Handles for solid-phase peptide synthesis

Methods in Enzymology

Volumn 289, Issue , 1997, Pages 126-174

  Songster, Michael F ^a   Barany, George ^b  

^a Solid Phase Sciences Inc   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE;

AMINO ACID ANALYSIS; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0030726646     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(97)89047-7     Document Type: Article

References (221)

1. R. B. Merrifield, J. Am. Chem. Soc. 85, 2149 (1963).
2. G. Barany and R. B. Merrifield, in "The Peptides" (E. Gross and J. Meienhofer, eds.), Vol. 2, p. 1. Academic Press, New York, 1979.
3. R. B. Merrifield, Science 232, 341 (1986).
4. G. Barany, N. Kneib-Cordonier, and D. G. Mullen, Int. J. Pept. Protein Res. 30, 705 (1987).
5. E. Atherton and R. C. Sheppard, "Solid Phase Peptide Synthesis: A Practical Approach." IRL, Oxford, 1989.
6. G. B. Fields, Z. Tian, and G. Barany, in "Synthetic Peptides: A User's Guide" (G. A. Grant, ed.), p. 259. Freeman, New York, 1992.
7. G. Barany and R. B. Merrifield, J. Am. Chem. Soc. 99, 7363 (1977).
8. L. A. Carpino and G. Y. Han, J. Org. Chem. 37, 3404 (1972).
9. G. B. Fields and R. L. Noble, Int. J. Pept. Protein Res. 35, 161 (1990).
10. E. Atherton, H. Fox, D. Harkiss, C. J. Logan, R. C. Sheppard, and B. J. Williams, J. Chem. Soc., Chem. Commun., 537 (1978).
11. C.-D. Chang, A. M. Felix, M. H. Jimenez, and J. Meienhofer, Int. J. Pept. Protein Res. 15, 485 (1980).
12. S.-S. Wang, J. Am. Chem. Soc. 95, 1328 (1973).
13. S.-S. Wang, J. P. Tam, B. S. H. Wang, and R. B. Merrifield, Int. J. Pept. Protein Res. 18, 459 (1981).
14. E. Atherton, C. J. Logan, and R. C. Sheppard, J. Chem. Soc., Perkin Trans. 1, 538 (1981).
15. R. C. Sheppard and B. J. Williams, Int. J. Pept. Protein Res. 20, 451 (1982).
16. F. Albericio and G. Barany, Int. J. Pept. Protein Res. 23, 342 (1984).
17. F. Albericio and G. Barany, Int. J. Pept. Protein Res. 26, 92 (1985).
18. M. S. Bernatowicz, T. Kearney, R. S. Neves, and H. Köster, Tetrahedron Lett. 30, 4341 (1989).
19. E. Atherton, D. L. J. Clive, and R. C. Sheppard, J. Am. Chem. Soc. 97, 6584 (1975).
20. G. R. Matsueda and E. Haber, Anal. Biochem. 104, 215 (1980).
21. F. Albericio, N. Kneib-Cordonier, S. Biancalana, L. Gera, R. I. Masada, D. Hudson, and G. Barany, J. Org. Chem. 55, 3730 (1990), and references cited therein.
22. F. Albericio and G. Barany, Int. J. Pept. Protein Res. 41, 307 (1993).
23. F. Albericio, P. Lloyd-Williams, and E. Giralt, Methods Enzymol. 289, [15], 1997 (this volume).
24. E. T. Kaiser, Acc. Chem. Res. 22, 47 (1989).
25. B. Riniker, A. Flörsheimer, H. Fretz, P. Sieber, and B. Kamber, Tetrahedron 49, 9307 (1993).
26. P. Lloyd-Williams, F. Albericio, and E. Giralt, Tetrahedron 49, 11065 (1993).
27. H. Benz, Synthesis, 337 (1994).
28. A. R. Mitchell, B. W. Erickson, M. N. Ryabtsev, R. S. Hodges, and R. B. Merrifield, J. Am. Chem. Soc. 98, 7357 (1976).
29. A. R. Mitchell, S. B. H. Kent, M. Engelhard, and R. B. Merrifield, J. Org. Chem. 43, 2845 (1978).
30. J. P. Tam, S. B. H. Kent, T. W. Wong, and R. B. Merrifield, Synthesis, 955 (1979).
31. A. Flörsheimer and B. Riniker, in "Peptides 1990" (E. Giralt and D. Andreu, eds.), p. 131. Escom, Leiden, The Netherlands, 1991.
32. M. Mergler, R. Tanner, J. Gosteli, and P. Grogg, Tetrahedron Lett. 29, 4005 (1988).
33. M. Mergler, R. Nyfeler, R. Tanner, J. Gosteli, and P. Grogg, Tetrahedron Lett. 29, 4009 (1988).
34. F. Albericio and G. Barany, Tetrahedron Lett. 32, 1015 (1991).
35. G. Barany and F. Albericio, in "Peptides 1990" (E. Giralt and D. Andreu, eds.), p. 139. Escom, Leiden, The Netherlands, 1991.
36. H. Rink, Tetrahedron Lett. 28, 3787 (1987).
37. K. Barlos, D. Gatos, J. Kallitsis, G. Papaphotiu, P. Sotiriu, Y. Wenqing, and W. Schäfer, Tetrahedron Lett. 30, 3943 (1989).
38. K. Barlos, O. Chatzi, D. Gatos, and G. Stavropoulos, Int. J. Pept. Protein Res. 37, 513 (1991).
39. M. F. Songster, "Design, Synthesis, and Implementation of Handles for Solid-Phase Peptide Synthesis," Ph.D. Thesis, University of Minnesota, Minneapolis (1996).
40. "The Peptides: Analysis, Synthesis, Biology" (E. Gross and J. Meienhofer, eds.), Vols. 1-9. Academic Press, New York, 1980.
41. N. Ling, F. Zeytin, P. Böhlen, F. Esch, P. Brazeau, W. B. Wehrenberg, A. Baird, and R. Guillemin, Annu. Rev. Biochem. 54, 403 (1985).
42. J. S. Morley, H. J. Tracey, and R. A. Gregory, Nature (London) 207, 1356 (1965).
43. P. G. Pietta, P. F. Cavallo, K. Takahashi, and G. Marshall, J. Org. Chem. 39, 44 (1974).
44. G. R. Matsueda and J. M. Stewart, Peptides 2, 45 (1981).
45. M. Bodanszky and J. T. Sheehan, Chem. Ind. (London), 1423 (1964).
46. M. Bodanszky and J. T. Sheehan, Chem. Ind. (London), 1597 (1966).
47. C. Ressler and V. du Vigneaud, J. Am. Chem. Soc. 76, 3107 (1954).
48. M. Zaoral and J. Rudinger, Collect. Czech. Chem. Commun. 20, 1183 (1955).
49. J. M. Stewart and J. D. Young, "Solid Phase Peptide Synthesis" 2nd Ed. Pierce, Rockford, Illinois, 1984.
50. M. Manning, J. Am. Chem. Soc. 90, 1348 (1968).
51. M. Bodanszky and J. Martinez, Synthesis, 333 (1981).
52. M. Christensen, O. Schou, and V. S. Pedersen, Acta Chem. Scand., Ser. B 35, 573 (1981).
53. P. Sieber, Tetrahedron Lett. 28, 2107 (1987).
54. H. C. Beyerman, H. Hindriks, and E. W. B. de Leer, Chem. Commun., 1668 (1968).
55. P. G. Pietta and G. R. Marshall, Chem. Commun., 650 (1970).
56. G. W. Tregear, H. D. Niall, J. T. Potts, S. E. Leeman, and M. M. Chang, Nature New Biol. 232, 87 (1971).
57. J. Rivier, W. Vale, R. Burgus, N. Ling, M. Amoss, R. Blackwell, and R. Guillemin, J. Med. Chem. 16, 545 (1973).
58. C. Peña, J. M. Stewart, A. C. Paladini, J. M. Dellacha, and J. A. Santomé, in "Peptides: Chemistry, Structure and Biology" (R. Walter and J. Meienhofer, eds.), p. 523. Ann Arbor Science, Ann Arbor, Michigan, 1976.
59. D. H. Coy and J. Gardner, Int. J. Pept. Protein Res. 15, 73 (1980).
60. C. G. Unson, D. Andreu, E. M. Gurzenda, and R. B. Merrifield, Proc. Natl. Acad. Sci. U.S.A. 84, 4083 (1987).
61. T. Inui, K. Hagiwara, K. Nakajima, T. Kimura, T. Nakajima, and S. Sakakibara, Pept. Res. 5, 140 (1992).
62. P. E. Thompson, H. H. Keah, P. T. Gomme, P. G. Stanton, and M. T. W. Hearn, Int. J. Pept. Protein Res. 46, 174 (1995).
63. F. Albericio and G. Barany, Int. J. Pept. Protein Res. 30, 206 (1987).
64. R. J. Bontems, P. Hegyes, S. L. Bontems, F. Albericio, and G. Barany, in "Peptides: Chemistry and Biology" (J. A. Smith and J. E. Rivier, eds.), p. 601. Escom, Leiden, The Netherlands, 1992.
65. Y. Han, S. L. Bontems, P. Hegyes, M. C. Munson, C. A. Minor, S. A. Kates, F. Albericio, and G. Barany, J. Org. Chem. 61, 6326 (1996), and references cited therein.
66. R. P. Hammer, F. Albericio, L. Gera, and G. Barany, Int. J. Pept. Protein Res. 36, 31 (1990).
67. M. S. Bernatowicz, S. B. Daniels, and H. Köster, Tetrahedron Lett. 30, 4645 (1989).
68. C. Blackburn and S. A. Kates, Methods Enzymol. 289, [9], 1997 (this volume).
69. Y. A. Ovchinnikov and V. T. Ivanov, in "The Proteins" (H. Neurath and R. L. Hill, eds.), p. 307. Academic Press, New York, 1982.
70. A. E. Tonelli, in "Cyclic Polymers" (J. A. Semlyen, ed.), p. 261. Elsevier, London, 1986.
71. V. J. Hruby, F. Al-Obeidi, and W. Kazmierski, Biochem. J. 268, 249 (1990).
72. J. Rizo and L. M. Gierasch, Annu. Rev. Biochem. 61, 387 (1992).
73. S. A. Kates, N. A. Solé, F. Albericio, and G. Barany, in "Peptides: Design, Synthesis, and Biological Activity" (C. Basava and G. M. Anantharamaiah, eds.), p. 39. Birkhaeuser, Boston, 1994.
74. R. Ramage, S. L. Irving, and C. Mclnnes, Tetrahedron Lett. 34, 6599 (1993).
75. R. Ramage, A. R. Brown, C. McInnes, S. L. Irving, S. G. Love, T. D. Pallin, T. W. Muir, G. Raphy, K. Shaw, F. O. Wahl, and J. Wilken, in "Innovation and Perspectives in Solid Phase Synthesis: Peptides, Proteins and Nucleic Acids: Biological and Biomedical Applications, 1994" (R. Epton, ed.), p. 1. Mayflower Worldwide, Birmingham, UK, 1994.
76. J. Honzl and J. Rudinger, Collect. Czech. Chem. Commun. 26, 2333 (1961).
77. H. B. Milne and C. F. Most, J. Org. Chem. 33, 169 (1968).
78. S. B. H. Kent, Methods Enzymol. 289, [13], 1997 (this volume); T. W. Muir, P. E. Dawson, M. C. Fitzgerald, and S. B. H. Kent, Methods Enzymol. 289, [24], 1997 (this volume); J. P. Tam and J. C. Spetzler, Methods Enzymol. 289, [28], 1997 (this volume).
79. S. B. H. Kent, Methods Enzymol. 289, [13], 1997 (this volume); T. W. Muir, P. E. Dawson, M. C. Fitzgerald, and S. B. H. Kent, Methods Enzymol. 289, [24], 1997 (this volume); J. P. Tam and J. C. Spetzler, Methods Enzymol. 289, [28], 1997 (this volume).
80. S. B. H. Kent, Methods Enzymol. 289, [13], 1997 (this volume); T. W. Muir, P. E. Dawson, M. C. Fitzgerald, and S. B. H. Kent, Methods Enzymol. 289, [24], 1997 (this volume); J. P. Tam and J. C. Spetzler, Methods Enzymol. 289, [28], 1997 (this volume).
81. P. Lloyd-Williams, F. Albericio, and E. Giralt, "Chemical Approaches to the Synthesis of Peptides and Proteins." CRC, Boca Raton, Florida, 1997.
82. D. R. Englebretsen, B. G. Garnham, D. A. Bergman, and P. F. Alewood, Tetrahedron Lett. 36, 8871 (1995).
83. E. Shaw, Physiol. Rev. 50, 244 (1970).
84. E. Shaw, Adv. Enzymol. 63, 271 (1990).
85. R. C. Thompson and E. R. Blout, Biochemistry 12, 44 (1973).
86. G. Schoellmann and E. Shaw, Biochemistry 2, 252 (1963).
87. E. Shaw, M. Mares-Guia, and W. Cohen, Biochemistry 4, 2219 (1965).
88. J. O. Westerick and R. Wolfenden, J. Biol. Chem. 247, 8195 (1972).
89. R. C. Thompson, Biochemistry 12, 47 (1973).
90. E. Sarubbi, P. F. Seneci, M. R. Angelastro, N. P. Peet, M. Denaro, and K. Islam, FEBS Lett. 319, 253 (1993).
91. É. Dufour, A. C. Storer, and R. Ménard, Biochemistry 34, 9136 (1995).
92. S. A. Thompson, P. R. Andrews, and R. P. Hanzlik, J. Med. Chem. 29, 104 (1986).
93. R. P. Hanzlik, J. Zygmunt, and J. B. Moon, Biochim. Biophys. Acta 1035, 62 (1990).
94. M. W. Pennington and P. Baur, Lett. Pept. Sci. 1, 143 (1994).
95. B. J. McRae, K. Kurachi, R. L. Heimark, K. Fujikawa, E. W. Davie, and J. C. Powers, Biochemistry 20, 7196 (1981).
96. B. J. McRae, T.-Y. Lin, and J. C. Powers, J. Biol. Chem. 256, 12362 (1981).
97. G. D. J. Green and E. Shaw, Anal. Biochem. 93, 223 (1979).
98. A. J. Whitmore, R. M. Daniel, and H. H. Petach, Tetrahedron Lett. 36, 475 (1995).
99. M. J. Castillo, K. Nakajima, M. Zimmerman, and J. C. Powers, Anal. Biochem. 99, 53 (1979).
100. A. J. Barrett and H. Kirschke, Methods Enzymol. 80, 535 (1981).
101. L. A. Reiter, Int. J. Pept. Protein Res. 43, 87 (1994).
102. J. C. H. M. Wijkmans, A. Nagel, and W. Bloemhoff, Lett. Pept. Sci. 3, 107 (1996).
103. T. Morita, H. Kato, S. Iwanaga, K. Takada, T. Kimura, and S. Sakakibara, J. Biochem. (Tokyo) 82, 1495 (1977).
104. L. C. Alves, P. C. Almeida, L. Franzoni, L. Juliano, and M. A. Juliano, Pept. Res. 9, 92 (1996).
105. D. A. Farmer and J. H. Hageman, J. Biol. Chem. 250, 7366 (1975).
106. Y. Hirata, M. H. S. Cezari, C. R. Nakaie, P. Boschcov, A. S. Ito, M. A. Juliano, and L. Juliano, Lett. Pept. Sci. 1, 299 (1994).
107. H. Umezawa, "Enzyme Inhibitors of Microbial Origin." University Park Press, Tokyo, 1972.
108. T. Aoyagi and H. Umezawa, in "Proteases and Biological Control" (E. Reich, D. B. Rifkin, and E. Shaw, eds.), p. 429. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York, 1975.
109. H. Umezawa, Annu. Rev. Microbiol. 36, 75 (1982).
110. J.-A. Fehrentz, M. Paris, A. Heitz, J. Velek, C.-F. Liu, F. Winternitz, and J. Martinez, Tetrahedron Lett. 36, 7871 (1995).
111. K. T. Chapman, Bioorg. Med. Chem. Lett. 2, 613 (1992).
112. R. T. Shuman, R. B. Rothenberger, C. S. Campbell, G. F. Smith, D. S. Gifford-Moore, and P. D. Gesellchen, J. Med. Chem. 36, 314 (1993).
113. J.-T. Woo, S. Sigeizumi, K. Yamaguchi, K. Sugimoto, T. Kobori, T. Tsuji, and K. Kondo, Bioorg. Med. Chem. Lett. 5, 1501 (1995).
114. S. W. Kaldor, M. Hammond, B. A. Dressman, J. M. Labus, F. W. Chadwell, A. D. Kline, and B. A. Heinz, Bioorg. Med. Chem. Lett. 5, 2021 (1995).
115. L. Bernardi, G. Bosisio, F. Chillemi, G. de Caro, R. de Castiglione, V. Erspamer, A. Glaesser, and O. Goffredo, Experientia 20, 306 (1964).
116. H. Takashima, W. Fraefel, and V. du Vigneaud, J. Am. Chem. Soc. 91, 6182 (1969).
117. M. Fujino, S. Kobayashi, M. Obayashi, S. Shinagawa, T. Fukuda, C. Kitada, R. Nakayama, I. Yamazaki, W. F. White, and R. H. Rippel, Biochem. Biophys. Res. Commun. 49, 863 (1972).
118. M. Fujino, S. Shinagawa, I. Yamazaki, S. Kobayashi, M. Obayashi, T. Fukuda, R. Nakayama, W. F. White, and R. H. Rippel, Arch. Biochem. Biophys. 154, 488 (1973).
119. S. A. St-Pierre, in "Neural and Endocrine Peptides and Receptors" (T. W. Moody, ed.), p. 653. Plenum, New York, 1986.
120. K. B. Mathur, in "Advances in the Biosciences. Volume 38. Current Status of Centrally Acting Peptides" (B. N. Dhawan, ed.), p. 37. Pergamon, Oxford, 1982.
121. M. J. Karten and J. E. Rivier, Endocr. Rev. 7, 44 (1986).
122. D. C. Heimbrook, W. S. Saari, N. L. Balishin, T. W. Fisher, A. Friedman, D. M. Kiefer, N. S. Rotberg, J. W. Wallen, and A. Oliff, J. Med. Chem. 34, 2102 (1991).
123. J. S. Morley, Annu. Rev. Pharmacol. Toxicol. 20, 81 (1980).
124. S. Bajusz, A. Patthy, Á. Kenessey, L. Gráf, J. I. Székely, and A. Z. Rónai, Biochem. Biophys. Res. Commun. 84, 1045 (1978).
125. S. A. Boyd, A. K. L. Fung, W. R. Baker, R. A. Mantei, Y.-L. Armiger, H. H. Stein, J. Cohen, D. A. Egan, J. L. Barlow, V. Klinghofer, K. M. Verburg, D. L. Martin, G. A. Young, J. S. Polakowski, D. J. Hoffman, K. W. Garren, T. J. Perun, and H. D. Kleinert, J. Med. Chem. 35, 1735 (1992).
126. D. H. Coy and A. V. Schally, Ann. Clin. Res. 10, 139 (1978).
127. B. J. Dhotre, S. Chaturvedi, and K. B. Mathur, Indian J. Chem., Sect. B 23B, 828 (1984).
128. J. R. Best, P. Byrne, R. Cotton, A. S. Dutta, B. Fleming, A. Garner, J. J. Gormley, C. F. Hayward, P. F. McLachlan, and P. B. Scholes, Drug Design Delivery 5, 267 (1990).
129. L.-H. Wang, D. H. Coy, J. E. Taylor, N.-Y. Jiang, S. H. Kim, J.-P. Moreau, S. C. Huang, S. A. Mantey, H. Frucht, and R. T. Jensen, Biochemistry 29, 616 (1990).
130. R. T. Jensen and D. H. Coy, Trends Pharmacol. Sci. 12, 13 (1991).
131. Y. Kiso, M. Yamaguchi, T. Akita, H. Moritoki, M. Takei, and H. Nakamura, Naturwissenschaften 68, 210 (1981).
132. J. L. Krstenansky, M. H. Payne, T. J. Owen, M. T. Yates, and S. J. T. Mao, Thromb. Res. 54, 319 (1989).
133. H. Wenschuh, M. Beyermann, H. Haber, J. K. Seydel, E. Krause, M. Bienert, L. A. Carpino, A. El-Faham, and F. Albericio, J. Org. Chem. 60, 405 (1995).
134. D. C. Heimbrook, W. S. Saari, N. L. Balishin, A. Friedman, K. S. Moore, M. W. Riemen, D. M. Kiefer, N. S. Rotberg, J. W. Wallen, and A. Oliff, J. Biol. Chem. 264, 11258 (1989).
135. H. Kodama, H. Uchida, T. Yasunaga, M. Kondo, T. Costa, and Y. Shimohigashi, J. Mol. Recognit. 3, 197 (1990).
136. Y. Kiso, T. Miyazaki, T. Akita, H. Moritoki, M. Takei, and H. Nakamura, FEBS Lett. 136, 101 (1981).
137. F. C. Buonomo, J. S. Tou, and L. A. Kaempfe, Life Sci. 48, 1953 (1991).
138. Z. Grzonka, Z. Palacz, L. Baran, E. Przegalinski, and G. Kupryszewski, Pol. J. Chem. 55, 1025 (1981).
139. E. V. Grishin, T. M. Volkova, and A. S. Arseniev, Toxicon 27, 541 (1989).
140. K. Suzuki, H. Fujita, Y. Sasaki, M. Shiratori, S. Sakurada, and K. Kisara, Chem. Pharm. Bull. 36, 4834 (1988).
141. H. Fujita, Y. Sasaki, H. Kohno, Y. Ohkubo, A. Ambo, K. Suzuki, and M. Hino, Chem. Pharm. Bull. 38, 2197 (1990).
142. D. H. Coy, J. A. Vilchez-Martinez, E. J. Coy, N. Nishi, A. Arimura, and A. V. Schally, Biochemistry 14, 1848 (1975).
143. R. F. Geraghty, G. B. Irvine, C. H. Williams, and G. A. Cottrell, Peptides 15, 73 (1994)
144. R. A. Smith, L. J. Copp, S. L. Donnelly, R. W. Spencer, and A. Krantz, Biochemistry 27, 6568 (1988).
145. P. D. Edwards, Tetrahedron Lett. 33, 4279 (1992).
146. B. Walker, N. McCarthy, A. Healy, T. Ye, and M. A. McKervey, Biochem. J. 293, 321 (1993).
147. I. J. Galpin, A. H. Wilby, and R. J. Beynon, in "Peptides 1982" (K. Bláha and P. Maloň, eds.), p. 649. de Gruyter, Berlin, 1983.
148. T. L. Graybill, R. E. Dolle, C. T. Helaszek, R. E. Miller, and M. A. Ator, Int. J. Pept. Protein Res. 44, 173 (1994).
149. A. Basak, F. Jean, N. G. Seidah, and C. Lazure, Int. J. Pept. Protein Res. 44, 253 (1994).
150. K. Folkers, C. Y. Bowers, W. B. Lutz, K. Friebel, T. Kubiak, B. Schircks, and G. Rampold, Z. Naturforsch. 37B, 1075 (1982).
151. R. R. Cook, B. J. McRae, and J. C. Powers, Arch. Biochem. Biophys. 234, 82 (1984).
152. M. Thorsen, B. Yde, U. Pedersen, K. Clausen, and S.-O. Lawesson, Tetrahedron 39, 3429 (1983).
153. A. J. Douglas, B. Walker, D. T. Elmore, and R. F. Murphy, Biochem. Soc. Trans. 15, 927 (1987).
154. M. Kruszyński, G. Kupryszewski, K. Misterek, and S. Gumulka, Pol. J. Pharmacol. Pharm. 42, 483 (1990).
155. D. E. Zembower, C. L. Neudauer, M. J. Wick, and M. M. Ames, Int. J. Pept. Protein Res. 47, 405 (1996).
156. R. W. Roeske and T. P. Hrinyo-Pavlina, in "Peptides: Chemistry and Biology" (G. R. Marshall, ed.), p. 273. Escom, Leiden, The Netherlands, 1988.
157. S. Bajusz, A. Z. Rónai, J. I. Székely, A. Turán, A. Juhász, A. Patthy, E. Miglécz, and I. Berzétei, FEBS Lett. 117, 308 (1980).
158. P. Mastalerz, L. Kupczyk-Subotkowska, Z. S. Herman, and G. Łaskawiec, Naturwissenschaften 69, 46 (1982).
159. A. Páldi, M. Móra, S. Bajusz, and L. Graf, Int. J. Pept. Protein Res. 29, 746 (1987).
160. M. Fujino, S. Shinagawa, M. Obayashi, S. Kobayashi, T. Fukuda, I. Yamazaki, R. Nakayama, W. F. White, and R. H. Rippel, J. Med. Chem. 16, 1144 (1973).
161. E. Kasafírek, I. Šutiaková, M. Bartík, and A. Šturc, Collect. Czech. Chem. Commun. 53, 2877 (1988).
162. L. Zhang, W. Rapp, C. Goldammer, and E. Bayer, in "Innovation and Perspectives in Solid Phase Synthesis: Peptides, Proteins and Nucleic Acids: Biological and Biomedical Applications, 1994" (R. Epton, ed.), p. 717. Mayflower Worldwide, Birmingham, UK, 1994.
163. S. Mammi and M. Goodman, Int. J. Pept. Protein Res. 28, 29 (1986).
164. J. Jurczak and A. Gołȩbiowski, Chem. Rev. 89, 149 (1989).
165. A. Ito, R. Takahashi, C. Miura, and Y. Baba, Chem. Pharm. Bull. 23, 3106 (1975).
166. P. Zlatoidsky, Helv. Chim. Acta 77, 150 (1994).
167. I. J. Galpin, A. H. Wilby, G. A. Place, and R. J. Beynon, Int. J. Peptide Protein Res. 23, 477 (1984).
168. K. Soai, H. Oyamada, and M. Takase, Bull. Chem. Soc. Jpn. 57, 2327 (1984).
169. G. Kokotos, Synthesis 299 (1990).
170. P. T. Ho and K.-y. Ngu, J. Org. Chem. 58, 2313 (1993).
171. B. A. Malcolm, C. Lowe, S. Shechosky, R. T. McKay, C. C. Yang, V. J. Shah, R. J. Simon, J. C. Vederas, and D. V. Smith, Biochemistry 34, 8172 (1995).
172. J.-A. Fehrentz, A. Heitz, and B. Castro, Int. J. Peptide Protein Res. 26, 236 (1985).
173. S. Bajusz, E. Barabás, E. Széll, and D. Bagdy, in "Peptides: Chemistry, Structure, and Biology" (R. Walter and J. Meienhofer, eds.), p. 603. Ann Arbor Science, Ann Arbor, Michigan, 1976.
174. R. C. Thompson, Methods Enzymol. 46, 220 (1977).
175. Y. Hamada and T. Shioiri, Chem. Pharm. Bull. 30, 1921 (1982).
176. A. Damodaran and R. B. Harris, J. Protein Chem. 14, 431 (1995).
177. K. Noda, M. Oda, M. Sato, and N. Yoshida, Int. J. Pept. Protein Res. 36, 197 (1990).
178. D. T. S. Rijkers, H. C. Hemker, G. H. I. Nefkens, and G. I. Tesser, Red. Trav. Chim. Pays-Bas 110, 347 (1991).
179. H. Nedev, H. Naharisoa, and T. Haertlé, Tetrahedron Lett. 34, 4201 (1993).
180. V. F. Pozdnev, Int. J. Pept. Protein Res. 44, 36 (1994).
181. M. Schutkowski, C. Mrestani-Klaus, and K. Neubert, Int. J. Pept. Protein Res. 45, 257 (1995).
182. D. H. Coy, E. J. Coy, A. V. Schally, J. A. Vilchez-Martinez, L. Debeljuk, W. H. Carter, and A. Arimura, Biochemistry 13, 323 (1974).
183. T. J. Lobl and L. L. Maggiora, J. Org. Chem. 53, 1979 (1988).
184. M. Mergler and R. Nyfeler, in "Innovation and Perspectives in Solid Phase Synthesis: Peptides, Polypeptides, and Oligonucleotides, 1992" (R. Epton, ed.), p. 429. Intercept, Andover, UK, 1992.
185. E. Nicolás, J. Clemente, M. Perelló, F. Albericio, E. Pedroso, and E. Giralt, Tetrahedron Lett. 33, 2183 (1992).
186. N. Voyer, A. Lavoie, M. Pinette, and J. Bernier, Tetrahedron Lett 35, 355 (1994).
187. F. Baleux, J. Daunis, R. Jacquier, and B. Calas, Tetrahedron Lett. 25, 5893 (1984).
188. B. Calas, J. Mery, J. Parello, and A. Cave, Tetrahedron 41, 5331 (1985).
189. M. Mergler and R. Nyfeler, in "Innovation and Perspectives in Solid Phase Synthesis: Peptides, Proteins and Nucleic Acids: Biological and Biomedical Applications, 1994" (R. Epton, ed.), p. 599. Mayflower Worldwide, Birmingham, UK, 1994.
190. T. Mizoguchi, K. Shigezane, and N. Takamura, Chem. Pharm. Bull. 18, 1465 (1970).
191. R. Epton, G. Marr, P. W. Small, and G. A. Willmore, Int. J. Biol. Macromol. 4, 62 (1982).
192. M. Mergler and R. Nyfeler, in "Peptides: Chemistry and Biology" (J. A. Smith and J. E. Rivier, eds.), p. 551. Escom, Leiden, The Netherlands, 1992.
193. K. U. Prasad, T. L. Trapane, D. Busath, G. Szabo, and D. W. Urry, Int. J. Pept. Protein Res. 19, 162 (1982).
194. G. B. Fields, C. G. Fields, J. Petefish, H. E. Van Wart, and T. A. Cross, Proc. Natl. Acad. Sci. U.S.A. 85, 1384 (1988).
195. W. B. Edwards, C. G. Fields, C. J. Anderson, T. S. Pajeau, M. J. Welch, and G. B. Fields, J. Med. Chem. 37, 3749 (1994).
196. W. F. DeGrado and E. T. Kaiser, J. Org. Chem. 45, 1295 (1980).
197. S. H. Nakagawa and E. T. Kaiser, J. Org. Chem. 48, 678 (1983).
198. P. T. Lansbury, Jr., J. C. Hendrix, and A. I. Coffman, Tetrahedron Lett. 30, 4915 (1989).
199. J. C. Hendrix, J. T. Jarrett, S. T. Anisfeld, and P. T. Lansbury, Jr., J. Org. Chem. 57, 3414 (1992).
200. L. M. Siemens, F. W. Rottnek, and L. S. Trzupek, J. Org. Chem. 55, 3507 (1990).
201. W. F. DeGrado and E. T. Kaiser, J. Org. Chem. 47, 3258 (1982).
202. A. W. Schwabacher and T. L. Maynard, Tetrahedron Lett. 34, 1269 (1993).
203. G. Ösapay and J. W. Taylor, J. Am. Chem. Soc. 112, 6046 (1990).
204. M. Mergler and R. Nyfeler, in "Peptides 1992" (C. H. Schneider and A. N. Eberle, eds.), p. 177. Escom, Leiden, The Netherlands, 1993.
205. J. Blake, Int. J. Pept. Protein Res. 17, 273 (1981).
206. D. Yamashiro and J. Blake, Int. J. Pept. Protein Res. 18, 383 (1981).
207. J. Blake and C. H. Li, Proc. Natl. Acad. Sci. U.S.A. 78, 4055 (1981).
208. D. Yamashiro and C. H. Li, Int. J. Pept. Protein Res. 31, 322 (1988).
209. L. E. Canne, S. M. Walker, and S. B. H. Kent, Tetrahedron Lett. 36, 1217 (1995).
210. W. Neugebauer and E. Escher, Helv. Chim. Acta 72, 1319 (1989).
211. J. Swistok, J. W. Tilley, W. Danho, R. Wagner, and K. Mulkerins, Tetrahedron Lett. 30, 5045 (1989).
212. W. Neugebauer, R. Brzezinski, and G. E. Willick, in "Peptides 1990" (E. Giralt and D. Andreu, eds.), p. 188. Escom, Leiden, The Netherlands, 1991.
213. F. Albericio, R. Van Abel, and G. Barany, Int. J. Pept. Protein Res. 35, 284 (1990).
214. S. A. Kates, N. A. Solé, C. R. Johnson, D. Hudson, G. Barany, and F. Albericio, Tetrahedron Lett. 34, 1549 (1993), and references cited therein.
215. J. Alsina, F. Rabanal, E. Giralt, and F. Albericio, Tetrahedron Lett. 35, 9633 (1994).
216. K. J. Jensen, M. F. Songster, J. Vágner, J. Alsina, F. Albericio, and G. Barany, in "Peptides: Chemistry, Structure and Biology" (T. P. Kaumaya and R. S. Hodges, eds.), p. 30. Mayflower Scientific, Kingswinford, UK, 1996.
217. K. J. Jensen, M. F. Songster, J. Vágner, J. Alsina, F. Albericio, and G. Barany, in "Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Chemical Libraries: Biomedical and Biological Applications, 1996" (R. Epton, ed.), p. 187. Mayflower Scientific, Kingswinford, UK, 1996.
218. M. F. Songster, J. Vágner, and G. Barany, Lett. Pept. Sci. 2, 265 (1996).
219. M. F. Songster, J. Vágner, and G. Barany, in "Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Chemical Libraries: Biomedical and Biological Applications, 1996" (R. Epton, ed.), p. 537. Mayflower Scientific, Kingswinford, UK, 1996.
220. S. K. Sharma, M. F. Songster, T. L. Colpitts, P. Hegyes, G. Barany, and F. J. Castellino, J. Org. Chem. 58, 4993 (1993).
221. M. F. Songster and G. Barany, in "Innovation and Perspectives in Solid Phase Synthesis: Peptides, Proteins and Nucleic Acids: Biological and Biomedical Applications, 1994" (R. Epton, ed.), p. 685. Mayflower Worldwide, Birmingham, UK, 1994.