2-氨基-4-羟基-6,7-二甲基-5,6,7,8-四氢蝶呤将苯丙氨酸非酶羟基化为酪氨酸
The non-enzymic hydroxylation of phenylalanine to tyrosine by 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine.
作者信息
Woolf L I, Jakubovic A, Chan-Henry E
出版信息
Biochem J. 1971 Nov;125(2):569-74. doi: 10.1042/bj1250569.
Abstract
- Phenylalanine is converted into tyrosine by incubation in air with 6,7-dimethyltetrahydropterin, which is a cofactor for the enzymic hydroxylation. This can cause serious inaccuracies in assays of phenylalanine hydroxylase. 2. The non-enzymic reaction is not specific for l-phenylalanine. 3. m-Tyrosine, o-tyrosine and dihydroxyphenylalanines are formed in addition to p-tyrosine; their chromatographic separation and assay are described. 4. l-[(14)C]Phenylalanine as purchased or soon after purification contains p- and m-tyrosine, both of which can cause errors in the assay of phenylalanine hydroxylase. 5. Catalase prevents the non-enzymic hydroxylation. Thiol compounds in low concentrations stimulate the reaction but in high concentrations are inhibitory. Fe(2+) and metal complexing agents have small stimulatory effects. 6. The mechanism of the non-enzymic reaction and its possible relation to the enzymic hydroxylation of phenylalanine are discussed; it is suggested that phenylalanine is attacked by a peroxide of the cofactor.
摘要
- 苯丙氨酸在空气中与6,7 - 二甲基四氢蝶呤一起温育时会转化为酪氨酸，6,7 - 二甲基四氢蝶呤是酶促羟基化反应的一种辅助因子。这可能会在苯丙氨酸羟化酶的测定中导致严重的误差。2. 非酶促反应对L - 苯丙氨酸不具有特异性。3. 除了对酪氨酸外，还会形成间酪氨酸、邻酪氨酸和二羟基苯丙氨酸；文中描述了它们的色谱分离和测定方法。4. 购买时或纯化后不久的L - [¹⁴C]苯丙氨酸含有对酪氨酸和间酪氨酸，这两者都会在苯丙氨酸羟化酶的测定中引起误差。5. 过氧化氢酶可防止非酶促羟基化反应。低浓度的硫醇化合物会刺激该反应，但高浓度时具有抑制作用。亚铁离子和金属络合剂有较小的刺激作用。6. 讨论了非酶促反应的机制及其与苯丙氨酸酶促羟基化反应可能的关系；有人提出苯丙氨酸会受到辅助因子过氧化物的攻击。
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本文引用的文献
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Hydroxylation-induced migration: the NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds.羟基化诱导的迁移：NIH 重排。近期实验揭示了芳香族化合物酶促羟基化一个意外且普遍的结果。
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[Non-enzymatic hydroxylation of phenylalanine to tyrosine using tetrahydrogenated pterines].[使用四氢蝶呤将苯丙氨酸非酶促羟基化为酪氨酸]
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