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Issue 12, 2017
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Enzymatic cascades for the stereo-complementary epimerisation of in situ generated epoxy alcohols

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Abstract

The synthesis of optically pure secondary epoxy alcohols from racemic allylic alcohols using a single whole-cell biocatalyst of recombinant Escherichia coli coexpressing three oxidoreductases is described. The cascade involves the concurrent action of a styrene monooxygenase that catalyzes the formation of the chiral epoxy group, and two alcohol dehydrogenases that fulfil the epimerisation of the hydroxy group. Two sets of alcohol dehydrogenases were each applied to couple with styrene monooxygenase in order to realize the epimerisation in a stereo-complementary manner. Excellent enantio- and diastereo-selectivities were achieved for most of the 12 substrates.

Graphical abstract: Enzymatic cascades for the stereo-complementary epimerisation of in situ generated epoxy alcohols

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Publication details

The article was received on 04 Jan 2017, accepted on 27 Feb 2017 and first published on 27 Feb 2017


Article type: Paper
DOI: 10.1039/C7OB00015D
Citation: Org. Biomol. Chem., 2017,15, 2562-2568
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    Enzymatic cascades for the stereo-complementary epimerisation of in situ generated epoxy alcohols

    Y. Liu, C. Guo, Y. Liu, H. Wang and Z. Wu, Org. Biomol. Chem., 2017, 15, 2562
    DOI: 10.1039/C7OB00015D

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