Use of Saccharomyces cerevisiae yeasts in the chemoselective bioreduction of (1E,4E)-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one in biphasic system

Journal of the Brazilian Chemical Society

César A. Schaefer¹  Vanessa D. Silva¹  Boris U. Stambuk²  Maria Da G. Nascimento¹ 

[1] ,Universidade Federal de Santa Catarina Departamento de Bioquímica Florianópolis SC ,Brazil

关键词: Saccharomyces cerevisiae;    α;    β-unsaturated carbonyl compounds;    bioreduction;    biphasic system;   

DOI  :  10.5935/0103-5053.20130140

来源: SciELO

【 摘 要 】

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.

【 授权许可】

CC BY   
 All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License