Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 47, Pages 16962-16971Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603824
Keywords
Alzheimer's disease; Ab peptides; copper complexes; dopamine; oxidation
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Funding
- Italian MIUR, through the PRIN (Programmi di Ricerca di Rilevante Interesse Nazionale) [2015T778JW]
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The oxidative reactivity of copper complexes with Ab peptides 1-16 and 1-28 (A beta 16 and A beta 28) against dopamine and related catechols under physiological conditions has been investigated in parallel with the competitive oxidative modification undergone by the peptides. It was found that both A beta 16 and A beta 28 markedly increase the oxidative reactivity of copper(II) towards the catechol compounds, up to a molar ratio of about 4: 1 of peptide/copper(II). Copper redox cycling during the catalytic activity induces the competitive modification of the peptide at selected amino acid residues. The main modifications consist of oxidation of His13/14 to 2-oxohistidine and Phe19/20 to ortho-tyrosine, and the formation of a covalent His6-catechol adduct. Competition by the endogenous peptide is rather efficient, as approximately one peptide molecule is oxidized every 10 molecules of 4-methylcatechol.
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