Enhanced microwave-assisted method for on-bead disulfide bond formation: Synthesis of α-comotoxin MII

Biopolymers

Volumn 92, Issue 1, 2009, Pages 23-34

  Galanis, Athanassios S ^a,b,c   Albericio, Fernando ^b,c   Grøtli, Morten ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b UNIVERSITY OF BARCELONA   (Spain)

^c INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

Author keywords

conotoxin MII; 2,2 dithiobis (5 nitropyridine); Conopeptide; Conotoxin; Disulfide bond; Microwave assisted heating; Solid phase peptide synthesis

Indexed keywords

CONOPEPTIDE; CONOTOXIN; DISULFIDE BOND; MICROWAVE ASSISTED HEATING; SOLID PHASE PEPTIDE SYNTHESIS;

CYCLIZATION; HEATING; MICROWAVES; RESINS;

AMINES;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CONOTOXINS; DISULFIDES; HYDROPHOBICITY; MICROWAVES; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; SOLUTIONS;

EID: 60149105961     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21116     Document Type: Article

References (39)

1. Bruckdorfer, T.; Marder, O.; Albericio, F. Curr Pharm Biotechnol 2004, 5, 29-43.
2. Sehgal, A. New Applications in Discovery, Manufacturing, and Therapeutics. In: Peptides 2006, Research and Markets, Ireland (2006).
3. Cupido, T.; Tulla-Puche, J.; Spengler, J.; Albericio, F. Curr Opin Drug Discov Dev 2007, 10, 768-783.
4. Curran, M. P.; Keating, G. M. Drugs 2005, 65, 2009-2035.
5. Barlocco, D. Curr Opin Invest Drugs 2001, 2, 1575-1581.
6. Prommer, E. Drugs Today 2006, 42, 369-378.
7. Annis, I.; Hargittai, B.; Barany, G. Methods Enzymol 1997, 289, 198-221.
8. Barany, G.; Angell, Y. M.; Annis, I.; Chen, L.; Gross, C. M.; Hargittai, B. In Innovations and Perspectives in Solid Phase Synthesis and Combinatorial Libraries; Epton, R., Ed.; Mayflower Scientific: Kingswinford, UK, 1998; pp 85-88.
9. Andreu, D.; Albericio, F.; Sole, N. A.; Munson, M. C.; Ferrer, M.; Barany, G. In Peptide Synthesis and Purification Protocols; Pennington, M. W.; Dunn, B. M., Eds.; Humana Press, Totowa, 1994; pp 91-169.
10. Moroder, L.; Besse, D.; Musiol, H. J.; Rudolph-Bohner, S.; Siedler, F. Biopolymers 1996, 40, 207-234.
11. Kellenberger, C.; Hietter, H.; Luu, B. Pept Res 1995, 6, 321-327.
12. Tam, J. P.; Wu, C. R.; Liu, W.; Zhang J. W. J Am Chem Soc 1991, 113, 6657-6662.
13. Albericio, F.; Hammer, R. P.; García-Echeverría, C.; Molins, M. A.; Chang, J. L.; Munson, M. C.; Pons, M.; Giralt, E.; Barany, G. Int J Pept Protein Res 1991, 37, 402-413.
14. Annis, I.; Chen, L.; Barany, G. J Am Chem Soc 1998, 120, 7226-7238.
15. Munson, M. C.; Barany, G. J Am Chem Soc 1993, 115, 10203-10210.
16. Edwards, W. B.; Fields, C. G.; Anderson, C. J.; Pajeau, T. S.; Welch, M. J.; Fields, G. B. J Med Chem 1994, 37, 3749-3757.
17. Han, Y.; Barany, G. J Org Chem 1997, 62, 3841-3848.
18. Cartier, G. E.; Yoshikami, D.; Gray, W. R.; Luo, S.; Olivera, B. M.; McIntosh, J. M. J Biol Chem 1996, 271, 7522-7528.
19. Harvey, S. C.; McIntosh, J. M.; Cartier, G. E.; Maddox, F. N.; Luetje, C. W. Mol Pharmacol 1997, 51, 336-342.
20. Galande, K.; Weissleder, R.; Tung, C.-H. J Comb Chem 2005, 7, 174-177.
21. Kappe, C. O.; Dallinger, D. Nat Rev Drug Discov 2006, 5, 51-63.
22. Cravotto, G.; Cintas, P. Chem Eur J 2007, 13, 1902-1909.
23. De La Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem Soc Rev 2005, 34, 164-178.
24. Grieco, P. Chimica Oggi 2004, 22, 18-20.
25. Murray, J. K.; Gellman, S. H. Nat Protocol 2007, 2, 624-631.
26. García-Martín, F.; Bayó-Puxan, N.; Cruz, L. J.; Bohling, J. C.; Albericio, F. QSAR Comb Sci 2007, 26, 1027-1035.
27. Murray, J. K.; Gellman, S. H. Org Lett 2005, 7, 1517-1520.
28. Rizzolo, F.; Sabatino, G.; Chelli, M.; Rovero, P.; Papini, A. M. Int J Pept Res Ther 2007, 13, 203-208.
29. Brandt, M.; Gammeltoft, S.; Jensen, K. J. Int J Pept Res Ther 2006, 12, 349-357.
30. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal Biochem 1970, 34, 595-598.
31. Vojkovsky, T. Pept Res 1995, 8, 236-237.
32. Fields, G. B.; Noble, R. L. Int J Pept Protein Res 1990, 35, 161-214.
33. Chan, W.; White, P. Fmoc Solid Phase Peptide Synthesis. A Practical Approach; Oxford University Press, Oxford, 2000.
34. Yu, H.-M.; Chen, S.-T.; Wang, K.-T. Org Chem 1992, 57, 4781-4784.
35. Rink, H. Tetrahedron Lett 1987, 28, 3787-3790.
36. Barlos, K.; Gatos, D.; Hatzi, O.; Koch, N.; Koutsogianni, S. Int J Pept Protein Res 1996, 47, 148-153.
37. Veber, D. F.; Milkowski, J. D.; Varga, S. L.; Denkewalter, R. G.; Hirschmann, R. J Am Chem Soc 1972, 94, 5456-5461.
38. Eritja, R.; Ziehler-Martin, J. P.; Walker, P. A.; Lee, T. D.; Legesse, K.; Albericio, F.; Kaplan, B. E. Tetrahedron 1987, 43, 2615-2680.
39. Bacsa, B.; Desai, B.; Dibó, G.; Kappe C. O. J Pept Sci 2006, 12, 633-638.