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Issue 2, 2017
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Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases

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Abstract

The asymmetric bioreduction of α,β-unsaturated γ-keto esters using ene-reductases from the Old Yellow Enzyme family proceeds with excellent stereoselectivity and high conversion levels, covering a broad range of acyclic and cyclic derivatives. Various strategies were employed to provide access to both enantiomers, which are versatile precursors of bioactive molecules. The regioselectivity of hydride addition on di-activated alkenes was elucidated by isotopic labeling experiments and showed strong preference for the keto moiety as activating/binding group as opposed to the ester. Finally, chemoenzymatic synthesis of (R)-2-(2-oxocyclohexyl)acetic acid was achieved in high ee on a preparative scale combining enzymatic reduction followed by ester hydrogenolysis.

Graphical abstract: Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases

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Publication details

The article was received on 06 Sep 2016, accepted on 21 Oct 2016 and first published on 21 Oct 2016


Article type: Paper
DOI: 10.1039/C6GC02493A
Citation: Green Chem., 2017,19, 511-518
  • Open access: Creative Commons BY license
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    Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases

    N. G. Turrini, R. C. Cioc, D. J. H. van der Niet, E. Ruijter, R. V. A. Orru, M. Hall and K. Faber, Green Chem., 2017, 19, 511
    DOI: 10.1039/C6GC02493A

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