Reaction of the model thiol 2-mercaptoethanol and glutathione with methylvinylmaleimide,a Michael acceptor with extended conjugation |
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| Affiliation: | 1. Department of Biochemistry Vanderbilt University School of Medicine, Nashville, Tennessee 37232 USA;2. Department of Chemistry Vanderbilt University School of Medicine, Nashville, Tennessee 37232 USA;3. Center in Molecular Toxicology, Vanderbilt University School of Medicine, Nashville, Tennessee 37232 USA;1. KU Leuven, University of Leuven, Department of Pharmaceutical and Pharmacological Sciences, Pharmaceutical Analysis, Herestraat 49, O&N2, PB 923, B-3000 Leuven, Belgium;2. Mekelle University, College of Health Sciences, Department of Pharmacy, P.O. Box 1871, Mekelle, Ethiopia;3. Topfond Pharmaceutical Co, Ltd., No.2 Guangming Road, Zhumadian, Henan, China;1. Cancer Research UK Cancer Therapeutics Unit, Division of Cancer Therapeutics, The Institute of Cancer Research, 15 Cotswold Road, London SM2 5NG, UK;2. Department of Data Science, The Institute of Cancer Research, 15 Cotswold Road, London SM2 5NG, UK;1. Department of Neurology and Neurosurgery, McGill University, Montréal, Quebec H3A 2B4, Canada;2. Centre de Recherche du Centre Hospitalier de Université de Montréal, Montréal, Quebec H2X 0A9, Canada;3. Department of Biochemistry and Molecular Medicine, Université de Montréal, Montréal, Quebec H3T 1J4, Canada;4. Department of Physics and Astronomy, University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada;5. Université Catholique de Louvain, 1348 Louvain-la-Neuve, Belgium;6. Université Pierre et Marie Curie, 75005 Paris, France;7. Department of Neurosciences, Université de Montréal, Montréal, Quebec H3T 1J4, Canada;8. Montreal Neurological Institute, McGill University, Montréal, Quebec H3A 2B4, Canada;9. Department of Pharmacology and Therapeutics, McGill University, Montréal, Quebec H3A 2B4, Canada;10. Department of Medicine (Neurology), University of British Columbia and Vancouver Coastal Health Research Institute, Brain Research Centre, Vancouver, British Columbia V6T 2B5, Canada;11. Human Health Therapeutics Portfolio, National Research Council of Canada, Ottawa, Ontario, K1A 0R6, Canada;12. Department of Chemistry, Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada;13. Tanz Centre for Research in Neurodegenerative Diseases, University of Toronto, Toronto, Ontario M5T 0S8, Canada |
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| Abstract: | Many α,β-unsaturated compounds are sufficiently reactive to condense with nucleophiles under physiological conditions and are potentially deleterious to cellular processes. These compounds react with thiols by nucleophilic attack to give 1,4 addition products. We have examined the products formed from the reaction of the model thiols HSCH2CH2OH and glutathione with methylvinylmaleimide, a Michael acceptor with extended conjugation. Glutathione produced exclusively a 1,6 addition product with methylvinylmaleimide. HSCH2CH2OH also formed a 1,6 nucleophilic addition product, as well as a disubstituted product resulting from apparent further 1,4 addition to the 1,6 addition product. Two other novel products which resulted from addition to the maleimide ring and addition at the vinyl carbon proximal to the maleimide ring were observed. |
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