Isothiocyanates (ITCs) are one of the enzymatic hydrolysis products of glucosinolates, which are abundant in crucifers such as broccoli; studies have shown that consumption of ITCs can reduce the risk of degenerative diseases. A synthetic ITC analogue, 2,2-diphenylethyl ITC, has displayed pronounced ability to inhibit mutant p53. The synthetic glucosinolate precursor to this ITC, 2,2-diphenylethyl glucosinolate, has been previously prepared by our group. Although 2,2-diphenylethyl glucosinolate is known to be a substrate for the enzyme myrosinase, kinetic characterization of its catalytic hydrolysis is incomplete. This current study describes (1) the Michaelis–Menten characterization of 2,2-diphenyethyl glucosinolate and (2) a parallel evaluation of this analogue and the natural analogue glucotropaeolin to evaluate effects of pH and temperature on rates of hydrolysis and product(s) formed. The results of this study demonstrate that the action of <i>Sinapis alba </i>myrosinase on natural and non-natural glucosinolates is consistent under the explored range of experimental conditions and in relation to previous accounts.

Enzymatic hydrolysis of 2,2-diphenylethyl glucosinolate

253rd National Meeting (2017)

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