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Chemoenzymatic Synthesis of Enantiopure Amino Alcohols from Simple Methyl Ketones |
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| Authors: | Jan Eric Neuburger Alina Gazizova Sven Tiedemann Prof. Dr. Jan von Langermann |
| Affiliation: | 1. Institute of Chemistry, Biocatalytic Synthesis Group, University of Rostock, Albert-Einstein-Str. 3 A, 18059 Rostock, Germany Contribution: Data curation (equal), Formal analysis (equal), Investigation (equal), Methodology (equal), Visualization (equal);2. Institute of Chemistry, Technical Chemistry, University of Rostock, Albert-Einstein-Str. 3 A, 18059 Rostock, Germany Contribution: Data curation (supporting), Formal analysis (supporting), Investigation (supporting), Methodology (equal), Writing - original draft (supporting);3. Institute of Chemistry, Biocatalytic Synthesis Group, University of Rostock, Albert-Einstein-Str. 3 A, 18059 Rostock, Germany Contribution: Data curation (supporting), Investigation (supporting);4. Institute of Chemistry, Biocatalytic Synthesis Group, University of Rostock, Albert-Einstein-Str. 3 A, 18059 Rostock, Germany |
| Abstract: | This study highlights the straight-forward synthesis of substituted 1,2-amino alcohols from simple and readily available aromatic methyl ketones. Starting from acetophenone derivatives, the straight-forward synthesis strategy involved an initial bromination of the alpha-positioned methyl group in the first step, followed by a simple hydrolysis to the hydroxyketone (2-hydroxyacetophenone). The hydroxylated intermediate was subsequently converted from Silicibacter pomeroyi to the final 1,2-amino alcohol by using the transaminase. The transaminase-catalyzed reaction proceeded with yields up to 62 % and always excellent enantiomeric excess of >99 %. Interestingly, the keto-enol-tautomerism of the hydroxyl ketone yields an unexpected amino alcohol isomer. |
| Keywords: | amino alcohol chemoenzymatic enantioselective enzyme tautomerism |