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Kinetics and Mechanism of Hydrolysis of 1-(2′-Acetoxybenzoyl)-2-deoxy-α-D-glucopyranose a, Novel Aspirin Prodrug

1979; Elsevier BV; Volume: 68; Issue: 3 Linguagem: Inglês

10.1002/jps.2600680311

1520-6017

Anwar Hussain, James Truelove, H.B. Kostenbauder,

Enzyme Catalysis and Immobilization

The formation rate of aspirin from the prodrug was determined as a function of the pH, temperature, and dielectric constant of the solvent spectrophotometrically and was confirmed by high-pressure liquid chromatography. Aspirin formation was first order with respect to the prodrug and zero order with respect to the hydroxide-ion concentrations. The hydrolysis rate was independent of buffer concentration but very sensitive to the dielectric constant of the solvents. The half-life for the formation of aspirin at 37 degrees was 7 min. The activation energy for the hydrolysis was 23.7 kcal/mole. The results suggest that the hydrolysis of the prodrug to aspirin proceeds by an SN1-type mechanism.