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• W2078981916 endingPage "3776" @default.
• W2078981916 startingPage "3769" @default.
• W2078981916 abstract "Kinetic isotope effects (KIEs) were measured for methyl glucoside (4) hydrolysis on unlabeled material by NMR. Twenty-eight (13)C KIEs were measured on the acid-catalyzed hydrolysis of alpha-4 and beta-4, as well as enzymatic hydrolyses with yeast alpha-glucosidase and almond beta-glucosidase. The 1-(13)C KIEs on the acid-catalyzed reactions of alpha-4 and beta-4, 1.007(2) and 1.010(6), respectively, were in excellent agreement with the previously reported values (1.007(1), 1.011(2): Bennet and Sinnott, J. Am. Chem. Soc. 1986, 108, 7287). Transition state analysis of the acid-catalyzed reactions using the (13)C KIEs, along with the previously reported (2)H KIEs, confirmed that both reactions proceed with a stepwise D(N)A(N) mechanism and showed that the glucosyl oxocarbenium ion intermediate exists in an E(3) sofa or (4)H(3) half-chair conformation. (13)C KIEs showed that the alpha-glucosidase reaction also proceeded through a D(N)*A(N) mechanism, with a 1-(13)C KIE of 1.010(4). The secondary (13)C KIEs showed evidence of distortions in the glucosyl ring at the transition state. For the beta-glucosidase-catalyzed reaction, the 1-(13)C KIE of 1.032(1) demonstrated a concerted A(N)D(N) mechanism. The pattern of secondary (13)C KIEs was similar to the acid-catalyzed reaction, showing no signs of distortion. KIE measurement at natural abundance makes it possible to determine KIEs much more quickly than previously, both by increasing the speed of KIE measurement and by obviating the need for synthesis of isotopically labeled compounds." @default.
• W2078981916 created "2016-06-24" @default.
• W2078981916 creator A5019935859 @default.
• W2078981916 creator A5040589637 @default.
• W2078981916 creator A5071290827 @default.
• W2078981916 date "2004-03-01" @default.
• W2078981916 modified "2023-10-03" @default.
• W2078981916 title "Probing the Transition States of Four Glucoside Hydrolyses with ¹³C Kinetic Isotope Effects Measured at Natural Abundance by NMR Spectroscopy" @default.
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• W2078981916 doi "https://doi.org/10.1021/ja0394028" @default.
• W2078981916 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15038730" @default.
• W2078981916 hasPublicationYear "2004" @default.
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