This work describes the chemoselective bioreduction of (1E,4E)-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one (1) mediated by baker's yeast (BY, Saccharomyces cerevisiae cells) in an aqueous/organic solvent biphasic system. The biotransformation of this compound was chemoselective and formed only the corresponding saturated ketone 1,5-bis(4-methoxyphenyl)-3-pentanone (2). The influence of various factors which may alter the bioreduction of 1, such as the type and percentage of co-solvents, use of six different S. cerevisiae yeast samples (four commercial and two industrial), variations in the substrate and yeast concentrations, temperature, pH and volume of aqueous and organic phases, was investigated. The best reaction conditions were 66.7 g L-1 of Fleischmann BY, 8.3 × 10-3 mol L-1 of substrate, pH 6.5 at 35 ºC in the presence of 2.5% (v/v) of N,N-dimethyl sulfoxide (DMSO) as an additive and a Vaq/Vorg ratio of 70/30. Under these conditions, the product 2 was recovered in conversions of 82% in 5 h reaction.
Saccharomyces cerevisiae; α,β-unsaturated carbonyl compounds; bioreduction; biphasic system
