The use of hydrogen peroxide for closing disulfide bridges in peptides

Russian Journal of Bioorganic Chemistry

Volumn 30, Issue 2, 2004, Pages 101-110

  Sidorova, M V ^a   Molokoedov, A S ^a   Az'muko, A A ^a   Kudryavtseva, E V ^a   Krause, E ^b   Ovchinnikov, M V ^a   Bespalova, Zh D ^a  

^a N N BLOKHIN NATIONAL MEDICAL RESEARCH CENTER OF ONCOLOGY   (Russian Federation)

^b LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

Author keywords

Chemical synthesis; Disulfide bond; Hydrogen peroxide; Natural peptides and their analogues

Indexed keywords

DISULFIDE; HISTIDYLALANYLGLYCYLCYSTEINYLLYSYLASPARAGINYLPHENYLALANYLPHENYLALANYL TRYPTOPHYLLYSYLTHREONYLPHENYLALANYLTHREONYLSERYLCYSTEINE HYDROXIDE; HISTIDYLCYSTEINYLSERYLCYSTEINYLSERYLLEUCYLMETHIONYLASPARTYLLYSYLGLUTAMYL CYSTEINYLVALYLTYROSYLPHENYLALANYLCYSTEINYLHISTIDYLLEUCYLASPARTYLHISTIDYL TRYPTOPHAN HYDROXIDE; HISTIDYLCYSTEINYLTHREONYLCYSTEINYLPHENYLALANYLTHREONYLTYROSYLLEUCYL ASPARTYLLYSYLGLUTAMYLCYSTEINYLVALYLTYROSYLTYROSYLCYSTEINYLHISTIDYLLEUCYL ASPARTYLHISTIDYLTRYPTOPHAN HYDROXIDE; HISTIDYLCYSTEINYLTYROSYLISOLEUCYLGLUTAMINYLASPARAGINYLCYSTEINYLPROLYL LEUCYLGLYCINAMIDE; HISTIDYLLEUCYLGLUTAMINYLASPARTYLGLUTAMINYLALANYLARGINYLLEUCYLASPARAGINYL SERYLTRYPTOPHYLGLYCYLCYSTEINYLALANYLPHENYLALANYLARGINYLGLUTAMINYLVALYLCYSTEINYL HISTIDYLTHREONYLTHREONYLVALINE HYDROXIDE; HISTIDYLSERYLLEUCYLARGINYLARGINYLSERYLSERYLCYSTEINYLPHENYLALANYLGLYCYL GLYCYLARGINYLISOLEUCYLASPARTYLARGINYLISOLEUCYLGLYCYLALANYLGLUTAMINYLSERYLGLYCYL LEUCYLGLYCYLCYSTEINYLASPARAGINYLSERYLPHENYLALANYLARGINYLTYROSINE HYDROXIDE; HISTIDYLSERYLSERYLCYSTEINYLPHENYLALANYLGLYCYLGLYCYLARGINYLISOLEUCYL ASPARTYLARGINYLISOLEUCYLGLYCYLALANYLGLUTAMINYLSERYLGLYCYLLEUCYLGLYCYLCYSTEINYL ASPARAGINYLSERYLPHENYLALANYLARGININE HYDROXIDE; HISTIDYLSERYLSERYLCYSTEINYLPHENYLALANYLGLYCYLGLYCYLARGINYLISOLEUCYL ASPARTYLARGINYLISOLEUCYLGLYCYLALANYLGLUTAMINYLSERYLGLYCYLLEUCYLGLYCYLCYSTEINYL ASPARAGINYLSERYLPHENYLALANYLARGINYLTYROSINE HYDROXIDE; HISTIDYLTRYPTOPHYLGLYCYLCYSTEINYLSERYLGLYCYLLYSYLLEUCYLISOLEUCYLCYSTEINYL THREONYLTHREONYLALANYLVALYLPROLYLTRYPTOPHYLASPARAGINYLALANINE HYDROXIDE; HYDROGEN PEROXIDE; IODINE; METHIONINE; OCTREOTIDE; OXYTOCIN; PEPTIDE; TRYPTOPHAN; TYROSINE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 3543132499     PISSN: 10681620     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUBI.0000023093.05123.31     Document Type: Article

References (20)

1. Andreu, D., Albericio, F., Sole, N.A., Munson, M.C., Ferrer, M., and Barany, G., Peptide Synthesis Protocols, Pennington, W. and Dunn, M.B., Eds., Totowa, NJ: Humana, 1994, pp. 91-169.
2. Sidorova, M.V., Kudryavtseva, E.V., and Evstigneeva, R.P., Usp. Khim., 1998, vol. 67, pp. 611-630.
3. Hardy, P.M., Ridge, B., Rydon, H.N., Dos, S.P., and Serräo, P.O., J. Chem. Soc. (C), 1971, pp. 1722-1731.
4. Moroder, L., Besse, D., Musiol, H.-J., Rudolph-Bohner, S., and Siedler, F., Biopolymers, 1996, vol. 40, pp. 207-234.
5. Misicka, A. and Hruby, V.J., Pol. J. Chem., 1994, vol. 68, pp. 893-899.
6. Kudryavtseva, E.V., Sidorova, M.V., Ovchinnikov, M.V., Bespalova, Zh.D., and Bushuev, V.N., J. Peptide Res., 1997, vol. 49, pp. 52-58.
7. Kudryavtseva, E.V., Sidorova, M.V., Molokoedov, A.S., Ovchinnikov, M.V., and Bespalova, Zh.D., Bioorg. Khim., 1999, vol. 25, pp. 107-116.
8. Kudryavtseva, E.V., Sidorova, M.V., Ovchinnikov, M.V., Bespalova, Zh.D., Bushuev, V.N., and Evstigneeva, R.P., Bioorg. Khim., 1996, vol. 22, pp. 370-375.
9. Papsuevich, O.S., Chipens, G.I., and Mikhailova, S.V., Neirogipofizarnye gormony (Neurohypophysial Hormones), Riga: Zinatne, 1986.
10. Sidorova, M.V., Kudryavtseva, E.V., Molokoedov, A.S., Ovchinnikov, M.V., and Bespalova, Zh.D., Bioorg. Khim., 1995, vol. 21, pp. 675-683.
11. Sidorova, M.V., Kudryavtseva, E.V., Antopol'skii, M.L., Pal'keeva, M.E., Ovchinnikov, M.V., and Bespalova, Zh.D., Bioorg. Khim., 1996, vol. 22, pp. 273-279.
12. Eichler, J. and Hougthen, R.A., Protein Peptide Lett., 1997, vol. 4, pp. 157-164.
13. Kudryavtseva, E.V., Sidorova, M.V., Ovchinnikov, M.V., and Bespalova, Zh.D., J. Peptide Sci., 2000, vol. 6, pp. 208-216.
14. King, D.S., Fields, G.G., and Fields, G.B., Int. J. Peptide Protein Res., 1990, vol. 36, pp. 255-266.
15. Hope, D.V., Murti, V.V.S., and du Vigneaud, V., J. Biol. Chem., 1962, vol. 237, pp. 1563-1566.
16. McCurdy, S.N., User Bulletin Peptide Synthesizer Applied Biosystems, 1988, no. 25.
17. Kumagaye, S.-I., Kuroda, H., Nakajima, K., Watanabe, T.X., Kimura, T., Masaki, T., and Sakakibara, S., Int. J. Peptide Protein Res., 1988, vol. 32, pp. 519-526.
18. Bauer, W. and Pless, J., Eur. Pat. Appl. 29 579 (1981); US Patent 4395403 (1983).
19. Ovchinnikov, M.V., Bespalova, Zh.D., Molokoedov, A.S., Titov, M.V., Revenko, I.V., Vinogradov, V.A., Korobov, N.V., and Zhukovskii, S.V., Bioorg. Khim., 1988, vol. 14, pp. 777-782.
20. Ovchinnikov, M.V., Bespalova, Z.D., Molokoedov, A.S., Titov, M.I., Revenko, I.V., Vinogradov, V.A., Korobov, N.V., and Zhukovskii, S.V., Collect. Czech. Chem. Commun., 1989, vol. 54, pp. 796-802.