Structural elucidation of the oxidation product of aminoethylcysteine ketimine decarboxylated dimer by peroxynitrite

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 H-1 NMR methods in D2O plus beta- or gamma-cyclodextrin. (C) 2004 Elsevier Ltd. All rights reserved.