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Production of chiral alcohols from prochiral ketones by microalgal photo-biocatalytic asymmetric reduction reaction

  • Biocatalysis
  • Published:
Journal of Industrial Microbiology & Biotechnology

Abstract

Microalgal photo-biocatalysis is a green technique for asymmetric synthesis. Asymmetric reduction of nonnatural prochiral ketones to produce chiral alcohols by microalgal photo-biocatalysis was studied in this work. Acetophenone (ACP) and ethyl acetoacetate (EAA) were chosen as model substrates for aromatic ketones and β-ketoesters, respectively. Two prokaryotic cyanophyta and two eukaryotic chlorophyta were selected as photo-biocatalysts. The results proved that nonnatural prochiral ketones can be reduced by microalgal photo-biocatalysis with high enantioselectivity. Illumination is indispensable to the photo-biocatalysis. For aromatic ketone, cyanophyta are eligible biocatalysts. For ACP asymmetric reduction reaction, about 45% yield and 97% e.e. can be achieved by the photo-biocatalysis reaction with Spirulina platensis as biocatalyst. On the contrary, chlorophyta are efficient biocatalysts for β-ketoester asymmetric reduction reaction among the four tested algae. For EAA asymmetric reduction reaction, about 70% yield and 90% e.e. can be achieved with Scenedesmus obliquus as biocatalyst. The microalgae used in this study outperformed other characterized biocatalysts such as microbial and plant cells.

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Acknowledgments

This work was partially supported by the Natural Science Foundation of Hubei Province of China (no. 2008CDB354), Scientific Program of China Hubei Provincial Science & Technology Department (no. 2008BCB203), and the open fund of Research Center of Green Manufacturing and Energy-Saving & Emission Reduction Technology in Wuhan University of Science and Technology (no. B1013).

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Authors and Affiliations

  1. College of Chemical Engineering and Technology, Wuhan University of Science and Technology, No. 154 postal box, Wuhan, 430081, China

    Zhong-Hua Yang, Li Luo, Xu Chang, Wei Zhou, Geng-Hua Chen & Yan Zhao

  2. Institute of Bioengineering, Zhejiang University of Technology, Hangzhou, 310014, Zhejiang, China

    Ya-Jun Wang

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  1. Zhong-Hua Yang
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  2. Li Luo
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Correspondence to Zhong-Hua Yang.

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Yang, ZH., Luo, L., Chang, X. et al. Production of chiral alcohols from prochiral ketones by microalgal photo-biocatalytic asymmetric reduction reaction. J Ind Microbiol Biotechnol 39, 835–841 (2012). https://doi.org/10.1007/s10295-012-1088-y

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  • DOI: https://doi.org/10.1007/s10295-012-1088-y

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