Solid-phase synthesis of difficult peptide sequences at elevated temperatures: A critical comparison of microwave and conventional heating technologies

Journal of Organic Chemistry

Volumn 73, Issue 19, 2008, Pages 7532-7542

  Bacsa, Bernadett ^a   Horváti, Kata ^b   Bõsze, Szilvia ^b   Andreae, Fritz ^c   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^c PiCHEM Forschungs und Entwicklungs GmbH   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; AMINATION; AMINO ACIDS; CHEMICAL REACTIONS; DIRECT ENERGY CONVERSION; ELECTRIC FIELDS; ELECTROMAGNETIC FIELD MEASUREMENT; ELECTROMAGNETIC FIELD THEORY; ELECTROMAGNETIC FIELDS; ELECTROMAGNETIC WAVES; ELECTROMAGNETISM; HEATING; IRRADIATION; MAGNETIC FIELDS; MICROWAVE IRRADIATION; MICROWAVES; ORGANIC ACIDS; RESINS; SYNTHESIS (CHEMICAL);

CHEMICAL EQUATIONS; CONVENTIONAL HEATING; COUPLING REAGENTS; DE-PROTECTION; ELEVATED TEMPERATURES; HEATED CONDITIONS; HYDROXYBENZOTRIAZOLE; MAIN EFFECTS; PEPTIDE SEQUENCING; PEPTIDE SYNTHESIS; REACTION TEMPERATURES; REACTION TIME; ROOM TEMPERATURES; SOLID-PHASE PEPTIDE SYNTHESIS; SOLID-PHASE SYNTHESIS;

AMINES;

BENZOTRIAZOLE DERIVATIVE; CYSTEINE; HISTIDINE; IMIDE; PEPTIDE; POLYSTYRENE;

AMINO ACID SEQUENCE; ARTICLE; COMPARATIVE STUDY; DEPROTECTION REACTION; ELECTROMAGNETIC FIELD; HEATING; MICROWAVE RADIATION; PEPTIDE SYNTHESIS; QUALITATIVE ANALYSIS; RACEMIZATION; ROOM TEMPERATURE; SOLID PHASE SYNTHESIS; TECHNOLOGY; TEMPERATURE MEASUREMENT;

CROSS-LINKING REAGENTS; ELECTROMAGNETIC FIELDS; HEATING; MICROWAVES; PEPTIDES; TEMPERATURE;

EID: 53049110370     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8013897     Document Type: Article

References (130)

1. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
2. (a) Chan, W.; White, P. D. Fmoc Solid Phase Peptide Synthesis: A Practical Approach; Oxford University Press: Oxford, U.K., 2000.
3. (b) Kates S. A.; Albericio, F. Solid-Phase Synthesis: A Practical Guide; CRC Press: Basel, Switzerland, 2000.
4. (c) Benoiton, N. L. Chemistry of Peptide Synthesis; CRC Press: Basel, Switzerland, 2006.
5. (a) Albericio, F.; Bofill, J. M.; El-Faham, A.; Kates, S. A. J. Org. Chem. 1998, 63, 9678-9683.
6. (b) Carpino, L.; El-Faham, A. Tetrahedron 1999, 55, 6813-6830.
7. (c) Albericio, F. Curr. Opin. Chem. Biol. 2004, 8, 211-221.
8. (d) Han, S. Y.; Kim, Y.-A. Tetrahedron 2004, 60, 2447-2467.
9. (e) Kamiński, Z. J.; Kolesińska, B.; Sabatino, G.; Chelli, M.; Rovero, P.; Blaszczyk, M.; Glǒwka, M. L.; Papini, A. M. J. Am. Chem. Soc. 2005, 127, 16912-16920.
10. (f) El-Faham, A.; Albericio, F. J. Org. Chem. 2008, 73, 2731-2737.
11. (a) Hyde, C.; Owen, J. D.; Quibell, M.; Sheppard, R. C. Int. J. Peptide Protein Res. 1994, 43, 431-440.
12. (b) Dettin, M.; Pegoraro, S.; Rovero, P.; Bicciato, S.; Bagno, A.; Di Bello, C. J. Peptide Res. 1997, 49, 103-111.
13. (c) Larsen, B. D.; Holm, A. J. Peptide Res. 1998, 52, 470-476.
14. (d) Henkel, B.; Bayer, E. J. Peptide Sci. 1998, 4, 461-470.
15. (e) McNamara, J. F.; Lombardo, H.; Pillai, S. K.; Jensen, I.; Albericio, F.; Kates, S. A. J. Peptide Sci. 2000, 6, 512-518.
16. (f) Carpino, L. A.; Krause, E.; Sferdean, C. D.; Schümann, M.; Fabian, H.; Bienert, M.; Beyermann, M. Tetrahedron Lett. 2004, 45, 7519-7523.
17. (a) MutterM.; Pillai, V. N. R.; Anzinger, Bayer, E.; Toniolo, C. In Proceedings of the 16th European Peptide Symposium; Brunfeldt, K., Ed.; Scripten Copenhagen, Denmark, 1981; pp 660-665.
18. (b) Hyde, C.; Johnson, T.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1992, 21, 1573-1575.
19. (a) Thaler, A.; Seebach, D.; Cardinaux, F. Helv. Chim. Acta 1991, 74, 628.
20. (b) Stewart, J. M.; Klis, W. A. In Innovation and Perspective in Solid Phase Synthesis: Peptides, Polypeptides and Oligonucleotides; Epton, R., Ed.; SPCC: Birmingham, U.K., 1991; pp 1-9.
21. (c) Hendrix, J. C.; Halverson, K. J.; Jarett, J. T.; Lansbury, P. T. J. Org. Chem. 1990, 55, 4517.
22. (a) Mutter, M.; Oppliger, H.; Zier, A. Macromol. Chem. Rapid Commun. 1992, 13, 151-157.
23. (a) Johnson, T.; Quibell, M.; Owen, D.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1993, 11, 369-372.
24. (b) Nicolas, E.; Pujades, M.; Bacardit, J.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 2317-2320.
25. (c) Zeng, W.; Regamey, P. O.; Rose, K.; Wang, Y.; Bayer, E. J. Peptide Res. 1997, 49, 273-279.
26. Pseudoproline derivatives: Whör, T.; Wahl, F.; Nefzi, A.; Sato, T.; Mutter, M. J. Am. Chem. Soc. 1996, 118, 9218-9227.
27. Sampson, W. R.; Patsiouras, H.; Ede, N. J. J. Peptide Sci. 1999, 5, 403-409.
28. Cremer, G. A.; Tariq, H.; Delmas, A. F. J. Peptide Sci. 2006, 12, 437-442.
29. Gacía-Martín, F.; White, P.; Steinauer, R.; Côté, S.; Tulla-Puche, J.; Albericio, F. Biopolymers 2006, 84, 566-575.
30. (b) Depsipeptide derivatives: Sohma, Y.; Sasaki, M.; Kimura, T.; Kiso, Y. Chem. Commun. 2004, 124125.
31. Coin, I.; Dölling, R.; Krause, E.; Bienert, M.; Beyermann, M.; Sferdean, C. D.; Carpino, L. A. J. Org. Chem. 2006, 71, 3171-6177.
32. Rivier, J. E.; Miranda, M. T. M. In Synthesis of Peptides and Peptidomimetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Georg Thieme: Stuttgart, Germany, 2002; Houben-Weyl, Vol. E22, pp 117-128.
33. (a) Tam, J. P. Int. J. Pept. Prot. Res. 1987, 29, 421-431.
34. (b) Barlos, K.; Papaionannou, D.; Patrianakou, S.; Tsegenidis, T. Liebigs Ann. Chem. 1986, 1950-1955.
35. (c) Lloyd, D. H.; Petrie, G. M.; Noble, R. L.; Tam, J. P. In Peptides: Chemistry, Structure and Biology. Proceedings of the 11th American Peptide Symposium; Rivier, J. E., Marshall, G. R., Eds.; Escom Science: Leiden, The Netherlands, 1990; pp 909-910.
36. (d) Wang, S.; Foutch, G. L. Chem. Eng. Sci. 1991, 46, 2373-2376.
37. (e) Tam, J. P.; Lu, Y.-A. J. Am. Chem. Soc. 1995, 117, 12058-12063.
38. (f) Kaplan, B. E.; Hefta, L. J.; Blake, R. C.; Swiderek, K. M.; Shively, J. E. J. Peptide Res. 1998, 52, 249-260.
39. (a) Rabinovich, A. K.; Rivier, J. E. Am. Biotech. Lab. 1994, 12, 48-51.
40. (b) Varanda, L. M.; Miranda, M. T. M. J. Peptide Res. 1997, 50, 102-108.
41. Souza, M. P.; Tavares, M. F. M.; Miranda, M. T. M. Tetrahedron 2004, 60, 4671-4681.
42. Reviews: (a) Collins, J. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 1141.
43. (b) Collins, J. M.; Collins, M. J. In Microwaves in Organic Synthesis, 2nd ed.; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2006; pp 898-958.
44. (a) Yu, H. M.; Chen, S-T.; Wang, K. T. J. Org. Chem. 1992, 57, 4781-4784.
45. (b) Santagada, V.; Fiorino, F.; Perissutti, E.; Severino, B.; De Filippis, V.; Vivenzio, B.; Caliendo, G. Tetrahedron Lett. 2001, 42, 5171-5173.
46. (c) Erdelyi, M.; Gogoll, A. Synthesis 2002, 11, 1592-1596.
47. (d) Finaru, A.; Berthault, A.; Basson, T.; Guillaumet, G.; Berteina-Raboin, S. Org. Lett. 2002, 4, 2613-2615.
48. (e) Zhang, H. B.; Chi, Y. S.; Huang, W. L.; Ni, S. J. Chin. Chem. Lett. 2007, 18, 902-904.
49. (f) Wisén, S.; Androsavich, J.; Evans, C. G.; Chang, L.; Gestwicki, J. E. Bioorg. Med. Chem. Lett. 2008, 18, 60-65.
50. (g) Bando, T.; Fujimoto, J.; Minoshima, M.; Shinohara, K.; Sasaki, S.; Kashiwazaki, G.; Mizumura, M.; Sugiyama, H. Bioorg. Med. Chem. 2007, 15, 6937-6942.
51. (h) Nagashima, I.; Shimizu, H.; Matsushita, T.; Nishimura, S.-I. Tetrahedron Lett. 2008, 49, 3413-3418.
52. (i) Katritzky, A. R.; Khashab, N. M.; Yoshioka, M.; Haase, D. N.; Wilson, K. R.; Johnson, J. V.; Chung, A.; Haskell-Luevano, C. Chem. Biol. Drug Des. 2007, 70, 465-468.
53. (j) Lecaillon, J.; Giles, P.; Subra, G.; Martinez, J.; Amblard, M. Tetrahedron Lett. 2008, 49, 4674-4676.
54. (k) Chi, Y.; Zhang, H.; Zhou, J.; Huang, W.; Ni, S. Lett. Org. Chem. 2008, 5, 399-402.
55. Bacsa, B.; Desai, B.; Dibó, G.; Kappe, C. O. J. Pept. Sci. 2006, 12, 633-638.
56. Bacsa, B.; Kappe, C. O. Nat. Protoc. 2007, 2, 2222-2227.
57. Fara, M. A.; Díaz-Mochón, H. J.; Bradley, M. Tetrahedron Lett. 2006, 47, 1011-1014.
58. Rizzolo, F.; Sabatino, G.; Chelli, M.; Rovero, P.; Papini, A. M. Int. J. Pept. Res. Ther. 2007, 13, 203-208.
59. Coantic, S.; Subra, G.; Martinez, J. Int. J. Pept. Res. Ther. 2008, 14, 143-147.
60. Abdel Rahman, S.; El-Kafrawy, A.; Hattaba, A.; Anwer, M. F. Amino Acids 2007, 33, 531-536.
61. For an example of microwave-assisted Boc-SPPS, see: Èemaar, M.; Craik, D. J. J. Peptide Sci. 2008, 14, 661-669.
62. Murray, J. K.; Gellman, S. H. Org. Lett. 2005, 7, 1517-1520.
63. (a) Murray, J. K.; Farooqi, B.; Sadowsky, J. D.; Scalf, M.; Freund, W. A.; Smith, L. M.; Chen, J.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 13271-13280.
64. (b) Murray, J. K.; Sadowsky, J. D.; Scalf, M.; Smith, L. M.; Tomita, Y.; Gellman, S. H. J. Comb. Chem. 2008, 10, 204-215.
65. (a) Murray, J. K.; Gellman, S. H. J. Comb. Chem. 2006, 8, 58-65.
66. (b) Murray, J. K.; Gellman, S. H. Nat. Protoc. 2007, 2, 624-631.
67. (a) Petersson, E. J.; Schepartz, A. J. Am. Chem. Soc. 2008, 130, 821-823.
68. (b) Miyake, R.; Tashiro, S.; Shiro, M.; Tanaka, K.; Shionoya, M. J. Am. Chem. Soc. 2008, 130, 5646-5647.
69. (a) Matsushita, T.; Hinou, H.; Kurogochi, M.; Shimizu, H.; Nishimura, S.-I. Org. Lett. 2005, 7, 877-880.
70. (b) Matsushita, T.; Hinou, H.; Fumoto, M.; Kurogochi, M.; Fujitani, N.; Shimizu, H.; Nishimura, S.-I. J. Org. Chem. 2006, 71, 3051-3063.
71. Brandt, M.; Gammeltoft, S.; Jensen, K. J. Int. J. Pept. Prot. Res. 2006, 12, 349-357.
72. (a) Olivos, H. J.; Alluri, P. G.; Reddy, M. M.; Salony, D.; Kodadek, T. Org. Lett. 2002, 4, 4057-4059.
73. (b) Gorske, B. C.; Jewell, S. A.; Guerard, E. J.; Blackwell, H. E. Org. Lett. 2005, 7, 1521-1524.
74. (c) Joshi, B. P.; Park, J.-W.; Kim, J.-M.; Lohani, C. R.; Cho, H.; Lee, K.-H. Tetrahedron Lett. 2008, 49, 98-101.
75. (d) Diaz-Mochon, J. J.; Fara, M. A.; Sanchez-Martin, R. M.; Bradley, M. Tetrahedron Lett. 2008, 49, 923-926.
76. (e) Fowler, S. A.; Stacy, D. M.; Blackwell, H. E. Org. Lett. 2008, 10, 2329-2332.
77. Monroe, S.; Feliu, L.; Planas, M.; Bardaji, E. Synlett 2006, 1311-1314.
78. Tullberg, M.; Luthman, K.; Grtli, M. J. Comb. Chem. 2006, 8, 915-922.
79. (a) Grieco, P.; Campiglia, P.; Gomez-Monterrey, I.; Lama, T.; Novellino, E. Synlett 2003, 2216-2218.
80. (b) Grieco, P.; Cai, M.; Liu, L.; Mayorov, A.; Chandler, K.; Trivedi, D.; Lin, G.; Campiglia, P.; Novellino, E.; Hruby, V. J. J. Med. Chem. 2008, 51, 2701-2707.
81. (c) Byk, G.; Cohen-Ohana, M.; Raichman, D. Biopolymers 2006, 81, 274-282.
82. (d) Chapman, R. N.; Arora, P. S. Org. Lett. 2006, 8, 5825-5828.
83. (e) Robinson, A. J.; Elaridi, J.; Van Lierop, B. J.; Mujcinovic, S.; Jackson, W. R. J. Pept. Sci. 2007, 13, 280-285.
84. (a) Campiglia, P.; Gomez-Monterrey, I.; Longobardo, L.; Lama, T.; Novellino, E.; Grieco, P. Tetrahedron Lett. 2004, 45, 1453-1456.
85. (b) Lama, T.; Campiglia, P.; Carotenuto, A.; Auriemma, L.; Gomez-Monterrey, I.; Novellino, E.; Grieco, P. J. Peptide Res. 2005, 66, 231-235.
86. (c) Park, M.-S.; Oh, H.-S.; Cho, H.; Lee, K.-H. Tetrahedron Lett. 2007, 48, 1053-1057.
87. (d) Nagaike, F.; Onuma, Y.; Kanazawa, C.; Hojo, H.; Ueki, A.; Nakahara, Y.; Nakahara, Y. Org. Lett. 2006, 8, 4465-4468.
88. (e) Grieco, P. Chim. Oggi 2004, 22, 18-20.
89. Merkx, R.; van Haren, M. J.; Rijkers, D. T. S.; Liskamp, R. M. J. J. Org. Chem. 2007, 72, 4574-4577.
90. Isidro-Llobet, A.; Alvarez, M.; Burger, K.; Spengler, J.; Albericio, F. Org. Lett. 2007, 9, 1429-1432.
91. García-Martín, F.; Bayó-Puxan, N.; Cruz, L. J.; Bohling, J. C.; Albericio, F. QSAR Comb. Sci. 2007, 26, 1027-1035.
92. (a) Paolini, I.; Nuti, F.; de la Cruz Pozo-Carrero, M.; Barbetti, F.; Kolesinska, B.; Kaminski, Z. J.; Chelli, M.; Papini, A. M. Tetrahedron Lett. 2007, 48, 2901-2904.
93. (b) Santagada, V.; Frecentese, F.; Fiorino, F.; Cirillo, D.; Perisutti, E.; Severino, B.; Terracciano, S.; Caliendo, G. QSAR Comb. Sci. 2004, 23, 899-901.
94. (c) Katritzky, A. R.; Todadze, E.; Angrish, P.; Draghici, B. J. Org. Chem. 2007, 72, 5794-5801.
95. (d) Cianci, J.; Baell, J. B.; Harvey, A. J. Tetrahedron Lett. 2007, 48, 5973-5975.
96. (e) Tantry, S. J.; Ramana Rao, R. V.; Suresh Babu, V. V. ARKIVOC 2006, 21-30.
97. (f) Porcheddu, A.; Ruda, G. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2003, 907-912.
98. (a) Sureshbabu, V. V.; Patil, B. S.; Venkataramanarao, R. J. Org. Chem. 2006, 71, 7697-7705.
99. (b) van Dijk, M.; Mustafa, K.; Dechesne, A. C.; van Nostrum, C. F.; Hennink, W. E.; Rijkers, D. T. S.; Liskamp, R. M. J. Biomacromolecules 2007, 8, 327-330.
100. (c) Rijkers, D. T. S.; van Esse, G. W.; Markx, R.; Brouwer, A. J.; Jacobs, H. J. F.; Pietrs, R. J.; Liskamp, R. M. J. Chem. Commun. 2005, 4581-4583.
101. (d) Campiglia, P.; Aquino, C.; Bertamino, A.; Sala, M.; Gomez-Monterrey, I. M.; Novellino, E.; Grieco, P. Tetrahedron Lett. 2008, 49, 731-734.
102. (a) Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213.
103. (b) Mingos, D. M. P.; Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
104. (a) De La Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164.
105. (b) Perreux, L.; Loupy, A. In Microwaves in Organic Synthesis, 2nd ed.; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2006; Chapter 4, pp 134-218.
106. Herrero, M. A.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 36.
107. Hachmann, J.; Lebl, M. Biopolymers 2006, 84, 340-347.
108. Rapp, W. In Combinatorial Peptide and Nonpeptide Libraries: A Handbook; Jung, G., Ed.; VCH: Weinheim, Germany, 1996; pp 425-464.
109. Camperi, S. A.; Marani, M. M.; Iannucci, N. B.; Côte, S.; Albericio, F.; Cascone, O. Tetrahedon Lett. 2005, 46, 1561-1564.
110. (a) Garcia-Martin, F.; Quintanar-Audelo, M.; Garcia-Ramos, Y.; Cruz, L. J.; Gravel, C.; Furie, R.; Côte, S.; Tulla-Puche, J.; Albericio, F. J. Comb. Chem. 2006, 8, 213-220.
111. (b) Garcia-Martin, F.; White, P.; Steinauer, R.; Côte, S.; Tulla-Puche, J.; Albericio, F. Biopolymers 2006, 84, 566-575.
112. (c) de la Torre, B. G.; Jakab, A.; Andreu, D. Int. J. Pept. Res. Ther. 2007, 13, 265-270.
113. Bernatowicz, M. S.; Daniels, S. B.; Köster, H. Tetrahedron Lett. 1989, 30, 4645-4648.
114. Caccamo, N.; Milano, S.; Di Sano, C.; Cigna, D.; Ivanyi, J.; Krensky, A. M.; Dieli, F.; Salerno, A. J. Infect. Dis. 2002, 186, 991-998.
115. Lebl, M.; Krchnak, V.; Lebl, G. Peptide Companion; San Diego, CA, 1995; http://www.5z.com/psp/software.shtml.
116. (a) Hosseini, M.; Stiasni, N.; Barbieri, V.; Kappe, C. O. J. Org. Chem. 2007, 72, 1417-1424.
117. (b) Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 4651-4658.
118. (c) Nüchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem. 2004, 6, 128-141.
119. (d) Nüchter, M.; Ondruschka, B.; Weiß, D.; Bonrath, W.; Gum, A. Chem. Eng. Technol. 2005, 28, 871-881.
120. (e) Leadbeater, N. E.; Pillsbury, S. J.; Shanahan, E.; Williams, V. A. Tetrahedron 2005, 61, 3565-3585.
121. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
122. The ability of a specific solvent to convert microwave energy into heat at a given frequency and temperature is determined by the so-called loss tangent (tan δ), expressed as the quotient tan δ = ε"/ ε′. A reaction medium with a high tan δ at the standard operating frequency of a microwave synthesis reactor (2.45 GHz) is required for good absorption and, consequently, for efficient heating. Solvents used for microwave synthesis can be classified as high (tan δ > 0.5), medium (tan δ 0.1-0.5), and low microwave absorbing (tan δ < 0.1). See ref 50 for further details.
123. de la Torre, B. G.; Jakab, A.; Andreu, D. Int. J. Pept. Res. Ther. 2007, 13, 265-270.
124. (a) Hogue Angeletti, R.; Bibbs, L.; Bonewald, L. F.; Fields, G. B.; Kelly, J. W.; McMurray, J. S.; Moore, W. T.; Weintraub, S. T. Techniques in Protein Chemistry VIII; Academic Press: San Diego, 1997.
125. (b) Han, Y.; Albericio, F.; Barany, G. J. Org. Chem. 1997, 7, 4307-4312.
126. (c) Van Den Nest, W.; Yuval, S.; Albericio, F. J. Pept. Sci. 2001, 7, 115-120.
127. Palasek, S. A.; Cox, Z. J.; Collins, J. M. J. Pept. Sci. 2007, 13, 143-148.
128. Frank, H.; Nicholson, G. J.; Bayer, E. J. Chromatogr. 1978, 167, 187-196.
129. Zasloff, M. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 5449-5453.
130. Wenschuh, H.; Beyermann, M.; Krause, E.; Brudel, M.; Winter, R.; Schuemann, M.; Carpino, L.; Bienert, M. J. Org. Chem. 1994, 59, 3275-3280.