar
  58. 55.
    Harington CR, Pitt-Rivers RV (1944) Biochem J 38: 417PubMedGoogle Scholar
  59. 56.
    Harington CR, Mead TH (1930) Biochem J 30: 1598Google Scholar
  60. 57.
    Weygand F, Zumach G (1962) Z Naturforsch 17b: 807Google Scholar
  61. 58.
    Kamber B, Rittel W (1968) Helv Chim Acta 51: 2061PubMedGoogle Scholar
  62. 59.
    Kamber B (1971) Helv Chim Acta 54: 398PubMedGoogle Scholar
  63. 60.
    Ressler C, du Vigneaud V (1954) J Amer Chem Soc 76: 3107Google Scholar
  64. 61.
    Wunsch E (1974) In: Houben-Weyl, Methoden der Organischen Chemie 4th ed, vol 15/1. Thieme, Stuttgart, p 800Google Scholar
  65. 62.
    Photaki I (1973) In: Katsoyannis P (ed) The Chemistry of Polypeptides. Plenum Press, New York, p 59Google Scholar
  66. 63.
    König W, Geiger R (1981) In: Eberle A, Geiger R, Wieland T (eds) Perspectives in Peptide Chemistry. Karger, Basel, p 31Google Scholar
  67. 64.
    Hiskey RG, Tucker WP (1962) J Amer Chem Soc 48: 4789Google Scholar
  68. 65.
    Hiskey RG, Mizoguchi T, Smithwick EL (1967) J Org Chem 32: 97PubMedGoogle Scholar
  69. 66.
    Hiskey RG, Sparrow TJ (1970) J Org Chem 35: 15Google Scholar
  70. 67.
    Hiskey RG, Ward BF Jr (1970) J Org Chem 35: 1118PubMedGoogle Scholar
  71. 68.
    Brois SJ, Pilot JF, Barnum HW (1970) J Amer Chem Soc 92: 7629Google Scholar
  72. 69.
    Kamber B (1973) Helv Chim Acta 56: 1370PubMedGoogle Scholar
  73. 70.
    Hiskey RG, Muthukumaraswamy N, Vunnam RR (1975) J Org Chem 40: 950PubMedGoogle Scholar
  74. 71.
    Abraham EP (1957) Biochemistry of Some Peptide and Steroid Antibiotics. Wiley, New YorkGoogle Scholar
  75. 72.
    Schwyzer R, Iselin B, Rittel W, Sieber P (1956) Helv Chim Acta 39: 872Google Scholar
  76. 73.
    Kopple KD (1972) J Pharmaceutical Sci 61: 1345Google Scholar
  77. 74.
    Schwyzer R, Sieber P (1958) HeIv Chim Acta 41: 2186Google Scholar
  78. 75.
    Schwyzer R, Sieber P (1957) Heiv Chim Acta 40: 624Google Scholar
  79. 76.
    Kato T, Izumiya N (1974) In: Weinstein B (ed) Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, vol 2. Dekker, New York, p 1Google Scholar
  80. 77.
    Ruttenberg MA, Mach B (1966) Biochemistry 5: 2864PubMedGoogle Scholar
  81. 78.
    Ziegler K, Eberle H, Ohlinger H (1933) Liebigs Ann Chem 504: 95Google Scholar
  82. 79.
    Waki M, Izumiya N (1967) J Amer Chem Soc 89: 1278Google Scholar
  83. 80.
    Bodanszky M, Henes JB (1975) Bioorg Chem 4: 212Google Scholar
  84. 81.
    Ramachandran GN, Chandrasekaran R (1972) In: Lande S (ed) Progress in Peptide Research, vol 2. Gordon and Breach, New York, p 195Google Scholar
  85. 82.
    Gerlach H, Ovchinnikov YA, Prelog V (1964) Helv Chim Acta 47: 2294Google Scholar
  86. 83.
    Wieland T, Faesel J, Faulstich H (1968) Liebigs Ann Chem 713: 201Google Scholar
  87. 84.
    Fahrenholz H, Faulstich H, Wieland T (1971) Liebigs Ann Chem 743: 83Google Scholar
  88. 85.
    Wieland T, Lapatsanis L, Faesel J, Konz W (1971) Liebigs Ann Chem 747: 194Google Scholar
  89. 86.
    Vogler K, Studer RO, Lergier W, Lanz P (1960) Helv Chim Acta 43: 1751Google Scholar
  90. 87.
    Wieland T, Ohly KW (1957) Liebigs Ann Chem 605: 179Google Scholar
  91. 88.
    König W, Geiger R (1969) Liebigs Ann Chem 727: 125Google Scholar
  92. 89.
    Brady SF, Varga SL, Freidinger RM, Schwenk DA, Mendlowski M, Holly FW, Veber DF (1979) J Org Chem 44: 3101Google Scholar
  93. 90.
    Shiori T, Ninomiya K, Yamada S (1972) J Amer Chem Soc 96: 2597Google Scholar
  94. 91.
    Isied SS, Kuehn CG, Lyon JM, Merrifield RB (1982) J Amer Chem Soc 104: 2632Google Scholar
  95. 92.
    Belleau B, Malek G (1968) J Amer Chem Soc 90: 1651Google Scholar
  96. 93.
    Woodward RB, Olofson RA (1961) J Amer Chem Soc 83: 1007Google Scholar
  97. 94.
    Bláha K, Rudinger J (1965) Collect Czechoslov Chem Commun 30: 3325Google Scholar
  98. 95.
    Hassal CH, Sanger DG, Handa BK (1971) J Chem Soc C, p 2814Google Scholar
  99. 96.
    Anderson GW, Blodinger J, Young RW, Welcher AD (1952) J Amer Chem Soc 74: 5304Google Scholar
  100. 97.
    Studer RO, Lergier W (1965) HeIv Chem Acta 48: 460Google Scholar
  101. 98.
    Fridkin M, Patchornik A, Katchalski E (1965) J Amer Chem Soc 87: 4646Google Scholar
  102. 99.
    Rothe M (1959) Acta Chim Acad Sci Hung 18: 449Google Scholar
  103. 100.
    Nutt RF, Veber DF, Saperstein R (1980) J Amer Chem Soc 102: 6539Google Scholar
  104. 101.
    Wade R, Winitz M, Greenstein JP (1956) J Amer Chem Soc 78: 373Google Scholar
  105. 102.
    Jarvis D, Rydon HN, Schofield JA (1961) J Chem Soc, p 1752Google Scholar
  106. 103.
    Guttmann S, Pless J, Sandrin E, Jaquenoud PA, Bossert H, Willems H (1968) Heiv Chim Acta 51: 1155Google Scholar
  107. 104.
    Kamber B, Rittel W (1969) HeIv Chim Acta 52: 1074Google Scholar
  108. 105.
    Inukai N, Nakano K, Murakami M (1968) Bull Chem Soc Jpn 41: 182PubMedGoogle Scholar
  109. 106.
    Kamber B (1971) HeIv Chim Acta 54: 927Google Scholar
  110. 107.
    Curtis RW (1958) Science 128: 661PubMedGoogle Scholar
  111. Anzai K, Curtis RW (1965) Phytochemistry 4: 263Google Scholar
  112. 108.
    Bodanszky M, Stahl GL (1974) Proc Nat Acad Sci USA 71: 2791PubMedGoogle Scholar
  113. Bodanszky M, Stahl GL (1975) Bioorg Chem 4: 93Google Scholar
  114. 109.
    Kurath P (1976) HeIv Chim Acta 59: 1127Google Scholar
  115. 110.
    Ludescher U, Schwyzer R (1972) HeIv Chim Acta 55: 2052Google Scholar
  116. 111.
    Wieland T (1986) Peptides of Poisonous Amanita Mushrooms, Springer, New YorkGoogle Scholar
  117. 112.
    Wieland T, Faulstich H, Fahrenholz F (1971) Liebigs Ann Chem 743: 77Google Scholar
  118. 113.
    Nebelin E, Faulstich H, Wieland T (1973) Liebigs Ann Chem, p 45Google Scholar
  119. 114.
    Faulstich H, Nebelin E, Wieland T (1973) Liebigs Ann Chem, p 50Google Scholar
  120. 115.
    Munekata E, Faulstich H, Wieland T (1977) J Amer Chem Soc 99: 6151Google Scholar
  121. 116.
    Klausner YS, Chorev M (1975) J Chem Soc Chem Commun, p 973Google Scholar
  122. 117.
    Ondetti MA, Thomas PL (1975) J Amer Chem Soc 87: 4373Google Scholar
  123. 118.
    Shemyakin MM, Aldanova NA, Vinogradova EI, Feigina MY (1963) Tetrahedron Lett, p 1921Google Scholar
  124. 119.
    Bonora GM, Toniolo C (1974) Biopolymers 13: 1055PubMedGoogle Scholar
  125. 120.
    Stewart FHC (1965) Austral J Chem 18: 887Google Scholar
  126. Stewart FHC (1966) ibid., 19:489, 1508Google Scholar
  127. 121.
    DeTar DF, Gouge M, Honsberg W, Honsberg U (1967) J Amer Chem Soc 89: 988Google Scholar
  128. 122.
    DeTar DF, Vajda T (1967) J Amer Chem Soc 89: 998Google Scholar
  129. 123.
    Kovacs J, Giannotti R, Kapoor A (1966) J Amer Chem Soc 88: 2282Google Scholar
  130. 124.
    Segal DM (1969) J Mol Biol 43: 497PubMedGoogle Scholar
  131. 125.
    Jones JH, Young GT (1968) J Chem Soc (C), p 436Google Scholar
  132. 126.
    Johnson BJ (1969) J Chem Soc (C), p 1412Google Scholar
  133. 127.
    Sakakibara S, Kishida Y, Kikuchi Y, Sakai R, Kakiuchi K (1968) Bull Chem Soc Jpn 41: 1273Google Scholar
  134. 128.
    Olsen BR, Berg RA, Sakakibara S, Kishida Y, Prockop DJ (1971) J Mol Biol 57: 589PubMedGoogle Scholar
  135. 129.
    Horiuichi K, Fujimoto D, Seto Y, Sakakibara S (1978) J Biochem 83: 261Google Scholar
  136. 130.
    Kemp DS, Bernstein ZW, McNeil GN (1974) J Org Chem 39: 2831PubMedGoogle Scholar
  137. 131.
    Jones JH (1977) In: Weinstein B (ed) Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, vol 4. Dekker, New York, p 29Google Scholar
  138. 132.
    Offord RE (1978) In: Offord RE, DiBello C (eds) Semisynthetic Peptides and Proteins. Academic, London, p 3Google Scholar
  139. Offord RE (1980) Semisynthetic Proteins, John Wiley. Chichester, New YorkGoogle Scholar
  140. 133.
    Corradin G, Harbury HA (1974) Biochem Biophys Res Commun 61: 1400PubMedGoogle Scholar
  141. 134.
    Dyckes DF, Creighton T, Sheppard RC (1974) Nature 247: 292Google Scholar
  142. 135.
    Gattner HG, Schmitt EW, Naithani VK (1975) Hoppe-Seyler’s Z Physiol Chem 356: 1465PubMedGoogle Scholar
  143. 136.
    Offord RE (1969) Nature 221: 37PubMedGoogle Scholar
  144. 137.
    Rees AR, Offord RE (1976) Biochem J 159: 467PubMedGoogle Scholar
  145. 138.
    Offord RE, Storey HT, Hayward CF, Johnson WH, Phasey MH, Rees AR, Wightman DA (1976) Biochem J 159: 480PubMedGoogle Scholar
  146. 139.
    Waldschmidt-Leitz E, Kühn K (1957) Chem Ber 84: 381Google Scholar
  147. 140.
    Sealock RW, Laskowski M, Jr (1969) Biochemistry 8: 3703PubMedGoogle Scholar
  148. 141.
    Kowalski D, Laskowski M, Jr (1976) Biochemistry 15: 1300–1309PubMedGoogle Scholar
  149. 142.
    Jering H, Tschesche H (1976) Eur J Biochem 61: 443, 453PubMedGoogle Scholar
  150. 143.
    Laskowski M, Jr (1978) In: Offord RE, DiBello C (eds) Semisynthetic Peptides and Proteins. Academic Press, London, p 263Google Scholar
  151. 144.
    Fruton JS (1982) In: Meister A (ed) Enzymology, vol 53. Wiley, New York, p 239Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1993

Authors and Affiliations

  • Miklos Bodanszky
    • 1
  1. 1.PrincetonUSA

Personalised recommendations