Hydrolysis of phosphotriesters: determination of transition states in parallel reactions by heavy-atom isotope effects

MA Anderson, H Shim, FM Raushel…

Index: Anderson; Shim; Raushel; Cleland Journal of the American Chemical Society, 2001 , vol. 123, # 38 p. 9246 - 9253

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Citation Number: 40

Abstract

The remote label method was used to measure primary and secondary 18O isotope effects in the alkaline hydrolysis of O, O-diethylphosphorylcholine iodide (DEPC) and the primary 18O effect in the alkaline hydrolysis of O, O-diethyl-m-nitrobenzyl phosphate (DE m NBP). Both the leaving group of interest (choline or m-nitrobenzyl alcohol) and ethanol can be ejected during hydrolysis due to the similarity of their p K values. The heavy-atom isotope ...