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The effect of dimethyl sulfoxide on the enantioselectivity in the pig liver esterase catalyzed hydrolysis of dialkylated propanedioic acid dimethyl esters
Affiliation:1. Department of Organic Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden;2. Department of Biochemistry and Biotechnology, Royal Institute of Technology, S-100 44 Stockholm, Sweden;1. Drug Delivery and Disposition, KU Leuven, Department of Pharmaceutical and Pharmacological Sciences, Belgium;2. University Hospitals Leuven, Department of Gastroenterology, Belgium;1. Department of Biotechnology, Panjab University, Chandigarh, India;2. National JALMA Institute for Leprosy & Other Mycobacterial Diseases, Agra, India;1. Polymer Electronics Research Center, School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand;2. The MacDiarmid Institute for Advanced Materials and Nanotechnology, Wellington 6140, New Zealand;3. Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, 700000 Viet Nam;4. IMS lab, Institute of Technology, University of Tartu, Nooruse 1, 50441 Tartu, Estonia;5. Centre for Electrochemistry and Intelligent Materials (CEMI), Universidad Politécnica de Cartagena, Aulario II, Paseo Alfonso XIII, E-30203, CartagenaMurcia, Spain;6. Conducting polymers in composites and applications Research Group, Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, Viet Nam;1. Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, Japan;2. School of Pharmacy, Tokyo University Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract:The effect of dimethyl sulfoxide (DMSO) on the enantioselectivity in the pig liver esterase (EC 3.1.1.1) catalyzed hydrolysis of dialkylated propanedioic acid diesters was studied. Increasing concentrations of DMSO increased the ratio of the (R)-enantiomers of the produced monoesters. This effect was not due to the change in pHapp caused by the solvent. The reaction rate was lowered to one-tenth of the rate without DMSO when the DMSO concentration was increased to 50%.
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