Acid-catalyzed hydrolysis of 5-enolpyruvylshikimate 3-phosphate (EPSP) and some simple models of its vinyl ether functional group

AJ Kresge, M Leibovitch, JA Sikorski

Index: Kresge, A. Jerry; Leibovitch, Mordechai; Sikorski, James A. Journal of the American Chemical Society, 1992 , vol. 114, # 7 p. 2618 - 2622

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Citation Number: 17

Abstract

Abstract: Rates of hydrolysis of the vinyl ether functional groups of 5-enolpyruvylshikimate 3- phosphate (EPSP), a-methoxyacrylic acid, and methyl a-methoxyacrylate were measured in concentrated and dilute mineral acid solutions and carboxylic acid buffers, and rate profiles were constructed from the data so obtained. The results for methyl a-methoxyacrylate show a monotonic decrease in reaction rate with decreasing solvent acidity, culminating in a first ...