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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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Supplementary files

Article information


Submitted
06 Sep 2016
Accepted
21 Oct 2016
First published
21 Oct 2016

This article is Open Access

Green Chem., 2017,19, 511-518
Article type
Paper

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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