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Appl. Sci. 2018, 8(8), 1334; https://doi.org/10.3390/app8081334

Yeast-Mediated Stereoselective Reduction of α-Acetylbutyrolactone

1
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Received: 17 July 2018 / Revised: 2 August 2018 / Accepted: 7 August 2018 / Published: 9 August 2018
(This article belongs to the Section Chemistry)
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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). View Full-Text
Keywords: yeast; biotransformation; α-acetylbutyrolactone yeast; biotransformation; α-acetylbutyrolactone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Mączka, W.; Wińska, K.; Grabarczyk, M.; Żarowska, B. Yeast-Mediated Stereoselective Reduction of α-Acetylbutyrolactone. Appl. Sci. 2018, 8, 1334.

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