Efficient methodology for the cyclization of linear peptide libraries via intramolecular S-alkylation using Multipin™ solid phase peptide synthesis

Journal of Peptide Science

Volumn 12, Issue 8, 2006, Pages 525-532

  Roberts, Kade D ^a,b   Lambert, John N ^a,c   Ede, Nicholas J ^b   Bray, Andrew M ^b,d  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b Mimotopes Pty Ltd   (Australia)

^c Biota Holdings Ltd   (Australia)

^d PharmaBank   (Australia)

Author keywords

Cyclic peptides; Cyclic thioethers; Cyclization of linear peptides; Multipin solid phase peptide synthesis; Peptide libraries; S alkylation; SynPhase

Indexed keywords

PEPTIDE DERIVATIVE; PEPTIDE LIBRARY; TYPE II SITE SPECIFIC DEOXYRIBONUCLEASE;

ALKYLATION; ARTICLE; CONTROLLED STUDY; CRYSTALLOGRAPHY; CYCLIZATION; ENZYME ACTIVE SITE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN MOTIF; PROTEIN STRUCTURE; SOLID PHASE SYNTHESIS;

ALKYLATION; AMINO ACID SEQUENCE; CHROMATOGRAPHY, LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; REPRODUCIBILITY OF RESULTS;

EID: 33747258349     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.761     Document Type: Article

References (55)

1. Roberts KD, Lambert JN, Ede NJ, Bray AM. Efficient synthesis of thioether-based cyclic peptide libraries. Tett. Lett. 1998, 39: 8357.
2. Roberts KD, Development of new methodologies for the synthesis and screening of type II restriction endonucleases. Thesis (PhD), 2003; University of Melbourne.
3. Roberts KD, Lambert JN, Ede NJ, Bray AM. Preparation of cyclic peptide libraries using intramolecular oxime formation. J. Pept. Sci. 2004; 10: 659.
4. Selent U, Ruter T, Kohler E, Lidetke M, Thielking V, Alves J, Oelgeschlager T, Wolfes H, Frens P, Pingoud A. A site-directed mutagenesis study to identify amino acid residues involved in the catalytic function of the restriction endonuclease, EcoRV. Biochemistry 1992; 31: 4808.
5. Winkler FK, Banner DW, Oefner C, Tsernoglou D, Brown RS, Bryan RK, Martin PD, Petratos K, Wilson KS. The crystal structure of EcoRV endonuclease and of its complexes with cognate and non-cognate DNA fragments. EMBO J. 1993; 12: 178.
6. 2+ binding to the active site of EcoRV endonuclease: a crystallographic study of complexes with substrate and product DNA at 2-Ang. resolution. Biochemistry 1995; 34: 683.
7. Vipond BI, Baldwin GS, Halford SE. Divalent metal ions at the active sites of the EcoRV and EcoRI restriction endonucleases. Biochemistry 1995; 34: 697.
8. Sam MD, Perona JJ. Catalytic roles of divalent metal ions in phosphoryl transfer by EcoRV endonuclease. Biochemistry 1999; 38: 6576.
9. Thomas MP, Brady RL, Halford SE, Sessions RB, Baldwin GS. Structural analysis of a mutational hot-spot in the EcoRV restriction endonuclease: a catalytic role for a main chain carbonyl group. Nucleic Acids Res. 1999; 27: 3438.
10. Baldwin GS, Sessions RB, Halford SE. DNA cleavage by the EcoRV restriction endonuclease: roles of divalent metal ions in specificity and catalysis. J. Mol. Biol. 1999; 288: 87.
11. Kim Y, Choi J, Grable JC, Greene PJ, Rosenberg JM. Refinement of EcoRI endonuclease crystal structure: a revised protein chain tracing. Science 1990; 249: 1307.
12. Grabowski G, Jeltsch A, Wolfes H, Maass G, Alves J. Site-directed mutagenesis in the catalytic centre of the restriction endonuclease EcoRI. Gene 1995; 157: 113.
13. Cheng X, Balendiran K, Schildkraut I, Anderson JE. Structure of PvuII endonuclease with cognate DNA. EMBO J. 1994; 13: 3927.
14. Horton JR, Cheng X. PvuII endonuclease contains two calcium ions in active sites. J. Mol. Biol. 2000; 300: 1049.
15. Dupureur CM, Conlan LH. A catalytically deficient active site variant of PvuII endonuclease binds Mg(II) ions. Biochemistry 2000; 39: 10921.
16. Newman M, Strzelecka T, Dorner LF, Schildkraut I, Aggarawal AK. Structure of restriction endonuclease BamHI and its relationship to EcoRI. Nature 1994; 388: 660.
17. Newman M, Strezlecka T, Dorner LF, Schildkraut I, Aggarawal AK. A. Structure of BamHI endonuclease bound to DNA; Partial folding and unfolding on. Science 1995; 269: 656.
18. Newman M, Lunnen K, Wilson G, Greci J, Schildkraut I, Phillips SE. Crystal structure of restriction endonuclease BglI bound to its interrupted DNA recognition sequence. EMBO J. 1998; 17: 5466.
19. Maclean D, Baldwin JJ, Itanov VT, Kato Y, Shaw A, Scheneider P, Gordon EM. Glossary of terms used in combinatorial chemistry. Pure Appl. Chem. 1999; 71: 2349.
20. Lambert JN, Mitchell JP, Roberts RD. Synthesis of cyclic peptides. J. Chem. Soc., Perkin Trans. I 2001; 471.
21. Li P, Roller PP, Xu J. Current synthetic approaches to peptide and peptidomimetic cyclization. Curr. Org. Chem. 2002; 6: 411.
22. Davies JS. The cyclization of peptides and depsipeptides. J. Pept. Sci. 2003; 9: 471.
23. Bourne GT, Golding SW, McGeary RP, Meutermans WDF, Jones A, Marshall GR, Alewood PF, Smythe ML. The development and application of a novel safety-catch linker for Boc-based assembly of libraries of cyclic peptides. J. Org. Chem. 2001; 66: 7706.
24. Ravin J, Bourne GT, Smythe ML. A safety catch linker for Fmoc-based assembly of constrained cyclic peptides. J. Pept. Sci. 2005; 11: 572.
25. Meutermans WDF, Bourne GT, Golding SW, Horton DA, Campitelli MR, Craik D, Scanlon M, Smythe ML. Difficult macrocyclizations; new strategies for synthesizing highly strained cyclic tetrapeptides. Org. Lett. 2003; 5: 2711.
26. Robey FA, Fields RL. Automated synthesis of N-bromoacetyl-modified peptides for the preparation of synthetic peptide polymers, peptide-protein conjugates, and cyclic peptides. Anal. Biochem. 1989; 177: 373.
27. Robey FA. Peptide Synthesis Protocols. Humana press: New Jersey, 1994.
28. Barker PL, Bullens S, Bunting S, Burdick DJ, Chan KS, Deisher T, Eigenbrot C, Gadek TR, Gantzos R, Lipari MT. Cyclic RDG peptide analogues as antiplatelet antithrombotics. J. Med. Chem. 1992; 35: 2040.
29. Bitan G, Zeltser I, Byk G, Halle D, Mashriki Y, Gluhov EV, Sukhotinsky I, Hanani M, Selinger Z, Gilon C. Backbone cyclization of the C-terminal part of substance P. part 1: the important role of the sulfur in position 11. J. Pept. Sci. 1996; 2: 261.
30. Akamatsu M, Roller PP, Chen L, Zhang ZY, Ye B, Burke TR. Potent inhibition of protein-tyrosine phosphatase by phosphotyrosine-mimic containing cyclic peptides. Bioorg. Med. Chem. 1997; 5: 157.
31. Olingo L, Lung FT, Sastry L, Bigeolw J, Cao T, Curran M, Burke TR, Wang S, Krga D, Roller PP, Ritcher King C Jr. Nonphosphorylated peptide ligands for the Grb2 Src homology 2 domain. J. Biol. Chem. 1997; 46: 29046.
32. Yu L, Lai Y, Wade JV, Coutts SM. A simple and efficient method for the synthesis of thioether cyclic peptides. Tet. Lett. 1998; 39: 6633.
33. Long Y, Voigt JH, Lung FT, Ritcher King C, Roller PP. Significant compensatory role of position Y-2 conferring high affinity to non-phosphorylated inhibitors of Grb2-Sh2 domain. Bioorg. Med. Chem. Lett. 1999; 9: 2267.
34. Fotouhi N, Joshi P, Tilley JW, Rowan K, Schwinge V, Wolitzky B. Cyclic thioether peptide mimetics as VCAM-VLA-4 antagonists. Bioorg. Med. Chem. Lett. 2000; 10: 1167.
35. 2-OH and design of potent Pmp-Containing Grb2-Sh2 Domain Antagonists. Org. Lett. 2003; 5: 3095.
36. 1A vasopressin receptor are structurally related to the second intracellular Rhopdopsin Loop: A combined 1H NMR and biochemical study. Biochemistry 2003; 42: 8204.
37. Long YQ, Lung FT, Roller PP. Global optimization of conformational constraints on non-phosphorylated cyclic peptide antagonists of the Grb2-SH2 domain. Bioorg. Med. Chem. 2003; 11: 3929.
38. Schlosser G, Mezo G, Kiss R, Vass E, Majer Z, Feijlbreif M, Perczel A, Bosze S, Welling-Wester S, Hudecz F. Synthesis, solution structure analysis and antibody binding of cyclic epitope peptides from glycoprotein D of herpes simplex virus type I. Biophys. Chem. 2003; 155.
39. Baidoo KE, Knight LC, Lin KS, Gabriel JL, Romano JE. Design and synthesis of a short-chain bitistatin analogue for imaging thrombi and emboli. Bioconjugate Chem. 2004; 15: 1068.
40. Tugyi R, Mezo G, Fellinger E, Andreu D, Hudecz F. The effect of cyclization on the enzymatic degradation of herpes simplex virus glycoprotein D derived epitope peptide. J. Pept. Sci. 2005; 11: 642.
41. 2+-binding loop of α-lactalbumin. Bioorg. Med. Chem. 2005; 13: 5310.
42. Mayer JP, Heil JR, Zhang J, Munson MC. An alternative solid-phase approach to C1-oxytocin. Tet. Lett. 1995; 95: 7387.
43. Gazal S, Gellerman G, Glukohov E, Gilon C. Synthesis of novel protected Nα (ω-thioalkyl) amino acid building nits and their incorporation in backbone cylic disulfide and thioetheric bridged peptides. J. Pept. Res. 2001; 58: 527.
44. Bondebjerg J, Grunnet M, Jespersen T, Meldal M. Solid phase synthesis and biological activity of a thioether analogue of conotoxin G1. ChemBioChem 2003; 4: 186.
45. Osapay G, Prokai L, Kim H, Medzihradszky KF, Coy DH, Liapakis G, Reisine T, Melacini G, Zhu Q, Wang SH, Mattern R, Goodman M. Lanthionine-somatostatin analogues: synthesis, characterization, biological activity, and enzymatic stability studies. J. Med. Chem. 1997; 40: 2241.
46. Chan WC, White PD. Fmoc Solid Phase Peptide Synthesis. Oxford university Press: New York, 2000.
47. Rasoul F, Ercole F, Pham Y, Bui CT, Wu Z, James SN, Trainor RW, Wickham G, Maeji JN. Grafted supports in solid phase synthesis. Biopolymers 2000; 55: 207.
48. Ede NJ. Multiple parallel synthesis of peptides on SynPhase™ grafted supports. J. Immunol. Methods 2002; 267: 3.
49. Parsons JG, Sheehan GS, Zemin W, James IW, Bray AM. A review of solid-phase organic synthesis on SynPhase™ Lanterns and SynPhase™ Crowns. Methods Enzymol. 2003; 389: 39.
50. Virgilio AA, Ellman JA. Simultaneous solid-phase synthesis of β-turn mimetics incorporating side-chain functionality. J. Am. Chem. Soc. 1994; 118: 11580.
51. Virgilio AA, Bray AM, Zhang W, Trinh L, Snyder M, Morrissey MM, Ellma JA. Synthesis and Evaluation of a library of peptidomimetics based upon the β-turn. Tetrahedron 1997; 53: 6635.
52. Barlos K, Gatos D, Hatzi O, Koch N, Koutsogianni S. Synthesis of the very acid-sensitive Fmoc-Cys(Mmt)-OH and its application in solid-phase peptide synthesis. Int. J. Pept. Protein Res. 1996; 47: 148.
53. NAr macrocyclizations to give turn-extended-turn peptidomimetics. Chem. Eur. J. 1999; 5: 3261.
54. Ellman G. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 1959; 82: 70.
55. Han Y, Albericio F, Barany G. Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis. J. Org. Chem. 1997; 62: 4307.