Yeast-Mediated Stereoselective Reduction of α-Acetylbutyrolactone

Abstract

α’-1’-Hydroxyethyl-γ-butyrolactone—a product of reduction of α-acetylbutyrolactone possesses two stereogenic centres and two reactive functionalities (an alcohol and an ester group). Additionally, this compound has a similar structure to γ-butyrolactone (GBL) which is psychoactive. In the present work, biotransformation using seven yeast strains was used to obtain anti stereoisomers of α’-1’-hydroxyethyl-γ-butyrolactone. The process was carried out in both growing and resting culture. The effect of media composition and organic solvent addition on stereoselectivity and effectiveness of biotransformation was also studied. After one day of transformation, optically pure (3R,1’R)-hydroxylactone was obtained by means of Yarrowia lipolytica P26A in YPG medium (yeast extract (1%), peptone (2%) and glucose (2%)). In turn, the use of resting cells culture of Candida viswanathi AM120 in the presence of 10% DES (deep eutectic solvent) allowed us to obtain a (3S,1’S)-enantiomer with de = 85% (diastereomeric excess) and ee 76% (enantiomeric excess).

Yarrowia lipolytica Yeast: A Treasure Trove of Enzymes for Biocatalytic Applications—A Review

“…Furthermore, such a method is particularly advantageous in terms of cost-effectiveness, ease of preparation, and the ability to effectively perform several types of reactions [14]. Table 1 demonstrates the past application of whole cells of Y. lipolytica as a biocatalyst in various reactions, including hydrogenation, reduction, and oxidation [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29].…”

Biocatalyzed Redox Processes Employing Green Reaction Media

“…The synthesis of optically pure α'-1-hydroxyethyl-γ-butyrolactone (33), valuable synthons in organic chemistry, has been recently developed by Maçzka et al by performing the reduction of α-acetylbutyrolactone (32) catalyzed by different yeasts (Scheme 13) [82]. Some Yarrowia strains as well as Candida viswanathi AM120 led to very good results, being obtained the anti diastereoisomers with high selectivity.…”

Positive Impact of Natural Deep Eutectic Solvents on the Biocatalytic Performance of 5-Hydroxymethyl-Furfural Oxidase

“…(NA)DESs have emerged in recent years as a valuable reaction medium for biocatalyzed reactions in which also redox enzymes can be employed [31,32]. The presence of different (NA)DES in these reactions can present a beneficial effect on the activity and stability of the biocatalysts [41], allowing improved enantio-and diastereoselectivities [42] and even reversal on biocatalyst enantiopreference [35]. Regarding the application of oxidases, a laccase from Bacillus HR03, a multi-copper-dependent oxidase, has been recently tested in the presence of different (NA)DES.…”