THE HYDROXYLATION OF THE SALICYLATE ANION BY A FENTON REACTION AND GAMMA-RADIOLYSIS - A CONSIDERATION OF THE RESPECTIVE MECHANISMS

被引：105

作者：

MASKOS, Z ^{[1
]}

RUSH, JD ^{[1
]}

KOPPENOL, WH ^{[1
]}

机构：

[1] LOUISIANA STATE UNIV,INST BIODYNAM,BATON ROUGE,LA 70803

来源：

FREE RADICAL BIOLOGY AND MEDICINE | 1990年 / 8卷 / 02期

关键词：

Dihydroxybenzoate; Fenton reaction; Hydroxyl radical; Hydroxylation; Radiolysis; Salicylate;

D O I：

10.1016/0891-5849(90)90088-Z

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：

The yield of 2,3- and 2,5-dihydroxybenzoates (dHB's) from the reaction of ·Oh radicals with salicylate (SA) ions has been measured as a function of pH and in the presence of oxidants. Under steady-state radiolysis conditions, the production of these products occures via the reactions ·OH + SA → HO-SA· (radical adduct) HO-SA· H+,OH+ → 2-carboxyphenoxyl radical (SA·) + H2O HO-SA· + SA· → 2,3-/2,5-dHB + SA The addition of the oxidants O2, Fe3+ edta, or Fe(CN)63- increases the relative yield of 2,5-dHB/2,3-dHB from about 0.2 to 1. A model to account for this effect is presented. Steady-state radiolyses of 3- and 4-hydroxybenzoate give dihydroxybenzoate products consistent with the phenol group being an ortho-para director in the electrophilic attack of the hydroxyl radical on the aromatic ring. A comparison of product distributions from the reaction of ferrous edta with hydrogen peroxide using salicylate as a scavenger strongly suggests that the same hydroxyl radical adducts are formed as in the reaction experiments. © 1990.

引用

页码：153 / 162

页数：10

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