Intramolecular catalysis of phosphodiester hydrolysis by two imidazoles.
作者： Elisa S Orth , Tiago AS Brandao , Bruno S Souza , Josefredo R Pliego , Boniek G Vaz
DOI: 10.1021/JA1034733
关键词: Stereochemistry 、 Nucleophile 、 Hydrolysis 、 Phosphodiester bond 、 Acid catalysis 、 Intramolecular force 、 Imidazole 、 Organic chemistry 、 Electrospray ionization 、 Chemistry 、 Catalysis
摘要: Two imidazole groups act together to catalyze the hydrolysis of phosphodiester bis(2-(1-methyl-1H-imidazolyl)phenyl) phosphate (BMIPP). A full investigation involving searching computational and electrospray ionization (ESI-MS-/MS) ultra mass spectrometry (LTQ-FT) experiments made possible a choice between two kinetically equivalent mechanisms. The preferred pathway, intramolecular nucleophilic catalysis by imidazole, assisted general acid imidazolium group, offers first simple model for mechanism used extensive phospholipase D superfamily.
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