Pentacovalent phosphorus in the hydrolysis of dibenzylphosphoenolpyruvate
Pentacovalent phosphorus in the hydrolysis of dibenzylphosphoenolpyruvate
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二苄基磷酸烯醇丙酮酸酯水解中的五共价磷
DOI：
10.1021/ja01048a046
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发表时间：
1969
影响因子：
15
通讯作者：
K. Schray
中科院分区：
文献类型：
--
作者：
S. Benkovic;K. Schray
我们研究了二苯基磷烯醇式丙酮酸(I)45和单苄基磷烯醇丙酮酸(II)4的水解反应，这两种反应是通过逐步失去苯甲醇进行的。苯甲醇释放的pH-速率曲线表明，I和II的水解反应物种必须含有质子化的羧基或其动力学等价物。为了进一步阐明该反应的机理，我们在羟胺存在下进行了实验，羟胺是一种可能的酰基捕捉剂。6在表I中，比较了在水中和0.67M羟胺中的水解产物。
We have investigated the hydrolysis of dibenzylphosphoenolpyruvic acid (I) 4 5and monobenzylphosphoenol-pyruvic acid (II) 4 which proceed via stepwise loss of benzyl alcohol. The pH-rate profiles for release of benzyl alcohol6 (1 mol from I) reveal that the hydro-lytically reactive species for I and II must involve a protonated carboxyl group or its kinetic equivalent. In order to further elucidate the mechanism of this reaction we have conducted experiments in the presence of hydroxylamine, a possible acyl trapping reagent. 6 In Table I the products of hydrolysis in water vs. 0.67 M hydroxylamine are compared.