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Published on: April 22, 2016
Biocatalytic racemization of sec-alcohols and alpha-hydroxyketones using lyophilized microbial cells
Bettina M Nestl1, Constance V Voss, Anne Bodlenner
1Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria.
Abstract:
Biocatalytic racemization of aliphatic and aryl-aliphatic sec-alcohols and alpha-hydroxyketones (acyloins) was accomplished using whole resting cells of bacteria, fungi, and one yeast. The mild (physiological) reaction conditions ensured the suppression of undesired side reactions, such as elimination or condensation. Cofactor and inhibitor studies suggest that the racemization proceeds through an equilibrium-controlled enzymatic oxidation-reduction sequence via the corresponding ketones or alpha-diketones, respectively, which were detected in various amounts. Ketone formation could be completely suppressed by exclusion of molecular oxygen. Figure Biocatalytic racemization whole microbial cells.
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