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Structural elucidation of the oxidation product of aminoethylcysteine ketimine decarboxylated dimer by peroxynitrite
Authors:Luisa Mannina,Sté  phane Viel,Silvestro Duprè  ,Mario Fontana,Antonio Antonucci
Affiliation:a Department of S.T.A.A.M., University of Molise, Via De Sanctis, 86100 Campobasso, Italy
b Institute of Chemical Methodologies, National Research Council, C.P.10, Via Salaria Km 29.300, 00016 Monterotondo St., Rome, Italy
c Department of Biochemical Sciences, and Institute of Molecular Biology and Pathology of CNR, University of Rome “La Sapienza”, P.le. Aldo Moro 5, 00185 Rome, Italy
d Department of Pharmaceutical Sciences, University of Chieti, Via dei Vestini 31, 66013 Chieti Scalo, Italy
Abstract:Aminoethylcysteine ketimine decarboxylated dimer (2) is a natural sulfur compound with antioxidant properties. 2 Inhibits some reactions mediated by peroxynitrite, a strong oxidizing and nitrating agent that reacts with several biomolecules. This work aims to elucidate the structure of the product resulting from the interaction of 2 with peroxynitrite using 1D and 2D NMR experiments and ion trap mass spectrometry. This product is a dimerized form of 2 and is hereafter referred to as 3. During the reactions leading to 2 and during the formation of 3, no chiral selection is operated; all optical isomers are present in D2O and have been evidenced by 1H NMR methods in D2O plus β- or γ-cyclodextrin.
Keywords:1H NMR   13C NMR   Aminoethylcysteine ketimine   Peroxynitrite   Chirality   Cyclodextrin
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