Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent

Böhmer, Wesley; Koenekoop, Lucien; Simon, Timothée; Mutti, Francesco G.

doi:10.3390/molecules25092140

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Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent

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Van ‘t Hoff Institute for Molecular Sciences, HIMS Biocat, University of Amsterdam, 1098 XH Amsterdam, The Netherlands

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Academic Editors: Antimo Gioiello and Bruno Cerra

Molecules 2020, 25(9), 2140; https://doi.org/10.3390/molecules25092140

Received: 6 April 2020 / Revised: 27 April 2020 / Accepted: 30 April 2020 / Published: 3 May 2020

(This article belongs to the Special Issue Enabling Chemical Technologies in Medicinal Chemistry)

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Abstract

Comprising approximately 40% of the commercially available optically active drugs, α-chiral amines are pivotal for pharmaceutical manufacture. In this context, the enzymatic asymmetric amination of ketones represents a more sustainable alternative than traditional chemical procedures for chiral amine synthesis. Notable advantages are higher atom-economy and selectivity, shorter synthesis routes, milder reaction conditions and the elimination of toxic catalysts. A parallel interconnected kinetic asymmetric transformation (PIKAT) is a cascade in which one or two enzymes use the same cofactor to convert two reagents into more useful products. Herein, we describe a PIKAT catalyzed by an immobilized ω-transaminase (ωTA) in neat toluene, which concurrently combines an asymmetric transamination of a ketone with an anti-parallel kinetic resolution of an amine racemate. The applicability of the PIKAT was tested on a set of prochiral ketones and racemic α-chiral amines in a 1:2 molar ratio, which yielded elevated conversions (up to >99%) and enantiomeric excess (ee, up to >99%) for the desired products. The progress of the conversion and ee was also monitored in a selected case. This is the first report of a PIKAT using an immobilized ωTA in a non-aqueous environment. View Full-Text

Keywords: biocatalysis; asymmetric catalysis; kinetic resolution; α-chiral amines; enzyme immobilization; EziG; cascades; PIKAT; transaminases; aminotransferases

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

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Böhmer, W.; Koenekoop, L.; Simon, T.; Mutti, F.G. Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent. Molecules 2020, 25, 2140. https://doi.org/10.3390/molecules25092140

AMA Style

Böhmer W, Koenekoop L, Simon T, Mutti FG. Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent. Molecules. 2020; 25(9):2140. https://doi.org/10.3390/molecules25092140

Chicago/Turabian Style

Böhmer, Wesley, Lucien Koenekoop, Timothée Simon, and Francesco G. Mutti. 2020. "Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent" Molecules 25, no. 9: 2140. https://doi.org/10.3390/molecules25092140

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Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent

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