Zu, Han; Gu, Jie; Zhang, Hui; Fan, Anwen; Nie, Yao; Xu, Yan published the artcile< Highly enantioselective synthesis of (R)-1,3-butanediol via deracemization of the corresponding racemate by a whole-cell stereoinverting cascade system>, Computed Properties of 6290-03-5, the main research area is R13 butanediol deracemization racemate stereoinverting cascade system; (R)-1,3-butanediol; Oxidation–reduction cascade; Racemate; Stereoselectivity; Whole-cell catalysis.
Abstract: Background: Deracemization, the transformation of the racemate into a single stereoisomeric product in 100% theor. yield, is an appealing but challenging option for the asym. synthesis of optically pure chiral compounds as important pharmaceutical intermediates. To enhance the synthesis of (R)-1,3-butanediol from the corresponding low-cost racemate with minimal substrate waste, we designed a stereoinverting cascade deracemization route and constructed the cascade reaction for the total conversion of racemic 1,3-butanediol into its (R)-enantiomer. This cascade reaction consisted of the absolutely enantioselective oxidation of (S)-1,3-butanediol by Candida parapsilosis QC-76 and the subsequent asym. reduction of the intermediate 4-hydroxy-2-butanone to (R)-1,3-butanediol by Pichia kudriavzevii QC-1. Results: The key reaction conditions including choice of cosubstrate, pH, temperature, and rotation speed were optimized systematically and determined as follows: adding acetone as the cosubstrate at pH 8.0, a temperature of 30°C, and rotation speed of 250 rpm for the first oxidation process; in the next reduction process, the optimal conditions were: adding glucose as the cosubstrate at pH 8.0, a temperature of 35°C, and rotation speed of 200 rpm. Conclusions: The step-by-step cascade reaction efficiently produced (R)-1,3-butanediol from the racemate by biosynthesis and shows promising application prospects.
Microbial Cell Factories published new progress about Candida parapsilosis. 6290-03-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H10O2, Computed Properties of 6290-03-5.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts