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Peptides pp 39-58 | Cite as

Solid-Phase Synthesis of Cyclic Peptides

  • Steven A. Kates
  • Núria A. Solé
  • Fernando Albericio
  • George Barany

Abstract

Interest in cyclic peptides dates back almost half a century to the discovery that the antibiotic gramicidin S is a cyclic decapeptide (Consden et al., 1947). Since then, numerous naturally occurring cyclic antibiotics and toxins have been found. Many of these are homodetic, that is, with only peptide (lactam) linkages connecting the constituent amino acid residues, whereas others are heterodetic, and include other functions such as disulfide, ester (lactone), ether, or thioether bridges that contribute to the ring(s). Duplication of the natural cycles, and the introduction of unnatural rings, have attracted the attention of chemists because of the extra level of synthetic complexity of such endeavors. Concurrently, a variety of biological studies have suggested that cyclic structures may exhibit improved metabolic stabilities, increased potencies, better receptor selectivities, and more controlled bioavailabilities. Further, the constrained geometries of cyclic peptides are conducive to conformational investigations, and for modeling and/or “locking” key secondary structural elements in protein folding. Early synthetic work focused on peptides with a small ring size, particularly cyclic hexapeptides. With the development of improved methods for peptide synthesis, larger ring sizes and more complex targets have become accessible.

Keywords

Cyclic Peptide Fmoc Chemistry Phosphonium Hexafluorophosphate Cyclic Decapeptide Lactam Bridge 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Albericio F, Hammer RP, García-Echeverría C, Molins MA, Chang JL, Munson MC, Pons M, Giralt E, Barany G (1991): Int J Pept Protein Res 37:402–413.PubMedCrossRefGoogle Scholar
  2. Albericio F, Barany G, Fields GB, Hudson D, Kates SA, Lyttle MH, Solé NA (1993): In: Peptides 1992, Proceedings of the 22d European Peptide Symposium, Schneider CH, Eberle AN, eds., pp. 191–193. Leiden: Escom.Google Scholar
  3. Albrecht E, Harada Y, Cooper GJS, Jones H, Lehman de Gaeta LS (1992): In: Peptides: Chemistry and Biology, Proceedings of the 12th American Peptide Symposium, Smith JA, Rivier JE, eds., pp. 441–442. Leiden: Escom.Google Scholar
  4. Andreu D, Albericio F, Solé NA, Munson MC, Ferrer M, Barany G: In: Peptide Synthesis and Purification Protocols, Pennington MW, Dunn BM, eds. Clifton, New Jersey: Humana Press (in press).Google Scholar
  5. Arttamangkul S, Aldrich JV: In: Peptides: Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium, Hodges RS, Smith JA, eds. Leiden: Escom (in press).Google Scholar
  6. Barany G, Albericio F (1985): J Am Chem Soc 107:4936–4942.CrossRefGoogle Scholar
  7. Barany G, Merrifield RB (1977): JAm Chem Soc 99:7363–7365.CrossRefGoogle Scholar
  8. Barany G, Merrifield RB (1979): In: The Peptides, Gross E, Meienhofer J, eds., pp. 1–284. New York: Academic Press.Google Scholar
  9. Barany G, Kneib-Cordonier N, Mullen DG (1987): Int J Pept Protein Res 30:705–739.PubMedCrossRefGoogle Scholar
  10. Barany G, Albericio F, Solé NA, Griffin GW, Kates SA, Hudson D (1993): In: Peptides 1992, Proceedings of the 22d European Peptide Symposium, Schneider CH, Eberle AN, eds., pp. 267–268. Leiden: Escom.Google Scholar
  11. Barlos K, Gatos D, Kutsogianni S, Papaphotiou G, Poulos C, Tsegenidis T (1991): Int J Pept Protein Res 38:562–568.PubMedCrossRefGoogle Scholar
  12. Bloomberg GB, Askin D, Gargaro AR, Tanner MJA (1993): Tetrahedron Lett 34:4709–4712.CrossRefGoogle Scholar
  13. Blout ER (1981): Biopolymers 20:1901–1912.CrossRefGoogle Scholar
  14. Bodanszky M (1984): Principles of Peptide Synthesis. Berlin: Springer-Verlag.CrossRefGoogle Scholar
  15. Bondi E, Fridkin M, Patchornik A (1968): IsrJ Chem 6:22p.Google Scholar
  16. Bouvier M, Taylor JW (1992): J Med Chem 35:1145–1155.PubMedCrossRefGoogle Scholar
  17. Brady SF, Paleveda WJ, Jr., Arison BH, Saperstein R, Brady EJ, Raynor K, Reisine T, Veber DF, Freidinger RM (1993): Tetrahedron 49:3449–3466.CrossRefGoogle Scholar
  18. Buchta R, Bondi E, Fridkin M (1986): Int J Pept Protein Res 28:289–297.PubMedCrossRefGoogle Scholar
  19. Büllesbach EE (1992): Kontakte (Darmstadt) 1:21–29.Google Scholar
  20. Canas M, Jodas G, Albericio F, Andreu D, García-Antón JM, Parente A, Ponsati B (1993): In: Peptides 1992, Proceedings of the 22d European Peptide Symposium, Schneider CH, Eberle AN, eds., pp. 401–402. Leiden: Escom.Google Scholar
  21. Carpino LA (1993): J Am Chem Soc 115:4397–4398.CrossRefGoogle Scholar
  22. Castro B, Dormoy JR, Evin G, Selve C (1975): Tetrahedron Lett 16:1219–1222.CrossRefGoogle Scholar
  23. Cavelier F, Daunis J, Jacquier R (1989): Bull Soc Chim Fr 788–798.Google Scholar
  24. Cavelier F, Daunis J, Jacquier R (1990): Bull Soc Chim Fr 210–225.Google Scholar
  25. Consden RJ, Gordon AH, Martin AJP, Synge RDM (1947): Biochem J 41:596–602.Google Scholar
  26. Coste J, Le-Nguyen D, Castro B (1990): Tetrahedron Lett 31:205–208.CrossRefGoogle Scholar
  27. Deadman U, Lu X, Moreno A, Rahman S, Chino N, Claeson G, Kakkar VV, Williams JA: In: Peptides: Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium, Hodges RS, Smith JA, eds. Leiden: Escom (in press).Google Scholar
  28. DeGrado WF, Kaiser ET (1980): JOrg Chem 45:1295–1300.CrossRefGoogle Scholar
  29. DeGrado WF, Kaiser ET (1982): JOrg Chem 47:3258–3261.CrossRefGoogle Scholar
  30. Edwards WB, Anderson CJ, Welch MJ, Fields CG, Fields GB: J Labelled Compd Radiopharm (in press).Google Scholar
  31. Eichler J, Bienert M, Stierandova A, Lebl M (1991): Pept Res 4:296–307.PubMedGoogle Scholar
  32. Eritja R, Ziehler-Martin JP, Walker PA, Lee TD, Legesse K, Albericio F, Kaplan BE (1987): Tetrahedron 43:2675–2680.CrossRefGoogle Scholar
  33. Felix AM, Wang C-T, Heimer EP, Fournier A (1988a): Int J Pept Protein Res 31:231–238.CrossRefGoogle Scholar
  34. Felix AM, Heimer EP, Wang C-T, Lambros TJ, Fournier A, Mowles TF, Maines S, Campbell RM, Wegrzynski BB, Toome V, Fry D, Madison VS (1988b): Int J Pept Protein Res 32:441–454.PubMedCrossRefGoogle Scholar
  35. Fields GB, Tian Z, Barany G (1992): In: Synthetic Peptides: A User’s Guide, Grant GA, ed., pp. 77–183. New York: Freeman.Google Scholar
  36. Flanigan E, Marshall GR (1970): Tetrahedron Lett 2403–2406.Google Scholar
  37. Freidinger RM, Veber DF, Hirschmann R, Paege LM (1980): Int J Pept Protein Res 16:464–470.PubMedCrossRefGoogle Scholar
  38. Fridkin M, Patchornik A, Katchalski E (1965): J Am Chem Soc 87:4646–4648.CrossRefGoogle Scholar
  39. Funakoshi S, Murayama E, Guo L, Fujii N, Yajima H (1988): J Chem Soc Chem Commun: 382–384. Google Scholar
  40. García-Echeverría C, Albericio F, Pons M, Barany G, Giralt E (1989): Tetrahedron Lett 30:2441–2444.CrossRefGoogle Scholar
  41. Gausepohl H, Pieles U, Frank RW (1992): In: Peptides: Chemistry and Biology, Proceedings of the 12th American Peptide Symposium, Smith JA, Rivier JE, eds., pp. 523–524. Leiden: Escom.Google Scholar
  42. Giralt E, Eritja R, Navalpotro C, Pedroso E (1984): An Quim 80:118–122.Google Scholar
  43. Giralt E, Eritja R, JosaJ, Kuklinski C, Pedroso E (1985): Synthesis 181–184.Google Scholar
  44. Gisin BF, Merrifield RB (1972): J Am Chem Soc 94:3102–3106.PubMedCrossRefGoogle Scholar
  45. Gray WR, Luque FA, Galyean R, Atherton E, Sheppard RC, Stone BL, Reyes A, Alford J, Mcintosh M, Olivera BM, Cruz LJ, Rivier J (1984): Biochemistry 23:2796–2802.PubMedCrossRefGoogle Scholar
  46. Hamada Y, Kato S, Shiori T (1985): Tetrahedron Lett 27:3223–3226.CrossRefGoogle Scholar
  47. Hill PS, Smith DD, Slaninova J, Hruby VJ (1990): J Am Chem Soc 112:3110–3113.CrossRefGoogle Scholar
  48. Hiskey RG (1981): In: The Peptides: Analysis, Synthesis, Biology, Gross E, Meienhofer J, eds., Vol. 3, pp. 137–167. New York: Academic Press.Google Scholar
  49. Ho P, Slavazza D, Chang D, Bassi K, Chang K (1990): In: Peptides: Chemistry, Structure and Biology, Proceedings of the 11th American Peptide Symposium, Rivier JE, Marshall GR, eds., pp. 993–995. Leiden: Escom.Google Scholar
  50. Hruby VJ (1982): Life Sci 31:189–199.PubMedCrossRefGoogle Scholar
  51. Hruby VJ: In: Peptides: Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium, Hodges RS, Smith JA, eds. Leiden: Escom (in press).Google Scholar
  52. Hruby VJ, Al-Obeidi F, Kazmierski W (1990a): Biochem J 268:249–262.PubMedGoogle Scholar
  53. Hruby VJ, Al-Obeidi F, Sanderson DG, Smith DD (1990b): In Innovation and Perspectives in Solid Phase Synthesis: Peptides, Polypeptides and Oligonucleotides, Epton R, ed., pp. 197–203. Birmingham, UK: S.P.C.C.Google Scholar
  54. Inukai N, Nakano K, Murakami M (1968): Bull Chem Socjpn 41:182–186.CrossRefGoogle Scholar
  55. Isied SS, Kuehn CG, Lyon JM, Merrifield RB (1982): J Am Chem Soc 104:2632–2634.CrossRefGoogle Scholar
  56. Kates SA, Solé NA, Johnson CR, Hudson D, Barany G, Albericio F (1993a): Tetrahedron Left 34:1549–1552.CrossRefGoogle Scholar
  57. Kates SA, Daniels SB, Albericio F (1993b): Anal Biochem 212:303–310.PubMedCrossRefGoogle Scholar
  58. Kessler H (1982): Angew Chem Int Ed Engl 21:512–523.CrossRefGoogle Scholar
  59. König W, Geiger R (1981): In: Perspectives in Peptide Chemistry, Eberle A, Geiger R, Wieland T, eds., pp. 31–44. Basel: Karger.Google Scholar
  60. Kopple KD (1972): J Pharm Sci 61:1345–1356.CrossRefGoogle Scholar
  61. Lebl M, Hruby VJ (1984): Tetrahedron Lett 25:2067–2068.CrossRefGoogle Scholar
  62. Lyttle MH, Hudson D (1992): In: Peptides: Chemistry and Biology, Proceedings of the 12th American Peptide Symposium, Smith JA, Rivier JE, eds., pp. 583–584. Leiden: Escom.Google Scholar
  63. Mazur S, Jayalekshmy P (1979): J Am Chem Soc 101:677–683.CrossRefGoogle Scholar
  64. McMurray JS (1991): Tetrahedron Lett 32:7679–7682.CrossRefGoogle Scholar
  65. Meldal M (1992): Tetrahedron Lett 33:3077–3080.CrossRefGoogle Scholar
  66. Mitchell AR, Merrifield RB (1985): In Peptides: Structure and Function, Proceedings of the 9th American Peptide Symposium, Deber CM, Hruby VJ, Kopple KD, eds., pp/.289–292. Rockford, Illinois: Pierce Chemical.Google Scholar
  67. Mott AW, Slomczynska U, Barany G (1986): In: Forum Peptides Le Cap d’Agde 1984, Castro B, Martinez J, eds., pp. 321–324. Nancy, France: Les Impressions Dohr.Google Scholar
  68. Munson MC, Barany G (1993): J Am Chem Soc 115:10203–10216.CrossRefGoogle Scholar
  69. Munson MC, Lebl M, Slaninová J, Barany G (1993): Pept Res 6:155–159.PubMedGoogle Scholar
  70. Munson MC, García-Echeverría C, Albericio F, Barany G (1992): JOrg Chem57:3013–3018.CrossRefGoogle Scholar
  71. Mutter M, Tuchscherer GG, Miller C, Altmann K-H, Carey RI, Wyss DF, Labhardt AM, Rivier JE (1992): J Am Chem Soc 114:1463–1470.CrossRefGoogle Scholar
  72. Neugebauer W, Willick G (1993): In: Peptides 1992, Proceedings of the 22d European Peptide Symposium, Schneider CH, Eberle AN, eds., pp. 395–396. Leiden: Escom.Google Scholar
  73. Nishino N, Xu M, Mihara H, Fujimoto T, Ueno Y, Kumagai H (1992a): Tetrahedron Lett 33:1479–1482.CrossRefGoogle Scholar
  74. Nishino N, Xu M, Mihara H, Fujimoto T, Ohba M, Ueno Y, Kumagai H (1992b): J Chem Soc Chem Commun: 180–181.Google Scholar
  75. Ösapay G, Taylor JW (1990): J Am Chem Soc 112:6046–6051.CrossRefGoogle Scholar
  76. Ösapay G, Profit A, Taylor JW (1990): Tetrahedron Lett 31:6121–6124.CrossRefGoogle Scholar
  77. Ösapay G, Bouvier M, Taylor JW (1991): In: Techniques in Protein Chemistry, Villafranca JJ, ed., pp. 221–321. San Diego: Academic Press.Google Scholar
  78. Ovchinnikov YA, Ivanov VT (1982): In: The Proteins, Neurath H, Hill RL, eds., pp. 307–642. New York: Academic Press.Google Scholar
  79. Photaki I (1976): In: Topics in Sulfur Chemistry, Senning A, ed., Vol. 1, pp. 111–183. Stuttgart: Georg Thieme.Google Scholar
  80. Plaué S (1990): Int J Pept Protein Res 35:510–517.PubMedCrossRefGoogle Scholar
  81. Ploux O, Chassaing G, Marquet A (1987): Int J Pept Protein Res 29:162–169.PubMedCrossRefGoogle Scholar
  82. Ponsati B, Giralt E, Andreu D (1990): Tetrahedron 46:8255–8266.CrossRefGoogle Scholar
  83. Rizo J, Gierasch LM (1992): Annu Rev Biochem 61:387–418.PubMedCrossRefGoogle Scholar
  84. Rothe M, Sander A, Fischer W, Mastle W, Nelson B (1977): In: Peptides, Proceedings of the 5th American Peptide Symposium, Goodman M, Meienhofer J, eds., pp. 506–509. New York: John Wiley.Google Scholar
  85. Rovero P, Quartara L, Fabbri G (1991): Tetrahedron Lett 32:2639–2642.CrossRefGoogle Scholar
  86. Royo M, García-Echeverría C, Giralt E, Eritja R, Albericio F (1992): Tetrahedron Lett 33:2391–2394.CrossRefGoogle Scholar
  87. Schiller PW, Nguyen TM-D, Lemieux C (1988): Tetrahedron 44:733–743.CrossRefGoogle Scholar
  88. Schiller PW, Nguyen TM-D, Miller J (1985): Int J Pept Protein Res 25:171–177.CrossRefGoogle Scholar
  89. Schiller PW, Nguyen TM-D, Maziak LA, Wilkes BC, Lemieux C (1987): J Med Chem 30:2094–2099.PubMedCrossRefGoogle Scholar
  90. Schiller PW, Weltrowska G, Nguyen TM-D, Lemieux C, Chung NN, Marsden BJ, Wilkes BC (1991):J Med Chem 34:3125–3132.PubMedCrossRefGoogle Scholar
  91. Schmidt U (1986): Pure Appl Chem 58:295–301.CrossRefGoogle Scholar
  92. Schwyzer R, Gorup B (1958): Helv Chim Acta 41:2199–2205.CrossRefGoogle Scholar
  93. Seidel C, Klein C, Empl B, Bayer H, Lin M, Batz H-G (1990): In: Peptides 1990, Proceedings of the 21st European Peptide Symposium, Giralt E, Andreu D, eds., pp. 236–237. Leiden: Escom.Google Scholar
  94. Small PW, Sherrington DC (1989): JChem Soc Chem Commun: 1589–1590.Google Scholar
  95. Smith DD, Slaninova J, Hruby VJ (1992): J Med Chem 35:1558–1563.CrossRefGoogle Scholar
  96. Solé NA, Kates SA, Albericio F, Barany G: In: Peptides: Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium, Hodges RS, Smith JA, eds. Leiden: Escom (in press).Google Scholar
  97. Spinella MJ, Malik AB, Everitt J, Andersen TT (1991): Proc Natl Acad Sci USA 88:7443–7446.PubMedCrossRefGoogle Scholar
  98. Tonelli AE (1986): In: Cyclic Polymers, Semlyen JA, ed., pp. 261–284. London: Elsevier.CrossRefGoogle Scholar
  99. Tromelin A, Fulachier M-H, Mourier G, Ménez A (1992): Tetrahedron Lett 33:5197–5200.CrossRefGoogle Scholar
  100. Trzeciak A, Bannwarth W (1992): Tetrahedron Lett 33:4557–4560.CrossRefGoogle Scholar
  101. Xu M, Nishino N, Mihara H, Fujimoto T, Izumiya N (1992): Chem Lett:191–194. Google Scholar
  102. Yajima H, Fujii N, Funakoshi S, Watanabe T, Murayama E, Otaka A (1988): Tetrahedron 44:805–819.CrossRefGoogle Scholar
  103. Zalipsky S, Albericio F, Barany G (1985): In: Peptides: Structure and Function, Proceedings of the 9th American Peptide Symposium, Deber CM, Hruby VJ, Kopple KD, eds., pp. 257–260. Rockford, Illinois: Pierce Chemical.Google Scholar

Copyright information

© Birkhäuser Boston 1994

Authors and Affiliations

  • Steven A. Kates
  • Núria A. Solé
  • Fernando Albericio
  • George Barany

There are no affiliations available

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