Asymmetric reduction of ketones by employing Rhodotorula sp. AS2.2241 and synthesis of the β-blocker (R)-nifenalol |
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| Affiliation: | 1. Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China;2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;1. Departamento de Química, Universidade de Evora, Rua Romão Ramalho, 59, 7000 Evora, Portugal;2. Centro de Química de Évora, Rua Romão Ramalho, 59, 7000 Évora, Portugal;3. Instituto de Ciências Agrárias e Ambientais Mediterrânicas (ICCAM), Apartado 94, 7002-554, Universidade de Évora, Portugal;4. Instituto de Investigação do Medicamento (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal;5. Center For Neurosciences and Cell Biology, University of Coimbra, Portugal;1. Key Laboratory of Environmental and Applied Microbiology, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China;2. Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu 610041, China;3. University of Chinese Academy of Sciences, Beijing 10049, China;1. College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea;2. Department of Synthetic Chemistry, Chong Kun Dang Research Institute, 315-20, Dongbaekjukjeon-daero, Giheung-gu, Yongin-si, Gyeonggi-do, Republic of Korea;1. College of Chemical Engineering, Fuzhou University, Fuzhou 350116, China;2. College of Biological Science and Engineering, Fuzhou University, Fuzhou 350116, China;3. Institute of Bioengineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China;4. School of Life Sciences, Northwestern Polytechnical University, Xi’an 710072, China;1. Institute of Bioengineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, PR China;2. Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, Hangzhou 310027, PR China |
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| Abstract: | A broad range of prochiral ketones were efficiently reduced to the corresponding optically active secondary alcohols using resting cells of Rhodotorula sp. AS2.2241. The microbial reduction system exhibited high activity and enantioselectivity in the reduction of various aromatic ketones and acetylpyridines (>97% ee), but moderate to high enantioselectivity in the reduction of α- and β-keto esters. (R)-Nifenalol, a β-adrenergic blocker, was also synthesized using 2-bromo-1(R)-(4-nitrophenyl)ethanol (97% ee) which was prepared through the asymmetric reduction of 2-bromo-1-(4-nitrophenyl)ethanone employing Rhodotorula sp. AS2.2241. The simple preparation and the high activity of the biocatalyst turned this system into a versatile tool for organic synthesis. |
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