Heterocycles 32. Efficient kinetic resolution of 1-(2-arylthiazol-4-yl)ethanols and their acetates using lipase B from Candida antarctica |
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| Institution: | 1. Iuliu Haţieganu University of Medicine and Pharmacy, Department of Organic Chemistry, Victor Babeş 41, Ro-400012 Cluj-Napoca, Romania;2. Babeş-Bolyai University of Cluj-Napoca, Department of Biochemistry and Biochemical Engineering, Arany János 11, Ro-400028 Cluj-Napoca, Romania;1. Beijing Bioprocess Key Laboratory, College of Life Science and Technology, Beijing University of Chemical Technology, Beijing, 100029, PR China;2. Amoy-BUCT Industrial of Bio-tech novation Institute, Amoy, 361026, PR China;3. State Key Laboratory of Chemical Resource Engineering, Institute of Materia Medica, College of Science, Beijing University of Chemical Technology, Beijing, 100029, PR China;1. Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India;2. School of Biotechnology, Jawaharlal Nehru University, New Delhi 110067, India;3. Departamento de Química Fundamental, Universidade da Coruña, Campus da Zapateira s/n, 15071 A Coruña, Spain;4. Department of Biotechnology, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India;1. Department of Organic Chemistry, Faculty of Chemistry, Uzhhorod National University, Fedinets'', Str. 53/1, 88000, Uzhhorod, Ukraine;2. State Scientific Institution “Institute for Single Crystals” NAS of Ukraine, 60 Nauky Ave, 61001, Kharkiv, Ukraine;1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, Saudi Arabia;2. Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019, Sesto Fiorentino, Florence, Italy;1. Florida International University, MAIDROC Laboratory, Department of Mechanical and Materials Engineering, 10555 West Flagler Street, Miami, FL 33174, USA;2. Indian Institute of Technology, Department of Materials Engineering, Kharagpur, W.B. 721302, India;3. North Carolina State University, Materials Science and Engineering Department, Raleigh, NC 27695, USA;4. Federal University of Rio de Janeiro/COPPE, Mechanical Engineering Department, Rio de Janeiro, Brazil;5. University of Trieste, Dipartimento di Ingegneria e Architettura, Via Valerio, 10, 34127 Trieste, Italy;6. SIGMA Technology, Electrozavodskaia St., 20, Moscow, 107023, Russia |
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| Abstract: | In this paper we describe the chemoenzymatic synthesis of new enantiomerically enriched (R)- and (S)-1-(2-arylthiazol-4-yl)ethanols and their acetates by enzymatic enantioselective acetylation of the racemic alcohols rac-2a–d and by methanolysis of the corresponding racemic esters rac-3a–d mediated by lipase B from Candida antarctica (CaL-B) in non-aqueous media. In terms of stereoselectivity and activity, both procedures, acylation and alcoholysis, gave similar good results (50% conversion, E ≫ 200). The absolute configuration of the kinetic resolution products was determined by a detailed 1H NMR study of the Mosher's derivatives of (S)-2b. |
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| Keywords: | Biocatalysis Kinetic resolution Thiazole Chiral secondary alcohols |
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