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Solid-Phase Synthesis of Cyclic Peptides

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Peptides

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.

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References

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • 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 

  • 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 

  • 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 

  • Barany G, Albericio F (1985): J Am Chem Soc 107:4936–4942.

    Article  CAS  Google Scholar 

  • Barany G, Merrifield RB (1977): JAm Chem Soc 99:7363–7365.

    Article  CAS  Google Scholar 

  • Barany G, Merrifield RB (1979): In: The Peptides, Gross E, Meienhofer J, eds., pp. 1–284. New York: Academic Press.

    Google Scholar 

  • Barany G, Kneib-Cordonier N, Mullen DG (1987): Int J Pept Protein Res 30:705–739.

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • Barlos K, Gatos D, Kutsogianni S, Papaphotiou G, Poulos C, Tsegenidis T (1991): Int J Pept Protein Res 38:562–568.

    Article  PubMed  CAS  Google Scholar 

  • Bloomberg GB, Askin D, Gargaro AR, Tanner MJA (1993): Tetrahedron Lett 34:4709–4712.

    Article  CAS  Google Scholar 

  • Blout ER (1981): Biopolymers 20:1901–1912.

    Article  CAS  Google Scholar 

  • Bodanszky M (1984): Principles of Peptide Synthesis. Berlin: Springer-Verlag.

    Book  Google Scholar 

  • Bondi E, Fridkin M, Patchornik A (1968): IsrJ Chem 6:22p.

    Google Scholar 

  • Bouvier M, Taylor JW (1992): J Med Chem 35:1145–1155.

    Article  PubMed  CAS  Google Scholar 

  • Brady SF, Paleveda WJ, Jr., Arison BH, Saperstein R, Brady EJ, Raynor K, Reisine T, Veber DF, Freidinger RM (1993): Tetrahedron 49:3449–3466.

    Article  CAS  Google Scholar 

  • Buchta R, Bondi E, Fridkin M (1986): Int J Pept Protein Res 28:289–297.

    Article  PubMed  CAS  Google Scholar 

  • Büllesbach EE (1992): Kontakte (Darmstadt) 1:21–29.

    Google Scholar 

  • 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 

  • Carpino LA (1993): J Am Chem Soc 115:4397–4398.

    Article  CAS  Google Scholar 

  • Castro B, Dormoy JR, Evin G, Selve C (1975): Tetrahedron Lett 16:1219–1222.

    Article  Google Scholar 

  • Cavelier F, Daunis J, Jacquier R (1989): Bull Soc Chim Fr 788–798.

    Google Scholar 

  • Cavelier F, Daunis J, Jacquier R (1990): Bull Soc Chim Fr 210–225.

    Google Scholar 

  • Consden RJ, Gordon AH, Martin AJP, Synge RDM (1947): Biochem J 41:596–602.

    CAS  Google Scholar 

  • Coste J, Le-Nguyen D, Castro B (1990): Tetrahedron Lett 31:205–208.

    Article  CAS  Google Scholar 

  • 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 

  • DeGrado WF, Kaiser ET (1980): JOrg Chem 45:1295–1300.

    Article  CAS  Google Scholar 

  • DeGrado WF, Kaiser ET (1982): JOrg Chem 47:3258–3261.

    Article  CAS  Google Scholar 

  • Edwards WB, Anderson CJ, Welch MJ, Fields CG, Fields GB: J Labelled Compd Radiopharm (in press).

    Google Scholar 

  • Eichler J, Bienert M, Stierandova A, Lebl M (1991): Pept Res 4:296–307.

    PubMed  CAS  Google Scholar 

  • Eritja R, Ziehler-Martin JP, Walker PA, Lee TD, Legesse K, Albericio F, Kaplan BE (1987): Tetrahedron 43:2675–2680.

    Article  CAS  Google Scholar 

  • Felix AM, Wang C-T, Heimer EP, Fournier A (1988a): Int J Pept Protein Res 31:231–238.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • Flanigan E, Marshall GR (1970): Tetrahedron Lett 2403–2406.

    Google Scholar 

  • Freidinger RM, Veber DF, Hirschmann R, Paege LM (1980): Int J Pept Protein Res 16:464–470.

    Article  PubMed  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Funakoshi S, Murayama E, Guo L, Fujii N, Yajima H (1988): J Chem Soc Chem Commun: 382–384.

    Google Scholar 

  • García-Echeverría C, Albericio F, Pons M, Barany G, Giralt E (1989): Tetrahedron Lett 30:2441–2444.

    Article  Google Scholar 

  • 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 

  • Giralt E, Eritja R, Navalpotro C, Pedroso E (1984): An Quim 80:118–122.

    CAS  Google Scholar 

  • Giralt E, Eritja R, JosaJ, Kuklinski C, Pedroso E (1985): Synthesis 181–184.

    Google Scholar 

  • Gisin BF, Merrifield RB (1972): J Am Chem Soc 94:3102–3106.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Hamada Y, Kato S, Shiori T (1985): Tetrahedron Lett 27:3223–3226.

    Article  Google Scholar 

  • Hill PS, Smith DD, Slaninova J, Hruby VJ (1990): J Am Chem Soc 112:3110–3113.

    Article  CAS  Google Scholar 

  • 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 

  • 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 

  • Hruby VJ (1982): Life Sci 31:189–199.

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • Hruby VJ, Al-Obeidi F, Kazmierski W (1990a): Biochem J 268:249–262.

    PubMed  CAS  Google Scholar 

  • 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 

  • Inukai N, Nakano K, Murakami M (1968): Bull Chem Socjpn 41:182–186.

    Article  CAS  Google Scholar 

  • Isied SS, Kuehn CG, Lyon JM, Merrifield RB (1982): J Am Chem Soc 104:2632–2634.

    Article  CAS  Google Scholar 

  • Kates SA, Solé NA, Johnson CR, Hudson D, Barany G, Albericio F (1993a): Tetrahedron Left 34:1549–1552.

    Article  CAS  Google Scholar 

  • Kates SA, Daniels SB, Albericio F (1993b): Anal Biochem 212:303–310.

    Article  PubMed  CAS  Google Scholar 

  • Kessler H (1982): Angew Chem Int Ed Engl 21:512–523.

    Article  Google Scholar 

  • König W, Geiger R (1981): In: Perspectives in Peptide Chemistry, Eberle A, Geiger R, Wieland T, eds., pp. 31–44. Basel: Karger.

    Google Scholar 

  • Kopple KD (1972): J Pharm Sci 61:1345–1356.

    Article  CAS  Google Scholar 

  • Lebl M, Hruby VJ (1984): Tetrahedron Lett 25:2067–2068.

    Article  CAS  Google Scholar 

  • 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 

  • Mazur S, Jayalekshmy P (1979): J Am Chem Soc 101:677–683.

    Article  CAS  Google Scholar 

  • McMurray JS (1991): Tetrahedron Lett 32:7679–7682.

    Article  CAS  Google Scholar 

  • Meldal M (1992): Tetrahedron Lett 33:3077–3080.

    Article  CAS  Google Scholar 

  • 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 

  • 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 

  • Munson MC, Barany G (1993): J Am Chem Soc 115:10203–10216.

    Article  CAS  Google Scholar 

  • Munson MC, Lebl M, Slaninová J, Barany G (1993): Pept Res 6:155–159.

    PubMed  CAS  Google Scholar 

  • Munson MC, García-Echeverría C, Albericio F, Barany G (1992): JOrg Chem57:3013–3018.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  • Ösapay G, Taylor JW (1990): J Am Chem Soc 112:6046–6051.

    Article  Google Scholar 

  • Ösapay G, Profit A, Taylor JW (1990): Tetrahedron Lett 31:6121–6124.

    Article  Google Scholar 

  • Ösapay G, Bouvier M, Taylor JW (1991): In: Techniques in Protein Chemistry, Villafranca JJ, ed., pp. 221–321. San Diego: Academic Press.

    Google Scholar 

  • Ovchinnikov YA, Ivanov VT (1982): In: The Proteins, Neurath H, Hill RL, eds., pp. 307–642. New York: Academic Press.

    Google Scholar 

  • Photaki I (1976): In: Topics in Sulfur Chemistry, Senning A, ed., Vol. 1, pp. 111–183. Stuttgart: Georg Thieme.

    Google Scholar 

  • Plaué S (1990): Int J Pept Protein Res 35:510–517.

    Article  PubMed  Google Scholar 

  • Ploux O, Chassaing G, Marquet A (1987): Int J Pept Protein Res 29:162–169.

    Article  PubMed  CAS  Google Scholar 

  • Ponsati B, Giralt E, Andreu D (1990): Tetrahedron 46:8255–8266.

    Article  CAS  Google Scholar 

  • Rizo J, Gierasch LM (1992): Annu Rev Biochem 61:387–418.

    Article  PubMed  CAS  Google Scholar 

  • 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 

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

    Article  CAS  Google Scholar 

  • Royo M, García-Echeverría C, Giralt E, Eritja R, Albericio F (1992): Tetrahedron Lett 33:2391–2394.

    Article  CAS  Google Scholar 

  • Schiller PW, Nguyen TM-D, Lemieux C (1988): Tetrahedron 44:733–743.

    Article  CAS  Google Scholar 

  • Schiller PW, Nguyen TM-D, Miller J (1985): Int J Pept Protein Res 25:171–177.

    Article  CAS  Google Scholar 

  • Schiller PW, Nguyen TM-D, Maziak LA, Wilkes BC, Lemieux C (1987): J Med Chem 30:2094–2099.

    Article  PubMed  CAS  Google Scholar 

  • Schiller PW, Weltrowska G, Nguyen TM-D, Lemieux C, Chung NN, Marsden BJ, Wilkes BC (1991):J Med Chem 34:3125–3132.

    Article  PubMed  CAS  Google Scholar 

  • Schmidt U (1986): Pure Appl Chem 58:295–301.

    Article  CAS  Google Scholar 

  • Schwyzer R, Gorup B (1958): Helv Chim Acta 41:2199–2205.

    Article  Google Scholar 

  • 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 

  • Small PW, Sherrington DC (1989): JChem Soc Chem Commun: 1589–1590.

    Google Scholar 

  • Smith DD, Slaninova J, Hruby VJ (1992): J Med Chem 35:1558–1563.

    Article  Google Scholar 

  • 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 

  • Spinella MJ, Malik AB, Everitt J, Andersen TT (1991): Proc Natl Acad Sci USA 88:7443–7446.

    Article  PubMed  CAS  Google Scholar 

  • Tonelli AE (1986): In: Cyclic Polymers, Semlyen JA, ed., pp. 261–284. London: Elsevier.

    Chapter  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Xu M, Nishino N, Mihara H, Fujimoto T, Izumiya N (1992): Chem Lett:191–194.

    Google Scholar 

  • Yajima H, Fujii N, Funakoshi S, Watanabe T, Murayama E, Otaka A (1988): Tetrahedron 44:805–819.

    Article  CAS  Google Scholar 

  • 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 

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Authors
  1. Steven A. Kates
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  2. Núria A. Solé
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  3. Fernando Albericio
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  4. George Barany
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Editors and Affiliations

  1. Novabiochem USA, 10394 Pacific Center Court, San Diego, CA, 92127, USA

    Channa Basava

  2. Atherosclerosis Research Unit, Department of Medicine, The University of Alabama at Birmingham, University Station, DREB 640, Birmingham, AL, 35924-0012, USA

    G. M. Anantharamaiah

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© 1994 Birkhäuser Boston

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Kates, S.A., Solé, N.A., Albericio, F., Barany, G. (1994). Solid-Phase Synthesis of Cyclic Peptides. In: Basava, C., Anantharamaiah, G.M. (eds) Peptides. Birkhäuser Boston. https://doi.org/10.1007/978-1-4615-8176-5_4

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  • DOI: https://doi.org/10.1007/978-1-4615-8176-5_4

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