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. 2021 Mar 12;26(6):1578.
doi: 10.3390/molecules26061578.

Microbial Synthesis of (S)- and (R)-Benzoin in Enantioselective Desymmetrization and Deracemization Catalyzed by Aureobasidium pullulans Included in the Blossom Protect™ Agent

Renata Kołodziejska  1 , Renata Studzińska  2 , Agnieszka Tafelska-Kaczmarek  3 , Hanna Pawluk  1 , Dominika Mlicka  1 , Alina Woźniak  1
Affiliations

Microbial Synthesis of (S)- and (R)-Benzoin in Enantioselective Desymmetrization and Deracemization Catalyzed by Aureobasidium pullulans Included in the Blossom Protect™ Agent

Renata Kołodziejska et al. Molecules. .

Abstract

In this study, we examined the Aureobasidium pullulans strains DSM 14940 and DSM 14941 included in the Blossom Protect™ agent to be used in the bioreduction reaction of a symmetrical dicarbonyl compound. Both chiral 2-hydroxy-1,2-diphenylethanone antipodes were obtained with a high enantiomeric purity. Mild conditions (phosphate buffer [pH 7.0, 7.2], 30 °C) were successfully employed in the synthesis of (S)-benzoin using two different methodologies: benzyl desymmetrization and rac-benzoin deracemization. Bioreduction carried out with higher reagent concentrations, lower pH values and prolonged reaction time, and in the presence of additives, enabled enrichment of the reaction mixture with (R)-benzoin. The described procedure is a potentially useful tool in the synthesis of chiral building blocks with a defined configuration in a simple and economical process with a lower environmental impact, enabling one-pot biotransformation.

Keywords: asymmetric; bioreduction; desymmetrization; microbial synthesis; microorganism; α-hydroxy ketones.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Biotransformation of a symmetrical diketone catalyzed by Blossom Protect™ containing live A. pullulans cells.
See this image and copyright information in PMC

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