Some peculiarities of synthesis of cysteine-containing peptides

Russian Chemical Reviews

Volumn 67, Issue 7, 1998, Pages 545-562

  Kudryavtseva, E V ^a   Sidorova, M V ^a   Evstigneeva, R P ^b  

^a INSTITUTE OF EXPERIMENTAL CARDIOLOGY   (Russian Federation)

^b MIREA RUSSIAN TECHNOLOGICAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008718507     PISSN: 0036021X     EISSN: None     Source Type: Journal    
DOI: 10.1070/RC1998v067n07ABEH000424     Document Type: Article

References (119)

1. I Photaki, in The Chemistry of Polypeptides (Ed. P Katsoyannis) (New York: Plenum, 1973)
2. D Andrey, F Albericio, N A Sole, M C Munson, M Ferrer, G Barany, in Peptide Synthesis Protocols (Eds M W Pennington, B M Dunn) (New Jersey: Hymana Press, 1994) p. 91
3. O S Papsuevich, G I Chipens, S V Mikhailova, in Neirogipofizarnye Gormony (Neurohypophysis Hormones) (Riga: Zinatne, 1986) p. 6
4. K Alitalo, P Partanen, A Vaheri (Eds) Synthetic Peptides in Biology and Medicine (Amsterdam: Elsevier, 1985)
5. J F W McOmie (Ed.) Protective Groups in Organic Chemistry (New York: Plenum, 1973)
6. R G Hiskey, in The Peptides Vol. 3 (Eds E Gross, J Meienhofer) (New York: Academic Press, 1981) p. 137
7. M C Munson, PhD Thesis, University of Minnesota, USA, 1993
8. G Barany, R B Merrifield, in The Peptides Vol. 2 (Eds E Gross, J Meienhofer) (New York: Academic Press, 1981) p. 3
9. N Fujii, A Otaka, S Funakoshi, K Bessho, T Watanabe, K Akaji, H Yajima Chem. Pharm. Bull. 35 2339 (1987)
10. M Yoshida, M Shimokura, Y Fyjiwara, T Fujisaki, K Akaji, Y Kiso Chem. Pharm. Bull. 38 382 (1990)
11. O A Tamamura, W Takada, Y Terakawa, H Yoshizawa, M Masuda, T Ibuka, T Murakami, H Nakashima Chem. Pharm. Bull. 43 12 (1995)
12. O Nishimura, C Kitada, M Fujino Chem. Pharm. Bull. 26 1576 (1978)
13. N Fujii, A Otaka, S Funakoshi, M Nomizu, K Akaji, H Yajima, I Yamamoto, K Torizuka, K Kitagawa, T Akita, K Ando, T Kawamoto, Y Shimonishi, T Takao Chem. Pharm. Bull. 34 613 (1986)
14. M C Munson, C Garcia-Echeverria, F Albericio, G Barany J. Org. Chem. 57 3013 (1992)
15. M C Munson, G Barany J. Am. Chem. Soc. 115 10203 (1993)
16. S N McCurdy Pep. Res. 2 147 (1989)
17. E E Bullesbach Kontakte (Darmstadt) 21 (1992)
18. N Fujii, A Otaka, T Watanabe, A Okamachi, N Tamamura, H Yajima, Y Inagaki, M Nomizu, K Asano J. Chem. Soc., Chem Commun. 283 (1989)
19. H-D Jakubke, H Jeschkeit Aminosäuren, Peptide, Proteine (Berlin: Academie-Verlag, 1982)
20. C Garcia-Echeverria, M A Molins, F Albericio, M Pons, E Giralt Int. J. Pept. Protein Res. 35 434 (1990)
21. M Royo, C Garcia-Echeverria, E Giralt, R Eritja, F Albericio Tetrahedron Lett. 33 2391 (1992)
22. N Fujii, A Otaka, S Funakoshi, H Yajima, O Nishimura Chem. Pharm. Bull. 34 869 (1986)
23. N Fujii, A Otaka, S Funakoshi, M Nomizu, K Akaji, H Yajima, K Kitagawa, T Akita, K Ando, T Kawamoto Chem. Pharm. Bull. 34 603 (1986)
24. Y Han, J Vagner, C M Gross, G Barany, in Proceedings of the 14th American Peptide Symposium (Abstracts of Reports) (Leiden: Escom, 1995) P061
25. H Yoshizawa, A Otaka, H Habashita, N Fujii Chem. Lett. 803 (1993)
26. A S J Stewart, C N C Drey J. Chem. Soc., Perkin Trans. 1 1753 (1990)
27. Shanlin Fu, F A Carver, L A P Kane-Maguire J. Organomet. Chem. 454 C11 (1993)
28. M Yoshida, K Akaji, T Tatsumi, S Iinuma, Y Fujiwara, T Kimura, Y Kiso Chem. Pharm. Bull. 38 273 (1990)
29. M Yoshida, T Tatsumi, Y Fujiwara, S Iinuma, T Kimura, K Akaji, Y Kiso Chem. Pharm. Bull. 38 1551 (1990)
30. Y Kiso, M Yoshida, Y Fujiwara, T Kimura, M Shimokura, K Akaji Chem. Pharm. Bull. 38 673 (1990)
31. Y Kiso, M Yoshida, T Kimura, Y Fujiwara, M Shimokura Tetrahedron Lett. 30 1979 (1989)
32. L Vesenkov, L Milev, A Dimitrova, in Proceeding of the 22nd European Peptide Symposium (Eds C H Schneider, A N Eberle) (Leiden: Escom, 1992) p. 421
33. M Royo, J Alsina, E Giralt, U Slomczynska, F Albericio, in Proceedings of the 13th American Peptide Symposium (Eds R S Hodges, J A Smith) (Leiden: Escom, 1994) p. 116
34. a
35. B H Rietman, R F R Peters, G I Tesser Synth. Commun. 24 1323 (1994)
36. K Nokihara, H Berndt J. Org. Chem. 43 4893 (1978)
37. R Eritja, J P Ziehler-Martin, P A Walker, T D Lee, K Legesse, F Albericio, B E Kaplan Tetrahedron 43 2675 (1987)
38. M Ueki, M Honda, Y Kazama, T Katoh Synthesis 21 (1994)
39. O Rosen, S Rubinraut, M Fridkin Int. J. Pept. Protein Res. 35 545 (1990)
40. F Albericio, D Andreu, E Giralt, C Navalpotro, E Pedroso, B Ponsati, M Ruiz-Gayo Int. J. Pept. Protein Res. 34 124 (1989)
41. R Matsueda, S Higashida, F Albericio, D Andreu, in The 29th Conference on Peptide Chemistry (Abstract of Reports). Osaka, 1991 p. 111
42. I Mangras, J Gostelli, E Rapp, R Nyfeler Int. J. Pept. Protein Res. 45 152 (1995)
43. E A Hallinan Int. J. Pept. Protein Res. 38 601 (1991)
44. G B Fields, R L Noble Int. J. Pept. Protein Res. 35 161 (1990)
45. B Walker, in Peptide Antigens (Ed. G B Wisdom) (Oxford: IRL Press, 1994) p. 27
46. H Nishio, T Kimura, S Sakakibara Tetrahedron Lett. 35 1239 (1994)
47. H Lamthank, H Virelizier, D Frayssinhes Pept. Res. 8 316 (1995)
48. H Lamthanh, C Roumestand, C Deprun, A Menez Int. J. Pept. Protein Res. 41 85 (1993)
49. L Lepsa, I Blaha, V Cerna, M Flegel, in 24th Symposium of the European Peptide Society (Abstract of Reports) (Edinburgh: Perkin Division, 1996) p. 126
50. M Bodanszky, in The Peptides Vol. 1 (Eds E Gross, J Meienhofer) (New York: Academic Press, 1981) p. 106
51. L Moroder, G Hubener, S Gohring-Romani, W Gohring, H-J Musiol, E Wunsch Tetrahedron 46 3305 (1990)
52. P M Hardy, B Ridge, H N Rydon, F O dos S P Serrao J. Chem. Soc. 1722 (1971)
53. Hung Lam Thank, G Mourier, A Menez, P Fromageot, in Second Forum on Peptides (Colloquies Inserm) (Montroge: J Lifbey Eurotext Ltd, 1989) p. 229
54. R G Almquist, S R Kadambi, D M Yasuda, F L Weitl, W E Polgar, L R Toll Int. J. Pept. Protein Res. 34 455 (1989)
55. E V Kudryavtseva, M V Sidorova, M V Ovchinnikov, Zh D Bespalova, V N Bushuev Int. J. Pept. Prot. Res. 49 52 (1997)
56. D Le-Nguyen, D Nalis, B Castro Int. J. Pept. Res. 34 492 (1989)
57. Cui-Rong Wu, J D Wade, G W Tregear Int. J. Pept. Protein Res. 31 47 (1988)
58. S-I Kumagaye, H Kuroda, K Nakajima, T X Watanabe, T Kimura, T Masaki, S Sakakibara Int. J. Pept. Protein Res. 32 519 (1988)
59. H Tamamura, A Otaka, J Nakamura, K Okubo, T Koide, K Ikeda, T Ibuka, N Fujii Int. J. Pept. Protein Res. 45 312 (1995)
60. J M Stewart, J D Young Solid Phase Peptide Synthesis (New York: Pierce Chem. Co., 1984)
61. D Laloo, M K Mahanti Oxyd. Commun. 11 231 (1988)
62. A Buku, N Yamin, D Gazis Int. J. Pept. Protein Res. 33 28 (1989)
63. C Haskell-Lecevano, N D Shenderovich, Sh D Sharma, G V Nikiforovich, Mac E Hadley, V J Hruby J. Med. Chem. 38 1736 (1995)
64. A Misicka, V J Hruby Pol. J. Chem. 68 893 (1994)
65. J Rivier, R Kaiser, R Galyean Biopolymers 17 1927 (1978)
66. A Buku, P Blandina, C Birr, D Gazis Int. J. Pept. Protein Res. 33 86 (1989)
67. N Fujii, A Otaka, A Okamachi, T Watanabe, H Arai, H Tamamura, S Funakoshi, H Yajima, in Proceedings of the 20th European Peptide Symposium (Eds G Jung, E Bayer) (Berlin: Walter de Gruyter, 1989) p. 58
68. A Otaka, T Koide, A Shide, N. Fujii Tetrahedron Lett. 32 1223 (1991)
69. J P Tam, Cui-Rong Wu, Wen Liu, Jing-Wen Zhang J. Am. Chem. Soc. 113 6657 (1991)
70. T Koide, A Otaka, N Fujii Chem. Pharm. Bull. 41 1030 (1993)
71. Chuan-Fa Liu, J P Tam Proc. Natl. Acad. Sci. USA 91 6584 (1994)
72. W C Schumb, C N Satterfield, R L Wentworth Hydrogen Peroxide (New York: Reinhold Publ. Co., 1958)
73. S Patai (Ed.) The Chemistry of Peroxides (Chichester: Wiley, 1983) p. 429
74. J D Roberts, M C Caserio Basic Principles of Organic Chemistry (New York: Benjamin Inc., 1964)
75. J Arroub, J Berges, Z Abedinzadeh, J Langlet, M Gardes-Albert Can. J. Chem. 72 2094 (1994)
76. Z Abedinzadeh, J Arroub, M Gardes-Albert Can J. Chem. 72 2102 (1994)
77. b
78. E V Kudryavtseva, Candidate Thesis in Chemical Sciences, M V Lomonosov Moscow Academy of Fine Chemical Technology, Moscow, 1997
79. L Kisfaludy, I Schon Acta Chim. Acad. Sci. Hung. 84 227 (1975)
80. Eur. P. 363 192; Chem. Abstr. 113 115 889 (1990)
81. G T Shulz, R H Schirmer Principles of Protein Structure (New York: Springer, 1979)
82. G Kupryszewski, U Ragnarsson, K Rolka, T Wilusz Int. J. Pept. Protein Res. 27 245 (1986)
83. S-Y Shin, M Shimizu, E Munekata Chem. Lett. 1997 (1994)
84. M W Pennington, W R Kem, R S Norton, B M Dunn Int. J. Pept. Protein Res. 36 335 (1990)
85. D L Rabenstein, P L Yeo J. Org. Chem. 59 4223 (1994)
86. M W Pennington, S M Festin, M L Maccecchini, in Proceedings of the 21st European Peptide Symposium (Abstracts of Reports) (Eds E Giralt, D Andreu) (Leiden: Escom, 1991) p. 164
87. B R Clarc, M Pai, in Proceedings of the 14th American Peptide Symposium (Abstracts of Reports) (Leiden: Escom, 1995) P090
88. Lin Chen, G Barany, in Proceedings of the 14th American Peptide Symposium (Abstracts of Reports) (Leiden: Escom, 1995) P119
89. F Albericio, R P Hammer, C Garcia-Echeverria, M A Molins, J L Chang, M C Munson, M Pons, E Giralt, G Barany Int. J. Pept. Protein Res. 37 402 (1991)
90. K Satoh, H Okuda, H Horimoto, H Kodama, M Kondo Bull. Chem. Soc. Jpn. 63 3467 (1990)
91. b
92. S Chaturvedi, Om P Bahl Int. J. Pept. Protein Res. 35 133 (1990)
93. R Drozdz, A N Eberle J. Pept. Sci. 1 58 (1995)
94. P Fourqet, E Bahraoni, J C Fontecilla-Camps Int. J. Pept. Protein Res. 32 81 (1988)
95. b
96. b
97. A Darbre (Ed.) Practical Protein Chemistry. A Handbook (New York: Wiley, 1987)
98. P Sieber, B Kamber, B Riniker, W Rittel Helv. Chim. Acta 63 2358 (1980)
99. P Bishop, J Chmielewski Tetrahedron Lett. 33 6263 (1992)
100. H Shih J. Org. Chem. 58 3003 (1993)
101. N Fujii, A Otaka, S Funakoshi, K Bessho, H Yajima J. Chem. Soc., Chem. Commun. 163 (1987)
102. W B Edwards, C G Fields, C J Anderson, T S Pajeau, M J Welch, G B Fields J. Med. Chem. 37 3749 (1994)
103. K Akaji, T Tatsumi, M Yoshida, T Kimura, Y Fujiwara, Y Kiso J. Chem. Soc., Chem. Commun. 167 (1991)
104. K Akaji, T Tatsumi, M Yoshida, T Kimura, Y Fujiwara, Y Kiso J. Am. Chem. Soc. 114 4137 (1992)
105. T Koide, A Otaka, H Suzuki, N Fujii Synlett 345 (1991)
106. K Akaji Yakugaku Kenkyn no Shinpo 11 25 (1995)
107. K Akaji, K Fujino, T Tatsumi, Y Kiso J. Am. Chem. Soc. 115 11384 (1993)
108. J V Castell, A Tun-Kyi Helv. Chim. Acta 62 2507 (1979)
109. A Fontana J. Chem. Soc., Chem. Commun. 976 (1975)
110. M S Bernatowicz, R Matsueda, G R Matsueda Int. J. Pept. Protein Res. 28 107 (1936)
111. D Le-Nguyen, J Rivier Int. J. Pept. Protein Res. 27 285 (1986)
112. S Romani, L Moroder, W Gohring, R Scharf, E Wunsch, Y A Barde, H Thoenen Int. J. Pept. Protein Res. 29 107 (1987)
113. E Wunsch, L Moroder, S Gohring-Romani, H-J Musiol, W Gohring, G Bovermann Int. J. Pept. Protein Res. 32 368 (1988)
114. H Yajima, N Fujii, S Funakoshi, T Watanabe, E Murayama, A Otaka Tetrahedron 44 805 (1988)
115. B Ponsati, M Ruiz-Gayo, E Giralt, F Albericio, D Andreu J. Am. Chem. Soc. 112 5345 (1990)
116. C Garcia-Echeverria, F Albericio, M Pons, G Barany, E Giralt Tetrahedron Lett. 30 2441 (1989)
117. Jpn. P. 06 256 385; Chem. Abstr. 122 56 591 (1995)
118. K Barlos, D Gatos, S Kutsogianni, G Papaphotiou, C Poulos, T Tsegenidis Int. J. Pept. Protein Res. 38 562 (1991)
119. M C Munson, M Lebl, J Slavinova, G Barany Pept. Res. 6 155 (1993)