Epimerization-free synthesis of cyclic peptide by use of the O-acyl isopeptide method

Journal of Peptide Science

Volumn 16, Issue 8, 2010, Pages 437-442

  Yoshiya, Taku ^a   Kawashima, Hiroyuki ^a   Hasegawa, Yuka ^a   Okamoto, Kazuhiro ^a   Kimura, Tooru ^a   Sohma, Youhei ^a   Kiso, Yoshiaki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Cyclic peptide; Epimerization; Isopeptide; O to N acyl migration; Racemization

Indexed keywords

CYCLIC O ACYL ISOPEPTIDE; CYCLOPEPTIDE; HEXAPEPTIDE; ISOPROTEIN; SILICA GEL; UNCLASSIFIED DRUG; PEPTIDE FRAGMENT;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CYCLIZATION; EPIMERIZATION; PRIORITY JOURNAL; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PEPTIDE FRAGMENTS; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 77957324874     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1261     Document Type: Article

References (33)

1. Veber DF, Freidinger RM, Perlow DS, Paleveda Jr WJ, Holly FW, Strachan RG, Nutt RF, Arison BH, Homnick C, Randall WC, Glitzer MS, Saperstein R, Hirschmann R. A potent cyclic hexapeptide analogue of somatostatin. Nature 1981; 292: 55-58.
2. Grieco P, Cai M, Liu L, Mayorov A, Chandler K, Trivedi D, Lin G, Campiglia P, Novellino E, Hruby VJ. Design and microwave-assisted synthesis of novel macrocyclic peptides active at melanocortin receptors: discovery of potent and selective hMC5R receptor antagonists. J.Med. Chem. 2008; 51: 2701-2707.
3. Mizuguchi T, Uchimura H, Kakizawa T, Kimura T, Yokoyama S, Kiso Y, Saito K. Inhibitory effect of a dimerization-arm-mimetic peptide on EGF receptor activation. Bioorg. Med. Chem. Lett. 2009; 19: 3279-3282.
4. Kessler H. Conformation and biological activity of cyclic peptides. Angew. Chem. Int. Ed. Engl. 1982; 21: 512-523.
5. Veber DF, Holly FW, Nutt RF, Bergstrand SJ, Brady SF, Hirschmann R, Glitzer MS, Saperstein R. Highly active cyclic and bicyclic somatostatin analogues of reduced ring size. Nature 1979; 280: 512-514.
6. Davies JS. The cyclization of peptides and depsipeptides. J. Pept. Sci. 2003; 9: 471-501.
7. Ehrlich A, Heyne H-U, Winter R, Beyermann, Haber H, Carpino LA, Bienert M. Cyclization of all-L-pentapeptides by means of 1-hydroxy- 7-azabenzotriazole-derived uronium and phosphonium reagents. J. Org. Chem. 1996; 61: 8831-8838.
8. Sohma Y, Sasaki M, Hayashi Y, Kimura T, Kiso Y. Novel and efficient synthesis of difficult sequence-containing peptides through O-N intramolecular acyl migration reaction of O-acyl isopeptides. Chem. Commun. 2004; 124-125.
9. Sohma Y, Yoshiya T, Taniguchi A, Kimura T, Hayashi Y, Kiso Y. Development of O-acyl isopeptide method. Biopolymers (Pept. Sci.) 2007; 88: 253-262.
10. Mutter M, Chandravarkar A, Boyat C, Lopez J, Dos Santos S, Mandal B, Mimna R, Murat K, Patiny L, Saucede L, Tuchscherer G. Switch peptides in statu nascendi: induction of conformational transitions relevant to degenerative diseases. Angew. Chem. Int. Ed. 2004; 43: 4172-4178.
11. Carpino LA, Krause E, Sferdean CD, Schuemann M, Fabian H, Bienert M, Beyermann M. Synthesis of "difficult" peptide sequences: application of a depsipeptide technique to the Jung-Redemann 10-and 26-mers and the amyloid peptide Aβ(1-42). Tetrahedron Lett. 2004; 45: 7519-7523.
12. Hentschel J, Krause E, Börner HG. Switch-peptides to trigger the peptide guided assembly of poly(ethylene oxide)-peptide conjugates into tape structures. J. Am. Chem. Soc. 2006; 128: 7722-7723.
13. Shigenaga A, Tsuji D, Nishioka N, Tsuda S, Itoh K, Otaka A. Synthesis of a stimulus-responsive processing device and its application to a nucleocytoplasmic shuttle peptide. ChemBioChem 2007; 8: 1929-1931.
14. Coin I, Beyermann M, Bienert M. Solid-phase peptide synthesis: from standard procedures to the synthesis of difficult sequences. Nat. Protoc. 2007; 2: 3247-3256.
15. Nepomniaschiy N, Grimminger V, Cohen A, DiGiovanni S, Lashuel HA, Brik A. Switch peptide via staudinger reaction. Org. Lett. 2008; 10: 5243-5246.
16. Vila-Perello M, Hori Y, Ribo M, Muir TW. Activation of protein splicing by protease- or light-triggered O to N Acyl migration. Angew. Chem. Int. Ed. 2008; 47: 7764-7767.
17. Kiso Y, Taniguchi A, Sohma Y. Click peptides, design and applications. In Wiley Encyclopedia of Chemical Biology, Vol. 1. Wiley: Hoboken, 2009; 379-383.
18. Boussert S, Diez-Perez I, Kogan MJ, de Oliveira E, Giralt E. An intramolecular O-N migration reaction on gold surfaces: toward the preparation of well-defined amyloid surfaces. ACS Nano 2009; 3: 3091-3097.
19. Taniguchi A, Sohma Y, Hirayama Y, Mukai H, Kimura T, Hayashi Y, Matsuzaki K, Kiso Y. "Click peptide": pH-triggered in situ production and aggregation of monomer Aβ(1-42). ChemBioChem 2009; 10: 710-715;
20. Spotlighted in Angew. Chem. Int. Ed. 2009; 48: 2444.
21. Bozso Z, Penke B, Simon D, Laczko I, Juhasz G, Szegedi V, Kasza A, Soos K, Hetenyi A, Weber E, Tohati H, Csete M, Zarandi M, Fulop L. Controlled in situ preparation of Aβ(1-42) oligomers from the isopeptide "iso-Aβ(1- 42)", physicochemical and biological characterization. Peptides 2010; 31: 248-256.
22. Cao P, Raleigh DP. Ester to amide switch peptides provide a simple method for preparing monomeric islet amyloid polypeptide under physiologically relevant conditions and facilitate investigations of amyloid formation. J. Am. Chem. Soc. 2010; 132: 4052-4053.
23. Yoshiya T, Sohma Y, Kimura T, Hayashi Y, Kiso Y. 'O-Acyl isopeptide method': racemization-free segment condensation in solid phase peptide synthesis. Tetrahedron Lett. 2006; 47: 7905-7909.
24. Yoshiya T, Kawashima H, Sohma Y, Kimura T, Kiso Y. O-Acyl isopeptide method: efficient synthesis of isopeptide segment and application to racemization-free segment condensation. Org. Biomol. Chem. 2009; 7: 2894-2904.
25. Coin I, Schmieder P, Bienert M, Beyermann M. J. Pept. Sci. 2008; 14: 299-306.
26. Lécaillon J, Gilles P, Subra G, Martinez J, Amblard M. Synthesis of cyclic peptides via O-N acyl migration. Tetrahedron Lett. 2008; 49: 4674-4676.
27. Carpino LA. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J. Am. Chem. Soc. 1993; 115: 4397-4398.
28. Carpino LA, El-Faham A. Effect of tertiary bases on O- benzotriazolyluronium salt-induced peptide segment coupling. J. Org. Chem. 1994; 59: 695-698.
29. Enholm E, Bharadwaj A. RGD mounted on an L-proline scaffold. Bioorg. Med. Chem. Lett. 2005; 15: 3470-3471.
30. Shioiri T, Ninomiya K, Yamada S. Diphenylphosphoryl azide. A new convenient reagent for a modified Curtius reaction and for the peptide synthesis. J. Am. Chem. Soc. 1972; 94: 6203-6205.
31. Brady SF, Freidinger RM, Paleveda WJ, Colton CD, Homnick CF, Whitter WL, Curley P, Nutt RF, Veber DF. Large-scale synthesis of a cyclic hexapeptide analogue of somatostatin. J. Org. Chem. 1987; 52: 764-769.
32. Taniguchi A, Yoshiya T, Abe N, Fukao F, Sohma Y, Kimura T, Hayashi Y, Kiso Y. 'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Aβ1-42 isopeptide using 'O-acyl isodipeptide unit'. J. Pept. Sci. 2007; 13: 868-874.
33. Stawikowski M, Cudic P. A novel strategy for the solid-phase synthesis of cyclic lipodepsipeptides. Tetrahedron Lett. 2006; 47: 8587-8590. (Pubitemid 44634600)