Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts

Abstract

We have developed biocatalytic methods for the stereoselective reduction of cyclic prochiral 1,3-diketones for the production of optically active β-hydroxyketones and/or 1,3-diols. The recombinant ketoreductase KRED1-Pglu (formulated as purified catalyst) and whole cells of wild type Escherichia coli DE3 Star were used as biocatalysts, displaying different and sometimes complementary stereoselectivity, thus allowing the preparation of stereochemically pure β-hydroxyketones (12–66% isolated yields, > 99% e.e.) and 1,3-diols (40–60% isolated yields, > 99% e.e.).

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Acknowledgements

The authors thank the University of Milan for funding the stay of Federica Dall’Oglio at the Biotechnology Forschungszentrum of Jülich.

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Correspondence to Andrea Pinto.

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Contente, M.L., Dall’Oglio, F., Annunziata, F. et al. Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts. Catal Lett 150, 1176–1185 (2020). https://doi.org/10.1007/s10562-019-03015-y

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Keywords

  • Biocatalytic reduction
  • 1-3 diketones
  • β-hydroxyketones
  • 1,3-Diols
  • Enzymatic
  • Whole cells