Nocardia species NRRL 5646 stereospecifically hydrates 4-vinylphenol (15) to S-1-(4'-hydroxyphenyl)ethanol (17), and further oxidizes 17 to 4'-hydroxyacetophenone (18). Labeled metabolites 17 and 18 obtained from incubations in D2O and H218O support initial enzymatic tautomerization of 15 to a reactive quinone methide (16), which adds water in the first reaction. Commitment to catalysis is high in the hydration reaction, while the alcohol dehydrogenation reaction appears to be reversible. The stereochemical features of water addition, alcohol oxidations, and ketone reductions with growing culture biocatalysis were established by chiral HPLC. Alcohol oxidations or ketone reductions in 12 000 × g supernatants preferentially require NADP+–NADPH,H+ as co-factors. The alcohol dehydrogenase has broad substrate specificity, favoring the oxidation of primary alkanols and 4-hydroxybenzyl alcohols.Key words : 4-vinylphenol, Nocardia sp., enantiospecific hydration, 1-(4'-hydroxyphenyl)ethanol, 4'-hydroxyacetophenone