Synthesis and study of (Z)-3-chlorophosphoenolpyruvate.

Synthesis and study of (Z)-3-chlorophosphoenolpyruvate.
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(Z)-3-氯磷酸烯醇丙酮酸酯的合成与研究。

DOI:
10.1016/0003-9861(90)90562-d
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发表时间:
1990
影响因子:
3.9
通讯作者:
M. O'Leary
M. O'Leary
中科院分区:
生物学3区
文献类型:
--
作者:
J. Liu;J. A. Peliska;M. O'Leary

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摘要以3,3-二氯丙酮酸和亚磷酸三甲酯为原料,经脱酯反应合成了(Z)-3-氯磷烯醇丙酮酸。该化合物是丙酮酸激酶和磷酸烯醇丙酮酸羧化酶的竞争性抑制剂。丙酮酸激酶在与化合物长时间孵育后不失活,但磷酸烯醇式丙酮酸羧化酶缓慢失活(t1 2= 5 h)。该化合物是两种酶的底物,丙酮酸激酶对该化合物的作用速度约为磷酸烯醇丙酮酸本身的0.1%。在磷酸烯醇式丙酮酸羧化酶的情况下,化合物转化为氯丙酮酸和氯丙酮酸乙酸的3:1混合物,总速率为磷酸烯醇式丙酮酸羧化速率的约25%。
Abstract (Z)-3-Chlorophosphoenolpyruvate has been synthesized by the reaction of 3, 3-dichloropyruvic acid with trimethylphosphite, followed by deesterification. This compound is a competitive inhibitor of pyruvate kinase and phosphoenolpyruvate carboxylase. Pyruvate kinase is not inactivated upon prolonged incubation with the compound, but phosphoenolpyruvate carboxylase is slowly inactivated t 1 2= 5 h). The compound is a substrate for both enzymes, being acted upon by pyruvate kinase approximately 0.1% as rapidly as phosphoenolpyruvate itself. In the case of phosphoenolpyruvate carboxylase, the compound is converted into a 3: 1 mixture of chloropyruvate and chlorooxalacetate, at an overall rate that is about 25% the carboxylation rate for phosphoenolpyruvate.
磷酸烯醇丙酮酸类似物与各种磷酸烯醇丙酮酸利用酶相互作用的立体选择性。
DOI: 10.1021/bi00299a012
发表时间: 1984
期刊: Biochemistry
影响因子: 2.9
作者:
Duffy,TH;Nowak,T
通讯作者: Nowak,T