Pseudopeptide synthesis via Fmoc solid-phase synthetic methodology

Mini-Reviews in Organic Chemistry

Volumn 4, Issue 4, 2007, Pages 268-280

  Cudic, Predrag ^a   Stawikowski, Maciej ^a  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

Author keywords

Fmoc solid phase synthesis; Isosteres; Peptidomimetics; Pseudopeptides

Indexed keywords

PEPTIDES;

FMOC SOLID-PHASE SYNTHESIS; ISOSTERE; PEPTIDE BONDS; PEPTIDOMIMETICS; PSEUDO-PEPTIDE; SOLID PHASE SYNTHESIS; SOLID PHASIS; SOLID-PHASE; STABLE PEPTIDES; SYNTHETIC METHODOLOGY;

SYNTHESIS (CHEMICAL);

EID: 36749021825     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019307782411716     Document Type: Article

References (110)

1. Marx, V. C&EN, 2005, 83, 17.
2. Adessi, C.; Soto, C. Curr. Med. Chem., 2002, 9, 963.
3. Sawyer, T.K. In Peptide and Protein Drug Analysis; Reid, R.E. Ed.; Marcel Dekker, Inc.: New York, 2000; Vol. 101, pp. 81-115.
4. Davies, J.S. J. Pept. Sci., 2003, 9, 471.
5. Lambert, J.N.; Mitchell, J.P.; Roberts, K.D. J. Chem. Soc. Perkin Trans., 2001, 1, 471.
6. Li, P.; Roller, P.P. Curr. Top. Med. Chem., 2002, 2, 325.
7. Blackburn, C.; Kates, S.A. Methods Enzymol., 1997, 289, 175.
8. Hruby, V.J.; Bonner, G. G. Methods Mol. Biol., 1994, 35, 201.
9. Kates, S.A.; Sole, N.A.; Albericio, F.; Barany, G. In Peptides: Design, Synthesis, and Biological Activity, Brikhauser: Boston: 1994; pp. 39-59.
10. Ahn, J.M.; Boyle, NA.; MacDonald, M.T.; Janda, K.D. Mini Rev. Med. Chem., 2002, 2, 463.
11. Synthesis of Peptidomimetics, Synthesis of Peptides and Peptidomimetics. Houben-Weyl, Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Ed.; Thieme: Stuttgard, New York, 2004; Vol. E 22c.
12. Spatula, A.F. In Peptides and Proteins, Weinstein, B., Ed.; Marcel Dekker Inc.: New York, 1983; Vol. 3, pp. 267-357.
13. Radkiewicz, J.; McAllister, M.A.; Goldstein, E.; Houk, K.N. J. Org. Chem., 1998, 63, 1419.
14. Moree, W.J.; Schouten, A.; Kroon, J.; Liskamp, R.M.J. Int. J. Pept. Protien Res., 1995, 45, 501.
15. Paik, S.; White, E.H. Tetrahedron, 1996, 52, 503.
16. Liskamp, R.M.J.; Kruijtzer A.W. Mole. Divers., 2004, 8, 79.
17. De Jong, R.; Rijkers, D.T.S.; Liskamp, R.M.J. Helv. Chim. Acta, 2002, 85, 4230.
18. De Bont, D.B.A.; Dijkstra, G.D.H.; Den Hartog, J.A.J.; Liskamp, R.M.J. Bioorg. Med. Chem. Lett., 1996, 6, 3035.
19. De Bont, D.B.A.; Sliedregt, K.M.; Hofmeyer, L.J.F.; Liskamp, R.M.J. Bioorg. Med. Chem., 1999, 7, 1043.
20. Moree, W.J.; Vand der Marel, G.A.; Liskamp, R.M.J. J. Org. Chem., 1995, 60, 5157.
21. Humijan, J.; Kotnik, M.; Boniface, A.; Solmajer. T.; Urleb, U.; Blanot, D.; Gobec, S. Tetrahedron, 2006, 62, 10980.
22. Humljan, J.; Gobec, S. Tetrahedron Lett. 2005, 46, 4069.
23. Brouwer, A.J.; Monnee, M.C.F.; Liskamp, R.M.J. Synthesis, 2000, 1579.
24. Monnee, M.C.F.; Marijne, M.F.; Brouwer, A.J.; Liskarnp, R.M.J. Tetrahedron Lett., 2000, 41, 7991.
25. Van Ameijde, J.; Liskamp, R.M.J. Tetrahedron Lett., 2000, 41, 1103.
26. Gennari, C.; Gude, M.; Potenza, D.; Piarulli, U. Chem. Eur. J., 1998, 4, 1924.
27. De Bont D.B.A.; Moree, W.J.; Liskamp, R.M.J. Bioorg. Med. Chem., 1996, 4, 667.
28. Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron Lett., 1991, 32, 923.
29. Krchnak, V.; Vagner, J.; Lebl, M. Int. J. Pept. Protein Res., 1988, 32, 415.
30. Bartlett, P.A.; Hanson, J.E.; Morgan, B.P.; Ellsworth, B.A. In Synthesis of Peptides and Peptidomimetics. Houben-Weyl, Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C. FAL; Thieme: Stuttgard, New York, 2004, Vol. E 22c. pp. 492-528.
31. Palacios, F.; Alonso, C.; de Jos Santos, J. Curr. Org. Chem., 2004, 8, 1481.
32. Bird, J.; De Mello, R.C.; Harper, G.P.; Hunter, D.J.; Karran, E.H.; Markwell, R.E.; Miles-Williams, A.J.; Rahman, S.S.; Ward, R.W. J. Med. Chem., 1994, 37, 158.
33. De Lombeart, S.; Erion, M.D.; Tan, J.; Blanchard, L.; El-Chehabi, L.; Ghai, R-D.; Sakane, Y.; Berry, C.; Trapani, A.J. J. Med. Chem., 1994, 37, 1498.
34. Barlett, P.A.; Hanson, J.E.; Giannousis, P.P. J. Org. Chem., 1990, 55, 6268.
35. Campbell, D.A.; Bermak, J.C. J. Am. Chem. Soc., 1994, 116, 6039.
36. Campbell, D.A.; Bermak, J.C. J. Org. Chem., 1994, 59, 658.
37. Campbell, D.A. J. Org. Chem., 1992, 57, 6331.
38. Champagne, J.-M.; Coste, J.; Jouin, P. Tetrahedron Lett., 1995, 36, 2079.
39. Champagne, J.-M.; Coate, J.; Jouin, P. Tetrahedron Lett., 1993, 34, 6743.
40. Seebach, D.; Charczuk, R.; Berber, C.; Renaud, P.; Bener, H.; Schneider, H. Helv. Chim. Acta, 1989, 72, 401.
41. Nicolau, K.C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc., 1997, 119, 449.
42. Gademann, K.; Seebach, D. Helv. Chim. Acta, 2001, 84, 2924.
43. Tamilarasu, N.; Hoq, I.; Rana, T.M. Bioorg. Med. Chem. Lett., 2001, 11, 505.
44. Appella, D.H.; Christianson, L.A., Karle, I.L., Powell, D.R.; Gellman, S.H. J. Am. Chem. Soc., 1996, 118, 13071.
45. Wang, X.; Espinosa, J.F.; Gellman, S.H. J. Am. Chem. Soc., 2000, 122, 4821.
46. Hanessian, S.; Luo, R.; Schaum, S.; Michcnik, S. J. Am. Chem. Soc., 1999, 120, 8569.
47. Hanessian, S.; Luo, X.; Schaum, R. Tetrahedron Lett., 1999, 40, 4925.
48. Seebach, D.; Ciceri, P.; Overhand, M.; Juan, B.; Rigo, D.; Oberer, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta, 1996, 79, 2043.
49. Seebach, D.; Sifferlen, T.; Mathieu, P.A.; Hane, A.M.; Krell, C.M.; Bierbaum, D.J.; Abele, S, Helv. Chim. Acta, 2000, 83, 2849.
50. Skurski, P.; Simons, J. J. Chem. Phys., 2001, 115, 8373.
51. Burgess, K.; Ibarzo, J.; Linthicum, D.S.; Russell, D.H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A.J. J. Am. Chem. Soc., 1997, 119, 1556.
52. Kim, J.-M.; Bi, Y.; Paikoff, S.J.; Scultz, P.G. Tetrahedron Lett., 1996, 37, 5305.
53. Guichard, G.; Semetey, V.; Rodriguez, M.; Briand, J.-P. Tetrahedron Lett., 2000, 41, 1553.
54. Boeijen, A.; van Ameijde, J.; Liskamp, R.M. J. Org. Chem., 2001, 66, 8454.
55. Boeijen, A.; Liskamp, R.M.J. Eur. J. Org. Chem., 1999, 2127.
56. Alsina, J.; Scott, W. L.; O'Donell, M.J. Tetrahedron Lett., 2005, 46, 3131.
57. Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J.M.; Houghten, R.A. J. Comb. Chem., 2002, 4, 175.
58. Shemyakin, M.M.; Shchukina, L.A.; Vinogradova, E.I.; Ravidel, G.A.; Ovchinnikov, Y.A. Experimentia, 1966, 22, 535.
59. Bramson, H.N.; Thomas, N.E.; Kaiser, E.T. J. Biol. Chem., 1985, 260, 15452.
60. Arad, O.; Goodman, M. Biopolymers, 1990, 29, 1633.
61. Coombs, G.S.; Rao, M.S.; Olson, A.J.; Dawson, P.E.; Madison, E.L. J. Biol. Chem., 1999, 274, 24074.
62. Davidson, B.S. Chem. Rev., 1993, 93, 1771.
63. Fusetani, N.; Matsunaga, S. Chem. Rev., 1993, 93, 1793.
64. Woo, A.J.; Strobl, W.R.; Priestley, N.D. Antimicrob. Agents Chemother., 1999, 43, 1662.
65. Kuisle, O.; Quinoa, E.; Riguera, R. Tetrahedron Lett., 1999, 40, 1203.
66. Kuisle, O.; Lolo, M.; Quinoa, E.; Riguera, R. Tetrahedron, 1999, 55, 14807.
67. Kuisle, O.; Quinoa, E.; Riguera, R. J. Org. Chem., 1999, 64, 8063.
68. Marder, O.; Albericio, F. Chim. Oggi, 2003, 6, 35.
69. Stawikowski, M.; Cudic, P. In Methods in Molecular Biology, Fields, G.B. Ed., Humana Press, Inc.: Totowa, 2006; Vol. 386, pp. 321-339.
70. Berry, J.D.; Digiovanna, V.C.; Metrick, S.S.; Murugan, R. Arkivoc, 2001, 201.
71. Stawikowski, M.; Cudic, P. Tetrahedron Lett., 2006, 47, 8587.
72. Park, B.-D.; Lee, Y-S. React. Funct. Polymers, 2000, 44, 41.
73. Hudson, D. J. Org. Chem. 1988, 53, 617.
74. Podlech, J. In Synthesis of Peptides and Peptidomimetics, Houben- Weyl, Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C. Ed.; Thieme: Stuttgart, New York, 2001; Vol. 22a, pp. 517-533.
75. Mouls, L.; Subra, G.; Enjabal. C.; Martinez, J.; Aubagnac, J.L. Tetrahedron Lett., 2004, 45, 1173.
76. Patch, J.A.; Kirshenbaum, K.; Seurynck, S.; Zuckermann, R.; Barron, A.E. In Pseudo-peptides in Drug Development. Neilsen, P.E., Ed.; Wiley-VCH Verlag: Weinheim, 2004; pp. 1-31.
77. Kwon, Y.U.; Kodadek, T. J. Am. Chem. Soc., 2007, 129, 1508.
78. Schröder, T.; Schmitz, K.; Niemeier, N.; Balaban, T.S.; Krug, H.F.; Schepers, U.; Bräse, S. Bioconjug. Chem. 2007, ASAP Article; DOI: 10.1021/bc0602073.
79. Miller, S.M.; Simmon, R.J.; Ng, S.; Zuckermann, R.N.; Kerr, J.M.; Moos, W.H. Drug Dev. Res., 1995, 35, 20.
80. Stawikowski, M.; Stawikowska, R.; Jaskiewicz, A.; Zablotna, E.; Rolka, K. Chembiochem, 2005, 6, 1057.
81. Simon, R.J.; Kania, R.S.; Zuckermann, R.N.; Huebner, V.D.; Jewell, D.A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C.K. Proc. Natl. Acad. Sci. USA, 1992, 89, 9367.
82. Kruijtzer, J.A.W.,, Hofmeyer, L.J.F.; Heerma, W.; Versluis, C.; Liskamp, R.M.J. Chem. Eur. J., 1998, 4, 1570.
83. Uno, T.; Beausoleil, E.; Goldsmith, R.A.; Levine, B.H.; Zuckermann, R.N. Tetrahedron Lett., 1999, 40, 1475.
84. Zuckermann, R.N.; Kerr, J.M.; Kent, S.B.H.; Moos, W.H. J. Am. Chem. Soc., 1992, 114, 10646.
85. Ostergaard, S.; Holm, A. Mol. Divers., 1997, 3, 17.
86. Boeijen, A.; Liskamp, R.M.J. Tetrahedron Lett., 1998, 39, 3589
87. Zega, A.; Urleb, U. Acta Chim. Slov., 2002, 49, 649.
88. Raynolds, C.H.; Horman, R.E. J. Am. Chem. Soc., 1996, 118, 9395.
89. Lee, H.J.; Lee, M.H.; Choi, Y.S.; Park, H.M.; Lee, K.B. J. Mol. Struct., 2003, 631, 101.
90. Gante, J. Synthesis, 1989, 405.
91. Hess, H.-J.; Moreland, W.T.; Laubach, G.D. J. Am. Chem. Soc., 1963, 85, 4041.
92. Niedrich, H. J. Prakt. Chem., 1972, 314, 749.
93. Oehme, P.; Bergmann, J.; Niedrich, H.; Jung, F.; Menzel, G.; Eichenstadt, M. Acta Biol. Med. Ger., 1970, 25, 613.
94. Han, H.; Yoon, J.; Janda, K.D. Bioorg. Med. Chem. Lett., 1998, 8, 117.
95. Dutta, A.S.; Furr, B.J.A. Ann. Rep. Med. Chem., 1985, 20, 203.
96. Zhang, W.J.; Berglund, A.; Kao, J.L.F.; Couty, J.P.; Gershengorn, M.C.; Marshall, J.R. J. Am. Chem. Soc., 2003, 125, 1221.
97. Vedel, M.; Diaz, J.; Cazaubon, C. European patent 2523126, 1983.
98. Quibell, M.; Turnell, W.G.; Johnson, T. J. Chem. Soc. Perkin Trans. 1, 1993, 294.
99. Liley, M.; Johnson, T. Tetrahedron Lett., 2000, 41, 3983.
100. Gibson, C.; Goodman, S.L.; Hahn, D.; Holzemann, G.; Kessler, H. J. Org. Chem., 1999, 64, 7388.
101. Boeglin, D.; Lubell, W.D. J. Comb. Chem., 2005, 7, 864.
102. Gray, C.J.; Quibell, M.; Bagget, N.; Hammerle, T. Int. J. Pept. Protein Res., 1992, 40, 351.
103. Lelais, G.; Seebach, D. Helv. Chim. Acta, 2003, 86, 4152.
104. Aubry, A.; Mangeot, J.P.; Vidal, J.; Collet, A.; Zerkout, S.; Marmud, M. Int. J. Pept. Protein Res., 1994, 43, 305.
105. Viret, J.; Collet, A.; Pichon-Pesme, V.; Aubry, A. New J. Chem., 1988, 12, 253.
106. Lecoq, A.; Marraud, M. Tetrahedron Lett., 1991, 24, 2765.
107. Guy, L.; Vidal, J.; Collet, A. J. Med. Chem., 1998, 41, 4833.
108. Bouillon, I.; Vanderesse, R.; Brosse, N.; Fabre, O.; Jamart-Grégoire, B. Tetrahedron, 2007, 63, 9635.
109. Bouillon, I.; Brosse, N.; Vanderesse, R.; Jamart-Grégoire, B. Tetrahedron, 2007, 63, 2223.
110. Zhang, L.; Goldammer, C.; Henkel, B.; Zuhl, F.; Panhaus, G.; Jungs, G.; Bayer, E. In Innovation and Perspectives in Solid Phase Synthesis; Epton,R., Ed.; Mayflower: Birmingham, 1994; pp. 711-716.