Rapid solid-phase synthesis of a calmodulin-binding peptide using controlled microwave irradiation

Nature Protocols

Volumn 2, Issue 9, 2007, Pages 2222-2227

  Bacsa, Bernadett ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CALMODULIN BINDING PROTEIN; NONAPEPTIDE; CALMODULIN; PEPTIDE;

ARTICLE; COUPLING FACTOR; DEPROTECTION REACTION; MICROWAVE IRRADIATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN PURIFICATION; REACTION TIME; ROOM TEMPERATURE; SOLID PHASE SYNTHESIS; TEMPERATURE SENSITIVITY; AMINO ACID SEQUENCE; BINDING SITE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METABOLISM; MICROWAVE RADIATION; RADIATION EXPOSURE; SYNTHESIS;

AMINO ACID SEQUENCE; BINDING SITES; CALMODULIN; COMBINATORIAL CHEMISTRY TECHNIQUES; MICROWAVES; PEPTIDES;

EID: 38449099548     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2007.300     Document Type: Article

References (28)

1. Marx, V. Watching peptide drugs grow up. Chem. Eng. News 83, 17-24 (2004).
2. Pichereau, C. & Allary, C. Therapeutic peptides under the spotlight. Euro. Biophorm. Rev. (WINTER), 88-93 (2005).
3. Chan, W.C. & White, P.D. Fmoc Solid Phase Peptide Synthesis (Oxford University Press, Oxford, 2000).
4. Hodge, P. Polymer-supported organic reactions: What takes places in the beads? Chem. Soc. Rev. 26, 417-424 (1997).
5. Günther, W., Matthias, U. & Birgitt, S. Medicinal chemistry: challenges and opportunities. Angew. Chem. Int. Ed. 40, 3341-3350 (2001).
6. Tam, J.P. & Lu, Y.-A. Coupling difficulty associated with interchain clustering and phase-transition in solid-phase peptide synthesis. J. Am. Chem. Soc. 117, 12058-12063 (1995).
7. Hyde, C., Johnson, T., Owen, D., Quibell, M. & Sheppard, R.C. Some 'difficult sequences' made easy: A study of interchain association in solid-phase peptide synthesis. Int. J. Peptide Protein Res. 43 431-440 (1994).
8. Kappe, C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 43, 6250-6284 (2004).
9. Kappe, C.O. & Stadler, A. Microwaves in Organic and Medicinal Chemistry (Wiley-VCH, Weinheim, Germany, 2005).
10. Loupy, A. (ed.) Microwaves in Organic Synthesis 2nd edn. (Wiley-VCH, Weinheim, Germany, 2006).
11. Kappe, C.O. & Dallinger, D. The impact of microwave synthesis on drug discovery. Nat Rev. Drug Discov. 5, 51-64 (2006).
12. Yu, H.M., Chen, S.-T. & Wang, K.T. Enhanced coupling efficiency in solid phase peptide synthesis by microwave irradiation. J. Org. Chem. 57, 4781-4784 (1992).
13. Erdelyi, M. & Gogoll, A. Rapid microwave-assisted solid-phase peptide synthesis. Synthesis 11, 1592-1596 (2002).
14. Matsushita, T., Hinou, H., Kurogochi, M., Shimizu, H. & Nishimura, S.I. Rapid microwave-assisted solid-phase glycopeptide synthesis. Org. Lett. 7, 877-880 (2005).
15. Brandt, M., Gammeltoft, S. & Jensen, K.J. Microwave heating for solid-phase peptide synthesis: General evaluation and application to 15-mer phosphopeptides. Int. J. Pept. Prot. Res. 12, 349-357 (2006).
16. Gorske, B.C., Jewell, S.A., Guerard, E.J. & Blackwell, H.E. Expedient synthesis and design strategies for new peptoid construction. Org. Lett. 7, 1521-1524 (2005).
17. Olivos, H.J., Alluri, P.G., Reddy, M.M., Salony, D. & Kodadek, T. Microwave-assisted solid-phase synthesis of peptoids. Org. Lett. 4, 4057-4059 (2002).
18. Fara, M.A., Díaz-Mochón, H.J. & Bradley, M. Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labelled peptides - a gentle heat goes a long way. Tetrahedron Lett. 47, 1011-1014 (2006).
19. Murray, J. K. & Gellman, S.H. Application of microwave irradiation to the synthesis of 14-helical β-peptides. Org. Lett. 7, 1517-1520 (2005).
20. Murray, J.K. et al. Efficient synthesis of a β-peptide combinatorial library with microwave irradiation. J. Am. Chem. Soc. 127, 13271-13280 (2005).
21. Murray, J.K. & Gellman, S.H. Microwave-assisted parallel synthesis of a 14-helical β-peptide Library. J. Comb. Chem. 8, 58-65 (2006).
22. Murray, J.K. & Gellman, S.H. Parallel synthesis of peptide libraries using microwave irradiation. Nat. Protoc. 2, 624-631 (2007).
23. Collins, J.M. & Collins, M.J. Microwave-enhanced solid-phase peptide synthesis. in Microwaves in Organic Synthesis 2nd edn. (ed. Loupy, A.) 898-958 (Wiley-VCH, Weinheim, Germany, 2006).
24. Palasek, S.A., Cox, Z.J. & Collins, J.M. Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis. J. Pept. Sci. 13, 143-148 (2007).
25. Collins, J.M. & Leadbeater, N.E. Microwave energy: A versatile tool for the biosciences. Org. Biomol. Chem. 5, 1141-1150 (2007).
26. Rizzolo, F., Sabatino, G., Chelli, M., Rovero, P. & Papini, A.M. A convenient microwave-enhanced solid-phase synthesis of difficult peptide sequence: Case study of Gramicidin A and CSF114(Glc). Int. J. Pept. Res. Ther. 13, 203-208 (2007).
27. Bacsa, B., Desai, B., Dibo, G. & Kappe, C.O. Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation. J. Pept. Sci. 12, 633-638 (2006).
28. Nevalainen, L.T. et al. Characterization of novel calmodulin-binding peptides with distinct inhibitory effects on calmodulin-dependent enzymes. Biochem. J. 321, 107-115 (1997).