Side reactions in peptide synthesis

Synthesis (Germany)

Volumn 1981, Issue 5, 1981, Pages 333-356

  Bodanszky, Miklos ^a   Martinez, Jean ^b  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b INSTITUT CHARLES GERHARDT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85004754595     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1981-29442     Document Type: Review

References (434)

1. E. Wunsch, in Houben-Weyl, Methoden der Organischen Chemie, 4th Edn., E. Miiller, Ed., Vol. 15, Georg Thieme Verlag, Stuttgart 1974.
2. K. Lubke, E. Schroder, G. Kloss, Chemie und Biochemie der Aminosauren, Peptide und Proteine, Georg Thieme Verlag, Stuttgart, 1975.
3. A. Hubbuch. Kontakte (Merck) 1979 (3), 14.
4. E. E. Bullesbach, Kontakte (Merck) 1980 (1), 23.
5. E. Fischer, Ber. Dtsch. Chem. Ges. 35, 1095 (1902).
6. F. Wessely, E. Kemm. Z. Physiol Chem. 174, 306 (1928).
7. F. Wessely, E. Kemm. J. Mayer, Z. Physiol. Chem. 180. 64 (1929).
8. S. Goldschmidt, M. Wick, Justus Liebigs Ann. Chem. 575, 217 (1952).
9. K. Schlogl, H. Fabtschowitz, Monatsh. Chem. 84, 937 (1953).
10. J. A. MacLaren, Aust. J. Chem. 11, 360 (1958).
11. C. A. Dekker, S. P. Taylor Jr., J. S. Fruton, J. Biol. Chem. 180, 155 (1949).
12. J. S. Fruton, M. Bergmann, J. Biol. Chem. 145. 253 (1942).
13. K. Heyns, G. Legler, Z. Physiol. Chem. 321, 161 (1960).
14. M. Goodman, K. C. Steuben, J. Am. Chem. Soc. 84, 1279 (1962).
15. T. Wieland, B. Heinke, Justus Liebigs Ann. Chem. 599. 70 (1956).
16. K. D. Kopple, R. J. Renick, J. Org. Chem. 23, 1565 (1958).
17. P. Schellenberg, J. Ulrich, Chem. Ber. 92, 1276 (1959).
18. H. Kotake, T. Saito. Bull. Chem. Soc. Jpn. 39, 853 (1966).
19. M. Zaoral, J. Rudinger, Collect. Czech. Chem. Commun. 26, 2316 (1961).
20. R. B. Merrifield, A. R. Mitchell, J. E. Clarke, J. Org. Chem. 39, 660 (1974).
21. H. C. Beyerman et at, in Peptides 1972, Proceedings of 12th European Peptide Symposium, H. Hanson and H. D. Jakubke. Eds., North Holland Publishing Co., Amsterdam, 1973, p. 170.
22. R. S. Dewey et al., J. Am. Chem. Soc. 90. 3254 (1968).
23. I. Muramatsu, T. Hirabayashi, A. Hagitani, Nippon Kagaku Zasshi 84, 855 (1963); C. A. 60, 12100 (1964).
24. J. I. Harris, T. S. Work, Biochem. J. 46, 582 (1950).
25. F. Weygand, R. Obermeier, Z. Naturforsch. [bj 23, 1390 (1968).
26. K. Esko, S. Karlsson, J. Porath, Acta Chem. Scand. 22. 3342 (1968).
27. J. W. Hinman, E. L. Caron, H. N. Christensen, J. Am. Chem. Soc. 72, 1620(1950).
28. J. C. Sheehan, G. P. Hess, J. Am. Chem. Soc. 77. 1067 (1955).
29. H. G. Khorana, Chem. Ind. (London) 1955, 1087.
30. M. Bodanszky, K. W. Funk, M. L. Fink, J. Org. Chem. 38, 3565 (1973).
31. G. Losse, G. Miiller, Chem. Ber. 94, 2768 (1961).
32. S. Shankman, S. Higa, J. Pharm. Sci. 51, 137 (1962).
33. S. Shankman, Y. Schvo, J. Am. Chem. Soc. 80, 1164 (1958).
34. R. Paul, G. W. Anderson, J. Org. Chem. 27, 2094 (1962).
35. M. Bodanszky, J. C. Tolle, Int. J. Peptide Protein Res. 10, 380 (1977).
36. N. Mitsuyasu, M. Waki, T. Kato, N. Izumiya, Mem. Fac. Sci. Kyushu Univ. Ser. C1970, 97; C. A. 73, 88154 (1970).
37. M. Bodanszky, G. F. Sigler, A. Bodanszky, J. Am. Chem. Soc. 95, 2352 (1973).
38. M. Bodanszky, J. Martinez, 1978, unpublished results.
39. E. E. Haley, B. J. Corcoran, F. E. Dorer, D. L. Buchanan, Biochemistry 5, 3229 (1966).
40. A. R. Battersby, J. C. Robinson, J. Chem. Soc. 1955, 259.
41. M. Bodanszky, M. A. Ondetti, S. D. Levine, J. Williams, J. Am. Chem. Soc. 89, 6753 (1967).
42. M. Bodanszky, J. Z. Kwei, Int. J. Peptide Protein Res. 12, 69 (1978).
43. M. Bodanszky, S. Natarajan, J. Org. Chem. 40, 2495 (1975).
44. S. Natarajan, M. Bodanszky, J. Org. Chem. 41. 1269 (1976).
45. M. Gordon, J. G. Miller, A. R. Day, j. Am. Chem. Soc. 70, 1946 (1948); 71, 1245 (1949).
46. R. B. Merrifield, in Recent Progress in Hormone Research 23, 451 (1967).
47. S. S. Wang el al., Int. J. Peptide Protein Res. 6, 103 (1974).
48. T. Baba, H. Sugiyama, S. Seto, Chem. Fharm. Bull. 21, 207 (1973).
49. K. Suzuki, K. Nitta, Y. Sasaki, Chem. Pharm. Bull. 24. 3025 (1976).
50. M. Bodanszky, J. C. Tolle, S. S. Deshmane, A. Bodanszky, Int. J. Peptide Protein Res. 12, 57 (1978).
51. C. C. Yang, R. B. Merrifield, J. Org. Chem. 41. 1032 (1976).
52. J. Blake, Int. J. Peptide Protein Res. 13, 418 (1979).
53. M. Bodanszky, J. Martinez, J. Org. Chem. 43, 3071 (1978).
54. P. Siebeir, B. Iselin, Helv. Chim. Acta 51, 622 (1968).
55. L. A. Carpino, G. Y. Han, J. Am. Chem Soc. 92, 5748 (1970).
56. L. A. Carpino, G. Y. Han, J. Org. Chem. 37, 3404 (1972).
57. J. Martinez, M. Bodanszky, Int. J. Peptide Protein Res. 12, 277 (1978).
58. R. Schwyzer et al., Helv. Chim. Acta 46, 1975 (1963).
59. S. Bajusz, T. Lazar, Z. Paulay, Acta Chim. Acad. Sci. Hung. 41, 329 (1964).
60. E. Wunsch, F. Drees, Chem. Ber. 99, 110 (1966).
61. M F. Chillemi, Gazz. Chim. Ital. 96, 359 (1966).
62. J. Bernhard, J. Cell. Comp. Physiol. (Suppl. 1) 195, 221 (1954).
63. R. W. Hanson, H. N. Rydon, J. Chem. Soc. 1964, 836.
64. G. Folsch, Acta Chem. Scand. 20, 459 (1966).
65. I. Muramatsu, Nippon Kagaku Zasshi 82. 83 (1961); C. A. 56, 10273 (1962).
66. F. E. King, D A. A. Kidd, .J. Chem. Soc. 1951, 2976.
67. S. W. Tanenbaum, J. Am. Chem. Soc. 75, 1754 (1953).
68. A. Menozzi, G. Appiani, Gazz. Chim. Ital. 22, 105 (1892); 24, 370 (1894).
69. E. Abderharden, K. Kautzsch, Z. Physiol Chem. 64, 447 (1909); 68, 487 (1910).
70. J. Rudinger, Collect. Czech. Chem. Commun. 19, 365 (1954).
71. R. J. Stedman, J. Am. Chem. Soc. 79, 4691 (1957).
72. H. Gibian, E. Klieger, Angew. Chem. 72, 708 (1960).
73. E. Taschner, C. Wasiliewski, J. F. Biernat, T. Sokolovska, Chimia (Aarau) 14, 371 (1960).
74. A. J. Hubert, R. Buyle, B. Hargitay, Helv. Chim. Acta 46, 1429 (1963).
75. G. M. Bonora et al., Biopolymers 13, 157 (1974).
76. W. J. LeQuesrie, G. T. Young, J. Chem. Soc. 1950, 1959.
77. H. Wilson, R. K. Cannan, J. Biol. Chem. 119, 309 (1937).
78. A. R. Battersby, J. C. Robinson, J. Chem. Soc. 1956, 2076.
79. D. W. Clayton, G. W. Kenner, R. C, Sheppard, J. Chem. Soc. 1956, 371.
80. D. W. Clayton, G. W. Kenner, Chem. Ind. (London) 1953, 1205.
81. J. Bayer, S. Dualszky, L. Kisfaludy, J. Chromatogr. 6, 155 (1961).
82. E. Schnabel, H. Klostermeyer, H. Berndt, Justus Liebigs Ann. Chem. 749, 90 (1971).
83. H. Zahn, H. Bremer, V. Sroka, J. Meienhofer, Z. Naturforsch. [b] 20, 646 (1965).
84. T. Shiba, T. Kaneko, Bull. Chem. Soc. Jpn. 33, 1721 (1960).
85. R. G. Denkewalter et al., J. Am. Chem. Soc. 88, 3163 (1966).
86. J. Melville, Biochem. J. 29, 179 (1935).
87. M. Bergmann, L. Zervas, J. S. Fruton, J. Biol. Chem. 115. 593 (1936).
88. J. Kovacs, K. Medzihradszky, V. Bruckner, Naturwissenschaften 41, 450 (1954); Acta Chim. Acad. Sci. Hung. 6, 183 (1955).
89. V. Bruckner, J. Kovacs, H. Nagy, M. Kajtar, Acta Chim. Acad. Sci. Hung. 6. 219 (1955).
90. V. Bruckner, J. Kovacs, K. Medzihradszky, Naturwissenschaften 42, 96 (1955).
91. V. Bruckner, J. Kovacs, Acta Chim. Acad. Sci. Hung. 12, 363 (1957).
92. V. Bruckner et al., Tetrahedron 2. 211 (1958).
93. V. Bruckner, M. Kajtar, Acta Chim. Acad. Sci. Hung. 21, 417 (1959).
94. V. Bruckner, A. Kotai, K. Kovaes, Acta Chim. Acad. Sci. Hung. 21, 427 (1959).
95. K. Medzihradszky, Collect. Czech. Chem. Commun. 24, 107 (1959).
96. W. J. LeQuesne, G. T. Young, J. Chem. Soc. 1954, 1950.
97. D. A. Rowlands, G. T. Young, Biochem. J. 65, 516 (1957).
98. H. Sachs, E. Brand, J. Am. Chem. Soc. 76, 1815 (1954).
99. L. Kisfaludy, Acta Chim. Acad. Sci. Hung. 24, 309 (1960).
100. F. E. King, D. A. A. Kidd, J. Chem. Soc. 1949, 3315.
101. F. E. King, B. S. Jackson, D. A. A. Kidd, J. Chem. Soc. 1951, 243.
102. F. E. King, J, W. Clark-Lewis, G. R. Smith, J. Chem. Soc. 1954, 1044.
103. F. E. King, J. W. Clark-Lewis, R. Wade, J. Chem. Soc. 1957, 880, 886.
104. R. B. Merrifield, J. Am. Chem. Soc. 85, 2149 (1963).
105. S. Sakakibara, Y. Shimonishi, Bull. Chem. Soc. Jpn. 38, 1412 (1965).
106. S. Sano, S. Kawanishi, Biochem. Biophys. Res. Commun. 51, 46 (1973).
107. K. P. Polzhofer, K. H. Ney, Tetrahedron 26, 3221 (1970).
108. S. Sano, S. Kawanishi, J. Am. Chem. Soc. 97, 3480 (1975).
109. R. S. Feinberg, R. B. Merrifield, J. Am. Chem. Soc. 97, 3480 (1975).
110. K. Suzuki, N. Endo, N. Sasaki, Chem. Pharm. Bull. 25, 2613 (1977).
111. R. Schwyzer et al., Helv. Chim. Acta 41, 1273, 1287 (1958).
112. A. B. Robinson, J. H. McKerron, P. Cary, Proc. Nat. Acad. Sci. U. S. 66, 753 (1970).
113. A. B. Robinson, S. Tedro, Int. J. Peptide Protein Res. 5, 275 (1973).
114. A. B. Robinson, Proc. Nat. Acad. Sci. U. S. 71, 885 (1974).
115. B. Riniker, R. Schwyzer, Helv. Chim. Acta 44, 685 (1961).
116. R. Roeske, J. Org. Chem. 28, 1251 (1963).
117. W. Konig, A. Volk, Chem. Ber. 110, 1 (1977).
118. B. Riniker, H. Brunner, R. Schwyzer, Angew. Chem. 74, 469 (1962); Angew. Chem. Int. Ed. Engl. 1, 405 (1962).
119. N. Inukae, K. Nakano, M. Murakami, Bull. Chem. Soc. Jpn. 41, 182 (1968).
120. E. Sondheimer, R. W. Holley, J. Am. Chem. Soc. 79, 3767 (1957).
121. R. A. Boissonnas, S. Guttmann, P. A. Jaquenoud, J. P. Waller, Helv. Chim. Acta 38, 1491 (1955).
122. C. Meyers, R. T. Havran, I. L. Schwartz, R. Walters, Chem. Ind. (London) 1969, 136.
123. R. S. Dewey, H. Barkemeyer, R. Hirschmann, Chem. Ind. (London) 1969, 1632.
124. M. Bodanszky, A. E. Yiotakis, unpublished results.
125. E. Sondheimer, R. W. Holley, J. Am. Chem. Soc. 76, 2816 (1954).
126. M. Ebata, J. Biochem. (Tokyo) 49, 110 (1961).
127. A. C. Chibnall, R. G. Westall, Biochem. J. 26, 122 (1932).
128. J. Rudinger, Z. Pravda, Collect. Czech. Chem. Commun. 23, 1947 (1958).
129. H. B. Vickery et al., Biochem. J. 29, 2710 (1935).
130. H. Takashima, V. du Vigneaud, R. B. Merrifield, J. Am. Chem Soc 90, 1323 (1968).
131. M. Manning, J. Am. Chem. Soc. 90, 1348 (1968).
132. H. C. Beyerman, T. S. Lie, C. J. van Veldhuizen in Peptides 1971, Proceedings of 11th European Peptide Symposium, H. Nesvadba, Ed., North Holland Publ., Amsterdam, 1973, p. 162.
133. J. T. Potts et al., Proc. Nat. Acad. Sci. U. S. 68, 63 (1971).
134. L. C. Dorman, D. A. Nelson, R. C. L. Chow, in Progress in Peptide Res. Vol. II, S. Lande, Ed., Gordon and Breach, New York 1972 p 65.
135. G. Barany, R. B. Merrifield, Cold Spring Harbor Symp. Quant Biol 37, 121 (1973).
136. E. Schroder, Justus Liebigs Ann. Chem. 681, 241 (1965).
137. E. Schnabel, H. Klostermeyer, J. Dahlmans, H. Zahn, Justus Liebigs Ann. Chem. 707, 227 (1967).
138. P. Pietta, I. Chillemi, A. Corbellini, Chem. Ber. 101, 3649 (1968).
139. E. Schnabel, H. Schuessler, Justus Liebigs Ann. Chem. 686. 229 (1965).
140. J. C . Sheehan, D. D. H. Yang, J. Am. Chem. Soc. 80, 1154 (1958).
141. E. Sondheimer, R. J. Semeraro, J Org. Chem. 26, 1847 (1961).
142. D. T. Gish, P. G. Katsoyannis, G. P. Hess, R. J. Stedman, J. Am. Chem. Soc. 78, 5954 (1956).
143. C. Ressler, J. Am. Chem. Soc. 78, 5956 (1956).
144. G. W. Anderson, J. Blodinger, R. W. Young, A. D. Welcher, J. Am. Chem. Soc. 74, 5304 (1952).
145. G. W. Anderson, R. W. Young, J. Am. Chem. Soc. 74, 5307 (1952).
146. G. W. Anderson, J. Blodinger, A. D. Welcher, J. Am. Chem. Soc. 74, 5309 (1952).
147. P. G. Katsoyannis, D. T. Gish, V. du Vigneaud, J. Am. Chem. Soc. 79, 4516 (1957).
148. P. G. Katsoyannis, D. T. Gish, G. P. Hess, V. du Vigneaud, J. Am. Chem. Soc. 80, 2558 (1958).
149. B. Liberek, Chem. Ind. (London) 1961. 987.
150. R. Wilchek. S. Ariely, A. Patchornik, J. Org. Chem. 33, 1258 (1968).
151. J. Stammer, J. Org. Chem. 26, 2556 (1961).
152. R. Paul, A. S. Kende, J. Am. Chem. Soc. 86, 741 (1964).
153. D. V. Kashelikar, C. Ressler, J. Am. Chem. Soc. 86, 2467 (1964).
154. C. Ressler, H. Ratzkin, J. Org. Chem. 26, 3356 (1961).
155. M. Zaoral, J. Rudinger, Collect. Czech. Chem. Commun. 24, 1993 (1959).
156. M. Bodanszky, V. du Vigneaud, J. Am. Chem. Soc. 81, 5688 (1959).
157. IM M. Bodanszky, V. du Vigneaud, Biochem. Preparations 10, 122 (1963).
158. A. R. Mitchell, R. B. Merrifield, J. Org. Chem. 41, 2015 (1976).
159. N. Fujii, S. Funakoshi, T. Sasaki, H. Yajima, Chem. Pharm. Bull. 25. 3096 (1977).
160. M. Bodanszky, C. A. Birkhimer, Chimia 14, 368 (1960).
161. B. C. Barras, D. T. Elmore, J. Chem. Soc. 1957, 4830.
162. J. D. Cipera, J. Org. Chem. 26, 206 (1961).
163. H M. Bodanszky, Ann. N. Y. Acad. Sci. 88, 655 (1960).
164. E. Schnabel, H. Klostermeyer, H. Berndt, Justus Liebigs Ann. Chem. 749, 90(1971).
165. Y. S. Klausner, M. Bodanszky, Bioorg. Chem. 2, 354 (1973).
166. B. Halpern, D. E. Nitecki, Tetrahedron Lett. 1967, 3031.
167. IM A. Yaron, S. F. Shlossman, Biochemistry 7, 2673 (1968).
168. O. Grahl-Nielsen, G. L. Tritsch, Biochemistry 8, 187 (1969).
169. A. Loffet, C. Dremier, Experientia 27, 1003 (1971).
170. D. Yamashiro, C. H. Li, J. Am. Chem. Soc. 95, 1310 (1973).
171. B. W. Erickson, R. B. Merrifield, J. Am. Chem. Soc. 95, 3757 (1973).
172. S. Sakakibara, T. Fukuda, Y. Kishida, I. Honda. Bull. Chem. Soc. Jpn. 43, 3322 (1970).
173. G. I. Tesser. in, Peptides 1974. Proceedings of 13th European Peptide Symposium, Y. Wolman, Ed., John Wiley & Sons, New York-Israel University Press, Jerusalem, 1975, p. 53.
174. G. I. Tesser, I. C. Balvert-Geers, Int. J. Peptide Protein Res. 7, 295 (1975).
175. I. Photaki, A. Yiotakis, J. Chem. Soc. Perkin Trans. I 1976, 259.
176. S. Guttmann, Helv. Chim. Acta 44, 721 (1961).
177. R. Hirschmann in, Peptides 1969. Proceedings of 10th European Peptide Symposium, E. Scoffone, Ed., North Holland Publ., Amsterdam, 1971, p. 138.
178. A. F. McKay, Chem. Rev. 51, 301 (1952).
179. W. Siedel, K. Sturm, R. Geiger, Chem. Ber. 96, 1436 (1963).
180. R. A. Boissonnas, S. Guttmann, P. A. Jaquenoud, Helv. Chim. Acta 43. 1349 (1960).
181. G. L. Tritsch, D. W. Woolley, J. Am. Chem. Soc. 82, 2787 (1960).
182. H. Kuenzi, M. Manneberg, R. O. Studer, Helv. Chim. Acta 57, 566 (1974).
183. D. Yamashiro, J. Blake, C. H. Li, J. Am. Chem. Soc. 94, 2855 (1972).
184. C. Gross, M. P. DeGarilhe, A. Costopanagiotis, R. Schwyzer, Helv. Chim. Acta 44, 2042 (1961).
185. P. M. Scopes, K. B. Walshaw, M. Welford, G. T. Young. J. Chem. Soc. 1965, 782.
186. A. Turan, A. Patthy, S. Bajusz, Acta Chim. Acad. Sci. Hung. 85, 327 (1975).
187. B. Iselin in, Peptides. Proceedings of 6th European Peptide Symposium, L. Zervas, Ed., Pergamon Press, Oxford, 1966, p. 27.
188. T. Hayakawa, Y. Fujiwara, J. Noguchi, Bull. Chem. Soc. Jpn. 40, 1205 (1967).
189. R. M. Freidinger, R. Hirschmann, D. F. Veber, J. Org. Chem. 43, 4800 (1978).
190. J. Pless, S. Guttmann in, Peptides. Proceedings of 8th European Peptide Symposium, H. C, Beyerman, A. van de Linde, W. Maassen van den Brink, Eds., North Holland Publ., Amsterdam, 1967. p. 50.
191. M. Bodanszky, J. T. Sheehan, Chem. Ind. (London) 1960, 1268.
192. L. Zervas, T. T. Otani, M. Winitz, J. P. Greenstein, J. Am. Chem. Soc. 81. 2878 (1959).
193. R. Paul, G. W. Anderson. F. M. Callahan, J. Org. Chem. 26, 3347 (1961).
194. W. R. Rittel, Helv. Chim. Acta 45, 2465 (1962).
195. E. Bayer et al.. J. Am. Chem. Soc. 92, 1735 (1970).
196. R. Geiger, G. Jager, W. Konig, A. Volk, Z. Naturforsch. [b] 24, 999 (1969).
197. R. H. Mazur, J. M. Schlatter, J. Org. Chem. 28, 1025 (1963).
198. J. M. Stewart, J. D. Young in, Solid Phase Peptide Synthesis, Freeman, San Francisco, Calif., 1969. p. 8.
199. E. Bricas, C. Nicot-Cutton, Bull. Soc. Chim. Fr. 26, 466 (1960).
200. H. Kappeler, Helv. Chim. Acta 44, 476 (1961).
201. K. D. Kopple, R. R. Jaraba, P. L. Bhatia, Biochemistry 2. 958 (1963).
202. D. Theodoropoulos. J. Org. Chem. 21, 1550 (1956).
203. C. H. Li, E. Schnabel, D. Chung, J. Am. Chem. Soc. 82, 2062 (1960).
204. R. Fletcher, J. H. Jones, W. I. Ramage, A. V. Stachulski in. Peptides 1978. Proceedings of 15th European Peptide Symposium, I. S. Siemion, G. Kupryszewski, Eds., Wroclaw Univ. Press, Wroclaw, Poland, 1979, p. 179.
205. F. Sakiyama, Bull. Chem. Soc. Jpn. 35, 1943 (1962).
206. J. C. Sheehan, K. Hasspacher, Y. L. Yeh, J. Am. Chem. Soc 81, 6086 (1959).
207. R. B. Merrifield, L. W. Wooley, J. Am. Chem. Soc. 78, 4646 (1956).
208. F. Schneider, Z. Physiol. Chem. 320, 82 (1960); 321, 38 (1960).
209. H. Rink, B. Riniker, Helv. Chim. Acta 57, 831 (1974).
210. D. Ben-Ishai, A. Berger, J. Org. Chem. 17, 1564 (1952).
211. G. W. Anderson, J. Blodinger, A. D. Welcher, J. Am. Chem. Soc. 74, 5309 (1952).
212. R. A. Boissonnas, I. Schumann, Helv. Chim. Acta 35, 2229 (1952).
213. E. D. Nicolaides, M. K. Craft, H. A. DeWald, J. Med. Chem. 6. 524 (1963).
214. E. D. Nicolaides, H. A. DeWald, J. Org. Chem. 28, 1926 (1963 ).
215. K. Okawa, Bull. Chem. Soc. Jpn. 30, 976 (1957).
216. J. C. Sheehan, M. Goodman, G. P. Hess, J. Am. Chem. Soc. 78, 1367 (1956).
217. M. Bodanszky in, Prebiotic and Biochemical Evolution, A. P. Kimball, J. Oro, Eds., North Holland Publ., Amsterdam, 1971, p. 217.
218. M. Bodanszky, M. A. Ondetti, Chem. Ind. (London) 1966, 26.
219. M. Bodanszky, Nature 175, 685 (1955).
220. H. Zahn, H. Brenner, R. Zabel, Z. Naturforsch. [b] 20, 53 (1965).
221. R. Garner, D. J. Schafer, G. T. Young in, Peptides 1969, Proceedings of 10th European Peptide Symposium, E. Scoffone, Ed., North Holland, Amsterdam, 1971. p. 102.
222. D. J. Schafer, G. T. Young, D. F. Elliott, R. Wade, J. Chem. Soc. [C] 1971, 46.
223. B R. Hogue-Angeletti, R. A. Bradshaw, G. R. Marshall, Int. I. Peptide Protein Res. 6, 321 (1974).
224. H. Hagenmaier, H. Frank, J. Chromatogr. Sci. 10. 663 (1972).
225. F. H. C. Stewart, Aust. J. Chem. 21, 477 (1968); 21, 1639 (1968).
226. M. Bodanszky et al., .J. Org. Chem. 42, 149 (1977).
227. Y. S. Klausner, M. Chorev, J. Chem. Soc. Chem. Commun. 1977, 973.
228. S. Sakakibara in, Peptides. Proceedings of 5th American Peptide Symposium, M. Goodman, J. Meienhofer, Eds., John Wiley & Sons, New York, 1977, p. 436.
229. S. K. Girin, Yu. P. Shvachkin, J. Gen. Chem. USSR 47, 1085, 1950 (1977); 48, 823 (1978).
230. J. Martinez, J. C. Tolle, M. Bodanszky, Int. J. Peptide Protein Res. 13, 22 (1979).
231. J. S. Fruton, J. Biol. Chem. 146, 463 (1942).
232. E. Baer, J. Maurukas, D. D. Clarke. Can. J. Chem. 34. 1182 (1956).
233. E. Schnabel, Justus Liebigs Ann. Chem. 659, 168 (1962).
234. P. G. Katsoyannis, A. M. Tometsko, C. Zalut, J. Am. Chem. Soc. 89, 4505 (1967).
235. T. Saito, Bull. Chem. Soc. Jpn. 37, 624 (1964).
236. J. C. Sheehan, Ann. N. Y. Acad. Sci. 88, 665 (1960).
237. W. Konig, R. Geiger, Chem. Ber. 103, 788 (1970).
238. J. I. Harris, J. S. Fruton, J. Biol. Chem. 191, 143 (1951).
239. B. F. Erlanger, H. Sachs, E. Brand, J. Am. Chem. Soc. 76, 1806 (1954).
240. H. Zahn, E. Schnabel, Justus Liebigs Ann. Chem. 605, 212 (1957).
241. K. Inouye, H. Otsuka, Bull. Chem. Soc. Jpn. 34, 1 (1961).
242. I. Photaki, J Am. Chem. Soc. 85, 1123 (1963).
243. G. Riley. J. Turnbull, W. Wilson, .J. Chem. Soc. 1957, 1373.
244. L. Benoiton, R. W. Hanson, H. N. Rydon, J. Chem. Soc. 1964, 824.
245. H. Zahn. G. Schmidt, Tetrahedron Lett. 1967, 5095.
246. M. Bergmann, E. Brand, F. Weinman. Z. Physiol. Chem. 131, 1 (1923).
247. M. Bergmann, A. Michaelis, Z. Physiol. Chem. 140, 128 (1924).
248. J. L. Bayley, Biochem. J. 60, 173 (1955).
249. L. A. Cohen, B. Witkop, Angew. Chem. 73, 253 (1961).
250. D. Theodoropoulos, H. Bennich, G. Folsch, O. Mellander, Nature 184, 270 (1959).
251. D. F. Elliot, Biochem. J. 50, 542 (1952).
252. K. Narita, J. Am. Chem. Soc. 81. 1751 (1959).
253. S. Fujiwara, S. Morinaga, K. Narita. Bull. Chem. Soc. Jpn. 35, 438 (1962).
254. K. H. Shin, K.. Sakakibara, W. Schneider, G. P. Hess, Biochem. Biophys. Res. Commun. 8, 288 (1962).
255. S. Sakakibara, K. H. Shin, G. P. Hess, J. Am. Chem. Soc. 84, 4921 (1962).
256. J. Lenard, G. P. Hess, J. Biol. Chem. 239, 3275 (1964).
257. K. lwai, T. Ando, Methods Enzymol. 11, 263 (1967).
258. F. Weygand, H. Rinno, Chem. Ber. 92, 517 (1959).
259. M. Fujirio, M. Wakimasu, S. Shinagawa, C. Kitada, H. Yajima, Chem. Pharm. Bull. 26, 539 (1978).
260. T. Wakamiya, Y. Tarumi, T. Shiba, Bull. Chem. Soc. Jpn. 47, 2686 (1974).
261. E. Fischer, Ber. Dtsch. Chem. Ges. 48, 93 (1915).
262. E. Abderhalden, A. Bahn, Z. Physiol. Chem. 219, 72 (1933).
263. E. Katchalski, M. Sela, J. Am. Chem. Soc. 75, 5284 (1953).
264. R. Paul, .J. Org. Chem. 28, 236 (1963).
265. J. Ramachandran, C. H. Li, J. Org. Chem. 28, 173 (1963).
266. K. Okawa, Bull. Chem. Soc. Jpn. 29, 488 (1956).
267. B. Iselin, Helv. Chim. Acta 45, 1510 (1962).
268. F Weygand, W. Steglich, Z Naturforsch. [b] 14, 472 (1959).
269. Y. Trudelle, G. Spach, Tetrahedron Lett. 1972, 3475.
270. S. Sakakibara et al., Bull. Chem. Soc. Jpn. 40, 2164 (1967).
271. Y. Kiso, H. Isawa, K. Kitagawa, T. Akita, Chem. Pharm. Bull. 26, 2562 (1978).
272. H. Yajima, N. Fujii, H. Ogawa, H. Kawatani, J. Chem. Soc. Chem. Commun. 1974, 107.
273. B. W. Erikson, R. B. Merrifield, J. Am. Chem. Soc. 95. 3750 (1973).
274. D. Yamashiro, C. H. Li, J. Org. Chem. 38, 591 (1973).
275. M. Engelhard, R. B. Merrifield, J. Am. Chem. Soc. 100, 5559 (1978).
276. O. Nishimura, M. Fujino, Chem. Pharm. Bull. 24, 1568 (1976).
277. M. Takeyama, K. Koyama, H. Yajima, in Peptide Chemistry 1978. N. lzumiya, Ed., Protein Research Foundation, Osaka, 1979, p. 1.
278. E. Schnabel, H. Zahn, Monatsh. Chem. 88, 646 (1957).
279. F. Sanger. Nature 171, 1025 (1953).
280. P. Ryle, F. Sanger, Biochem. J. 60, 535 (1955).
281. R. E. Benesch, R. Benesch, J. Am. Chem. Soc. 80, 1666 (1958).
282. W. Lunkenheimer, H. Zahn, Justus Liebigs Ann. Chem. 740, 1 (1970).
283. L. Zervas, J. Photaki, N. Ghelis, J. Am. Chem. Soc. 85, 1337 (1963).
284. M. Sokolovsky, M. Wilchek, A. Patchornik, J. Am. Chem. Soc. 86, 1202 (1964).
285. K. Hammerstrom, W. Lunkenheimer, H. Zahn, Macromol. Chem. 133, 41 (1970).
286. I. Phocas, P. C. Yovanidis, I. Photaki, L. Zervas, J. Chem. Soc. [C] 1967, 1506.
287. M. Guarneri et al., Gazz. Chim. Ital. 101, 375 (1971).
288. L. A. Shchukina, L. A. Davankova, N. N. Suvorov, A. D. Neklyudov, J. Gen. Chem. USSR 40, 1657 (1970).
289. M. Bergmann, G. Michaelis, Ber. Dtsch. Chem. Ges. 63, 987 (1930).
290. C. Berse, R. Boucher, L. Piche, .J. Org. Chem. 22, 805 (1957).
291. M. A. Ondetti, M. Bodanszky, Chem. Ind (London) 1962, 697.
292. R. Kuhn, H.J. Hass, Angew. Chem. 67, 785 (1955).
293. L. A. Carpino et al., J. Org. Chem. 35, 3291 (1970).
294. G. L. Southard, B. R. Zaborowski, J. M. Pettee, J. Am. Chem. Soc. 93, 3302 (1971).
295. J. Meienhofer, K. Kuromizu, Tetrahedron Lett. 1974, 3259.
296. K. Kuromizu, J. Meienhofer, J. Am. Chem. Soc. 95, 4978 (1974).
297. A. M. Felix, M. H. Jimenez, T. Mowles, J. Meienhofer. Int. J. Peptide Protein Res. 11, 329 (1978).
298. P. G. Katsoyannis, Am. J. Med. 40, 652 (1966).
299. J. M. Manning, A. Marglin, S. Moore, in Progress in Peptide Research, Vol. 2, S. Lande. Ed., Gordon and Breach, New York 1972, p. 173.
300. H. T. Clarke, J. M. Inouye, J. Biol. Chem. 94, 541 (1931).
301. V. du Vigneaud, M. F. Bartlett, A. Johl, J. Am. Chem. Soc. 79, 5572 (1957).
302. J. M. Swan, Nature 78, 643 (1957).
303. M. Bodanszky, A. Bodanszky, J. Antibiotics 27, 312 (1974).
304. R. G. Hiskey, R. A. Upham, G. M. Beverly, W. C. Jones Jr., J. Org. Chem. 35, 513 (1970).
305. J. A. MacLaren, W. E. Savige, M. J. Swan, Aust. J. Chem. 11, 345 (1958).
306. B. Hegedus, Helv. Chim. Acta 31, 737 (1968).
307. R. Roeske, F. H. C. Stewart, R. J. Stedman, V. du Vigneaud, J. Am. Chem. Soc. 78, 5883 (1956).
308. G. F. Holland, L. A. Cohen, J. Am. Chem. Soc. 80, 3765 (1958).
309. J. Honzl, J. Rudinger, Collect. Czech. Chem. Commun. 26, 2333 (1961).
310. K. C. Hooper, H. N. Rydon, J. A. Schofield, G. S. Heaton, J. Chem. Soc. 1956, 3148.
311. E. Schnabel, in Peptides, Proceedings of 5th European Peptide Symposium, G. T. Young, Ed., Pergamon Press, New York, 1963, p. 77.
312. K. Hofmann, W. Haas, M. J. Smithers, G. Zanetti, J. Am. Chem. Soc. 87, 631 (1965).
313. K. P. Polzhofer, K. H. Ney, Tetrahedron 27, 1997 (1971).
314. W. E. Savige, A. Fontana, in Methods in Enzymology, Vol. 47, C. W. Hirs, Ed., Academic Press, New York, 1978, p. 453.
315. R. A. Houghten, C. H. Li, in Peptides, Proceedings 5th American Peptide Symposium, M. Goodman, J. Meienhofer, Eds., John Wiley & Sons, New York, 1977, p. 458.
316. B. Iselin, Helv. Chim. Acta 44, 61 (1961).
317. K. Norris, J. Halstrom, K. Brunfeldt, Acta Chem. Scand. 25, 945 (1971).
318. P. Sieber et al., Helv. Chim. Acta 53, 2135 (1970).
319. B. F. Lundt, N. L. Johansen, A. Volund, J. Markussen, Int. J. Peptide Protein Res. 12, 258 (1978).
320. D. F. Veber et al., J. Am. Chem. Soc. 91, 506 (1969).
321. R. L. Noble, D. Yamashiro, C. H. Li, J. Am. Chem. Soc. 98. 2324 (1976).
322. G. Toennis, J. J. Kolb, J. Am. Chem. Soc. 67, 849 (1945).
323. C. A. Dekker, J. S. Fruton, J. Biol. Chem. 173, 471 (1948).
324. N. F. Albertson, F. C. McKay, J Am. Chem. Soc. 75, 5323 (1953).
325. F. C. McKay, N. F. Albertson, J. Am. Chem. Soc. 79, 4686 (1957).
326. O. Gawron, F. Draus, J. Org. Chem. 23, 1040 (1958).
327. G. F. Zhukova, G. A. Ravdel, L. A. Shchukina, J. Gen. Chem. USSR 40, 2750 (1970).
328. H. Irie et al., Chem. Pharm. Bull. 25, 2929 (1977); J. Chem. Soc. Chem. Commun. 1976, 922.
329. F. Naider, Z. Bohak, Biochemistry 11, 3208 (1972).
330. J. L. M. Syrier, H. C. Beyerman, in Peptides 1974, Proceedings of 13th European Peptide Symposium, Y. Wolman, Ed., John Wiley & Sons, New York-Israel Univ. Press, Jerusalem, 1975, p. 105.
331. E. Bayer, G. Jung, H. Hagenmaier, Tetrahedron 24, 4853 (1968).
332. H. Yajima et al., Chem. Pharm. Bull. 24, 492 (1976).
333. S. Guttmann, R. A. Boissonnas, Helv. Chim. Acta 42, 1257 (1959).
334. F. Chillemi, Gazz. Chim. Ital. 93, 1079 (1963).
335. R. B. Merrifield, J. Org. Chem. 29, 3100 (1964).
336. M. Bodanszky, N. Chandramouli, unpublished results.
337. J. A. Stekol, J. Biol. Chem. 140, 827 (1941).
338. K. Hoffmann, A. Johl, A. F. Furlenmeier, H. Kappeler. J. Am. Chem. Soc. 79, 1636 (1957).
339. M. Brenner, R. W. Pfister, Helv. Chim. Acta 34, 2085 (1951).
340. V. du Vigneaud, H. M. Dyer, J. Harmon, J. Biol. Chem. 101, 714 (1933).
341. K. Medzihradszky et al., Acta Chim. Acad. Sci. Hung. 30, 105 (1962).
342. C. H. Li et al., J. Am. Chem. Soc. 83, 4449 (1961).
343. H. Yajima et al., Chem. Pharm. Bull. 16, 1342 (1968).
344. H. Medzihradszky-Schweiger, K. Medzihradszky, Acta Chim. Acad. Sci. Hung. 50, 339 (1966).
345. H. Medzihradszky-Schweiger, Acta Chim. Acad. Sci. Hung. 76, 437 (1973).
346. W. Grassmann, E. Wunsch, Chem. Ber. 91, 462 (1958).
347. E. P. Grommers, J. F. Arens, Reel. Trav. Chim. Pays-Bas 78, 558 (1959).
348. M. Goodmann, K. C. Steuben, J. Org. Chem. 24, 112 (1959).
349. S. S. Brown, R. Wade, J. Chem. Soc. 1962, 3280.
350. M. Bodanszky. unpublished results.
351. G. C. Windridge, E. C. Jorgensen, J. Am. Chem. Soc. 93. 6318 (1971).
352. A. Fontana, C. Toniolo, Fortschr. Chem. Org. Naturst. 33, 309 (1976).
353. R. A. Boissonnas et al., Helv. Chim. Acta 41, 1867 (1958).
354. D. Theodoropoulos, J. S. Fruton, Biochemistry 1, 933 (1962). '.
355. H. Yajima, H. Kawatani, H. Watanabe, Chem. Pharm. Bull. 18, 1279 (1970).
356. E. Wunsch, Collect. Czech. Chem. Commun. 24, 60 (1959).
357. A. Fontana, F. Marchiori, L. Moroder, E. Scoffone, Gazz. Chim. Ital. 96, 1313 (1966).
358. C. H. Li, D. Yamashiro, J. Am. Chem. Soc. 92, 7608 (1970).
359. J. M. Stewart, G. R. Matsueda, in Chemistry and Biology of Peptides, Proceedings of 3rd American Peptide Symposium, J. Meienhofer, Ed., Ann Arbor Sci. PubL, Ann Arbor, Mich., 1972, p. 221.
360. K. Noda, E. Gross, in Chemistry and Biology of Peptides, Proceedings of 3rd American Peptide Symposium, J. Meienhofer, Ed., Ann Arbor Sci. Publ., Ann Arbor, Mich., 1972, p. 241.
361. J. J. Sharp, A. B. Robinson, M. D. Kamen, .J. Am. Chem. Soc. 95, 6097 (1973).
362. J. Blake, K. T. Wang, C. H. Li, Biochemistry 11, 438 (1972).
363. N. Chino, Y. Masui, S. Sakakibara, in Peptide Chemistry 1977, T. Shiba, Ed., Protein Res. Found., Osaka, 1978, p. 27.
364. W. Bauer, J. Pless, in Peptides, Chemistry, Structure and Biology, Proceedings of 4th American Peptide Symposium, R. Walter, J. Meienhofer, Eds., Ann Arbor Sci. Publ., Ann Arbor, Mich., 1975, p. 341.
365. M. Ohno, S. Tsukamoto, S. Makisumi, N. Izumiya, Bull. Chem. Soc. Jpn. 45, 2852 (1972).
366. K. Suzuki, N. Endo, N. Kazuo, Y. Sasaki, Chem. Pharm. Bull. 26. 2198 (1978).
367. A. Previero, M. A. Coletti-Previero, J. C. Cavadore, Biochim. Biophys. Acta 147, 453 (1967).
368. D. Yamashiro, C. H. Li, J. Org. Chem. 38, 2594 (1973).
369. M. Ohno, S. Tsukamoto, N. Izumiya, J. Chem. Soc. Chem. Commun. 1972, 663.
370. H. Zahn, D. Brandenburg, Justus Liebigs Ann. Chem. 692, 220 (1966).
371. K. L. Agarwal, G. W. Kenner, R. C. Sheppard, J. Chem. Soc. [C] 1969, 954.
372. B. Keil, J. Zikan, L. Rexova, F. Sorm, Collect. Czech. Chem. Commun. 27, 1678 (1962).
373. J. C. Anderson et al., Acta Chim. Hung. 44, 187 (1965).
374. A. Fontana, F. Marchiori, R. Rocehi, P. Pajetta, Gazz. Chim. Etill. 96, 1301 (1966).
375. E. Scoffone, A. Fontana, R. Rocehi, Biochemistry 7, 971 (1968).
376. E. Wiinsch, A. Fontana, F. Drees, Z. Naturforsch. [b] 22, 607 (1967).
377. J. wieland, O. Weiber, E. Fischer, G. Horlein, Justus Liebigs Ann. Chem. 587, 146 (1954), .
378. A. Fontana, F. Marchiori, L. Moroder. E. Scoffone, Tetrahedron Lett. 1966, 2985.
379. M. Juillerat, J. P. Bargetzi, Helv. Chim. Acta 59, 855 (1976).
380. A. Tun-Kyi, Helv. Chim. Acta 61, 1086 (1978).
381. W. Kessler, B. Iselin, Helv. Chim. Acta 49, 1330 (1966).
382. P. Sieber, in Peptides 1968. Proceedings of 9th European Peptide Symposium, E. Bricas, Ed., North Holland Publ. Co., Amsterdam, 1968, p. 236.
383. Yu. B. Alakhov, A. A. Kiryushkin, V. M. Lipkin, G. W. A. Milne, J. Chem. Soc. [C] 1970, 406.
384. E. Wiinsch, E. Jaeger, M. Deffner, R. Scharf, Z. Physiol. Chem. 353, 1716 (1972).
385. E. Wiinsch, E. Jaeger, L. Kisfaludy, M. Low, Angew. Chem. 89, 330 (1977); Angew. Chem. Int. Ed. Engl. 16, 317 (1977).
386. E. Jaeger et al., Z. Physiol. Chem. 359, 1617 (1978).
387. E. Jaeger, P. Thamm, S. Knof, E. Wiinsch, Z. Physiol. Chem. 359, 1629 (1978).
388. M. Low et al., Z. Physiol. Chem. 359, 1637 (1978).
389. M. Low, L. Kisfaludy, P. Sohar, Z Physiol. Chem. 359, 1643 (1978).
390. H. Ogawa, T. Sasaki, H. Irie, H. Yajima, Chem. Pharm. Bull. 26, 3144 (1978).
391. G. W. Kenner, G. A. Moore. R. Ramage, Tetrahedron Lett. 1976, 3623.
392. A. Previero, M. A. Coletti-Previero, L. G. Barry, Can. J. Chem. 46, 3404 (1968).
393. R. A. Uphaus, L. I. Grossweiner, J. J. Katz, K. D. Kopple, Science 129, 641 (1959).
394. Y. Omori et al., Chem. Lett. 1976, 805.
395. N. C. Davis, J. Biol. Chem. 223, 935 (1956).
396. A. Patchornik, in Peptides. Proceedings of 5th European Peptide Symposium, G. T. Young, Ed., Pergamon Press, New York, 1963, p. 54.
397. M. Wilchek, S. Sand, A. Patchornik, Biochim. Biophys. Acta 104, 616 (1965).
398. W. F. Benisek, R. D. Cole, Biochem. Biophys. Res. Commun. 20, 655 (1965).
399. J. Ramachandran, D Chung, C. H. Li, J. Am. Chem. Soc. 87. 2696 (1965).
400. C. Ressler, D. V. Kashelikar, J. Am. Chem. Soc. 88, 2025 (1966).
401. A. Marglin, R. B. Merrifield, J. Am. Chem. Soc. 88, 5051 (1966).
402. K. Jost, J. Rudinger, Collect. Czech. Chem. Commun. 32, 1229 (1978).
403. P. G. Katsoyannis et al., J. Am. Chem. Soc. 93, 5871 (1971).
404. A. Marglin, hit. J. Peptide Protein Res. 4. 47 (1972).
405. M. W. Bossert, P. A. Jaquenoud, in Peptides 1974. Proceedings of 13th European Peptide Symposium, Y. Wolman, F.d., John Wiley & Sons, New York-Israel Univ. Press, Jerusalem, 1975, p. 233.
406. S. Guttmann, in Peptides. Proceedings 5th European Peptide Symposium, G. T. Young, Ed., Pergamon Press, New York, 1963, p. 41.
407. S. Bajusz, K. Medzihradszky, in Peptides. Proceedings of 5th European Peptide Symposium, G. T. Young, Ed., Pergamon Press, New York, 1963, p. 49.
408. E. Abderhalden, H. Nienburg, I'ermentforschung 13, 573 (1933).
409. E. L. Smith, M. Bergmann, .J. Biol. Chem. 153, 627 (1944).
410. R. E. Neumann, E. L. Smith, .J. Biol. Chem. 193, 97 (1951).
411. T. Wieland, B. Heinke, Justus Liebigs Ann. Chem. 615, 184 (1958).
412. S. Sakakibara, Y. Nagai, Bull. Chem. Soc. Jpn. 33, 1537 (1960).
413. E. Wiinsch, in Peptides. Proceedings 5th European Peptide Symposium, G. T. Young, Ed., Pergamon Press, New York, 1963, p. 89.
414. M. A. Ondetti et al., Biochemistry 10, 4033 (1971).
415. J. Meienhofer, J. Am. Chem. Soc. 92, 3711 (1970).
416. G. Lucente, G. Fiorenti, D. Rossi, Gazz. Chim. Ital. 101, 109 (1971).
417. M. Goodman. K. C. Stuben, J. Org. Chem. 27, 3409 (1962).
418. F. Conti, G. Lucente, A. Romeo, G. Zanotti, Int. J. Peptide Protein Res. 5, 353 (1973).
419. B. F. Gisin, R. B. Merrifield, J. Am. Chem. Soc. 94, 3102 (1972).
420. M. C. Khosla. R. R. Smeby, F. M. Bumpus, J. Am. Chem. Soc. 94, 4721 (1972).
421. H. Hagenmaier, H. Frank, Z. Physiol. Chem. 353, 1979 (1972).
422. M. Rothe, J. Mazanek, Angew. Chem. 84, 290 (1972); Angew. Chem. Int. Ed. Engl. 11, 293 (1972); Justus Liebigs Ann. Chem. 439, 59 (1974).
423. O. Schou, D. Bucher, F. Nebelin, Z. Physiol. Chem. 357, 103 (1976).
424. M. Christensen, O. Schou, Internal. J. Peptide Protein Res. 12, 121 (1978).
425. R. B. Merrifield, Biochemistry 3, 1385 (1964).
426. T. R. Govindachari, S. Rajappa, A. S. Akerkar, V. S. Iyer, Tetrahedron 23, 4811 (1967).
427. J. Savrda, J. Org. Chem. 42, 3199 (1977).
428. J. P. Tam et al., Tetrahedron Lett. 1979. 4033.
429. I. Schon, L. Kisfaludy, Int. J. Peptide Protein Res. 14, 485 (1979).
430. P. Sorup, H. Braae, P. Villemoes, T. Christensen, Acta Chem. Scand. B 33, 653 (1979).
431. S. K. Girin. Yu. P. Shvachkin, Zhur. Obsch. Khim. 49, 451 (1979).
432. F. S. Tjoeng, J. P. Tam, R. B. Merrifield, Int. J. Peptide Protein Res. 14, 262 (1979).
433. S. Mojsov, A. R. Mitchell, R. B. Merrifield, .J. Org. Chem. 45, 555 (1980).
434. G. Barany, R. B. Merrifield, in The Peptides, E. Gross, J. Meienhofer, Eds., Vol. 2, Academic Press, New York, 1979, p. 1.