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The flavoenzyme vanillyl-alcohol oxidase (VAO) catalyzes the conversion of 4-alkylphenols through the initial formation of p-quinone methide intermediates. These electrophilic species are stereospecifically attacked by water to yield (R)-1-(4′-hydroxyphenyl)alcohols or rearranged in a competing reaction to 1-(4′-hydroxyphenyl)alkenes. Here, we show that the product spectrum of VAO can be controlled...