Intramolecular Catalysis of Phosphodiester Hydrolysis by Two Imidazoles,Journal of the American Chemical Society

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Intramolecular Catalysis of Phosphodiester Hydrolysis by Two Imidazoles
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2010-06-23 , DOI: 10.1021/ja1034733
Elisa S. Orth ₁ , Tiago A. S. Brandão ₁ , Bruno S. Souza ₁ , Josefredo R. Pliego ₁ , Boniek G. Vaz ₁ , Marcos N. Eberlin ₁ , Anthony J. Kirby ₁ , Faruk Nome ₁

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Two imidazole groups act together to catalyze the hydrolysis of the phosphodiester bis(2-(1-methyl-1H-imidazolyl)phenyl) phosphate (BMIPP). A full investigation involving searching computational and electrospray ionization (ESI-MS-/MS) and ultra mass spectrometry (LTQ-FT) experiments made possible a choice between two kinetically equivalent mechanisms. The preferred pathway, involving intramolecular nucleophilic catalysis by imidazole, assisted by intramolecular general acid catalysis by the imidazolium group, offers the first simple model for the mechanism used by the extensive phospholipase D superfamily.

中文翻译：

两种咪唑对磷酸二酯水解的分子内催化

两个咪唑基团共同作用以催化磷酸二酯双（2-（1-甲基-1H-咪唑基）苯基）磷酸酯（BMIPP）的水解。一项涉及搜索计算和电喷雾电离 (ESI-MS-/MS) 和超质谱 (LTQ-FT) 实验的全面调查使得在两种动力学等效机制之间进行选择成为可能。首选途径，包括咪唑的分子内亲核催化，辅以咪唑鎓基团的分子内一般酸催化，为广泛的磷脂酶 D 超家族使用的机制提供了第一个简单模型。

更新日期：2010-06-23

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