IngentaConnect Copper catalysed oxidation of amino acids and Alzheimer's disease

Authors: Feda E. Ali¹; Kevin J. Barnham²; Colin J. Barrow¹; Frances Separovic³

Source: Letters in Peptide Science, Volume 10, Number 5, 2003 , pp. 405-412(8)

Publisher: Springer

Abstract:

Metal-catalyzed oxidation (MCO) can lead to damage of bio-molecules and is implicated in neurodegenerative diseases, such as Alzheimer’s disease (AD). The amino acid residues, tyrosine, histidine and methionine, have been proposed to play important roles in metal mediated oxidative stress and subsequent reactions of amyloid peptide (A) a major contributor in the pathogenesis of AD. The MCO of A residues, particularly histidine, methionine and tyrosine, are reviewed. MCO of A histidine and tyrosine residues can facilitate oligomerization and may play a role in both amyloid formation and A neurotoxicity. Further work is needed to determine the importance of A oxidation in AD and the role of A oxidation products and oxidative stress in disease progression. The mechanisms of A MCO are complex and multiple reaction products can form. Further study is needed to determine the mechanisms by which A MCO occurs in vivo. In addition, new analytical methods are required to monitor the formation of A MCO products formed during AD. The copper–H₂O₂ redox system provides a chemical model by which A MCO can be studied in vitro and can be used to produce oxidatively modified amino acid residues for use as standards in developing new analytical methods to monitor A MCO.

Keywords: amino acid; dityrosine; DOPA; metal-catalyzed oxidation; methionine sulfoxide; oxidative stress

Document Type: Research article

DOI: 10.1007/s10989-004-2391-x

Affiliations: 1: School of Chemistry, University of Melbourne, VIC 3010, Australia 2: Department of Pathology, University of Melbourne, VIC 3010, Australia 3: School of Chemistry, University of Melbourne, VIC 3010, Australia (), Email: fs@unimelb.edu.au

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Copper catalysed oxidation of amino acids and Alzheimer’s disease