The enantioselectivity of reduction of ethyl 4-halo-3-oxobutanoate catalyzed by Geotrichum candidum depends on the cofactor |
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| Affiliation: | 1. Dipartimento di Ingegneria Civile, Ambientale, Aerospaziale, dei Materiali, Università degli Studi di Palermo, Viale delle Scienze, Edificio 8, 90128, Palermo, Italy;2. Dipartimento di Ingegneria Civile, Ambientale e Architettura, Università degli Studi di Cagliari, Viale Marengo, 2, 09123, Cagliari, Italy;1. Department of Chemistry, Baselius College, Kottayam, 686001, Kerala, India;2. School of Pure & Applied Physics, Mahatma Gandhi University, 686560, Kerala, India;3. School of Health Science, University of KwaZulu-Natal, Westville, Durban, 4001, South Africa;4. Division of Drug Design and Medicinal Chemistry Research Lab, Department of Pharmaceutical Chemistry, Ahalia School of Pharmacy, Palakkad, 678557, Kerala, India;5. Department of Pharmaceutical Chemistry, Al Shifa College of Pharmacy, Perinthalmanna, 679325, Kerala, India;1. Department of Biodiversity and Molecular Ecology, Research and Innovation Centre, Fondazione Edmund Mach, Italy;2. Institute of Plant Physiology and Genetics, Bulgarian Academy of Sciences, Bulgaria;3. Faculty of Biology, Sofia University, Bulgaria;4. Department of Food Quality and Nutrition, Volatile Compound Facility, Research and Innovation Centre, Fondazione Edmund Mach, Italy;5. Department of Sustainable Agro-ecosystems and Bio-resources, Research and Innovation Centre, Fondazione Edmund Mach, Italy;6. Institute of Ecology, University of Innsbruck, Austria;7. The National Research Council of Italy (CNR), Department of Biology, Agriculture and Food Sciences, Rome, Italy;1. Laboratory of Synthetic and Materials Chemistry, Manipal Centre for Natural Sciences, Manipal University, Karnataka 576104, India;2. Department of Physics, TKM College of Arts and Science, Karicode, Kollam, Kerala, 69100, India;3. University of Novi Sad, Faculty of Sciences, Department of Physics, Trg D. Obradovića 4, Novi Sad, 21000 Serbia;4. University of Novi Sad, Faculty of Sciences, Department of Chemistry, Biochemistry and Environmental Protection, Trg D. Obradovića 3, Novi Sad, 21000, Serbia |
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| Abstract: | Enantioselective reductions of ethyl 3-oxobutanoates with fermenting cells or acetone treated cells of Geotrichum candidum gave 3-hydroxyesters with different ee and different predominant configurations depending on reaction conditions. Ethyl 4-bromo-3-oxobutanoate was reduced with APG4 and NADH to give predominantly ethyl (R)-4-bromo-3 hydroxybutanoate while the (S)-configuration was predominant when NADPH was the cofactor. Moreover, when the catalyst was heated before the reaction, the ee was increased indicating that the enzyme giving the (S)-alcohol is more thermolabile than the other. |
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