Imino [4+4] cycloaddition products as exclusive and biologically relevant acrolein-amine conjugates are intermediates of 3-formyl-3,4-dehydropiperidine (FDP), an acrolein biomarker |
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| Institution: | 1. Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan;2. Department of Chemistry Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi 560-0043, Japan;3. Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, Kazan 420008, Russia;1. Australian Centre for Research on Separation Sciences (ACROSS), School of Science and Health, University of Western Sydney (Parramatta), NSW 1797, Australia;2. Centre for Chemistry and Biotechnology; School of Life and Environmental Sciences, Deakin University, Victoria 3216, Australia;1. ICTM-Center for Chemistry, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia;2. Faculty of Chemistry University of Belgrade, Studentski trg 12-16, 11158 Belgrade, Serbia;3. Disease Glycomics Team and RIKEN, Saitama 351-0198, Japan;4. Structural Glycobiology Team, RIKEN-Max Planck Joint Research Center, Global Research Cluster, and RIKEN, Saitama 351-0198, Japan;5. Biofunctional Synthetic Chemistry Laboratory, RIKEN, Saitama 351-0198, Japan,;6. Department of Applied Bioorganic Chemistry, Gifu University, Gifu 501-1193, Japan,;12. Division of Biological Chemistry and Biologicals, National Institute of Health Sciences, Tokyo 158-8501, Japan |
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| Abstract: | We demonstrated synthetically that the eight-membered heterocycles 2,6,9-triazabicyclo3.3.1]nonanes and 1,5-diazacyclooctanes are the initial and exclusive products of the reaction, through an imino 4+4] cycloaddition, of biologically relevant amines with acrolein. The stabilities of the aminoacetals within the eight-membered heterocycles determined whether the product was subsequently transformed gradually into the 3-formyl-3,4-dehydropiperidine (FDP), which is widely used as an oxidative stress marker. The reactivity profiles discovered in this study suggested that some of the imino 4+4] cycloaddition products are reactive intermediates of FDP and contribute to the mechanisms underlying the oxidative stress response to acrolein. |
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| Keywords: | Acrolein Biologically relevant amine Biomarker 1 5-Diazacyclooctane 3-Formyl-3 4-dehydropiperidine (FDP) Imino [4+4] cycloaddition 2 6 9-Triazabicyclo[3 3 1]nonane |
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