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  • Title: Direct detection of the internal acyl migration reactions of benzoic acid 1-O-acylglucuronide by 13C-labeling and nuclear magnetic resonance spectroscopy.
    Author: Akira K, Taira T, Shinohara Y.
    Journal: J Pharmacol Toxicol Methods; 1997 Jun; 37(4):237-43. PubMed ID: 9279779.
    Abstract:
    1-O-Acyl-beta-D-glucopyranuronates can undergo irreversible binding to proteins mainly through internal acyl migration reactions, which may have toxicological significance. A new method based on the 13C-labeling and nuclear magnetic resonance (NMR) spectroscopy has been developed to study the reactivity of the 1-O-acyl-beta-D-glucopyranuronate of benzoic acid. In phosphate buffer (pH 7.4) solution at 37 degrees C, the glucuronide showed apparent first-order degradation kinetics (T1/2, 125 min), and concurrent and sequential appearance of 2-, 3- and 4-O-acyl isomers as both alpha- and beta-anomers was observed. The isomeric glucuronides were identified by two-dimensional NMR of the reaction mixture. The direct approach using 13C-labeling and NMR could also provide insights into the reactivities of other labile drug acylglucuronides and their isomeric glucuronides.
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