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Issue 2, 2009
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Biocatalytical production of (5S)-hydroxy-2-hexanone

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Abstract

Biocatalytical approaches have been investigated in order to improve accessibility of the bifunctional chiral building block (5S)-hydroxy-2-hexanone ((S)-2). As a result, a new synthetic route starting from 2,5-hexanedione (1) was developed for (S)-2, which is produced with high enantioselectivity (ee >99%). Since (S)-2 can be reduced further to furnish (2S,5S)-hexanediol ((2S,5S)-3), chemoselectivity is a major issue. Among the tested biocatalysts the whole-cell system S. cerevisiae L13 surpasses the bacterial dehydrogenase ADH-T in terms of chemoselectivity. The use of whole-cells of S. cerevisiae L13 affords (S)-2 from prochiral 1 with 85% yield, which is 21% more than the value obtained with ADH-T. This is due to the different reaction rates of monoreduction (12) and consecutive reduction (23) of the respective biocatalysts. In order to optimise the performance of the whole-cell-bioreduction 12 with S. cerevisiae, the system was studied in detail, revealing interactions between cell-physiology and xenobiotic substrate and by-products, respectively. This study compares the whole-cell biocatalytic route with the enzymatic route to enantiopure (S)-2 and investigates factors determining performance and outcome of the bioreductions.

Graphical abstract: Biocatalytical production of (5S)-hydroxy-2-hexanone

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Publication details

The article was received on 18 Sep 2008, accepted on 16 Oct 2008 and first published on 17 Nov 2008


Article type: Paper
DOI: 10.1039/B816364B
Citation: Org. Biomol. Chem., 2009,7, 304-314
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    Biocatalytical production of (5S)-hydroxy-2-hexanone

    M. Katzberg, K. Wechler, M. Müller, P. Dünkelmann, J. Stohrer, W. Hummel and M. Bertau, Org. Biomol. Chem., 2009, 7, 304
    DOI: 10.1039/B816364B

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