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      Continuous Flow Bioamination of Ketones in Organic Solvents at Controlled Water Activity using Immobilized ω‐Transaminases

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          Abstract

          Compared with biocatalysis in aqueous media, the use of enzymes in neat organic solvents enables increased solubility of hydrophobic substrates and can lead to more favorable thermodynamic equilibria, avoidance of possible hydrolytic side reactions and easier product recovery. ω‐Transaminases from Arthrobacter sp. (AsR−ωTA) and Chromobacterium violaceum (Cv−ωTA) were immobilized on controlled porosity glass metal‐ion affinity beads (EziG) and applied in neat organic solvents for the amination of 1‐phenoxypropan‐2‐one with 2‐propylamine. The reaction system was investigated in terms of type of carrier material, organic solvents and reaction temperature. Optimal conditions were found with more hydrophobic carrier materials and toluene as reaction solvent. The system's water activity (a w) was controlled via salt hydrate pairs during both the biocatalyst immobilization step and the progress of the reaction in different non‐polar solvents. Notably, the two immobilized ωTAs displayed different optimal values of a w, namely 0.7 for EziG 3−AsR−ωTA and 0.2 for EziG 3−Cv−ωTA. In general, high catalytic activity was observed in various organic solvents even when a high substrate concentration (450–550 mM) and only one equivalent of 2‐propylamine were applied. Under batch conditions, a chemical turnover (TTN) above 13000 was obtained over four subsequent reaction cycles with the same batch of EziG‐immobilized ωTA. Finally, the applicability of the immobilized biocatalyst in neat organic solvents was further demonstrated in a continuous flow packed‐bed reactor. The flow reactor showed excellent performance without observable loss of enzymatic catalytic activity over several days of operation. In general, ca. 70% conversion was obtained in 72 hours using a 1.82 mL flow reactor and toluene as flow solvent, thus affording a space‐time yield of 1.99 g L −1 h −1. Conversion reached above 90% when the reaction was run up to 120 hours.

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          Author and article information

          Contributors
          f.mutti@uva.nl
          Journal
          Adv Synth Catal
          Adv. Synth. Catal
          10.1002/(ISSN)1615-4169
          ADSC
          Advanced Synthesis & Catalysis
          John Wiley and Sons Inc. (Hoboken )
          1615-4150
          1615-4169
          17 February 2020
          27 April 2020
          : 362
          : 9 ( doiID: 10.1002/adsc.v362.9 )
          : 1858-1867
          Affiliations
          [ 1 ] Van't Hoff Institute for Molecular Sciences, HIMS-Biocat University of Amsterdam Science Park 904 1098 XH Amsterdam The Netherlands
          [ 2 ] EnginZyme AB Tomtebodavägen 6 171 65 Solna Sweden
          Article
          ADSC201901274
          10.1002/adsc.201901274
          7217232
          658f6339-a4b6-4e4e-8028-e7a0606b469a
          © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

          This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

          History
          : 02 October 2019
          : 21 January 2020
          Page count
          Figures: 6, Tables: 1, References: 124, Pages: 10, Words: 0
          Funding
          Funded by: European Research Council (ERC)
          Funded by: European Union's Horizon 2020 Research and Innovation programme
          Award ID: 638271
          Funded by: NWO Sector Plan for Physics and Chemistry
          Categories
          Full Paper
          Full Papers
          Very Important Publication
          Custom metadata
          2.0
          April 27, 2020
          Converter:WILEY_ML3GV2_TO_JATSPMC version:5.8.1 mode:remove_FC converted:12.05.2020

          Catalysis
          asymmetric synthesis,biocatalysis,α-chiral amines,flow chemistry,transaminases
          Catalysis
          asymmetric synthesis, biocatalysis, α-chiral amines, flow chemistry, transaminases

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