Bioactive Macrocyclic Peptides and Peptide Mimics

Modern Supramolecular Chemistry: Strategies for Macrocycle Synthesis

Volumn , Issue , 2008, Pages 1-27

  Liskamp, Rob M J ^a   Rijkers, Dirk T S ^a   Bakker, Saskia E ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Bioactive macrocyclic peptide mimics; Bioactive macrocyclic peptides; Macrocycle synthesis; Modern supramolecular chemistry; Selected cyclic peptides

Indexed keywords

EID: 79960588868     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527621484.ch1     Document Type: Chapter

References (83)

1. Boger, D.L. (2001) Med. Res. Rev., 21 (5), 356-381;
2. Nicolaou, K.C., Boddy, C.N.C., Bräse, S. and Winssinger, N. (1999) Angew. Chem., 111, 2230-2287. Angew. Chem. Int. Ed., 38, 2096-2152;
3. Rao, A.V.R., Gurjar, M.K., Reddy, K.L. and Rao, A.S. (1995) Chem. Rev., 95, 2135-2167.
4. Chatterjee, C., Paul, M., Xie, L. and van der Donk, W.A. (2005) Chem. Rev., 105, 633-684.
5. Haubner, R., Finsinger, D. and Kessler, H. (1997) Angew. Chem., 109,1440-1456; Angew. Chem. Int. Ed., 36, 1374-1389.
6. Rüegger, A., Kuhn, M., Lichti, H., Loosli, H.-R., Huguenin, R., Quiquerez, C. and von Wartburg, A. (1976) Helv. Chim. Acta, 59, 1075-1092.
7. Fusetani, N., Matsunaga, S., Matsumoto, H. and Takebayashi, Y. (1990) J. Am. Chem. Soc., 112, 7053-7054.
8. Froideveaux, S. and Eberle, A.N. (2002) Biopolymers (Peptide Science), 66, 161-183.
9. X-ray structure of octreotide: Pohl, E., Heine, A., Sheldrick, G.M., Dauter, Z., Wilson, K.S., Kallen, J., Huber, W. and Pfäffli, P.J. (1995) Acta Crystallogr., Sect. D, 51, 48-59.
10. Rohl, C.A., Chakrabartty, A. and Baldwin, R.L. (1996) Protein Science, 5, 2623-2637.
11. Benfield, A.P., Teresk, M.G., Plake, H.R., DeLorbe, J.E., Millspaugh, L.E. and Martin, S.F. (2006) Angew. Chem., 118, 6984-6989; Angew. Chem. Int. Ed., 45, 6830-6835;
12. de Mol, N.J., Catalina, M.I., Dekker, F.J., Fischer, M.J.E., Heck, A.J.R. and Liskamp, R.M.J. (2005) ChemBioChem., 6, 2261-2270.
13. Knox, J.R. and Pratt, R.F. (1990) Antimicrob. Agents Chemother., 34, 1342-1347.
14. Mackay, J.P., Gerhard, U., Beauregard, D.A., Maplestone, R.A. and Williams, D. H. (1994) J. Am. Chem. Soc., 116, 45734580.
15. Williams, D.H., Maguire, A.J., Tsuzuki, W. and Westwell, M.S. (1998) Science, 280, 711-714.
16. Mackay, J.P., Gerhard, U., Beauregard, D.A., Westwell, M.S., Searle, M.S. and Williams, D.H. (1994) J. Am. Chem. Soc., 116, 4581-4590.
17. Süssmuth, R.D. (2002) ChemBioChem, 3, 295-298;
18. Walsh, C. T., Fisher, S.L., Park, I.-S., Prahalad, M. and Wu, Z. (1996) Chem. Biol, 3, 21-28.
19. Printsevskaya, S.S., Pavlov, A.Y., Olsufyeva, E.N., Mirchnink, E.P., Isakova, E.B., Reznikova, M.I., Goldman, R.C., Branstrom, A.A., Baizman, E.R., Longley, C.B., Sztaricskai, F., Batta, G. and Preobrazhenskaya, M.N. (2002) J. Med. Chem., 45,1340-1347;
20. Crowley, B.M., Mori, Y., McComas, C.C., Tang, D. and Boger, D.L. (2004) J. Am. Chem. Soc., 126, 4310-4317;
21. Boger, D.L., Kim, S. H., Mori, Y., Weng, J.-H., Rogel, O., Castle, S.L. and McAtee, J.J. (2001) J. Am. Chem. Soc., 123, 1862-1871.
22. Xu, R., Greiveldinger, G., Marenus, L.E., Cooper, A. and Ellman, J.A. (1999) J. Am. Chem. Soc., 121, 4898-4899.
23. Bois-Choussy, M., Neuville, L., Beugelmans, R. and Zhu, J. (1996) J. Org. Chem., 61, 9309-9322.
24. Arnusch, C.J. and Pieters, R.J. (2003) Eur.J. Org. Chem., 3131-3138.
25. ten Brink, H.T., Rijkers, D.T.S. and Liskamp, R.M.J. (2006) J. Org. Chem, 71, 1817-1824.
26. ten Brink H.T., Rijkers D.T.S., Kemmink J., Hilbers H.W. and Liskamp R.M.J. (2004) Org. Biomol. Chem., 2, 2658-2663.
27. Gross, E. and Morell, J.L. (1971) J. Am. Chem. Soc., 93, 4634-4635.
28. Ramseier, H.R. (1960) Arch. Microbiol., 37, 57-94.
29. Ruhr, E. and Sahl, H.-G. (1985) Antimicrob. Agents Chemother., 27, 841-845.
30. Linnett, P.E. and Strominger, J.L. (1973) Antimicrob. Agents Chemother., 4, 231-236.
31. Reisinger, P., Seidel, H., Tschesche, H. and Hammes, W.P. (1980) Arch. Microbiol., 127, 187-193.
32. Breukink, E., Wiedemann, I., van Kraaij, C., Kuipers, O.P., Sahl, H.-G. and de Kruijff, B. (1999) Science, 286,2361-2364.
33. Hoffmann, A., Pag, U., Wiedemann, I. and Sahl, H.-G. (2001) Il Farmaco, 57, 685-691.
34. Brötz, H., Josten, M., Wiedemann, I., Schneider, U., Götz, F., Bierbaum, G. and Sahl, H.-G. (1998) Mol. Microbiol., 30, 317-327.
35. Chan, W.C., Leyland, M., Clark, J., Dodd, H.M., Lian, L.-Y., Gasson, M.J., Bycroft, B.W. and Roberts, G.C.K. (1996) FEBS Lett., 390, 129-132.
36. Wiedemann, I., Breukink, E., van Kraaij, C., Kuipers, O.P., Bierbaum, G., de Kruijff, B. and Sahl, H.-G. (2001) J. Biol. Chem., 276, 1772-1779.
37. Hsu, S.-T.D., Breukink, E., de Kruijff, B., Kaptein, R., Bonvin, A.M.J.J. and van Nuland, N.A.J. (2002) Biochemistry, 41, 7670-7676.
38. Hsu, S.-T.D., Breukink, E., Tischenko, E., Lutters, M.A.G., de Kruijff, B., Kaptein, R., Bonvin, A.M.J.J. and van Nuland, N.A.J. (2004) Nat. Struct. Mol. Biol., 11, 963-967.
39. van Heusden, H.E., de Kruijff, B. and Breukink, E. (2002) Biochemistry, 41, 12171-12178.
40. Hasper, H.E., de Kruijff, B. and Breukink, E. (2004) Biochemistry, 43, 11567-11575.
41. Hasper, H.E., Kramer, N.E., Smith, J.L., Hillman, J.D., Zachariah, C., Kuipers, O. P., de Kruijff, B. and Breukink, E. (2006) Science, 313, 1636-1637.
42. Ghalit, N., Rijkers, D.T.S., Kemmink, J., Versluis, C. and Liskamp, R.M.J. (2005) Chem. Commun., 192-194;
43. Ghalit, N., Poot, A.J., Fürstner, A. and Rijkers, D.T.S. and Liskamp, R.M.J. (2005) Org. Lett., 7, 2961-2964;
44. Ghalit, N., Rijkers, D.T.S. and Liskamp, R.M.J. (2006) J. Mol. Catal. A: Chem., 254, 68-77;
45. Ghalit, N., Kemmink, J., Hilbers, H.W., Versluis, C., Rijkers, D.T. S. and Liskamp, R.M.J. (2007) Org. Biomol. Chem., 5, 924-934.
46. For a solid phase synthesis: Angell, Y.M., Thomas, T.L., Flentke, G.R. and Rich, D. H. (1995) J. Am. Chem. Soc., 117, 7279-7280.
47. Huai, Q., Kim, H.-Y., Liu, Y., Zhao, Y., Mondragon, A., Liu, J.O. and Ke, H. (2002) Proc. Natl. Acad. Sci. U.S.A., 99, 12037-12042.
48. For a review on sponge peptides: Fusetani, N. and Matsunaga, S. (1993) Chem. Rev., 93, 1793-1806.
49. Since the original paper by Fusetani and Matsunaga [39], Hagihara and Schreiber reassigned the stereochemistry of the vinylogous tyrosine-and a-ketoarginine residue to be of the S-configuration Hagihara, M. and Schreiber, S.L. (1992) J. Am. Chem. Soc., 114, 6570-6571.
50. Maryanoff, B.E., Qiu, X., Padmanabhan, K.P., Tulinsky, A., Almond, H.R. Jr., Andrade-Gordon, P., Greco, M.N., Kauffman, J.A., Nicolaou, K. C., Liu, A., Brungs, P.H. and Fusetani, N. (1993) Proc. Natl. Acad. Sci. U.S.A., 90, 8048-8052;
51. Lee, A.Y., Hagihara, M., Karmacharya, R., Albers, M.W., Schreiber, S.L.and Clardy J. (1993) J.Am. Chem. Soc., 115, 12619-12620;
52. Ganesh, V., Lee, A. Y., Clardy, J. and Tulinsky, A. (1996) Protein Sci., 5, 825-835.
53. Bode, W., Mayr, I., Baumann, U., Huber, R., Stone, S.R. and Hofsteenge, J. (1989) EMBO J., 8, 3467-3475.
54. Wipf, P. and Kim, H. (1993) J. Org. Chem., 58, 5592-5594;
55. Deng, J., Hamada, Y., Shioiri, T., Matsunaga, S. and Fusetani, N. (1994) Angew. Chem., 106, 1811-1813; Angew. Chem. Int. Ed. Engl., 33, 1729-1731;
56. Maryanoff, B.E., Greco, M.N., Zhang, H.-C., Andrade-Gordon, P., Kauffman, J.A., Nicolaou, K. C., Liu, A. and Brungs, P.H. (1995) J. Am. Chem. Soc., 117, 1225-1239;
57. Bastiaans, H.H.M., van der Baan, J.L. and Ottenheijm, H.C.J. (1997) J. Org. Chem., 62, 3880-3889.
58. Maryanoff, B.E., Zhang, H.-C., Greco, M.N., Glover, K.A., Kauffman, J.A. and Andrade-Gordon, P. (1995) Bioorg. Med. Chem., 3, 1025-1038;
59. Nakao, Y., Matsunaga, S. and Fusetani, N. (1995) Bioorg. Med. Chem., 3, 1115-1122.
60. For a review see: Gustafsson, D., Bylund, R., Antonsson, T., Nilsson, I., Nyström, J.-E., Eriksson, U., Bredberg, U. and Teger-Nilsson, A.-C. (2004) Nat. Rev. Drug Discovery, 3, 649-659.
61. Plow, E.F., Haas, T.A., Zhang, L., Loftus, J. Smith, J.W. (2000) J. Chem. Biol., 275, 21785-21788;
62. Gottschalk, K.-E. and Kessler, H. (2002) Angew. Chem., 114, 3919-3927; Angew. Chem. Int. Ed., 41, 3767-3774.
63. Hynes, R.O. (1992) Cell, 69, 11-25;
64. Brooks, P.C., Clark, R.A. and Cheresh, D.A. (1994) Science, 264, 569-571;
65. Hynes, R.O. (2002) Nat. Med., 8, 918-921.
66. Xiong, J.-P., Stehle, T., Zhang, R., Joachimiak, A., Frech, M., Goodman, S. L. and Arnaout, M.A. (2002) Science, 296, 151-155.
67. Brooks, P.C., Montgomery, A.M.P., Rosenfeld, M., Reisfeld, R.A., Hu, T., Klier, G. and Cheresh, D.A. (1994) Cell, 79, 1157-1164.
68. Hood, J.D., Bednarski, M., Frausto, R., Guccione, S., Reisfeld, R.A., Xiang, R. and Cheresh, D.A. (2002) Science, 296, 2404-2407.
69. Gurrath, M., Müller, G., Kessler, H., Aumailley, M. and Timpl, R. (1992) Eur. J. Biochem., 210, 911-921.
70. Haubner, R., Gratias, R., Diefenbach, B., Goodman, S.L., Jonczyk, A. and Kessler, H. (1996) J. Am. Chem. Soc., 118, 7461-7472.
71. Haubner, R., Wester, H.-J., Reuning, U., Senekowitsch-Schmidtke, R., Diefenbach, B., Kessler, H., Stöcklin, G. and Schwaiger, M. (1999) J. Nucl. Med., 40, 1061-1071.
72. For the chemical synthesis of Echistatin, see: Garsky, V.M., Lumma, P.K., Freidinger, R.M., Pitzenberger, S.M., Randall, W.C., Veber, D.F., Gould, R.J. and Friedman, P.A. (1989) Proc. Natl. Acad. Sci. U.S.A., 86, 4022-4026;
73. For the structural elucidation by NMR, see: Saudek, V., Atkinson, R.A. and Pelton, J.T. (1991) Biochemistry, 30, 7369-7372.
74. Liu, B.A., Jablonowski, K., Raina, M., Arcé, M., Pawson, T. and Nash, P.D. (2006) Mol. Cell, 22, 851-868;
75. Machida, K. and Mayer, B.J. (2005) Biochim. Biophys. Acta, 1747, 1-25.
76. Overduin, M., Rios, C.B., Mayer, B.J., Baltimore, D. and Cowburn, D. (1992) Cell, 70, 697-704;
77. Waksman, G., Kominos, D., Robertson, S.C., Pant, N., Baltimore, D., Birge, R.B., Cowburn, D., Hanafusa, H., Mayer, B.J., Overduin, M., Resh, M.D., Rios, C.B., Silverman, L. and Kuriyan, J. (1992) Nature, 358, 646-653;
78. Booker, G.W., Breeze, A.L., Downing, A.K., Panayotou, G., Gout, I., Waterfield, M.D. and Campbell, I.D. (1992) Nature, 358, 684-687.
79. Ogura, K., Shiga, T., Yuzawa, S., Yokochi, M., Burke, T.R. and Inagaki, F., unpublished results: PDB access code: 1X0N.
80. Gao, Y., Voigt, J., Wu, J.X., Yang, D. and Burke, T.R. Jr. (2001) Bioorg. Med. Chem. Lett., 11, 1889-1892.
81. Shi, Z.-D., Lee, K., Liu, H., Zhang, M., Roberts, L.R., Worthy, K.M., Fivash, M. J., Fisher, R.J., Yang, D. and Burke, T.R. Jr. (2003) Biochem. Biophys. Res. Commun., 310, 378-383.
82. Shi, Z.-D., Wei, C.-Q., Lee, K., Liu, H., Zhang, M., Araki, T., Roberts, L.R., Worthy, K.M., Fisher, R.J., Neel, B.G., Kelley, J.A., Yang, D. and Burke, T.R. Jr. (2004) J. Med. Chem., 47, 2166-2169.
83. Dekker, F.J., de Mol, N.J., Fischer, M.J. E., Kemmink, J. and Liskamp, R.M.J. (2003) Org. Biomol. Chem., 1, 3297-3303.