Skip to main content
Log in

Exploring privileged structures: The combinatorial synthesis of cyclic peptides

  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

Head-to-tail cyclic peptides have been reported to bind to multiple, unrelated classesof receptor with high affinity. They may therefore be considered to beprivileged structures. This review outlines the strategies by which bothmacrocyclic cyclic peptides and cyclic dipeptides or diketopiperazines havebeen synthesised in combinatorial libraries. It also briefly outlines someof the biological applications of these molecules, thereby justifying theirinclusion as privileged structures.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Goodman, N., Curr. Opin. Biotechnol., 13 (2002) 68–71.

    Google Scholar 

  2. Burley, S.K., Nat. Str. Biol., 7 (Suppl) (2000) 932–934.

    Google Scholar 

  3. Kreider, B.L., Annu. Rep. Med. Chem., 36 (2001) 227–235.

    Google Scholar 

  4. Caron, P.R., Mullican, M.D., Mashal, R.D., Wilson, K.P., Su, M.S., Murcko, M.A., Curr. Opin. Chem. Biol., 5 (2001) 464–470.

    Google Scholar 

  5. Schreiber, S.L., Bioorg. Med. Chem., 6 (1998) 1127–1152.

    Google Scholar 

  6. Wolcke, J., Ullmann, D., Drug Discov. Today, 6 (2001) 637–646.

    Google Scholar 

  7. Darvas, F., Dorman, G., Urge, L., Szabo, I., Ronai, Z., Sasvari-Szekely, M., Pure Appl. Chem., 73 (2001) 1487–1498.

    Google Scholar 

  8. Dean, P.M., Zanders, E.D., Bailey, D.S., Trends Biotechnol., 19 (2001) 288–292.

    Google Scholar 

  9. Hann, M.M., Leach, A.R., Harper, G., J. Chem. Inf. Comput. Sci., 41 (2001) 856–864.

    Google Scholar 

  10. Leach, A.R., Hann, M.M., Drug Discov. Today, 5 (2000) 326–336.

    Google Scholar 

  11. Deisenhofer, J., Biochemistry, 20 (1981) 2361–2370.

    Google Scholar 

  12. Sauer-Eriksson, A.E., Kleywegt, G.J., Uhlen, M., Jones, T.A., Structure, 3 (1995) 265–278.

    Google Scholar 

  13. Corper, A.L., Sohi, M.K., Bonagura, V.R., Steinitz, M., Jefferis, R., Feinstein, A., Beale, D., Taussig, M.J., Sutton, B.J., Nat. Struct. Biol., 4 (1997) 374–381.

    Google Scholar 

  14. Burmeister, W.P., Huber, A.H., Bjorkman, P.J., Nature, 372 (1994) 379–383.

    Google Scholar 

  15. DeLano, W.L., Ultsch, M.H., de Vos, A.M., Wells, J.A., Science, 287 (2000) 1279–1283.

    Google Scholar 

  16. Rose, G.D., Gierasch, L.M., Smith, J.A., Adv. Protein. Chem., 37 (1985) 1–109.

    Google Scholar 

  17. Andrianov, A.M., Mol. Biol., 33 (1999) 534–538.

    Google Scholar 

  18. Li, S.Z., Lee, J.H., Lee, W., Yoon, C.J., Baik, J.H., Lim. S.K., Eur. J. Biochem., 265 (1999) 430–440.

    Google Scholar 

  19. Freidinger, R.M., Veber, D.F., Perlow, D.S., Brooks, J.R., Science, 210 (1980) 656–658.

    Google Scholar 

  20. Wilmot, C.M., Thornton, J.M., J. Mol. Biol., 203 (1988) 221–232.

    Google Scholar 

  21. Wilmot, C.M., Thornton, J.M., Protein Eng., 3(6) (1990) 479–493.

    Google Scholar 

  22. Richardson, J.S., Adv. Protein. Chem., 34 (1981) 167–339.

    Google Scholar 

  23. Venkatachalam, C.M., Biopolymers, 6 (1968) 1425–1436.

    Google Scholar 

  24. Lewis, P.N., Momany, F.A., Scheraga, H.A., Biochim. Biophys. Acta, 303 (1973) 211–229.

    Google Scholar 

  25. Hutchinson, E.G., Thornton, J.M., Protein Sci., 3 (1994) 2207–2216.

    Google Scholar 

  26. Ball, J.B., Andrews, P.R., Alewood, P.F., Hughes, R.A., Fed. Eur. Biochem. Soc., 273 (1990) 15–18.

    Google Scholar 

  27. Ball, J.B., Hughes, R.A., Alewood, P.F., Andrews, P.R., Tetrahedron, 49 (1993) 3467–3478.

    Google Scholar 

  28. Garland, S.L., Dean, P.M., J. Comput. Aided Mol. Des., 13 (1999) 469–483.

    Google Scholar 

  29. Garland, S.L., Dean, P.M., J. Comput. Aided Mol. Des., 13 (1999) 485–498.

    Google Scholar 

  30. Ball, J.B., Alewood, P.F., J. Mol. Recognit., 3 (1990) 55–56.

    Google Scholar 

  31. Li, W., Burgess, K., Tetrahedron Lett., 40 (1999) 6527–6530.

    Google Scholar 

  32. Halab, L., Lubell, W.D., J. Org. Chem., 64 (1999) 3312–3321.

    Google Scholar 

  33. Terrett, N., Drug Discov. Today, 4 (1999) 141–141.

    Google Scholar 

  34. Gardner, R.R., Liang, G.B., Gellman, S.H., J. Am. Chem. Soc., 121 (1999) 1806–1816.

    Google Scholar 

  35. Lombardi, A., D'Auria, G., Maglio, O., Nastri, F., Quartara, L., Pedone, C., Pavone, V., J. Am. Chem. Soc., 120 (1998) 5879–5886.

    Google Scholar 

  36. Fink, B.E., Kym, P.R., Katzenellenbogen, J.A., J. Am. Chem. Soc., 120 (1998) 4334–4344.

    Google Scholar 

  37. Souers, A.J., Ellman, J.A., Tetrahedron, 57 (2001) 7431–7448.

    Google Scholar 

  38. Slomczynska, U., Chalmers, D.K., Cornille, F., Smythe, M.L., Beusen, D.D., Moeller, K.D., Marshall, G.R., J. Org. Chem., 61 (1996) 1198–1204.

    Google Scholar 

  39. Cornille, F., Slomczynska, U., Smythe, M.L., Beusen, D.D., Moeller, K.D., Marshall, G.R., J. Am. Chem. Soc., 117 (1995) 909–917.

    Google Scholar 

  40. Evans, B.E., Rittle, K.E., Bock, M.G., Dipardo, R.M., Freidinger, R.M., Whitter, W.L., Lundell, G.F., Veber, D.F., Anderson, P.S., Chang, R.S.L., Lotti, V.J., Cerino, D.J., Chen, T.B., Kling, P.J., Kunkel, K.A., Springer, J.P., Hirshfield, J., J. Med. Chem., 31 (1988) 2235–2246.

    Google Scholar 

  41. Patchett, A.A., Nargund, R.P., Annu. Rep. Med. Chem., 35 (2000) 289–298.

    Google Scholar 

  42. Mason, J.S., Morize, I., Menard, P.R., Cheney, D.L., Hulme, C., Labaudiniere, R.F., J.Med. Chem., 42 (1999) 3251–3264.

    Google Scholar 

  43. Fecik, R.A., Frank, K.E., Gentry, E.J., Menon, S.R., Mitscher, L.A., Telikepalli, H., Med. Res. Rev, 18 (1998) 149–185.

    Google Scholar 

  44. Yang, L., Berk, S.C., Rohrer, S.P., Mosley, R.T., Guo, L., Underwood, D.J., Arison, B.H., Birzin, E.T., Hayes, E.C., Mitra, S.W., Parmar, R.M., Cheng, K., Wu, T.J., Butler, B.S., Foor, F., Pasternak, A., Pan, Y., Silva, M., Freidinger, R.M., Smith, R.G., Chapman, K., Schaeffer, J.M., Patchett, A.A., Proc. Natl. Acad. Sci. U. S. A., 95 (1998) 10836–10841.

    Google Scholar 

  45. Patchett, A.A., Nargund, R.P., Tata, J.R., Chen, M.H., Barakat, K.J., Johnston, D.B.R., Cheng, K., Chan, W.W.S., Butler, B., Hickey, G., Jacks, T., Schleim, K., Pong, S.S., Chaung, L.Y.P., Chen, H.Y., Frazier, E., Leung, K.H., S.H.L., C., Smith, R.G., Proc. Natl. Acad. Sci. USA, 92 (1995) 7001–7005.

    Google Scholar 

  46. Smith, A.B.I., Cho, Y.S., Zawacki, L.E., Hirschmann, R., Pettit, G.R., Org. Lett., 3 (2001) 4063–4066.

    Google Scholar 

  47. Hirschmann, R., Hynes, J.J., Cichy-Knight, M.A., van Rijn, R.D., Sprengeler, P.A., Spoors, P.G., Shakespeare, W.C., Pietranico-Cole, S., Barbosa, J., Liu, J., Yao, W., Rohrer, S., Smith, A.B.I., J. Med. Chem., 41 (1998) 1382–1391.

    Google Scholar 

  48. Hirschmann, R., Ducry, L., Smith, A.B.I., J. Org. Chem., 65 (2000) 8307–8316.

    Google Scholar 

  49. Liu, J., Underwood, D.J., Cascieri, M.A., Rohrer, S.P., Cantin, L.-D., Chicchi, G., Smith, A.B.I., Hirschmann, R., J. Med. Chem., 43 (2000) 3827–3831.

    Google Scholar 

  50. Abrous, L., Hynes, J.J., Friedrich, S.R., Smith, A.B.I., Hirschmann, R. Org. Lett., 3 (2001) 1089–1092.

    Google Scholar 

  51. Nicolaou, K.C., Pfefferkorn, J.A., Mitchell, H.J., Roecker, A.J., Barluenga, S., Cao, G.Q., Affleck, R.L., Lillig, J.E., J. Am. Chem. Soc., 122 (2000) 9954–9967.

    Google Scholar 

  52. Nicolaou, K.C., Pfefferkorn, J.A., Roecker, A.J., Cao, G.Q., Barluenga, S., Mitchell, H.J., J. Am. Chem. Soc., 122 (2000) 9939–9953.

    Google Scholar 

  53. Emmel, E.A., Verweij, C.L., Durand, D.B., Higgins, K.M., Lacy, E., Crabtree, G.R., Science, 246 (1989) 1617–1620.

    Google Scholar 

  54. Mootz, H.D., Marahiel, M.A., J. Bacteriol., 179 (1997) 6843–6850.

    Google Scholar 

  55. Kratzschmar, J., Krause, M., Marahiel, M.A., J. Bacteriol., 171 (1989) 5422–5429.

    Google Scholar 

  56. Sanchez-Quesada, J., Ghadiri, M.R., Bayley, H., Braha, O., J. Am. Chem. Soc., 122 (2000) 11757–11766.

    Google Scholar 

  57. Wieland, T., Int. J. Peptide Protein Res., 22 (1983) 257–276.

    Google Scholar 

  58. Hirschmann, R., Yao, W.Q., Cascieri, M.A., Strader, C.D., Maechler, L., Cichy-Knight, M.A., Hynes, J., van Rijn, R.D., Sprengeler, P.A., Smith, A.B., J. Med. Chem., 39 (1996) 2441–2448.

    Google Scholar 

  59. Rohrer, S.P., Schaeffer, J.M., J. Physiol. Paris, 94 (2000) 211–215.

    Google Scholar 

  60. Quartara, L., Pavone, V., Pedone, C., Lombardi, A., Renzetti, A.R., Maggi, C.A., Regul. Pept., 65 (1996) 55–59.

    Google Scholar 

  61. Schiller, P.W., Berezowska, I., Nguyen, T.M.-D., Schmidt, R., Lemieux, C., Chung, N.N., Falcone-Hindley, M.L., Yao, W., Liu, J., Iwama, S., Smith, A.B., Hirschmann, R., J. Med. Chem., 43 (2000) 551–559.

    Google Scholar 

  62. Boer, J., Gottschling, D., Schuster, A., Semmrich, M., Holzmann, B., Kessler, H., J. Med. Chem., 44 (2001) 2586–2592.

    Google Scholar 

  63. Braun, V., Bös, C., Braun, M., Killmann, H., J. Infect. Dis., 183 Suppl 1 (2001) S12–S16.

    Google Scholar 

  64. Braun, V., Killmann, H., Benz, R., FEBS Lett., 346 (1994) 59–64.

    Google Scholar 

  65. Tkacz, J.S., DiDomenico, B., Curr. Opin. Microbiol., 4 (2001) 540–545.

    Google Scholar 

  66. Belvisi, L., Bernardi, A., Checchia, A., Manzoni, L., Potenza, D., Scolastico, C., Castorina, M., Cupelli, A., Giannini, G., Carminati, P., Pisano, C., Org. Lett., 3 (2001) 1001–1004.

    Google Scholar 

  67. Spatola, A.F., Crozet, Y., deWit, D., Yanagisawa, M., J. Med. Chem., 39 (1996) 3842–3846.

    Google Scholar 

  68. Yoshida, M., Furumai, R., Nishiyama, M., Komatsu, Y., Nishino, N., Horinouchi, S., Cancer Chemother. Pharmacol., 48 Suppl 1 (2001) S20- S26.

  69. Yoshida, M., Horinouchi, S., Beppu, T., Bioessays, 17 (1995) 423–430.

    Google Scholar 

  70. Lax, A.R., Shepherd, H.S., ACS Symp. Ser., 380 (1988) 24–34

    Google Scholar 

  71. Lax, A.R., Shepherd, H.S., Edwards, J.V., Weed Technol., 2 (1988) 540–544.

    Google Scholar 

  72. Edwards, J.V., Dailey, O.D., Bland, J.M., Cutler, H.G., ACS Symp. Ser., 380 (1998) 35–56.

    Google Scholar 

  73. Bernardi, E., Cros, S., Viallefont, P., Lazaro, R., Bull. Soc. Chim. Fr., 131 (1994) 944–948.

    Google Scholar 

  74. Shute, R.E., Kawai, M., Rich, D.H., Tetrahedron, 44 (1988) 685–695.

    Google Scholar 

  75. Kawai, M., Jasensky, R.D., Rich, D.H., J. Am. Chem. Soc., 105 (1983) 4456–4462.

    Google Scholar 

  76. Liesch, J.M., Sweeley, C.C., Staffeld, G.D., Anderson, M.S., Weber, D.J., Scheffer, R.P., Tetrahedron, 38 (1982) 45–48.

    Google Scholar 

  77. Hruby, V.J., Wilke, S., Al-Obeidi, F., Jiao, D., Lin, Y., React. Polym., (1994) 231–241.

  78. Kates, S.A., Sole, N.A., Albericio, F., Barany, G., In Basava, C., Anantharamaiah, G.M. (Eds.), In Peptides: Design, Synthesis, and Biological Activity, Birkhäuser, Boston, USA, 1994, pp. 39–58.

    Google Scholar 

  79. Plaué, S., Int. J. Pept. Protein Res., 35 (1990) 510–517.

    Google Scholar 

  80. Backes, B.J., Ellman, J.A., Curr. Opin. Chem. Biol., 1 (1997) 86–93.

    Google Scholar 

  81. Alewood, P.F., Alewood, D., Miranda, L.P., Love, S., Meutermans, W.D.F., Wilson, D., Methods in Enzymol., 289 (1997) 14–29.

    Google Scholar 

  82. Cabrele, C., Langer, M., Beck-Sickinger, A.G., J. Org. Chem., 64 (1999) 4353–4361.

    Google Scholar 

  83. Rovero, P., Quartara, L., Fabbri, G., Tetrahedron Lett., 32 (1991) 2639–2642.

    Google Scholar 

  84. Spatola, A.F., Darlak, K., Romanovskis, P., Tetrahedron Lett., 37 (1996) 591–594.

    Google Scholar 

  85. Sugiura, T., Hamada, Y., Shioiri, T., Tetrahedron Lett., 28 (1987) 2251–2254.

    Google Scholar 

  86. Valero, M.L., Giralt, E., Andreu, D., Tetrahedron Lett., 37 (1996) 4229–4232.

    Google Scholar 

  87. Lee, J.H., Griffin, J.H., Nicas, T.I., J. Org. Chem., 61 (1996) 3983–3986.

    Google Scholar 

  88. Tromelin, A., Fulachier, M.-H., Mourier, G., Ménez, A., Tetrahedron Lett., 33 (1992) 5197–5200.

    Google Scholar 

  89. Trzeciak, A., Bannwarth, W., Tetrahedron Lett., 33 (1992) 4557–4560.

    Google Scholar 

  90. Kates, S.A., Sole, N.A., Johnson, C.R., Hudson, D., Barany, G., Albericio, F., Tetrahedron Lett., 34 (1993) 1549–1552.

    Google Scholar 

  91. McMurray, J.S., Tetrahedron Lett., 32 (1991) 7679–7682.

    Google Scholar 

  92. McMurray, J.S., Lewis, C.A., Obeyesekere, N.U., Pept. Res., 7 (1994) 195–206.

    Google Scholar 

  93. Sabatino, G., Chelli, M., Mazzucco, S., Ginanneschi, M., Papini, A.M., Tetrahedron Lett., 40 (1999) 809–812.

    Google Scholar 

  94. Kobayashi, K., Hayashi, K., J. Am. Chem. Soc., 112 (1990) 6051–6053.

    Google Scholar 

  95. Alsina, J., Rabanal, F., Giralt, E., Albericio, F., Tetrahedron Lett., 35 (1994) 9633–9636.

    Google Scholar 

  96. Romanovskis, P., Spatola, A.F., J. Pept. Res., 52 (1998) 356–374.

    Google Scholar 

  97. Alsina, J., Rabanal, F., Chiva, C., Giralt, E., Albericio, F., Tetrahedron, 54 (1998) 10125–10152.

    Google Scholar 

  98. Lee, Y., Silverman, R.B., J. Am. Chem. Soc., 121 (1999) 8407–8408.

    Google Scholar 

  99. Jensen, K.L., Alsina, J., Songster, M.F., Vágner, J., Albericio, F., Barany, G., J. Am. Chem. Soc., 120 (1998) 5441–5452.

    Google Scholar 

  100. Jensen, K.J., Songster, M.F., Vágner, J., Alsina, J., Albericio, F., Barany, G., In Kaumaya, P.T.P., Hodges, R.S. (Eds.), Peptides: Chemistry, Structure and Biology: Proceedings of the 14th American Peptide Symposium, Mayflower Scientific, Kinswinford, U.K., 1996, pp. 30–32.

    Google Scholar 

  101. del Fresno, M., Alsina, J., Royo, M., Barany, G., Albericio, F., Tetrahedron Lett., 39 (1998) 2639–2642.

    Google Scholar 

  102. Bourne, G.T., Golding, S.W., Meutermans, W.D.F., Smythe, M.L., Lett. Pept. Sci., 7 (2001) 311–316.

    Google Scholar 

  103. Bourne, G.T., Meutermans, W.D.F., Alewood, P.F., McGeary, R.P., Scanlon, M., Watson, A.A., Smythe, M.L., J. Org. Chem., 64 (1999) 3095–3101.

    Google Scholar 

  104. Bourne, G.T., Meutermans, W.D.F., Smythe, M.L., Tetrahedron Lett., 40 (1999) 7271–7274.

    Google Scholar 

  105. Okayama, T., Burritt, A., Hruby, V.J., Lett., 2 (2000) 1787–1790.

    Google Scholar 

  106. Ehrlich, A., Heyne, H.-U., Winter, R., Beyermann, M., Haber, H., Carpino, L.A., Bienert, M., J. Org. Chem., 61 (1996) 8831–8838.

    Google Scholar 

  107. Ehrlich, A., Klose, J., Heyne, H.-U., Beyermann, M., Carpino, L.A., Bienert, M., In Kaumaya, P.T.P.H., Robert S. (Eds.), Pept.: Chem., Struct. Biol., Proc. Am. Pept. Symp., 14th, Mayflower Scientific, Kingswinford, UK, 1996, pp. 75–76.

    Google Scholar 

  108. Fridkin, M., Patchornik, A., Katchalski, E., J. Am. Chem. Soc., 90 (1968) 2953–2957.

    Google Scholar 

  109. Fridkin, M., Patchornik, A., Katchalski, E., J. Am. Chem. Soc., 87 (1965) 4646–4648.

    Google Scholar 

  110. DeGrado, W.F., Kaiser, E.T., J. Org. Chem., 45 (1980) 1295–1300.

    Google Scholar 

  111. DeGrado, W.F., Kaiser, E.T., J. Org. Chem., 47 (1982) 3258–3261.

    Google Scholar 

  112. Kaiser, E.T., Mihara, H., Laforet, G., Kelly, J.W., Walters, L., Findeis, M.A., Sasaki, T., Science, 243 (1989) 187–192.

    Google Scholar 

  113. Ösapay, G., Profit, A., Taylor, J.W., Tetrahedron Lett., 31 (1990) 6121–6124.

    Google Scholar 

  114. Ösapay, G., Taylor, J.W., J. Am. Chem. Soc., 112 (1990) 6046–6051.

    Google Scholar 

  115. Nishino, N., Xu, M., Mihara, H., Fujimoto, T., Ueno, Y., Kumagai, H., Tetrahedron Lett., 33 (1992) 1479–1482.

    Google Scholar 

  116. Nishino, N., Xu, M., Mihara, H., Fujimoto, T., Ohba, M., Ueno, Y., Kumagai, H., J. Chem. Soc., Chem. Commun., (1992) 180–181.

  117. Kapurniotu, A., Taylor, J.W., Tetrahedron Lett., 34 (1993) 7031–7034.

    Google Scholar 

  118. Zhang, L.H., Ma, P., Tetrahedron Lett., 35 (1994) 5765–5768.

    Google Scholar 

  119. Mihara, H., Yamabe, S., Niidome, T., Aoyagi, H., Kumagai, H., Tetrahedron Lett., 36 (1995) 4837–4840.

    Google Scholar 

  120. Nishino, N., Hayashida, J., Arai, T., Mihara, H., Ueno, Y., Kumagai, H., J. Chem. Soc., Perkin Trans. 1, 9 (1996) 939–946.

    Google Scholar 

  121. Lee, B.H., Tetrahedron Lett., 38 (1997) 757–760.

    Google Scholar 

  122. Wu, X., Grathwohl, M., Schmidt, R.R., Org. Lett., 3 (2001) 747–750.

    Google Scholar 

  123. Richter, L.S., Tom, J.Y.K., Burnier, J.P., Tetrahedron Lett., 35 (1994) 5547–5550.

    Google Scholar 

  124. Bourne, G.T., Golding, S.W., McGeary, R.P., Meutermans, W.D.F., Jones, A., Marshall, G.R., Alewood, P.F., Smythe, M.L., J. Org. Chem., 66 (2001) 7706–7713.

    Google Scholar 

  125. Bourne, G.T., McGeary, R.P., Golding, S.W., Meutermans, W.D.F., Alewood, P.F., Smythe, M.L., In Fields, G.B., Tam, J.P., Barany, G. (Eds.), Peptides for the New Millennium: Proceedings of the 16th American Peptide Symposium, Kluwer Academic Publishers, Dordrecht, Netherlands, 2000, pp. 98–99.

    Google Scholar 

  126. Flanigan, E., PhD Thesis, Marshall, G.R., Tetrahedron Lett., 27 (1970) 2403–2406.

    Google Scholar 

  127. Flanigan, E., PhD Thesis, Washington University, St. Louis., 1971.

    Google Scholar 

  128. Marshall, D.L., Liener, I.E., J. Org. Chem., 35 (1970) 867–868.

    Google Scholar 

  129. Pátek, M., Int. J. Pept. Protein Res., 42 (1993) 97–117.

    Google Scholar 

  130. Kiso, Y., Fukui, T., Tanaka, S., Kimura, T., Akaji, K., Tetrahedron Lett., 35 (1994) 3571–3574.

    Google Scholar 

  131. Hoffmann, S., Frank, R., Tetrahedron Lett., 35 (1994) 7763–7766.

    Google Scholar 

  132. Chan, W.C., Bycroft, B.W., Evans, D.J., White, P.D., J. Chem. Soc., Chem. Commun., 21 (1995) 2209–2210.

    Google Scholar 

  133. Kimura, T., Fukui, T., Tanaka, S., Akaji, K., Kiso, Y., Chem. Pharm. Bull., 45 (1997) 18–26.

    Google Scholar 

  134. Hulme, C., Peng, J., Morton, G., Salvino, J.M., Herpin, T. Labaudiniere, R., Tetrahedron Lett., 39 (1998) 7227–7230.

    Google Scholar 

  135. Breitenbucher, J.G., Johnson, C.R., Haight, M., Phelan, J.C., Tetrahedron Lett., 39 (1998) 1295–1298.

    Google Scholar 

  136. Beech, C.L., Coope, J.F., Fairley, G., Gilbert, P.S., Main, B.G., Plé, K., J. Org. Chem., 66 (2001) 2240–2245.

    Google Scholar 

  137. Cano, M., Ladlow, M., Balasubramanian, S., J. Org. Chem., 67 (2002) 129–135.

    Google Scholar 

  138. Miller, M.W., Vice, S.F., McCombie, S.W., Tetrahedron Lett., 39 (1998) 3429–3432.

    Google Scholar 

  139. Panke, G., Frank, R., Tetrahedron Lett., 39 (1998) 17–18.

    Google Scholar 

  140. Pátek, M., Lebl, M., Tetrahedron Lett., 32 (1991) 3891–3894.

    Google Scholar 

  141. Pátek, M., Lebl, M., Biopolymers, 47 (1998) 353–363.

    Google Scholar 

  142. Rothe, M., Sander, A., Fischer, W., Mästle, W., Nelson, B., In Goodman, M., Meienhofer, J. (Eds.), Peptides: Proceedings of the 5th American Peptide Symposium, JohnWiley and Sons, New York, USA, 1977, pp. 506–509.

    Google Scholar 

  143. Routledge, A., Abell, C., Balasubramanian, S., Tetrahedron Lett., 38 (1997) 1227–1230.

    Google Scholar 

  144. Sola, R., Saguer, P., David, M.,-L., Pascal, R., J. Chem. Soc., Chem. Comm., 23 (1993) 1786–1788.

    Google Scholar 

  145. Sola, R., Mery, J., Pascal, R., Tetrahedron Lett., 37 (1996) 9195–9198.

    Google Scholar 

  146. Todd, M.H., Oliver, S.F., Abell, C., Org. Lett., 1 (1999) 1149–1151.

    Google Scholar 

  147. Wade, W.S., Yang, F., Sowin, T.J., J. Comb. Chem., 2 (2000) 266–275.

    Google Scholar 

  148. Kenner, G.W., McDermott, J.R., Sheppard, R.C., J. Chem. Soc., Chem. Comm., (1971) 636–637.

  149. Fitzpatrick, L.J., Rivero, R.A., Tetrahedron Lett., 38 (1997) 7479–7482.

    Google Scholar 

  150. Backes, B.J., Ellman, J.A., J. Am. Chem. Soc., 116 (1994) 11171–11172.

    Google Scholar 

  151. Backes, B.J., Ellman, J.A., J. Org. Chem., 64 (1999) 2322–2330.

    Google Scholar 

  152. Maclean, D., Hale, R., Chen, M., Org. Lett., 3 (2001) 2977–2980.

    Google Scholar 

  153. Backes, B.J., Virgilio, A.A., Ellman, J.A., J. Am. Chem. Soc., 118 (1996) 3055–3056.

    Google Scholar 

  154. Bannwarth, W., Küng, E., Vorherr, T., Bioorg. Med. Chem. Lett., 6 (1996) 2141–2146.

    Google Scholar 

  155. Gough, S.L., Clemens, I.R., Seale, P.W., In Bajusz, S., Hudecz, F. (Eds.), Peptides 1998, Proceedings of the 25th European Peptide Symposium, Akademiai Kiado, Budapest, Hungary, 1999, pp. 770–771.

    Google Scholar 

  156. Meutermans, W.D.F., Golding, S.W., Bourne, G.T., Miranda, L.P., Dooley, M.J., Alewood, P.F., Smythe, M.L., J. Am. Chem. Soc., 121 (1999) 9790–9796.

    Google Scholar 

  157. Prasad, C., Peptides, 16 (1995) 151–164.

    Google Scholar 

  158. Szardenings, A.K., Burkoth, T.S., Lu, H.H., Tien, D.W., Campbell, D.A., Tetrahedron, 53 (1997) 6573–6593.

    Google Scholar 

  159. Loughlin, W.A., Marshall, R.L., Carreiro, A., Elson, K.E., Bioorg. Med. Chem. Lett., 10 (2000) 91–94.

    Google Scholar 

  160. Cui, C., Kakeya, H., Osada, H., Tetrahedron, 52 (1996) 12651–12666.

    Google Scholar 

  161. Wang, H., Ganesan, A., Org. Lett., 1 (1999) 1647–1649.

    Google Scholar 

  162. Funabashi, Y., Horiguchi, T., Iinuma, S., Tanida, S., Harada, S., J. Antibiot., 47 (1994) 1202–1218.

    Google Scholar 

  163. Royo, M., Van Den Nest, W., del Fresno, M., Frieden, A., Yahalom, D., Rosenblatt, M., Chorev, M., Albericio, F., Tetrahedron Lett., 42 (2001) 7387–7391.

    Google Scholar 

  164. Szardenings, A.K., Harris, D., Lam, S., Shi, L.H., Tien, D., Wang, Y.W., Patel, D.V., Navre, M., Campbell, D.A., J.Med. Chem., 41 (1998) 2194–2200.

    Google Scholar 

  165. Goodfellow, V.S., Laudeman, C.P., Gerrity, J.I., Burkard, M., Strobel, E., Zuzack, J.S., McLeod, D.A., Mol. Divers., 2 (1996) 97–102.

    Google Scholar 

  166. van Loevezijn, A., Allen, J.D., Schinkel, A.H., Koomen, G.J., Bioorg. Med. Chem. Lett., 11 (2000) 29–32.

    Google Scholar 

  167. Nefzi, A., Giulianotti, M.A., Houghten, R.A., Tetrahedron, 56 (2000) 3319–3326.

    Google Scholar 

  168. Cody, W.L., Cai, C., Doherty, A.M., Edmunds, J.J., He, J.X., Narasimhan, L.S., Plummer, J.S., Rapundalo, S.T., Rubin, J.R., Van Huis, C.A., St-Denis, Y., Winocour, P.D., Siddiqui, M.A., Bioorg. Med. Chem. Lett., 9 (1999) 2497–2502.

    Google Scholar 

  169. Baures, P.W., Ojala, W.H., Costain, W.J., Ott, M.C., Pradhan, A., Gleason, W.B., Mishra, R.K., Johnson, R.L., J. Med. Chem., 40 (1997) 3594–3600.

    Google Scholar 

  170. Lopez-Rodriguez, M.L., Morcillo, M.J., Fernandez, E., Porras, E., Orensanz, L., Beneytez, M.E., Manzanares, J., Fuentes, J.A., J. Med. Chem., 44 (2001) 186–197.

    Google Scholar 

  171. Liebscher, J., Jin, S.D., Chem. Soc. Rev., 28 (1999) 251–259.

    Google Scholar 

  172. Ienaga, K., Nakamura, K., Kurohashi, M., Nakanishi, T., Ichii, T., Phytochemistry, 29 (1990) 35–39.

    Google Scholar 

  173. Rajappa, S., Natekar, M.V., In Kratritzky, A.R. (Eds.), Adv. Heterocycl. Chem., Academic Press, San Diego, 1993, Vol. 57, pp. 187–289.

    Google Scholar 

  174. Szardenings, A.K., Antonenko, V., Campbell, D.A., DeFrancisco, N., Ida, S., Shi, L., Sharkov, N., Tien, D., Wang, Y.W., Navre, M., J. Med. Chem., 42 (1999) 1348–1357.

    Google Scholar 

  175. Gordon, D.W., Steele, J., Bioorg. Med. Chem. Lett., 5 (1995) 47–50.

    Google Scholar 

  176. Smith, R.A., Bobko, M.A., Lee, W., Bioorg. Med. Chem. Lett., 8 (1998) 2369–2374.

    Google Scholar 

  177. Golebiowski, A., Klopfenstein, S.R., Chen, J.J., Shao, X., Tetrahedron Lett., 41 (2000) 4841–4844.

    Google Scholar 

  178. Bianco, A., Sonksen, C.P., Roepstorff, P., Briand, J.P., J. Org. Chem., 65 (2000) 2179–2187.

    Google Scholar 

  179. Groth, T., Meldal, M., J. Comb. Chem., 3 (2001) 45–63.

    Google Scholar 

  180. Lin, X.D., Dorr, H., Nuss, J.M., Tetrahedron Lett., 41 (2000) 3309–3313.

    Google Scholar 

  181. Chucholowski, A., Masquelin, T., Obrecht, D., Stadlwieser, J., Villalgordo, J.M., Chimia, 50 (1996) 525–530.

    Google Scholar 

  182. Hulme, C., Morrissette, M.M., Volz, F.A., Burns, C.J., Tetrahedron Lett., 39 (1998) 1113–1116.

    Google Scholar 

  183. Falorni, M., Giacomelli, G., Porcheddu, A., Taddei, M., Eur. J. Org. Chem., (2000) 1669–1675.

  184. Falorni, M., Giacomelli, G., Nieddu, F., Taddei, M., Tetrahedron Lett., 38 (1997) 4663–4666.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Horton, D.A., Bourne, G.T. & Smythe, M.L. Exploring privileged structures: The combinatorial synthesis of cyclic peptides. Mol Divers 5, 289–304 (2000). https://doi.org/10.1023/A:1021365402751

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1021365402751

Navigation