Phosphoryl-transfer reactions of phosphodiesters: Characterization of transition states by heavy-atom isotope effects

AC Hengge, WW Cleland

Index: Hengge, Alvan C.; Cleland Journal of the American Chemical Society, 1991 , vol. 113, # 15 p. 5835 - 5841

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Citation Number: 46

Abstract

Abstract: The secondary I8O and I5N isotope effects have been measured for phosphoryl- transfer reactions of the phosphodiester 3, 3-dimethyl pnitrophenyl phosphate under conditions of acid and alkaline hydrolysis, cleavage by 0-cyclodextrin, and cleavage by snake venom phosphodiesterase. Isotopic labeling and other experiments show that these reactions proceed by an sN2 (P) mechanism. The secondary I8O isotope effect measures ...