Journal article
Transition State Analysis of Acid-Catalyzed dAMP Hydrolysis
Abstract
Multiple kinetic isotope effects (KIEs) on deoxyadenosine monophosphate (dAMP) hydrolysis in 0.1 M HCl were used to determine the transition state (TS) structure and probe its intrinsic reactivity. The experimental KIEs revealed a stepwise (SN1) mechanism, with a discrete oxacarbenium ion intermediate. This is the first direct evidence for the deoxyribosyl oxacarbenium ion in solution. In 50% methanol/0.1 M HCl the products were deoxyribose …
Authors
McCann JAB; Berti PJ
Journal
Journal of the American Chemical Society, Vol. 129, No. 22, pp. 7055–7064
Publisher
American Chemical Society (ACS)
Publication Date
June 6, 2007
DOI
10.1021/ja067371l
ISSN
0002-7863