(S)-1-(4-Hydroxyphenyl)ethanol and (S)-1-(4-hydroxyphenyl)propanol were synthesized with enantiomeric excesses of 96.6% and 95.2%, respectively, from the corresponding 4-alkylphenols by eugenol dehydrogenase from Pseudomonas fluorescens E118. The enantioselectivity of the enzyme was shown to be pH- dependent.
Wieser, M., Furukawa, H., Morita, H., Yoshida, T., & Nagasawa, T. (1999). Synthesis of (S)-1-(4-hydroxyphenyl)alcohols by eugenol dehydrogenase from Pseudomonas fluorescens E118. Tetrahedron Asymmetry, 10(9), 1627–1630. https://doi.org/10.1016/S0957-4166(99)00164-0