Lactones 34 [1]. Application of alcohol dehydrogenase from horse liver (HLADH) in enantioselective synthesis of δ- and ɛ-lactones |
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| Institution: | 1. Center for Bioengineering and Biotechnology, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao, 266580, China;2. College of Chemistry and Materials, Fujian Normal University, Fuzhou, 350007, China;1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. Central Scientific and Research Technological Institute ‘Technomash’, 121108 Moscow, Russian Federation;3. Photochemistry Center, Russian Academy of Sciences, 119421 Moscow, Russian Federation;1. Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany;2. Institute of Biomaterial Science and Berlin-Brandenburg Center for Regenerative Therapies (BCRT), Helmholtz-Zentrum Geesthacht, Kantstraße 55, 14513 Teltow, Germany;1. New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore, Karnataka 560064, India;2. Theoretical Sciences Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore, Karnataka 560064, India;4. Cleveland Center for Membrane and Structural Biology, School of Medicine, Case Western Reserve University, Cleveland, OH; and;2. Laboratory of Hematology and Flow Cytometry, Department of Hematology, Military Institute of Medicine, Warsaw, Poland |
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| Abstract: | The ability of horse liver alcohol dehydrogenase (HLADH) to the enantioselective oxidation of primary–primary, primary–secondary and primary-tertiary aliphatic 1,5- and 1,6-diols 1a–i was studied. No enantioselectivity of the transformations of primary–primary 1,6-diols 1a–d to ɛ-lactones 4a–d was observed. Regioselective oxidation of primary–secondary 1,6-diols 1e,f and 1,5-diols 1h,i afforded enantiomerically enriched ɛ-lactones 4e,f and δ-lactones 4h,i. ɛ-Lactones 4e,f were formed with higher enantiomeric excesses (e.e. = 85–99%). Enzymatic oxidation of primary–tertiary 1,6-diol 1g did not give lactone product. |
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