酪氨酸和3,4-二羟基苯丙氨酸（多巴）的膦酸类似物会影响蘑菇酪氨酸酶的活性。

Phosphonic analogues of tyrosine and 3,4-dihydroxyphenylalanine (dopa) influence mushroom tyrosinase activity.

作者信息

Lejczak B, Kafarski P, Makowiecka E

出版信息

Biochem J. 1987 Feb 15;242(1):81-8. doi: 10.1042/bj2420081.

DOI:10.1042/bj2420081

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1147667/

Abstract

A series of phosphonic analogues of tyrosine and 3,4-dihydroxyphenylalanine (dopa) were synthesized in order to study their interaction with mushroom tyrosinase. 1-Amino-2-(3,4-dihydroxyphenyl)ethylphosphonic acid and 1-amino-2-(3,4-dimethoxyphenyl)ethylphosphonic acid turned out to be substrates for mushroom tyrosinase with Km values of 3.3 mM and 9.3 mM respectively. Shortening of the alkyl chain by one methylene group gave amino-(3,4-dihydroxyphenyl)methylphosphonic acid, one of the most powerful known inhibitors of this enzyme. This compound, racemic as well as in its optically active forms, exerts a mixed type of inhibition with an affinity for the enzyme one order of magnitude greater than that of the natural substrate.

摘要

为了研究酪氨酸和3,4-二羟基苯丙氨酸（多巴）的一系列膦酸类似物与蘑菇酪氨酸酶的相互作用，合成了这些类似物。结果表明，1-氨基-2-(3,4-二羟基苯基)乙基膦酸和1-氨基-2-(3,4-二甲氧基苯基)乙基膦酸是蘑菇酪氨酸酶的底物，其米氏常数（Km）分别为3.3 mM和9.3 mM。烷基链缩短一个亚甲基得到氨基-(3,4-二羟基苯基)甲基膦酸，它是该酶已知的最有效的抑制剂之一。该化合物，无论是外消旋体还是其旋光活性形式，都表现出混合型抑制作用，对酶的亲和力比天然底物高一个数量级。

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The synthesis of a DOPA analogue, 1-amino-2-(3, 4-dihydroxyphenyl)-ethylphosphonic acid and distribution studies in mice bearing the Harding-Passey melanoma.一种多巴类似物1-氨基-2-(3,4-二羟基苯基)乙基膦酸的合成及其在荷Harding-Passey黑色素瘤小鼠体内的分布研究。

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