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Issue 8, 2015
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Biocatalyzed asymmetric reduction of benzils to either benzoins or hydrobenzoins: pH dependent switch

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Abstract

Enantiopure benzoins and hydrobenzoins are precursors of various pharmaceuticals and biologically active compounds. In addition, hydrobenzoins are precursors of chiral ligands and auxiliaries in stereoselective organic synthesis. Biocatalytic reduction of benzils is a straightforward approach to prepare these molecules. However, known methods are not selective and lead to formation of a mixture of benzoin and hydrobenzoin, requiring expensive separation procedures. Here, we describe an enzyme system Talaromyces flavus, which exhibited excellent pH dependent selectivity for the conversion of benzil to either benzoin or hydrobenzion in high ee. Thus, (S)-benzoin was the exclusive product at pH 5.0 (ee >99%), whereas at pH 7.0, (S,S)-hydrobenzoin (ee >99%, dl/meso 97 : 3) was the exclusive product. The observed pH dependent selectivity was shown to be due to the presence of multiple enzymes in Talaromyces flavus, which specifically accepted either benzil or benzoin as a substrate and exhibited different pH profiles of their activity. The biocatalyst efficiently reduced a variety of symmetrical and unsymmetrical benzils. Moreover, a 36.4 kDa benzoin reductase was purified, the N-terminal sequence of which did not show a significant similarity to any of the known reductase/dehydrogenase in the database. The protein therefore appears to be a novel reductase.

Graphical abstract: Biocatalyzed asymmetric reduction of benzils to either benzoins or hydrobenzoins: pH dependent switch

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Supplementary files

Article information


Submitted
01 Feb 2015
Accepted
26 May 2015
First published
26 May 2015

Catal. Sci. Technol., 2015,5, 4017-4028
Article type
Paper
Author version available

Biocatalyzed asymmetric reduction of benzils to either benzoins or hydrobenzoins: pH dependent switch

M. Pal, G. Srivastava, A. N. Sharma, S. Kaur and R. S. Jolly, Catal. Sci. Technol., 2015, 5, 4017
DOI: 10.1039/C5CY00158G

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