Journal article
Transition State Analysis of Acid-Catalyzed Hydrolysis of an Enol Ether, Enolpyruvylshikimate 3‑Phosphate (EPSP)
Abstract
Proton transfer to carbon represents a significant catalytic challenge because of the large intrinsic energetic barrier and the frequently unfavorable thermodynamics. Multiple kinetic isotope effects (KIEs) were measured for acid-catalyzed hydrolysis of the enol ether functionality of enolpyruvylshikimate 3-phosphate (EPSP) as a nonenzymatic analog of the EPSP synthase (AroA) reaction. The large solvent deuterium KIE demonstrated that …
Authors
Lou M; Gilpin ME; Burger SK; Malik AM; Gawuga V; Popović V; Capretta A; Berti PJ
Journal
Journal of the American Chemical Society, Vol. 134, No. 31, pp. 12947–12957
Publisher
American Chemical Society (ACS)
Publication Date
August 8, 2012
DOI
10.1021/ja3043382
ISSN
0002-7863