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Immature fruits and leaves of black cherry (Prunus serotina Ehrh.) accumulate the cyanogenic glucoside prunasin (the β-glucoside of (R)-mandelonitrile). Cell-free extracts from these tissues catalysed the stereospecific glucosylation of (R,S)-mandelonitrile to (β)-prunasin at rates of 0.2-2.0 μmol/h/mg protein. Uridine diphosphate glucose (K m  = 0.32 mᴍ) acted as glucose donor. The optimum concentration of (R,S)-mandelonitrile was 20 mᴍ. Highest activity was exhibited at pH 7.0-8.0 in Tris-phosphate buffer, and no additional cofactors were required. β- Mercaptoethanol (14.5 mᴍ), provided in the homogenization medium to prevent browning of homogenates, did not stimulate the rate of prunasin production. In addition to (R)-mandelonitrile (100%), significant activity was shown towards mandelamide (21%), benzyl alcohol (15%), mandelic acid (8%) and benzoic acid (153%), but not towards prunasin. Mandelonitrile glucosyltransferase activity was most stable at - 20 °C in the presence of 10% glycerol.

Prunasin Biosynthesis by Cell-Free Extracts from Black Cherry (Prunus serotina Ehrh.) Fruits and Leaves