Intramolecular catalysis of phosphodiester hydrolysis by two imidazoles

…, JR Pliego, BG Vaz, MN Eberlin, AJ Kirby…

Index: Orth, Elisa S.; Brandao, Tiago A.S.; Souza, Bruno S.; Pliego, Josefredo R.; Vaz, Boniek G.; Eberlin, Marcos N.; Kirby, Anthony J.; Nome, Faruk Journal of the American Chemical Society, 2010 , vol. 132, # 24 p. 8513 - 8523

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Citation Number: 36

Abstract

Two imidazole groups act together to catalyze the hydrolysis of the phosphodiester bis (2-(1- methyl-1 H-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, ...