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Asymmetric synthesis of the chiral synthon ethyl (S)-4-chloro-3-hydroxybutanoate using Lactobacillus kefir
Affiliation:1. Warsaw University, Department of Chemistry, Pasteur 1 Str., 02-093 Warsaw, Poland;2. Medical University of Warsaw, 2nd Faculty of Medicine, Department of Biochemistry, 61 Zwirki i Wigury Av., 02-091 Warsaw, Poland;1. Siberian Federal University, 79 Svobodny Ave., Krasnoyarsk, 660041, Russia;2. Laboratory of Crystal Physics, Kirensky Institute of Physics, Federal Research Center KSC SB RAS, bld. 38 Akademgorodok 50, Krasnoyarsk, 660036, Russia;3. Department of Physics, Far Eastern State Transport University, 47 Seryshev Str., Khabarovsk, 680021, Russia;4. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky, Irkutsk 664033, Russia;1. School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, China;2. National-Local Joint Engineering Laboratory for Energy Conservation of Chemical Process Integration and Resources Utilization, Tianjin 300130, China
Abstract:Lactobacillus kefir was used as the whole cell biocatalyst for the asymmetric reduction of ethyl 4-chloro acetoacetate 1 to the chiral synthon ethyl (S)-4-chloro-3-hydroxybutanoate 2. Ketoester 1 was obtained as micro-droplets, without the use of an organic solvent as substrate reservoir. 2 (1.2 M) was produced using 2-propanol as co-substrate with a final yield of 97% within 14 h. A high space-time yield and a high specific product capacity of 85.7 mmol/L h and of 24 mmol/gDCW were measured. The enantiomeric excess of the (S)-alcohol 2 was 99.5%.
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