New chiral building blocks from acetovanillone using lipase A and B from Candida antarctica |
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| Institution: | 1. Department of Actinobacteria Metabolic Engineering Group, Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Campus C2 3, 66123 Saarbrücken, Germany;2. Institute for Organic Chemistry II, University Siegen, Adolf-Reichwein-Str. 2, 57076 Siegen, Germany;3. Institute for Pharmaceutical Biology and Biotechnology, Albert-Ludwigs University Freiburg, Stefan-Meier-Str. 19, 79104 Freiburg, Germany;1. College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, People''s Republic of China;2. Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, People''s Republic of China;1. Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE 50740-540, Brazil;2. Centro de Educação e Saúde, Universidade Federal de Campina Grande, Olho D’agua da Bica, s/n, Cuité, PB 58175-000, Brazil;1. Ege University, Department of Chemistry, Catalyst Research Laboratory, 35100 Bornova, Izmir, Turkey;2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Semenov Av. 1, Chernogolovka, 142432 Moscow Region, Russia;3. N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia |
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| Abstract: | Acetovanillone has been used as the starting material for the synthesis of a series of secondary alcohols, which were resolved by lipase catalyzed esterification. 1-(4-Benzyloxy-3-methoxyphenyl)ethanol was efficiently resolved using immobilized lipase B from Candida antarctica (Novozym 435, CAL-B), whereas immobilized lipase A from C. antarctica (Novozym 735, CAL-A) was the lipase of choice for the resolution of the corresponding 2-bromo- and 2-chloro-derivatives. The enantioenriched alcohols are new building blocks for potential use in the synthesis of bioactive compounds. |
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