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Abstract
The /sup 18/O isotope-induced shift in /sup 13/C NMR spectroscopy was used to elucidate the point of bond cleavage in the acid-catalyzed hydrolysis of sucrose. Sucrose was hydrolyzed in the presence of H/sub 2//sup 18/O, and the incorporation of /sup 18/O into the several anomeric products was simultaneously assayed as a function of time. While the equilibrium ratio of /sup 18/O was detected in the fructose anomers throughout the course of the hydrolysis, the percentage incorporation of /sup 18/O into the glucose anomers slowly increased to the equilibrium ratio. Independent experimental evidence was obtained with /sup 1/H NMR; the ratio of ..beta..-glucose to ..cap alpha..-glucose was observed to increase from an initially detected value of less than 2:3 to the equilibrium value of greater than 3:2 during the hydrolysis reaction. The data from the NMR experiments were quantitated and compared to theoretical models based on hydrolysis mechanisms involving fructosyl-oxygen bond cleavage and glucosyl-oxygen bond cleavage. The results clearly indicate fructosyl-oxygen bond cleavage under the reaction conditions employed. 39 references, 4 figures.
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