Chemo-enzymatic synthesis of (R)- and (S)-3,4-dichlorophenylbutanolide intermediate in the synthesis of sertraline |
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| Institution: | 1. Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Ministry of Education), and School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China;2. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China;3. Chemistry Department, York University, 4700 Keele Street, Toronto, ON, M3J1P3, Canada;1. Université de Toulouse; INSA, UPS, INP; LISBP, 135 Avenue de Rangueil, F-31077 Toulouse, France;2. INRA, UMR792 Ingénierie des Systèmes Biologiques et des Procédés, F-31400 Toulouse, France;3. CNRS, UMR5504, F-31400 Toulouse, France;4. Université de Toulouse; INPT, UPS; Laboratoire de Génie Chimique UMR CNRS 5503; 4, Allée Emile Monso, F-31030 Toulouse, France;5. IDTQ−Grupo Vinculado PLAPIQUI−CONICET-FCEFyN, Universidad Nacional de Córdoba, X5016GCA, Av. Vélez Sarsfield 1611, Córdoba, Argentina;1. Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China;2. Chemistry Department, College of Saint Benedict and Saint John’s University, MN 56374, USA |
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| Abstract: | 3,4-Dichlorophenacylchloride was reduced with whole cell biocatalysts to give the (R)- or (S)-chlorohydrine in high yields and good to high enantiomeric excess. Yields and enantiomeric purity of the (S)-enantiomer were increased to 95 and >98%, respectively, using growing cells from Geotrichum candidum (CBS 233.76) in the presence of hydrophobic adsorbing resins at 4 g/l. The latter compound was transformed into (R)-3,4-dichlorophenylbutanolide, intermediate in the synthesis of (+)-cis-1S,4S-sertraline. |
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