Aromatic hydroxylation and nitration of phenylalanine and tyrosine by peroxynitrite

FEBS Letters

Kaur, Harparkash²  Cross, Carroll E.¹  Halliwell, Barry¹  O'Neill, Charles A.¹  van der Vliet, Albert¹ 

[1] Division of Pulmonary/Critical Care Medicine, UC Davis Medical Center, Sacramento, CA 95817, USA;Neurodegerative Diseases Research Group, Pharmacology Department, King's College, Manresa Road, London SW3 6LX, UK

关键词: Peroxynitrite;    Hydroxyl radical;    Phenylalanine;    Tyrosine;    Nitrotyrosine;    Dityrosine;   

DOI  :  10.1016/0014-5793(94)80391-9

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

Peroxynitrite is a highly reactive species, generated from Superoxide and nitric oxide. Some effects of peroxynitrite are ascribed to the molecule itself, but decomposition products of the protonated form, peroxynitrous acid, may account for much of its reactivity in biological systems. Suggested products include highly-reactive hydroxyl radicals, but thermodynamic calculations have been used to claim that free hydroxyl radicals cannot be formed from peroxynitrite. We utilized aromatic hydroxylation of phenylalanine as a specific detector of hydroxyl radicals, and found that incubation of phenylalanine with peroxynitrite leads to a small amount of p-, m- and o-tyrosine, specific products of attack by this radical. Products of nitration of phenylalanine and tyrosine were also detected, as was dityrosine. Peroxynitrite decomposition generates several reactive species, including some that can nitrate aromatic rings. Formation of nitro-aromatic compounds may be a useful marker of peroxynitrite generation in biological systems.

【 授权许可】

Unknown