Lipase-catalyzed enantioselective acylation of 3-benzyloxypropane-1,2-diol in supercritical carbon dioxide |
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| Institution: | 1. Department of Chemical Engineering, Budapest University of Technology and Economics, M?egyetem Rakpart 3, H-1111 Budapest, Hungary;2. Institute for Organic Chemistry and Research Group for Alkaloid Chemistry, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest, Hungary;3. VITUKI Ltd., Kvassay Jen? út 1, H-1095 Budapest, Hungary;1. Department of Applied Physics, Sri Venkateswara College of Engineering, Chennai 602117, India;2. Department of Physics, Sriram Engineering College, Chennai 602024, India;3. Department of Physics, Kalasalingam University, Krishnankoil 626126, India;4. Department of Physics, Presidency College, Chennai 600005, India;1. Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507 & FR3038, ENSICAEN, Normandie Université, Université de Caen Basse-Normandie, 6 Bd du Maréchal Juin, Caen 14050, France;2. Normandie Université, COBRA, UMR 6014 & FR 3038; Université de Rouen; INSA Rouen; CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France;3. CNRS, Institut de Pharmacologie et de Biologie Structurale, 205 Route de Narbonne, 31077 Toulouse, France;4. Université de Toulouse, UPS, IPBS, 205 Route de Narbonne, 31077 Toulouse, France;1. Department of Medicinal Chemistry, Sichuan Medical University, Luzhou 646000, PR China;2. Key Laboratory of Medicinal Electrophysiology of Ministry of Education, Sichuan Medical University, Luzhou 646000, PR China;1. Department of Marine Life Sciences, School of Marine Biomedical Sciences, Jeju National University, Jeju Self-Governing Province 63243, Republic of Korea;2. Fish Vaccine Research Center, Jeju National University, Jeju Self-Governing Province 63243, Republic of Korea;3. Department of Veterinary Medicine, College of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa 252-8570, Japan;4. Informatics Development & Management Group, Korea Institute of Oriental Medicine, 1672 Yuseongdae-ro, Yuseong-gu, Daejeon 34054, Republic of Korea;1. Wellcome Trust Centre for Neuroimaging, Institute of Neurology, University College London, London, WC1N 3BG, UK;2. Max Planck-University College London Centre for Computational Psychiatry and Ageing Research, London, WC1B 5EH, UK;3. Department of Systems Neuroscience, Medical Center Hamburg-Eppendorf, Hamburg, Germany;4. Department of Neurophysics, Max Planck Institute for Human Cognitive and Brain Sciences, 04103, Leipzig, Germany |
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| Abstract: | Lipase-catalyzed acylation of 3-benzyloxypropane-1,2-diol with vinyl acetate as acyl donor using different lipases porcine pancreas lipase (PPL), Lipase AK “Amano”, Lipase PS “Amano”, and crude enzymes from Trichoderma reesei RUT-C30, Thermoascus thermophilus (NRRL5208), Talaromyces emersonii (NRLL3221)] was studied in supercritical carbon dioxide (scCO2). In the reactions catalyzed by different lipases different amounts of monoacetate and diacetate products along with minor amounts of cyclic acetals forming from the diol and acetaldehyde were obtained.Application of Lipase AK led to the highest conversion (84.7%) and the highest enantiomeric excess values (eemonoacetates = 38%, eediacetate = 85%). Effect of water content of scCO2 on the productivity and the enantiomer selectivity of the reactions with Lipase AK was also investigated. |
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