Photochemical desulfurization of thiols and disulfides |
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| Institution: | 1. Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona, Spain;2. Unit for Glycoconjugate Chemistry, C.S.I.C., Jordi Girona 18-26, 08034 Barcelona, Spain;1. Department of Basic Sciences, Touro University-California, Vallejo, CA 94592, United States;2. Department of Pharmaceutical Chemistry, University of California San Francisco, CA 94143, United States;3. Southern Research Institute, 431 Aviation Way, Frederick, MD 21701, United States;4. Department of Biophysics and Biochemistry, University of California San Francisco, CA 94143, United States;1. School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001, China;2. Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001, China;3. Henan Provincial Key Laboratory of Children’s Genetics and Metabolic Diseases, Children’s Hospital Affiliated to Zhengzhou University, Zhengzhou Children’s Hospital, Zhengzhou University, Zhengzhou 450018, China;3. From the Institute of Medical Physics and Biophysics, University of Leipzig, Härtelstrasse 16/18, 04107 Leipzig, Germany and;4. the Institute of Pharmacy, Medicinal Chemistry, Freie Universität Berlin, Königin-Luise-Strasse 2+4, 14195 Berlin, Germany |
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| Abstract: | A visible light-induced desulfurization process for thiols and disulfides using triethylphosphite and triethylborane is reported. The reaction can be effected on a range of organic molecules having either primary, secondary or tertiary thiol groups and disulfides without the need of protecting groups. Thus, after treating l-cystine 7, l-cystine dimethylester 8, thioctic amide 9 and glutathione disulfide 10, first with tributylphosphine, later with triethylborane/triethylphosphite under irradiation in a one-pot reaction, the corresponding desulfurized compounds l-Ala, l-Ala, 1-octanamide and γ-l-Glu-l-Ala-Gly, respectively, are prepared in high yields with retention of configuration. |
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