Lee, Myungmo and Neukirchen, Saskia and Cabrele, Chiara and Reiser, Oliver (2017) Visible-light photoredox-catalyzed desulfurization of thiol- and disulfide-containing amino acids and small peptides. JOURNAL OF PEPTIDE SCIENCE, 23 (7-8). pp. 556-562. ISSN 1075-2617, 1099-1387
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A scalable protocol for the desulfurization of cysteine by using visible light, the photocatalyst Ir(dF(CF3)ppy)(2)(dtb-bpy)PF6 and triethylphosphite under biphasic reaction conditions has been developed. The loading of the catalyst can be as low as 0.01mol%, which can be efficiently removed during the workup (0.3ppm), giving rise to the corresponding desulfurized product in high yields. This method has been applied also to cystine, penicillamine, and reduced and oxidized glutathione. The desulfurization has been found to be pH sensitive, with an optimal pH value of 6.5 and 7.0 for the cysteine derivatives and glutathione, respectively. In addition, during the desulfurization of a decapeptide containing cysteine and methionine, concurrent oxidation of the two sulfur-containing residues to disulfide and sulfoxide has been observed. Therefore, whereas the presented protocol allows a straightforward visible light-mediated desulfurization of simple thiols by using very low catalyst loading and a cost-effective trialkylphosphite as thiyl radical trapping agent, its application to complex substrates needs to be carefully validated. Copyright (c) 2017 European Peptide Society and John Wiley & Sons, Ltd.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | NATIVE CHEMICAL LIGATION; TRIALKYL PHOSPHITES; PHOTOCHEMICAL DESULFURIZATION; 2-SUBSTITUTED BENZOTHIAZOLES; DEOXYGENATION; CYSTEINE; ERYTHROPOIETIN; PROTEINS; ALCOHOLS; BONDS; desulfurization; photocatalysis; photoredox; iridium; cysteine; glutathione; penicillamine |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:16 |
| Last Modified: | 01 Mar 2019 11:02 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1587 |
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