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

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

• desymmetrization
• bioreduction
• microbial synthesis
• asymmetric
• microorganism
• α-hydroxy ketones