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Reversible Blocking of Amino and Carboxyl Groups

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Principles of Peptide Synthesis

Part of the book series: Springer Laboratory ((SLM))

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Abstract

In the preparation of even the smallest peptide, it becomes obvious that certain functional groups must be blocked. If amino acid H2N—CHR—COOH (A) has to be coupled with amino acid H2N—CHR′—COOH (B) to produce the dipeptide H2N—CHR—CO—NH—CHR′—COOH (AB), then, in order to acylate the amino group of the amino-component (B), we have to activate the carboxyl group of the carboxyl-component (A). The activated carboxyl-component, H2N—CHR—CO—X, can acylate, however, not only the amino-component (B), but also some still unreacted molecules of A, to yield, instead of the desired compound AB, rather a derivative of AA:

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References

  1. Photaki K, Yiotakis AE (1976) In: Perkin I. J Chem Soc, p 259

    Google Scholar 

  2. Bodanszky M, Fink ML, Klausner YS, Natarajan S, Tatemoto K, Yiotakis AE, Bodanszky A (1977) J Org Chem 42: 149

    PubMed  CAS  Google Scholar 

  3. Fischer E (1902) Ber dtsch Chem Ges 35: 1095

    CAS  Google Scholar 

  4. Wessely F, Kemm E (1928) Hoppe-Seilers Z Physiol Chem 174:306; Wessely F, Kemm E, Mayer J (1929) ibid., 180: 64

    Google Scholar 

  5. MacLaren JA (1958) Aust J Chem 11: 360

    CAS  Google Scholar 

  6. Bergmann M, Zervas L (1932) Ber dtsch Chem Ges 65: 1192

    Google Scholar 

  7. Rosenmund KW, Zetzsche F, Heise F (1921) Ber dtsch Chem Ges 54: 2038

    Google Scholar 

  8. Fischer E (1915) Ber dtsch Chem Ges 48: 93

    CAS  Google Scholar 

  9. du Vigneaud V, Audrieth LF, Loring HS (1930) J Amer Chem Soc 52: 4500

    Google Scholar 

  10. du Vigneaud V, Behrens OK (1937) J Biol Chem 117: 27

    Google Scholar 

  11. Sifferd RH, du Vigneaud V (1935) J Biol Chem 108: 753

    CAS  Google Scholar 

  12. Kuromizu K, Meienhofer J (1974) J Amer Chem Soc 96:4978; cf. also Felix AM, Jimenez MH, Mowles T, Meienhofer J (1980) Org Synth 59: 159

    Google Scholar 

  13. Anantaramaiah GM, Sivanandaiah KM (1977) J Chem Soc (Perkin I), 490; cf. also Jackson AE, Johnstone AW (1977) Synthesis, 685

    Google Scholar 

  14. Felix AM, Heimer EP, Lambros TJ, Tzougraki C, Meienhofer J (1978) J Org Chem 43: 4194

    CAS  Google Scholar 

  15. Anwer MK, Khan SA, Sivanandaiah KM (1978) Synthesis, 751

    Google Scholar 

  16. Sivanandaiah KM, Gurusiddappa S (1979) J Chem Res (S), 108

    Google Scholar 

  17. Pless J, Guttmann S (1967) In: Beyermann HC, Van de Linde A, Maassen van den Brink W (eds) Peptides 1966. North Holland Publ, Amsterdam, p 50

    Google Scholar 

  18. Hayakawa T, Fujiwara Y, Noguchi J (1967) Bull Chem Soc Jpn 40: 1205

    PubMed  CAS  Google Scholar 

  19. Freidinger RM, Hirschmann R, Veber DF (1978) J Org Chem 43: 4800

    CAS  Google Scholar 

  20. Clubb ME, Scopes PM, Young GT (1960) Chimia 14:373; cf. also Scopes PM, Walshaw KB, Welford M, Young GT ( 1965 ) J Chem, Soc 782

    Google Scholar 

  21. Kollonitsch J, Gabor V, Hajos A (1956) Nature 177:841; Kollonitsch J, Hajos A, Gabor V (1956) Chem Ber 89: 2288

    CAS  Google Scholar 

  22. Kamber B, Rittel W (1968) Helv Chim Acta 51: 2061

    PubMed  CAS  Google Scholar 

  23. Veber DF, Milkowski JD, Varga S, Denkewalter RG, Hirschmann R (1972) J Amer Chem Soc 94: 5456

    CAS  Google Scholar 

  24. Ben-Ishai D, Berger A (1952) J Org Chem 17: 1564

    CAS  Google Scholar 

  25. Weygand F, Hunger K (1962) Chem Ber 95:1; cf. also ref. 27

    Google Scholar 

  26. Carpino LA (1957) J Amer Chem Soc 79: 98

    CAS  Google Scholar 

  27. McKay FC, Albertson NF (1957) J Amer Chem Soc 79: 4686

    CAS  Google Scholar 

  28. Anderson GW, McGregor AC (1957) J Amer Chem Soc 79: 6180

    CAS  Google Scholar 

  29. Sieber P, Iselin B (1968) Helv Chim Acta 51: 614, 622

    PubMed  CAS  Google Scholar 

  30. Yajima H, Fujii N, Ogawa H, Irie H, Shinagawa S, Fujino M (1977) In: Nakajima T (ed) Peptide Chemistry 1976. Osaka, Protein Res Foundation, p 57

    Google Scholar 

  31. Kenner GW, Moore GA, Ramage R (1976) Tetrahedron Lett, 3623

    Google Scholar 

  32. Crane CW, Rydon HN (1947) J Chem Soc, 766

    Google Scholar 

  33. Mamalis P, Rydon HN (1955) J Chem Soc, 1049

    Google Scholar 

  34. Carpino LA, Han GY (1970) J Amer Chem Soc 92: 5748

    CAS  Google Scholar 

  35. Carpino LA, Han GY (1972) J Org Chem 37:3404; (1973) ibid., 38: 4218

    Google Scholar 

  36. Goerdeler J, Holst A (1959) Angew Chem 71: 775

    CAS  Google Scholar 

  37. Zervas L, Borovas D, Gazis E (1963) J Amer Chem Soc 85: 3660

    CAS  Google Scholar 

  38. Ekström MB, Sjöberg B (1965) Acta Chem Scand 19: 1245

    PubMed  Google Scholar 

  39. Fontana A, Marchiori F, Moroder L, Scoffone E (1966) Tetrahedron Lett, p 2985

    Google Scholar 

  40. Brandenburg D (1966) Tetrahedron Lett 6201

    Google Scholar 

  41. Kessler W, Iselin B (1966) Helv Chim Acta 49: 1330

    CAS  Google Scholar 

  42. Juillerat M, Bargetzi JP (1976) Helv Chim Acta 59: 855

    PubMed  CAS  Google Scholar 

  43. Tun-Kyi A (1978) Helv Chim Acta 61: 1086

    CAS  Google Scholar 

  44. Carpino LA, Tsao JH, Ringsdorf H, Fell E, Hettisch G (1978) J Chem Soc Chem Commun, 358

    Google Scholar 

  45. D’Souza L, Day RA (1968) Science 160: 882

    PubMed  Google Scholar 

  46. Chamberlin JW (1966) J Org Chem 31: 1658

    CAS  Google Scholar 

  47. Wieland T, Birr C (1966) In: Beyerman HC, Van de Linde A, Maassen van den Brink (eds) Peptides, Proc 8th Eur Peptide Symp, Nordwijk, 1966. North Holland Publ, Amsterdam, p 103

    Google Scholar 

  48. Patchornik A, Amit B, Woodward RB (1970) J Amer Chem Soc 92: 6333

    CAS  Google Scholar 

  49. Sheehan JC, Umezawa K (1973) J Org Chem 38: 3771

    CAS  Google Scholar 

  50. Sheehan JC, Wilson RM, Oxford AW (1971) J Amer Chem Soc 93: 7222

    CAS  Google Scholar 

  51. Rich DH, Gurwara SK (1975) J Amer Chem Soc 97: 1575

    CAS  Google Scholar 

  52. Jering H, Schorp G, Tschesche H (1974) Hoppe-Seyler’s Z. Physiol Chem 355: 1129

    CAS  Google Scholar 

  53. Kloss G, Schröder E (1964) Hoppe-Seyler’s Z. Physiol Chem 336: 248

    CAS  Google Scholar 

  54. Royer GP, Anantharamaiah GM (1979) J Amer Chem Soc 101: 3394

    CAS  Google Scholar 

  55. Barton MA, Lemieux RU, Savoie JY (1973) J Amer Chem Soc 95: 4501

    CAS  Google Scholar 

  56. Prestidge RL, Harding DRK, Battersby JE, Hancock WS (1975) J Org Chem 40: 3287

    PubMed  CAS  Google Scholar 

  57. Gross E, Witkop B (1962) J Biol Chem 237: 1856

    PubMed  CAS  Google Scholar 

  58. Sjöberg BOH, Ekström BA (1962) Belg Pat 620519; (1963) Chem Abstr 59:P 11502a

    Google Scholar 

  59. Bayer E, Schmidt K (1973) Tetrahedron Lett, 2051

    Google Scholar 

  60. Bodanszky M, Natarajan S (1975) J Org Chem 40:2495; cf. also Natarajan S, Bodanszky M (1976) ibid. 41: 1269

    Google Scholar 

  61. Sakakibara S (1977) In: Goodman M, Meienhofer J (eds) Peptides, Proc Fifth Amer Pept Symp. Wiley, New York, p 436

    Google Scholar 

  62. Haslam E (1980) Tetrahedron 36: 2409

    CAS  Google Scholar 

  63. Roeske RW (1981) In: Gross E, Meienhofer J (eds) The Peptides, vol 3. Academic, New York, p 102

    Google Scholar 

  64. Schwartz H, Arakawa K (1959) J Amer Chem Soc 81: 5691

    Google Scholar 

  65. Schwyzer R, Sieber P (1959) Hely Chim Acta 42: 972

    CAS  Google Scholar 

  66. Kisfaludy L, Löw M (1965) Acta Chim Hung 44: 33

    CAS  Google Scholar 

  67. Guttmann S, Pless J (1965) Angew Chem 77: 53

    Google Scholar 

  68. Stewart FHC (1965) Austral J Chem 18: 1877

    CAS  Google Scholar 

  69. Stewart FHC (1966) Austral J Chem 19:1067; (1967) ibid. 20: 2243

    Google Scholar 

  70. Stewart FHC (1971) Austral J Chem 24: 2193

    CAS  Google Scholar 

  71. Stelakatos GC, Solomos-Aravidis C, Karayannakis P, Kolovos MG, Photaki I (1981) In: Brunfeldt K (ed) Peptides 1980, Scriptór, Copenhagen, p 133

    Google Scholar 

  72. Wieland T, Racky W (1968) Chimia 22: 375

    CAS  Google Scholar 

  73. Stewart FHC (1965) Austral J Chem 18: 1699

    CAS  Google Scholar 

  74. Camble R, Garner R, Young GT (1969) J Chem Soc, 1911

    Google Scholar 

  75. Burton J, Fletcher GA, Young GT (1971) Chem Commun, 1057

    Google Scholar 

  76. Merrifield RB (1963) J Amer Chem Soc 85: 2149

    CAS  Google Scholar 

  77. Bethell M, Bigley DB, Kenner GW (1963) Chem Ind (London), 653; cf. also Hardegger E, El Heweihi Z, Robinet FG (1948) Helv Chim Acta 31: 439

    Google Scholar 

  78. Aboderin AA, Delpierre GR, Fruton JS (1965) J Amer Chem Soc 87: 5469

    CAS  Google Scholar 

  79. Abderhalden E, Suzuki S (1928) Hoppe-Seyler’s Z. Physiol Chem 176: 601

    Google Scholar 

  80. Miller HK, Waelsch H (1952) J Amer Chem Soc 74: 1092

    CAS  Google Scholar 

  81. Cipera JD, Nicholls RVV (1955) Chem Ind, 16

    Google Scholar 

  82. Kollonitsch J. Vita J (1956) Nature 178: 1307

    CAS  Google Scholar 

  83. Büchi H, Steen K, Eschenmoser A (1964) Angew Chem 3: 62

    Google Scholar 

  84. Gisin BF (1973) Helv Chim Acta 56: 1476

    CAS  Google Scholar 

  85. Stewart FCH (1968) Austral J Chem 21: 2543

    CAS  Google Scholar 

  86. Wang SS (1973) J Amer Chem Soc 95:1328; cf. also Bodanszky M, Fagan DT (1977) Int J Peptide Protein Res 10: 375

    Google Scholar 

  87. Bywood R, Gallagher G, Sharma GK, Walker D (1975) J Chem Soc Perkin I, 2019; cf. also Homer L, Fernekes H (1961) Chem Ber 94: 712

    Google Scholar 

  88. Stelakatos GC, Paganou A, Zervas L (1966) J Chem Soc (C), 1191

    Google Scholar 

  89. Hiskey RG, Adams JB (1965) J Amer Chem Soc 87: 3969

    CAS  Google Scholar 

  90. Ho TL, Olah GA (1976) Angew Chem Int Ed 15: 774

    Google Scholar 

  91. Jung ME, Lyster MA (1977) J Amer Chem Soc 99: 968

    CAS  Google Scholar 

  92. Kornblum N, Scott A (1974) J Amer Chem Soc 96: 590

    CAS  Google Scholar 

  93. Curtius T, Goebel F (1888) J prakt Chem [2] 37: 150

    Google Scholar 

  94. Fischer E (1906) Ber dtsch Chem Ges 39: 2893

    CAS  Google Scholar 

  95. Brenner M, Huber W (1953) Heiv Chim Acta 36: 1109

    CAS  Google Scholar 

  96. Hanby WE, Waley SG, Watson J (1950) J Chem Soc, p 3239

    Google Scholar 

  97. Rachele JR (1963) J Org Chem 28: 2898

    CAS  Google Scholar 

  98. Bodanszky M, Bodanszky A (1984) The practice of peptide synthesis. Springer Verlag Berlin Beidelberg, New York, p 33

    Google Scholar 

  99. Taschner E. Wasiliewski C (1961) Liebigs Ann Chem 640: 142

    CAS  Google Scholar 

  100. Guttmann S, Boissonnas RA (1958) Hely Chim Acta 41: 1852

    CAS  Google Scholar 

  101. McLaren JA (1958) Austral J Chem 11: 360

    Google Scholar 

  102. Kenner GW, Seely JH (1972) J Amer Chem Soc 94: 3259

    CAS  Google Scholar 

  103. McDermott JR, Benoiton NL (1973) Can J Chem 51: 1915

    CAS  Google Scholar 

  104. Bartlett PA, Johnson WS (1970) Tetrahedron Lett, p 4459

    Google Scholar 

  105. Sheehan JC, Daves GD Jr (1964) J Org Chem 29: 2006

    CAS  Google Scholar 

  106. Nefkens GHL, Tesser GI, Nivard RJF (1963) Rec Tray Chim Pays-Bas 82: 941

    CAS  Google Scholar 

  107. Taylor-Papadimitriou J, Yovanidis C, Paganou A, Zervas L (1967) J Chem Soc C, p 1830

    Google Scholar 

  108. Tam JP, Cunningham-Rundles WF, Erickson BW, Merrifield RB (1977) Tetrahedron Lett, p 4001

    Google Scholar 

  109. Bodanszky M, Martinez J (1978) J Org Chem 43: 3071

    CAS  Google Scholar 

  110. Ledger R, Stewart FHC (1967) Austral J Chem 20: 787

    CAS  Google Scholar 

  111. Hendrickson JB, Kandall C (1970) Tetrahedron Lett, p 343

    Google Scholar 

  112. Eckstein F (1965) Angew Chem Int Ed 4: 876

    CAS  Google Scholar 

  113. Woodward RB (1966) Angew Chem 78: 557

    Google Scholar 

  114. Bates GS, Diakur J, Masamune S (1976) Tetrahedron Letters, p 4423

    Google Scholar 

  115. Trzupek LS, Go A, Kopple KD (1979) J Org Chem 44: 4577

    CAS  Google Scholar 

  116. Ueda K (1979) Bull Chem Soc Jpn 52: 1879

    CAS  Google Scholar 

  117. Taschner E, Liberek B (1959) Bull Acad Pol Sci (Ser Sci Chim Geol Geogr) 7: 877

    CAS  Google Scholar 

  118. Ohno M, Anfinsen CB (1970) J Amer Chem Soc 92: 4098

    CAS  Google Scholar 

  119. Amaral M, Barrett GC, Rydon HN, Willett JE (1966) J Chem Soc C, p 807

    Google Scholar 

  120. Miller AW, Stirling CJM (1968) J Chem Soc C, p 2612

    Google Scholar 

  121. Amaral MJSA (1969) J Chem Soc C, p 2495

    Google Scholar 

  122. Diaz J, Guegan R, Beaumont M, Benoit J, Clement J, Fauchard C, Galtier D, Milian J, Muneaux C, Maneaux Y, Vedel M, Schwyzer R (1979) Bioorg Chem 8: 429

    CAS  Google Scholar 

  123. Sieber P (1977) Hely Chim Acta 60: 2711

    CAS  Google Scholar 

  124. Riniker B, Eisler K, Kamber B, Müller H, Rittel W, Sieber P (1979) In: Siemion IZ, Kupryszewski G (eds) Peptides 1978, Wroclaw Univ, Wroclaw, p 631

    Google Scholar 

  125. Roeske RW (1963) J Org Chem 28: 1251

    CAS  Google Scholar 

  126. Roeske R (1959) Chem Ind (London), p 1121

    Google Scholar 

  127. Taschner E, Chimiak A, Bator B, Sokolowska T (1961) Liebigs Ann Chem 646: 134

    CAS  Google Scholar 

  128. Losse G, Zeidler D, Grieshaber T (1968) Liebigs Ann Chem 715: 196

    CAS  Google Scholar 

  129. Birkofer L, Ritter A (1960) Chem Ber 93:424; cf. also Rühlmann K, Hills J (1965) Liebigs Ann Chem 683: 211

    Google Scholar 

  130. Schnabel E, Oberdorf A (1968) In: Bricas E (ed) Peptides 1968. North Holland Publ, Amsterdam, p 261

    Google Scholar 

  131. Blotny G, Taschner E (1966) Bull Acad Polon Sci Ser Sci Chim 14: 615

    CAS  Google Scholar 

  132. Gordon M, Miller JG, Day AR (1948) J Amer Chem Soc 70: 1946

    CAS  Google Scholar 

  133. Kenner GW (1959) Angew Chem 71: 741

    Google Scholar 

  134. Galpin IJ, Handa BK, Hudson D, Jackson AG, Kenner GW, Ohlsen SR, Ramage R, Singh B, Tyson RG (1976) In: Loffet A (ed) Peptides 1976. Edition de l’Université de Bruxelles, p 246

    Google Scholar 

  135. Chaudhury AM, Kenner GW, Moore S, Ramage SR, Richards PM, Thorpe WD (1976) In: Loffet A (ed) Peptides 1976. Editions de l’Université de Bruxelles, Belgium, p 257

    Google Scholar 

  136. Taschner E, Blotny G, Bator B, Wasielewski C (1964) Bull Acad Polon Sci Ser Sci Chem 12: 755

    CAS  Google Scholar 

  137. Barth A (1965) Liebigs Ann Chem 683: 216

    CAS  Google Scholar 

  138. Ito H (1979) Synthesis, p 465

    Google Scholar 

  139. Bodanszky M (1955) Nature 175:685; cf. also (1957) Acta Chim Hung 10: 335

    Google Scholar 

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

    CAS  Google Scholar 

  141. Goodman M, Steuben KC (1959) J Amer Chem Soc 81:3980; (1962) 84: 1279

    Google Scholar 

  142. Iselin B, Schwyzer R (1960) HeIv Chim. Acta 43: 1760

    Google Scholar 

  143. Jones JH, Young GT (1968) J Chem Soc C, p 437

    Google Scholar 

  144. Johnson BJ, Jacobs PM (1968) Chem Commun, p 73

    Google Scholar 

  145. Johnson BJ, Trask EG (1968) J Org Chem 33: 4521

    PubMed  CAS  Google Scholar 

  146. Cheung HT, Blout ER (1965) J Org Chem 30: 315

    PubMed  CAS  Google Scholar 

  147. Bennett EL, Niemann C (1948) J Amer Chem Soc 70: 2610

    CAS  Google Scholar 

  148. Milne HB, Stevens CM (1950) J Amer Chem Soc 72: 1742

    CAS  Google Scholar 

  149. Waldschmidt-Leitz E, Kühn K (1951) Chem Ber 84: 381

    CAS  Google Scholar 

  150. Milne HB, Peng CH (1957) J Amer Chem Soc 79: 645

    CAS  Google Scholar 

  151. Milne HB, Most CF Jr (1968) J Org Chem 33: 169

    PubMed  CAS  Google Scholar 

  152. Lewalter J, Birr C (1970) Liebigs Ann Chem 740: 48

    CAS  Google Scholar 

  153. Wolman Y, Gallop PM, Patchornik A (1961) J Amer Chem Soc 83:1263; Wolman Y, Gallop PM, Patchornik A, Berger A (1962) ibid., 84: 1889

    Google Scholar 

  154. Kelly RB (1963) J Org Chem 28: 453

    CAS  Google Scholar 

  155. Milne HB, Kilday W (1965) J Org Chem 30:64; Milne HB, Carpenter FH (1968) ibid., 33: 4476

    Google Scholar 

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

    CAS  Google Scholar 

  157. Barton DHR, Girijavallabhan M, Sammes PG (1972) J Chem Soc Perkin I, p 929

    Google Scholar 

  158. Hofmann K, Magee MZ, Lindenmann A (1950) J Amer Chem Soc 72: 2814

    CAS  Google Scholar 

  159. Schwyzer R (1959) Angew Chem 71: 742

    Google Scholar 

  160. Preston J, Weinstein B (1967) Experientia 24: 265

    Google Scholar 

  161. Wang SS (1973) J Amer Chem Soc 95: 1328

    CAS  Google Scholar 

  162. Macrae R, Young GT (1974) J Chem Soc Chem Commun, p 446

    Google Scholar 

  163. Bierzycka D, Biernat JF (1970) Roczniki Chem 44: 2477

    Google Scholar 

  164. Yajima H, Kiso Y (1971) Chem Pharm Bull 19: 420

    CAS  Google Scholar 

  165. Velluz L, Amiard G, Heymes R (1954) Bull Soc Chim France, p 1012

    Google Scholar 

  166. Velluz L, Anatol J, Amiard G (1954) Bull Soc Chim France, p 1449

    Google Scholar 

  167. Liwschitz Y, Zilkha A (1954) J Amer Chem Soc 76: 3698

    CAS  Google Scholar 

  168. Liwschitz Y, Zilkha A, Amiel Y (1956) J Amer Chem Soc 78: 3067

    Google Scholar 

  169. Quitt P, Hellerbach J, Vogler K (1963) HeIv Chim Acta 46:327; cf. also Scheibler H, Baumgarten P (1922) Ber dtsch Chem Ges 55: 1358

    Google Scholar 

  170. Hanson RW, Law HD (1965) J Chem Soc, p 7285

    Google Scholar 

  171. Helferich B, Moog L, Jünger A (1925) Ber dtsch Chem Ges 58: 872

    Google Scholar 

  172. Hillmann-Elies A, Hillmann G, Jatzkewitz J (1953) Z. Naturforsch 8b: 445

    Google Scholar 

  173. Amiard G, Heymes R, Velluz L (1955) Bull Soc Chim France 191: 1464

    Google Scholar 

  174. Zervas L, Theodoropoulos DM (1956) J Amer Chem Soc 78: 1359

    CAS  Google Scholar 

  175. Schnabel E (1964) Liebigs Ann Chem 673: 171

    CAS  Google Scholar 

  176. Bezas B, Zervas L (1961) J Amer Chem Soc 83: 719

    CAS  Google Scholar 

  177. Guttmann S (1963) Heiv Chim Acta 46: 1975

    Google Scholar 

  178. Hiskey RG, Beacham LM, Matl VG (1972) J Org Chem 37: 2472, 2478

    PubMed  CAS  Google Scholar 

  179. Halstrßm J, Brunfeldt K (1972) Hoppe-Seyler’s Z. Physiol Chem 353: 1204

    Google Scholar 

  180. Riniker B, Kamber B, Sieber P (1974) Hely Chim Acta 57: 831

    Google Scholar 

  181. Bergmann M, Ennslin H, Zervas L (1925) Ber dtsch Chem Ges 58: 1034

    Google Scholar 

  182. Bergmann M, Zervas L (1926) Hoppe-Seyler’s Z. Physiol Chem 152: 282

    CAS  Google Scholar 

  183. Wieland T, Schäfer W (1952) Liebigs Ann Chem 576: 104

    CAS  Google Scholar 

  184. McIntire FC (1947) J Amer Chem Soc 69:1377; cf. also Zervas L, Konstas S (1960) Chem Ber 93: 435

    Google Scholar 

  185. Sheehan JC, Grenda VJ (1962) J Amer Chem Soc 84: 2417

    Google Scholar 

  186. Hope AP, Halpern B (1972) Tetrahedron Lett, 2261; (1976) Austral J Chem 29: 1591

    CAS  Google Scholar 

  187. Abdipranoto A, Hope AP, Halpern B (1977) Austral J Chem 30: 2711

    CAS  Google Scholar 

  188. Halpern B, James LB (1964) Austral J Chem 17:1282; Halpern B (1965) ibid., 18:417; Halpern B, Cross AB (1965) Chem Ind, p 1183

    Google Scholar 

  189. Deer A, Fried JH, Halpern B (1967) Austral J Chem 20: 797

    CAS  Google Scholar 

  190. Dane E, Drees F, Konrad P, Dockner T (1962) Angew Chem 74: 873

    CAS  Google Scholar 

  191. Dane E, Dockner T (1965) Chem Ber 98: 780

    Google Scholar 

  192. Dane E, Dockner T (1964) Angew Chem Int Ed 3: 439

    Google Scholar 

  193. Balog A, Breazu D, Vargha E, Gönczy F, Beu L (1970) Rev Roumaine Chem 15: 1375

    CAS  Google Scholar 

  194. Yamashiro D, Aaning HL, du Vigneaud V (1968) Proc Natl Acad Sci USA 54: 166

    Google Scholar 

  195. Yamashiro D, du Vigneaud V (1968) J Amer Chem Soc 90: 487

    CAS  Google Scholar 

  196. Hardy PM, Samworth DJ (1977) J Chem Soc Perkin I, p 1954

    Google Scholar 

  197. Sheehan JC, Guziec FS (1972) J Amer Chem Soc 94:6561; (1973) J Org Chem 38: 3034

    Google Scholar 

  198. Fischer E, Warburg O (1905) Ber dtsch Chem Ges 38:3997; cf. also Curtius T (1883)ibid., 16: 753

    Google Scholar 

  199. du Vigneaud V, Dorfmann R, Loring H (1932) J Biol Chem 98: 577

    Google Scholar 

  200. Stoll A, Petrzilka T (1952) Helv Chim Acta 35: 589

    CAS  Google Scholar 

  201. Hofmann K, Stutz E, Spühler G, Yajima A, Schwartz ET (1960) J Amer Chem Soc 82: 3727

    CAS  Google Scholar 

  202. Okawa K, Hase S (1963) Bull Chem Soc Jpn 36: 754

    CAS  Google Scholar 

  203. Muramatsu I, Itoi M, Tsuji M, Hagitani A (1964) Bull Chem Soc Jpn 37: 756

    CAS  Google Scholar 

  204. Thomas JO (1967) Tetrahedron Lett, p 335

    Google Scholar 

  205. Sheehan JC, Yang DDH (1958) J Amer Chem Soc 80: 1154, 1158

    CAS  Google Scholar 

  206. Losse G, Zönnchen W (1960) Liebigs Ann Chem 636: 140

    CAS  Google Scholar 

  207. Geiger R, Siedel W (1968) Chem Ber 101: 3386

    CAS  Google Scholar 

  208. Geiger R, Siedel W (1969) Chem Ber 102: 2487

    CAS  Google Scholar 

  209. Losse G, Nadolski D (1964) J Pract Chem 24: 118

    CAS  Google Scholar 

  210. Lefrancier P, Bricas E (1965) Bull Soc Chim France, p 3668

    Google Scholar 

  211. Sigmund F, Wessely F (1925) Hoppe-Seyler’s Z. Physiol Chem 147: 91

    Google Scholar 

  212. Bartlett PD, Jones RH (1957) J Amer Chem Soc 79: 2153

    CAS  Google Scholar 

  213. Bartlett PD, Dittmer DC (1957) J Amer Chem Soc 79: 2159

    CAS  Google Scholar 

  214. Denkewalter RG, Schwam H, Strachan RG, Beesley TE, Veber DF, Schoenewaldt EF, Barkemeyer H, Paleveda WJ Jr, Jacob TA, Hirschmann R (1966) J Amer Chem Soc 88: 3163

    CAS  Google Scholar 

  215. Holley RW, Holley AD (1952) J Amer Chem Soc 74: 3069

    CAS  Google Scholar 

  216. Masaki M, Kitahara T, Kurita H, Oata M (1968) J Amer Chem Soc 90: 4508

    CAS  Google Scholar 

  217. Fontana A, Scoffone E (1968) Gazetta Chim Ital 98: 1261

    CAS  Google Scholar 

  218. Steglich W, Batz HG (1971) Angew Chem Int Ed 10: 75

    CAS  Google Scholar 

  219. Glass JD, Pelzig M, Pande CS (1979) Int J Peptide Protein Res 13: 28

    CAS  Google Scholar 

  220. Undheim K, Fjelstad E (1973) J Chem Soc Perkin I, p 829

    Google Scholar 

  221. Panetta CA (1969) J Org Chem 34: 2773

    CAS  Google Scholar 

  222. Cuiban F (1972) Rev Romaine Chem 17:897; (1973) 18: 449

    Google Scholar 

  223. Wieland T (1965) Acta Chim Acad Sci Hung 44: 5

    CAS  Google Scholar 

  224. D’Angeli F, Filiva F, Scoffone E (1965) Tetrahedron Lett, p 605

    Google Scholar 

  225. Di Bello F, Giormani V, D’Angeli F (1969) J Chem Soc (C), p 350

    Google Scholar 

  226. Di Bello C, Filiva F, D’Angeli F (1971) J Org Chem 36: 1818

    Google Scholar 

  227. Weygand F, Csendes E (1952) Angew Chem 64: 136

    CAS  Google Scholar 

  228. Weygand F, Geiger R (1956) Chem Ber 89: 647

    CAS  Google Scholar 

  229. Schallenberg EE, Calvin M (1955) J Amer Chem Soc 77:2779; cf. also Hauptschein M, Stokes CS, Nodiff EA (1952) ibid., 74: 4005

    Google Scholar 

  230. Weygand F, Geiger R (1959) Chem Ber 92: 2099

    CAS  Google Scholar 

  231. Weygand F, Röpsch A (1959) Chem Ber 92: 2095

    CAS  Google Scholar 

  232. Benoiton L, Rydon HN, Willett JE (1960) Chem Ind (London), p 1060

    Google Scholar 

  233. Panetta CA, Casanova TG (1970) J Org Chem 35: 4275

    PubMed  CAS  Google Scholar 

  234. Goldberger RF, Anfinsen CB (1902) Biochemistry 1: 401

    Google Scholar 

  235. Weygand F, Frauendorfer E (1970) Chem Ber 103: 2437

    PubMed  CAS  Google Scholar 

  236. Hubbuch A, Danho W, Zahn H (1977) In: Goodman M, Meienhofer J (eds) Peptides. Wiley, New York, p 550

    Google Scholar 

  237. Meyers C, Glass JD (1975) Proc Natl Acad Sci USA 72: 2193

    PubMed  CAS  Google Scholar 

  238. Busse WD, Hansen SR, Carpenter FH (1974) J Amer Chem Soc 96: 5949

    CAS  Google Scholar 

  239. Lawson WB, Gross E, Folk CM, Witkop B (1962) J Amer Chem Soc 84: 1715

    CAS  Google Scholar 

  240. Kidd DAA, King FE (1948) Nature 162:776; cf. also King FE, Kidd DAA (1949) J Chem Soc, p 3315

    Google Scholar 

  241. Sheehan JC, Frank VS (1949) J Amer Chem Soc 71: 1856

    CAS  Google Scholar 

  242. Fling M, Minard FN, Fox SW (1947) J Amer Chem Soc 69: 2466

    CAS  Google Scholar 

  243. Billman JH, Harting WF (1948) J Amer Chem Soc 70: 1473

    CAS  Google Scholar 

  244. Nefkens GHL (1960) Nature 185: 309

    PubMed  CAS  Google Scholar 

  245. Nefkens GHL, Tesser GI, Nivard RJF (1960) Rec Tray Chim Pays Bas 79: 688

    Google Scholar 

  246. Ing HR, Manske RHF (1926) J Chem Soc, p 2348

    Google Scholar 

  247. Schumann I, Boissonnas RA (1952) Helv Chim Acta 35: 2235

    CAS  Google Scholar 

  248. Keller O, Rudinger J (1975) Helv Chim Acta 58: 531

    PubMed  CAS  Google Scholar 

  249. Barany G, Merrifield RB (1977) J Amer Chem Soc 99: 7363

    CAS  Google Scholar 

  250. Barany G, Merrifield RB (1980) J Amer Chem Soc 102: 3084

    CAS  Google Scholar 

  251. Geiger R, König W (1981) In: Gross E, Meienhofer J (eds) The Peptides, vol 3. Academic, New York, p 3

    Google Scholar 

  252. Wünsch E (1974) In: Wunsch E (ed) Methoden der Org Chem (Houben-Weil), vol 15/1. Thieme, Stuttgart, p 46

    Google Scholar 

  253. Boissonnas RA, Preitner G (1953) Helv Chim Acta 36: 875

    CAS  Google Scholar 

  254. Kisfaludy L, Dualszky S (1960) Acta Chim Acad Sci Hung 24: 301

    CAS  Google Scholar 

  255. Blâha K, Rudinger J (1965) Coll Czech Chem Commun 30: 585

    Google Scholar 

  256. Meienhofer J (1966) In: Zervas L (ed) Peptides Proc 6th Eur Peptide Symp, Athens, 1963. Pergamon, Oxford, p 55

    Google Scholar 

  257. Erickson BW, Merrifield RB (1973) J Amer Chem Soc 95: 3757

    CAS  Google Scholar 

  258. Channing DM, Turner PB, Young GT (1951) Nature 167: 457

    Google Scholar 

  259. Yamashiro D, Li CH (1973) J Amer Chem Soc 95: 1310

    CAS  Google Scholar 

  260. Carpenter FH, Gish DT (1952) J Amer Chem Soc 74: 3818

    CAS  Google Scholar 

  261. Gish DT, Carpenter FH (1953) J Amer Chem Soc 75: 950

    CAS  Google Scholar 

  262. Amit B, Zehavi U, Patchornik A (1974) Israel J Chem 12: 103

    CAS  Google Scholar 

  263. Noda K, Terada S, Izumiya N (1970) Bull Chem Soc Jpn 43: 1883

    CAS  Google Scholar 

  264. Letsinger RL, Kornet MJ (1963) J Amer Chem Soc 85: 3045

    CAS  Google Scholar 

  265. Schwyzer R, Sieber P, Zatsko K (1958) Helv Chim Acta 41: 491

    CAS  Google Scholar 

  266. Losse G, Jeschkeit H, Willenberg E (1974) Angew Chem Int Ed 3: 307

    Google Scholar 

  267. Jeschkeit H, Losse G, Neubert K (1966) Chem Ber 99: 2803

    CAS  Google Scholar 

  268. Veber DF, Paleveda WJ Jr, Lee YC, Hirschmann R (1977) Org Chem 42: 3286

    CAS  Google Scholar 

  269. Coyle S, Keller O, Young GT (1975) J Chem Soc Chem Commun, p 939

    Google Scholar 

  270. Sakakibara S, Fukuda T, Kishida Y, Honda I (1970) Bull Chem Soc Jpn 43: 3322

    CAS  Google Scholar 

  271. Jäger G, Geiger R (1973) Liebigs Ann Chem, p 1535

    Google Scholar 

  272. Fujino M, Shinagawa S, Nishimura O, Fukuda T (1972) Chem Pharm Bull 20: 1017

    CAS  Google Scholar 

  273. Hiskey RG, Smithwick EL (1967) J Amer Chem Soc 89: 437

    CAS  Google Scholar 

  274. Sakakibara S, Shin M, Fujino M, Shimonishi Y, Inouye S, Inukai N (1965) Bull Chem Soc Jpn 38: 1522

    PubMed  CAS  Google Scholar 

  275. Sakakibara S, Itoh M (1967) Bull Chem Soc Jpn 40: 646

    PubMed  CAS  Google Scholar 

  276. Birr C, Lochinger W, Stahnke G, Lang P (1972) Liebigs Ann Chem 763: 162

    CAS  Google Scholar 

  277. Coyle S, Keller O, Young GT (1979) J Chem Soc Perkin I, p 1459

    Google Scholar 

  278. Kalbacher H, Voelter W (1978) Angew Chem Int Ed 17: 944

    Google Scholar 

  279. Tun-Kyi A, Schwyzer R (1976) Helv Chim Acta 59: 1642

    PubMed  CAS  Google Scholar 

  280. Brady SF, Hirschmann R, Veber DF (1977) J Org Chem 42: 143

    PubMed  CAS  Google Scholar 

  281. Bailey WJ, Griffith JR (1964) Polym Prepr 5: 266

    CAS  Google Scholar 

  282. Haas WL, Krumkalns EV, Gerzon K (1966) J Amer Chem Soc 88: 1988

    CAS  Google Scholar 

  283. Kader AT, Stirling CJM (1964) J Chem Soc, p 258

    Google Scholar 

  284. Tesser GI, Balvert-Geers IC (1975) Int J Peptide Protein Res 7: 295

    CAS  Google Scholar 

  285. Kunz H (1976) Chem Ber 109: 2670, 3693

    CAS  Google Scholar 

  286. Kemp DS, Hoyng CF (1975) Tetrahedron Lett, p 4625

    Google Scholar 

  287. Wakselman M, Guibé-Jampel E (1973) Chem Commun, p 593

    Google Scholar 

  288. Woodward RB, Heusler K, Gosteli J, Naegeli P, Oppolzer W, Ramage R, Ranganathan S, Vorbrüggen H (1966) J Amer Chem Soc 88: 852

    CAS  Google Scholar 

  289. Wünsch E, Spangenberg R (1971) Chem Ber 104: 2427

    Google Scholar 

  290. Stevens CM, Watanabe R (1950) J Amer Chem Soc 72: 725

    CAS  Google Scholar 

  291. Olofson RA, Yamamoto YS, Wancowicz DJ (1977) Tetrahedron Lett, p 1563

    Google Scholar 

  292. Carpino LA, Parameswaran KN, Kirkley RK, Spiewak JW, Schmitz E (1970) J Org Chem 35: 3291

    CAS  Google Scholar 

  293. Southard GL, Zaborowski BR, Pettee JM (1971) J Amer Chem Soc 93: 3302

    CAS  Google Scholar 

  294. Cassady DR, Easton NR (1964) J Org Chem 29: 2032

    CAS  Google Scholar 

  295. Brechbühler H, Büchi H, Hatz E, Schreiber J, Eschenmoser A (1965) Helv Chim Acta 48: 1746

    Google Scholar 

  296. Schellenberg P, Schühle H (1961) Angew Chem 73: 770

    Google Scholar 

  297. Kemp DS, Roberts DC (1975) Tetrahedron Lett, 4629

    Google Scholar 

  298. Stevenson D, Young GT (1967) Chem Commun, p 900

    Google Scholar 

  299. Stevenson D, Young GT (1969) J Chem Soc (C), 2389

    Google Scholar 

  300. Ehrensvärd GCH (1947) Nature 159: 500

    Google Scholar 

  301. Lindenmann A, Khan NH, Hofmann K (1952) J Amer Chem Soc 74: 476

    CAS  Google Scholar 

  302. Barany G (1982) Int J Peptide Protein Res 19: 321

    CAS  Google Scholar 

  303. Wünsch E, Moroder L, Nyfeler R, Jaeger E (1982) Hoppe-Seyler’s Z. Physiol Chem 363: 197

    Google Scholar 

  304. Carter HE, Frank RL, Johnston HW (1955) In: Horning EC (ed) Organic Syntheses Coll, vol. III. Wiley, New York, p 167

    Google Scholar 

  305. Greenstein JP, Winitz M (1961) The Chemistry of Amino Acids. Wiley, New York, p 887

    Google Scholar 

  306. Zahn H, Falkenburg HR (1960) Liebigs Ann Chem 636:117; cf. also Zahn H, Schmidt F (1960) Makromol Chem 36: 1

    Google Scholar 

  307. Sofuku S, Mizimura M, Hagitani A (1969) Bull Chem Soc Jpn 42: 278

    CAS  Google Scholar 

  308. Sofuku S, Mizimura M, Hagitani A (1970) Bull Chem Soc Jpn 43: 177

    CAS  Google Scholar 

  309. Sakakibara S, Honda I, Naruse M, Kanaoka M (1969) Experientia 25: 576

    PubMed  CAS  Google Scholar 

  310. Carpino LA (1957) J Amer Chem Soc 79: 4427

    CAS  Google Scholar 

  311. Carpino LA, Giza CA, Carpino BA (1959) J Amer Chem Soc 81: 995

    Google Scholar 

  312. Schnabel E (1967) Liebigs Ann Chem 702: 188

    CAS  Google Scholar 

  313. Polzhofer KP (1969) Tetrahedron Lett, p 2305

    Google Scholar 

  314. Grzonka Z, Lammek B (1974) Synthesis 9: 661

    Google Scholar 

  315. Khan SA, Sivanandaiah KM (1977) Indian J Chem 15B: 80

    CAS  Google Scholar 

  316. Sieber P, Iselin B (1969) Helv Chim Acta 52: 1525

    PubMed  CAS  Google Scholar 

  317. Schnabel E, Schmidt G, Klauke E (1971) Liebigs Ann Chem 743: 69

    CAS  Google Scholar 

  318. Schnabel E, Herzog H, Hoffmann P, Klauke E, Ugi I (1968) Experientia 7:380; (1968) Liebigs Ann Chem 716: 175

    CAS  Google Scholar 

  319. Moroder L, Wackerle L, Wünsch E (1976) Hoppe-Seyler’s Z. Physiol Chem 357: 1647

    CAS  Google Scholar 

  320. Tarbell DS, Insalaco MA (1968) Proc Natl Acad Sci USA 57: 233

    Google Scholar 

  321. Tarbell DS, Uamamoto Y, Pope BM (1972) Proc Natl Acad Sci USA 69: 730

    PubMed  CAS  Google Scholar 

  322. Moroder L, Hallett A, Wünsch E, Keller O, Wersin G (1976) Hoppe-Seyler’s Z. Physiol Chem 357: 1651

    CAS  Google Scholar 

  323. Staab HA, Benz W (1961) Angew Chem 73: 66

    CAS  Google Scholar 

  324. Carpino LA (1964) J Org Chem 29: 2820

    CAS  Google Scholar 

  325. Broadbent W, Morley J, Stone JE (1967) J Chem Soc C, p 2632

    Google Scholar 

  326. Klieger E (1969) Liebigs Ann Chem 724: 204

    CAS  Google Scholar 

  327. Fujino M, Hatanaka C (1967) Chem Pharm Bull 15: 2015

    PubMed  CAS  Google Scholar 

  328. Frankel M, Ladkany D, Gilon C, Wolman Y (1964) Tetrahedron Lett, p 4765

    Google Scholar 

  329. Gross H, Bilk L (1969) Liebigs Ann Chem 716: 212

    Google Scholar 

  330. Jones JH, Young GT (1966) Chem Ind, p 1722

    Google Scholar 

  331. Itoh M, Hagiwara D, Kamiya T (1975) Tetrahedron Lett, p 4393

    Google Scholar 

  332. Duggan AJ, Roberts FE (1979) Tetrahedron Lett, p 595

    Google Scholar 

  333. Nagasawa T, Kuriowa K, Narita K, Isowa Y (1973) Bull Chem Soc Jpn 46: 1269

    CAS  Google Scholar 

  334. Klee W, Brenner M (1961) Helv Chem Acta 44: 2151

    Google Scholar 

  335. Bram G (1973) Tetrahedron Lett, p 469

    Google Scholar 

  336. Guibe’-Jampel E, Wakselman M (1971) Chem Commun, p 267

    Google Scholar 

  337. Rzeszotarska B, Palka G (1968) Bull Acad Polonaise des Sciences Ser Sci Chim 16: 23

    CAS  Google Scholar 

  338. Rzeszotarska B, Wiejak S (1968) Angew Chem 80: 364

    Google Scholar 

  339. Wunsch E, Moroder L, Keller O (1981) Hoppe-Seyler’s Z. Physiol Chem 362: 1789

    Google Scholar 

  340. Bodanszky M, Tolle JC unpublished

    Google Scholar 

  341. Atherton E, Bury C, Sheppard RC, Williams BJ (1979) Tetrahedron Lett, p 3041

    Google Scholar 

  342. Martinez J, Tolle JC, Bodanszky M (1979) J Org Chem 44: 3596

    CAS  Google Scholar 

  343. Medzihradszky-Schweiger H, Medzihradszky K (1966) Acta Chim Hung 50: 339

    CAS  Google Scholar 

  344. Medzihradszky-Schweiger H (1973) Acta Chim Hung 76: 437

    CAS  Google Scholar 

  345. Bodanszky M, Martinez J, Priestley GP, Gardner JD, Mutt V (1978) J Med Chem 21: 1030

    PubMed  CAS  Google Scholar 

  346. Bodanszky M, Bodanszky A, Deshmane SS, Martinez J, Said SI (1979) Bioorg Chem 8: 399

    CAS  Google Scholar 

  347. Medzihradszky-Schweiger H (1972) Ann Univ Sci Budapestiensis de Rolando Eötvös Nominatae, Sectio Chimica 13: 35

    Google Scholar 

  348. Losse G, Stiehl HU (1981) Z Chem 21: 188

    CAS  Google Scholar 

  349. Tzougraki C, Makofske RC, Gabriel TF, Wang SS, Kutny R, Meienhofer J (1978) J Amer Chem Soc 100: 6248

    CAS  Google Scholar 

  350. Lundt BF, Johansen NL, VOlund A, Markussen J (1978) Int J Pept Protein Res 12: 258

    PubMed  CAS  Google Scholar 

  351. Weygand F, Steglich W (1959) Z Naturforsch 14b: 472

    Google Scholar 

  352. Bodanszky M, Klausner YS, Lin CY, Mutt V, Said SI (1974) J Amer Chem Soc 96: 4973

    CAS  Google Scholar 

  353. Kiso Y, Ukawa K, Akita T (1980) J Chem Soc Chem Commun, p 101

    Google Scholar 

  354. Schwyzer R, Kappeler H, Iselin B, Rittel W, Zuber H (1959) HeIv Chim Acta 42: 1702

    CAS  Google Scholar 

  355. Stewart JM, Woolley DW (1960) Nature 206: 619

    Google Scholar 

  356. White J (1934) J Biol Chem 106: 141

    CAS  Google Scholar 

  357. Idelson M, Blout ER (1958) J Amer Chem Soc 80: 4631

    CAS  Google Scholar 

  358. Brenner M, Curtius HG (1963) HeIv Chim Acta 46: 2126

    CAS  Google Scholar 

  359. Chauvette RR, Pennington PA, Ryan CW, Cooper RDE, Jose L, Wright IG, Van Heyningen EM, Huffmann GW (1971) J Org Chem 36: 1259

    Google Scholar 

  360. Yajima H, Fujii N, Ogawa H, Kawatani H (1974) J Chem Soc Chem Commun, p 407

    Google Scholar 

  361. Halpern B, Nitecki DE (1967) Tetrahedron Lett, p 3031

    Google Scholar 

  362. Loffet A, Dremier C (1971) Experientia 27: 1003

    CAS  Google Scholar 

  363. Hiskey RG, Beacham LM III, Matl VG, Smith JN, Williams EB Jr, Thomas AM, Wolters ET (1971) J Org Chem 36: 488

    PubMed  CAS  Google Scholar 

  364. Felix AM (1974) J Org Chem 39: 1427

    CAS  Google Scholar 

  365. Pless J, Bauer W (1973) Angew Chem 85: 142

    CAS  Google Scholar 

  366. Sakakibara S, Shimonishi Y (1965) Bull Chem Soc Jpn 38: 1412

    PubMed  CAS  Google Scholar 

  367. Olah GA, Nojima M, Kerekes I (1973) Synthesis, 779; Matsuura S, Niu CH, Cohen JS (1976) J Chem Soc Chem Commun, p 451

    Google Scholar 

  368. Sakakibara S, Shin KH, Hess GP (1962) J Amer Chem Soc 84: 4921

    CAS  Google Scholar 

  369. Yasima H, Fujii N (1983) In: Gross E, Meienhofer N (eds) The Peptides, vol 5. Academic, New York, p 65

    Google Scholar 

  370. Homer RB, Moodie RB, Rydon HN (1965) J Chem Soc, p 4403

    Google Scholar 

  371. Blâha K, Rudinger J (1965) Collect Czechoslov Shem Commun 30: 599

    Google Scholar 

  372. König W, Geiger R (1972) In: Meienhofer J (ed) Chemistry and Biology of Peptides, Ann Arbor Sci Publ, Ann Arbor, Michigan, p 343

    Google Scholar 

  373. Kutassy S, Kajtâr J, Medzihradszky-Schweiger H (1968) Acta Chim Hung 57: 123

    CAS  Google Scholar 

  374. Carpino LA (1966) Chem Commun, 858

    Google Scholar 

  375. Bodanszky M, Deshmane SS, Martinez J (1979) J Org Chem 44: 1622

    CAS  Google Scholar 

  376. Carpino LA, Williams JR (1978) J Chem Soc Chem Commun, p 450

    Google Scholar 

  377. Eckert H, Schrauzer GN, Ugi I (1975) Tetrahedron 31: 1399

    CAS  Google Scholar 

  378. Eckert H, Ugi I (1976) Angew Chem 88:717; (1976) Angew Chem Int Ed 15: 681

    Google Scholar 

  379. Grimshaw J (1965) J Chem Soc, p 7136

    Google Scholar 

  380. Schönheimer R (1926) Hoppe-Seyler’s Z. Physiol Chem 154: 203

    Google Scholar 

  381. Rudinger J (1973) In: Katsoyannis PG (ed) The Chemistry of Polypeptides. Plenum, New York, p 87

    Google Scholar 

  382. Mazur RH, Plume G (1968) Experientia 24: 661

    PubMed  CAS  Google Scholar 

  383. Weisblat DI, Magerlein BJ, Meyers DR (1953) J Amer Chem Soc 75: 3630

    CAS  Google Scholar 

  384. Poduska K, Rudinger J, Sorm F (1955) Collect Czech Chem Commun 20: 1174

    CAS  Google Scholar 

  385. Rudinger J, Maassen van den Brink-Zimmermannova H (1973) Helv Chim Acta 56: 2216

    CAS  Google Scholar 

  386. Homer L, Neumann H (1965) Chem Ber 98: 3462

    Google Scholar 

  387. Okumura K, Iwasaki T, Matsuoka M, Matsumoto K (1971) Chem Ind, p 929

    Google Scholar 

  388. Hamada T, Nishida A, Matsumoto Y, Yonemitsu O (1980) J Amer Chem Soc 102: 3978

    CAS  Google Scholar 

  389. Wiley RH, Davis HL, Gensheimer DE, Smith NR (1952) J Amer Chem Soc 74: 936

    CAS  Google Scholar 

  390. Wiley RH, Davis RP (1954) J Amer Chem Soc 76: 3496

    CAS  Google Scholar 

  391. Beecham AF (1955) Chem Ind, p 1120

    Google Scholar 

  392. Beecham AF (1957) J Amer Chem Soc 79: 3257, 3262

    CAS  Google Scholar 

  393. Milne HB, Peng CH (1957) J Amer Chem Soc 79: 639

    CAS  Google Scholar 

  394. Fukuda T, Kitada C, Fujino M (1978) J Chem Soc Chem Commun, p 220

    Google Scholar 

  395. Hendrickson JB, Bergeron R (1970) Tetrahedron Lett, p 345

    Google Scholar 

  396. Ito H, Ogawa K, Iida T, Ichikizaki I (1978) Chem Pharm Bull 26: 296

    CAS  Google Scholar 

  397. Wolman Y (1967) Israel J Chem 5: 231

    CAS  Google Scholar 

  398. Savrda J, Veyrat DH (1970) J Chem Soc (C), p 2180

    Google Scholar 

  399. Spangenberg R, Thamm P, Wunsch E (1971) Hoppe-Seyler’s Z. Physiol Chem 352: 655

    CAS  Google Scholar 

  400. Poduska K, Maassen van den Brink-Zimmermannovâ H (1968) Coll Czech Chem Commun 33: 3769

    CAS  Google Scholar 

  401. Poduska K (1968) Coll Czech Chem Commun 33: 3779

    CAS  Google Scholar 

  402. Meienhofer J (1965) Nature 205: 73

    CAS  Google Scholar 

  403. Wünsch E, Spangenberg R (1972) Chem Ber 105: 740

    PubMed  Google Scholar 

  404. Stern M, Warshawsky A, Fridkin M (1981) Int J Peptide Protein Res 17: 531

    CAS  Google Scholar 

  405. Foss O (1947) Acta Chem Scand 1: 307

    CAS  Google Scholar 

  406. Polzhoffer KP, Nay KH (1971) Tetrahedron 27: 1997

    Google Scholar 

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

    PubMed  Google Scholar 

  408. Bodanszky M, Bednarek MA, Bodanszky A (1982) Int J Peptide Protein Res 20: 387

    CAS  Google Scholar 

  409. Mitin YV, Vlasov GP (1968) Dokl Akad Nauk SSSR 179: 353

    CAS  Google Scholar 

  410. Savrda J, Veyrat DH (1968) Tetrahedron Letters 6253

    Google Scholar 

  411. Wunsch E, Fontana A, Drees F (1967) Z Naturforsch 22b: 607

    Google Scholar 

  412. Phocas I, Yovanidis C, Photaki I, Zervas L (1967) J Chem Soc (C), p 1506

    Google Scholar 

  413. Zervas L, Dilaris L (1955) J Amer Chem Soc 77: 5354

    CAS  Google Scholar 

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Bodanszky, M. (1993). Reversible Blocking of Amino and Carboxyl Groups. In: Principles of Peptide Synthesis. Springer Laboratory. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-78056-1_3

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