Metal catalyzed oxidation of tyrosine residues by different oxidation systems of copper/hydrogen peroxide

被引:53
作者
Ali, FE
Barnham, KJ [1 ]
Barrow, CJ
Separovic, F
机构
[1] Univ Melbourne, Dept Pathol, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia
关键词
metal catalyzed oxidation; oxidative stress; copper; hydrogen peroxide; tyrosine; dityrosine; DOPA;
D O I
10.1016/j.jinorgbio.2003.10.002
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Metal-catalysed oxidation (MCO) reactions result in the formation of reactive oxygen species (ROS) in biological systems. These ROS cause oxidative stress that contributes to a number of pathological processes leading to a variety of diseases. Tyrosine is one residue that is very susceptible to oxidative modification and the formation of dityrosine (DT) and 3,4-dihydroxyphenylalanine (DOPA) have been widely reported in a number of diseases. However, the mechanisms of MCO of tyrosine in biological systems are poorly understood and require further investigation. In this study we investigated the mechanism of DT and DOPA formation by MCO using N-acetyl tyrosine ethyl ester as a model for tyrosine in proteins and peptides. The results showed that DT formation could be observed upon Cu(2')+/H(2)O(2) oxidation at pH 7.4. Our results indicate that it is unlikely to be via Fenton chemistry since Cu(+)/H(2)O(2) oxidative conditions did not lead to the formation of DT. (C) 2003 Elsevier Inc. All rights reserved.
引用
收藏
页码:173 / 184
页数:12
相关论文
共 67 条
[1]   FORMATION OF DITYROSINE CROSS-LINKS IN PROTEINS BY OXIDATION OF TYROSINE RESIDUES [J].
AESCHBACH, R ;
AMADO, R ;
NEUKOM, H .
BIOCHIMICA ET BIOPHYSICA ACTA, 1976, 439 (02) :292-301
[2]  
Ando Y, 1998, HISTOL HISTOPATHOL, V13, P845, DOI 10.14670/HH-13.845
[3]   Neurodegenerative disorders in humans: the role of glutathione in oxidative stress-mediated neuronal death [J].
Bains, JS ;
Shaw, CA .
BRAIN RESEARCH REVIEWS, 1997, 25 (03) :335-358
[4]   Dityrosine bridge formation and thyroid hormone synthesis are tightly linked and are both dependent on N-glycans [J].
Baudry, N ;
Lejeune, PJ ;
Niccoli, P ;
Vinet, L ;
Carayon, P ;
Mallet, B .
FEBS LETTERS, 1996, 396 (2-3) :223-226
[5]   ARE REACTIVE OXYGEN SPECIES INVOLVED IN ALZHEIMERS-DISEASE [J].
BENZI, G ;
MORETTI, A .
NEUROBIOLOGY OF AGING, 1995, 16 (04) :661-674
[6]   Does human βA4 exert a protective function against oxidative stress in Alzheimer's disease? [J].
Berthon, G .
MEDICAL HYPOTHESES, 2000, 54 (04) :672-677
[7]  
Bondy SC, 1996, TOXICOLOGY METALS, P699
[8]  
BRACKMAN W, 1955, RECL TRAV CHIM PAY B, V74, P937
[9]   QUINONE TANNING IN THE ANIMAL KINGDOM [J].
BURTON, H ;
STOVES, JL .
NATURE, 1950, 165 (4197) :569-570
[10]   Metals and neuroscience [J].
Bush, AI .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2000, 4 (02) :184-191