Regio- and enantioselective bioreduction of methyleneketoesters using both polymeric resin and cellulose matrix |
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| Affiliation: | 1. Department of Biochemistry, Stellenbosch University, Stellenbosch, South Africa;2. Department of Anatomical Pathology, Tohoku University School of Graduate Medicine, Sendai, Japan;1. Dipartimento di Scienze Farmaceutiche, Sez. Chimica Generale e Organica ‘A. Marchesini’, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy;2. Dipartimento di Scienze per gli Alimenti, la Nutrizione, l’Ambiente, Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy;1. Regional Centre of Advanced Technologies and Materials, Department of Analytical Chemistry, Faculty of Science, Palacký University in Olomouc, 17. Listopadu 12, Olomouc CZ-77146, Czech Republic;2. Department of Forensic Medicine and Medical Law, Faculty Hospital, Hněvotínská 3, Olomouc CZ-77515, Czech Republic |
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| Abstract: | Methyleneketoesters were prepared in >90% yield by performing an IBX oxidation of Morita–Baylis–Hillman adducts. A methodology was developed to achieve methyl 3-aryl-3-keto-2-methylenepropanoate reduction using a screening of yeast strains in three different reaction procedures to obtain products with both high yield and diastereoselectivity. The reactions conducted in water provided inferior yields (50%) for substrates 2b–c. Employing Amberlite® XAD7HP which was a substrate reservoir that also immediately extracted the products from the reaction medium after their formation, syn-4a–c and anti-4a–c were isolated in 60–70% yield, with high stereoselectivity (98–99% ee). The best results were obtained using substrates adsorbed on filter paper which provided products yields above 70%, a 99% ee and a diastereomoeric ratio (syn-4: anti-4) 9:1. Cellulose matrix has excellent potential to be successfully employed in general biocatalytic reactions. |
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| Keywords: | Methyleneketoesters Baylis–Hillman adducts Cellulose matrix |
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