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The use of marine-derived fungi for preparation of enantiomerically pure alcohols

Abstract

A highly enantioselective and minimally polluting approach to optically pure chiral alcohols is developed using cheap, readily available and sustainable marine-derived fungi as catalysts. An evaluation of the synthetic potential of 13 Chinese marine fungi was performed to screen for enantioselective reduction of 13 aromatic ketones from different compound classes as substrates. Good yields and excellent enantioselectivities were achieved with this method. In details, first the effects of several crucial variables on the bioreduction of aromatic ketones with whole cells of marine fungi were explored systematically. Next, we obtained insight into the substrate scope of the tested fungi under the optimized conditions, and selected reduction processes were performed at a commercial scale of up to 1000 mL to determine scalability, which led to excellent yields and enantioselectivities. Last, ketone reductases from two prioritized fungi exhibited good recyclability, with those of Rhodotorula mucilageinosa giving a > 95% yield with up to 99% ee during 3 cycles and those of Rhodotorula rubra giving a > 95% yield with up to 99% ee during 9 cycles.

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Acknowledgements

This study was funded by the Basic Research Program of Sun Yat-Sen University (Grant Nos. 17lgpy58 and 17lgzd12), Natural Science Foundation of Guangdong Province (Grant Nos. 42000-18823950 and 42000-18823952), the National Natural Science Foundation of China (Grant Nos. 21272289,41606167, 41706148, and 51709287), China’s Marine Commonweal Research Project (Grant No. 201305017), and the special financial fund of innovative development of marine economic demonstration project (Grant No. GD2012-D01-001).

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Correspondence to Bi-Shuang Chen.

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This article does not contain any studies with human participants or animals performed by any of the authors.

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Liu, H., de Souza, F.Z.R., Liu, L. et al. The use of marine-derived fungi for preparation of enantiomerically pure alcohols. Appl Microbiol Biotechnol 102, 1317–1330 (2018). https://doi.org/10.1007/s00253-017-8707-5

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  • DOI: https://doi.org/10.1007/s00253-017-8707-5

Keywords

  • Chiral alcohols
  • Marine fungi
  • Enantioselective reduction
  • Scalability
  • Recyclability