Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions

Heinks T, Paulus J, Koopmeiners S, Beuel T, Sewald N, Höhne M, Bornscheuer UT, Fischer von Mollard G (2022)
ChemBioChem 23(16): e202200329.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Chiral and enantiopure amines can be produced by enantioselective transaminases via kinetic resolution of amine racemates. This transamination reaction requires stoichiometric amounts of co-substrate. A dual-enzyme recycling system overcomes this limitation: L-amino acid oxidases (LAAO) recycle the accumulating co-product of ( S )-selective transaminases in the kinetic resolution of racemic amines to produce pure ( R )-amines. However, availability of suitable LAAOs is limited. Here we use the heterologously produced, highly active fungal hcLAAO4 with broad substrate spectrum. H 2 O 2 as by-product of hcLAAO4 is detoxified by a catalase. The final system allows using sub-stoichiometric amounts of 1mol% of the transaminase co-substrate as well as the initial application of L-amino acids instead of alpha-keto acids. With an optimized protocol, synthetic potential of this kinetic resolution cascade was proven at the preparative scale (>90mg) by the synthesis of highly enantiomerically pure ( R )-methylbenzylamine (>99%ee) at complete conversion (50%). © 2022 Wiley-VCH GmbH.
Erscheinungsjahr
2022
Zeitschriftentitel
ChemBioChem
Band
23
Ausgabe
16
Art.-Nr.
e202200329
eISSN
1439-7633
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Open-Access-Publikationskosten wurden durch die Universität Bielefeld im Rahmen des DEAL-Vertrags gefördert.
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https://pub.uni-bielefeld.de/record/2963945

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Heinks T, Paulus J, Koopmeiners S, et al. Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions. ChemBioChem. 2022;23(16): e202200329.
Heinks, T., Paulus, J., Koopmeiners, S., Beuel, T., Sewald, N., Höhne, M., Bornscheuer, U. T., et al. (2022). Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions. ChemBioChem, 23(16), e202200329. https://doi.org/10.1002/cbic.202200329
Heinks, Tobias, Paulus, Jannik, Koopmeiners, Simon, Beuel, Tobias, Sewald, Norbert, Höhne, Matthias, Bornscheuer, Uwe T, and Fischer von Mollard, Gabriele. 2022. “Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions”. ChemBioChem 23 (16): e202200329.
Heinks, T., Paulus, J., Koopmeiners, S., Beuel, T., Sewald, N., Höhne, M., Bornscheuer, U. T., and Fischer von Mollard, G. (2022). Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions. ChemBioChem 23:e202200329.
Heinks, T., et al., 2022. Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions. ChemBioChem, 23(16): e202200329.
T. Heinks, et al., “Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions”, ChemBioChem, vol. 23, 2022, : e202200329.
Heinks, T., Paulus, J., Koopmeiners, S., Beuel, T., Sewald, N., Höhne, M., Bornscheuer, U.T., Fischer von Mollard, G.: Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions. ChemBioChem. 23, : e202200329 (2022).
Heinks, Tobias, Paulus, Jannik, Koopmeiners, Simon, Beuel, Tobias, Sewald, Norbert, Höhne, Matthias, Bornscheuer, Uwe T, and Fischer von Mollard, Gabriele. “Recombinant L-Amino Acid Oxidase with broad substrate spectrum for Co-Substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions”. ChemBioChem 23.16 (2022): e202200329.
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