Controlled syntheses of natural and disulfide-mispaired regioisomers of α-conotoxin SI

Journal of Peptide Research

Volumn 54, Issue 6, 1999, Pages 468-479

  Hargittai, B ^a   Barany, G ^a  

^a University of Minnesota   (United States)

Author keywords

Conotoxin SI; Disulfide bridges; Disulfide mispaired regioisomers; Orthogonal synthesis

Indexed keywords

CONOTOXIN;

ARTICLE; DISULFIDE BOND; ISOMER; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN MODIFICATION; PROTEIN STABILITY;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CONOTOXINS; DISULFIDES; STEREOISOMERISM;

GASTROPODA;

EID: 0032760184     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00127.x     Document Type: Article

References (37)

1. Hargittai, B. & Barany, G. (1999) Intentional syntheses of disulfide-mispaired isomers of a-conotoxin SI and SIA. In Peptides: Frontiers of Peptide Science (Proceedings of the Fifteeneth American Peptide Symposium) (Tam, J.P. & Kaumaya, P.T.P., eds.). Kluwer, Dordrecht, The Netherlands. pp. 271-272.
2. Barany, G., Angell, Y.M., Annis, I., Chen, L., Gross, C.M. & Hargittai, B. (1999) Current strategies for disulfide bridge formation in synthetic peptides and proteins. In Innovations and Perspectives in Solid Phase Synthesis and Combinatorial Libraries, 1998 (Epton, R., ed.). Mayflower Scientific Ltd, Kingswinford, UK, pp. 85-88.
3. Hargittai, B., Groebe, D.R., Abramson, S.N. & Barany, G. (1999) Chemical syntheses and biological activities of α-conotoxin SI analogues: roles of disulfide bridges as judged by intentional misparing and lactam replacement. In Peptides-98: Proceedings of the Twenty-Fifth European Peptide Symposium (Hudecz, F. & Bajusz, S., eds.). Akadémia Kiadó, Budapest, Hungary, pp. 492-493.
4. Andreu, D., Albericio, F., Solé, N.A., Munson, M.C., Ferrer, M. & Barany, G. (1994) Formation of disulfide bonds in synthetic peptides and proteins. In Peptide Synthesis and Purification Protocols (Pennington, M.W. & Dunn, B.M., eds.). Humana Press, Clifton, NJ, pp. 91-169.
5. Moroder, L., Besse, D., Musiol, H.J., Rudolph-Böhner, S. & Siedler, F. (1996) Oxidative folding of cystine-rich peptides vs regioselective cysteine pairing strategies. Biopolymers (Peptide Science) 40, 207-234.
6. Annis, I., Hargittai, B. & Barany, G. (1998) Disulfide bond formation in peptides. Methods Enzymol. 289, 198-221.
7. Munson, M.C. & Barany, G. (1993) Synthesis of α-conotoxin SI, a bicyclic tridecapeptide amide with two disulfide bridges: illustration of novel protection schemes and oxidation strategies. J. Am. Chem. Soc. 115, 10203-10210.
8. Zafaralla, G.C., Ramilo, C., Gray, W.R., Karlstrom, R., Olivera, B.M. & Cruz, L.J. (1988) Phylogenetic specificity of cholinergic ligands: α-conotoxin SI. Biochemistry 27, 7102-7105.
9. Olivera, B.M., Rivier, J., Clark, C., Ramilo, C.A., Corpuz, G.P., Abogadie, F.C., Mena, E.E., Woodward, S.R., Hillyard, D.R. & Cruz, L.J. (1990) Diversity of Conus neuropeptides. Science 249, 257-263.
10. Groebe, D.R., Dumm, J.M., Levitan, E.S. & Abramson, S.N. (1995) α-Conotoxins selectively inhibit one of the two acctylcholine binding sites of nicotinic receptors. Mol. Pharmacol. 48, 105-111.
11. Nishiuchi, Y. & Sakakibara, S. (1982) Primary and secondary structure of conotoxin GI, a neurotoxic tridecapeptide from a marine snail. FEBS Lett. 48, 260-262.
12. Nishiuchi, Y. & Sakakibara, S. (1984) Synthesis of conotoxin MI and GII: structure-activity relationship of conotoxins. In Peptide Chemistry 1983 (Munekata, E., ed.). Protein Research Foundation, Osaka, Japan, pp. 191-196.
13. Hemmasi, B., Watanabe, T.X., Kimura, T. & Sakakibara, S. (1993) Solution synthesis of α-conotoxin SI and its biological activity. In Peptide Chemistry 1992: Proceedings of the 2nd Japanese Symposium on Peptide Chemistry (Yanaihara, H., ed.). ESCOM, Leiden, The Netherlands, pp. 155-157.
14. Gehrmann, J., Alewood, P.F. & Craik, D.J. (1998) Structure determination of the three disulfide bond isomers of α-conotoxin GI: a model for the role of disulfide bonds in structural stability. J. Mol. Biol. 278, 401-415.
15. Hunt, J.T., Lee, V.G., Liu, E.C.K., Moreland, S., McMullen, D., Webb, M.L. & Bolgar, M. (1993) Control of peptide disulfide regioisomer formation by mixed cysteine-penicillamine bridges. Int. J. Peptide Protein Res. 42, 249-258.
16. Spetzler, J.C., Rao, C. & Tam, J.P. (1994) A novel strategy for the synthesis of the cysteine-rich protective antigen of the malaria merozoite surface protein (MSP-1). Int. J. Peptide Protein Res. 43, 351-358.
17. Chen, H., Pyluck, A.L., Janik, M. & Sampson, N.S. (1998) Peptides corresponding to the epidermal growth factor-like domain of mouse fertilin: synthesis and biological activity. Biopolymers (Peptide Sci.) 47, 299-307.
18. Merrifield, R.B. (1986) Solid-phase synthesis (Nobel lecture). Science 232, 341-347.
19. Fields, G.B., Tian, Z. & Barany, G. (1992) Principles and practice of solid-phase peptide synthesis. In: Synthetic Peptides: A User's Guide (Grant, G.A., ed.). W.H. Freeman, New York, pp. 77-183.
20. Albericio, F., Kneib-Cordonier, N., Biancalana, S., Gera, L., Masada, R.I., Hudson, D. & Barany, G. (1990) Preparation and application of the 5-[4-(9-fluorenylmethyloxycarbonyl) aminomethyl-3,5-dimethoxyphenoxy]valeric acid (PAL) handle for the solid-phase synthesis of C-terminal peptide amides under mild condition. J. Org. Chem. 55, 3730-3743.
21. α-9-fluorenylmethyloxycarbonyl (Fmoc) strategy of peptide synthesis. J. Org. Chem. 62, 3841-3848.
22. Veber, D.F., Milkowski, J.D., Varga, S.L., Denkewalter, R.G. & Hirschmann, R. (1972) Acetamidomethyl. A novel thiol protecting group for cysteine. J. Am. Chem. Soc. 94, 5456-5461.
23. King, D.S., Fields, C.G. & Fields, G.B. (1990) A cleavage method which minimizes side reactions following Fmoc solid-phase peptide synthesis. Int. J. Peptide Protein Res. 36, 255-266.
24. 8]-dynorphin A. J. Org. Chem. 57, 5399-5403.
25. Van Abel, R.J., Tang, Y.-Q., Rao, V.S.V., Dobbs, C.H., Tran, D., Barany, G. & Selsted, M.E. (1995) Synthesis and characterization of indolicidin, a tryptophan-rich antimicrobial peptide from bovine neutrophils. Int. J. Peptide Protein Res. 45, 401-409.
26. Wallace, T.J. (1964) Reactions of thiols with sulfoxides. I. Scope of the reaction and synthetic applications. J. Am. Chem. Soc. 86, 2018-2021.
27. Tam, J.P., Wu, C.R., Liu, W. & Zhang, J.W. (1991) Disulfide bond formation in peptides by dimethyl sulfuxide. Scope and applications. J. Am. Chem. Soc. 113, 6657-6662.
28. Fujii, N., Otaka, A., Funakoshi, S., Bessho, K., Watanabe, T., Akaji, K. & Yajima, H. (1987) Studies on peptides. CLI. Syntheses of cystine peptides by oxidation of S-protected cysteine-peptides with thallium(III) trifluoroacetate. Chem. Pharm. Bull. 35, 2339-2347.
29. Kamber, B., Hartmann, A., Eisler, K., Riniker, B., Rink, H., Sieber, P. & Rittel, W. (1980) The synthesis of cystine peptides by iodine oxidation of S-trityl-cysteine and S-acetamidomethyl-cysteine peptides. Helv. Chim. Acta 63, 899-915.
30. Koide, T., Otaka, A., Suzuki, H. & Fujii, N. (1991) Selective conversion of S-protected cysteine derivatives to cystine by various sulphoxide-silyl compound/trifluoroacetic acid systems. Synlett 345-346.
31. Akaji, K., Tatsumi, T, Yoshida, M., Kimura, T., Fujiwara, Y. & Kiso, Y. (1992) Disulfide bond formation using the silyl chloride-sulfoxide system for the synthesis of a cystine peptide. J. Am. Chem. Soc. 114, 4137-4143.
32. Akaji, K., Nishiuchi, H. & Kiso, Y. (1995) Synthesis of human endothelin-1 by regioselective disulfide formation using the silyl chloride-sulfoxide system. Tetrahedron Lett. 36, 1875-1878.
33. Albericio, F., Hammer, R.P., Garcia-Echeverría, C., Molins, M.A., Chang, J.L., Munson, M.C., Pons, M., Giralt, E. & Barany, G. (1991) Cyclization of disulfide-containing peptides in solid-phase synthesis. Int. J. Peptide Protein Res. 37, 402-413.
34. Mazur, S. & Jayalekshmy, P. (1979) Chemistry of polymer-bound o-benzyne. Frequency of encounter between substituents on cross linked polystyrenes. J. Am. Chem. Soc. 101, 677-683.
35. Barany, G. & Merrifield, R.B. (1979) Solidphase peptide synthesis. In The Peptides-Analysis, Synthesis, Biology Vol. 2 [Gross, E. & Meienhofer, J., eds.). Academic Press, New York, pp. 1-284. (particularly pp. 27-29).
36. Misicka, A. & Hruby, V.J. (1994) Optimization of disulfide bond formation. Polish J. Chem. 68, 893-899.
37. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34, 595-598.