The Use of Hydrogen Peroxide for Closing Disulfide Bridges in Peptides |
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Authors: | M V Sidorova A S Molokoedov A A Az'muko E V Kudryavtseva E Krause M V Ovchinnikov Zh D Bespalova |
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Institution: | (1) Cardiological Research and Production Association, Russian Ministry of Health, ul. Tret'ya Cherepkovskaya 15a, Moscow, 121552, Russia;(2) Institute of Molecular Pharmacology, Berlin, Germany |
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Abstract: | The use of hydrogen peroxide for the formation of disulfide bridges was studied in 15 peptides of various lengths and structures. The oxidation of peptide thiols by hydrogen peroxide was shown to proceed under mild conditions without noticeable side reactions of Trp, Tyr, and Met residues. Yields of the corresponding cyclic disulfides were high and mostly exceeded those obtained with other oxidative agents, in particular, iodine. It was established that the use of hydrogen peroxide in organic medium also provided sufficiently high yields when large-scale syntheses of oxytocin and octreotide (up to 10 g) were carried out. |
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Keywords: | chemical synthesis disulfide bond hydrogen peroxide natural peptides and their analogues |
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