Stereochemistry in oxidation of allylic alcohols by cell-free system of callus induced from Cannabis sativa L.

In the cell-free system of callus induced from Cannabis sativa L. (Moraceae), the pro-R hydrogen from C-1 methylene of primary allylic alcohols such as trans-cinnamyl alcohol and geraniol was abstracted. In an example of secondary allylic alcohols biotransformations, S-(-)-isophorol of the racemate was biotransformed to isophorone, and (+)-trans-verbenol of four isomers, such as (+)-and (-)-trans-verbenol, and (+)-and (-)-cis-verbenol, was preferentially biotransformed to (+)-verbenone. We reported previously that the enzyme which catalyzed the oxidation of these allylic alcohols in the cell-free system of Cannabis callus was an alcohol oxidase.