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Article

Asymmetric Synthesis of Optically Pure Aliphatic Amines with an Engineered Robust ω-Transaminase

by
Linhan Dong
1,2,
Qinglong Meng
1,
Carlos Ramírez-Palacios
1,3,
Hein J. Wijma
1,
Siewert J. Marrink
3 and
Dick B. Janssen
1,*
1
Biotransformation and Biocatalysis Group, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
2
College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun 130012, China
3
Molecular Dynamics Group, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands
*
Author to whom correspondence should be addressed.
Catalysts 2020, 10(11), 1310; https://doi.org/10.3390/catal10111310
Submission received: 12 October 2020 / Revised: 30 October 2020 / Accepted: 8 November 2020 / Published: 12 November 2020
(This article belongs to the Section Biocatalysis)
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Abstract

The production of chiral amines by transaminase-catalyzed amination of ketones is an important application of biocatalysis in synthetic chemistry. It requires transaminases that show high enantioselectivity in asymmetric conversion of the ketone precursors. A robust derivative of ω-transaminase from Pseudomonasjessenii (PjTA-R6) that naturally acts on aliphatic substrates was constructed previously by our group. Here, we explore the catalytic potential of this thermostable enzyme for the synthesis of optically pure aliphatic amines and compare it to the well-studied transaminases from Vibrio fluvialis (VfTA) and Chromobacterium violaceum (CvTA). The product yields indicated improved performance of PjTA-R6 over the other transaminases, and in most cases, the optical purity of the produced amine was above 99% enantiomeric excess (e.e.). Structural analysis revealed that the substrate binding poses were influenced and restricted by the switching arginine and that this accounted for differences in substrate specificities. Rosetta docking calculations with external aldimine structures showed a correlation between docking scores and synthetic yields. The results show that PjTA-R6 is a promising biocatalyst for the asymmetric synthesis of aliphatic amines with a product spectrum that can be explained by its structural features.
Keywords: transamination; asymmetric synthesis; alkanamines; transaminase; computational modeling transamination; asymmetric synthesis; alkanamines; transaminase; computational modeling
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MDPI and ACS Style

Dong, L.; Meng, Q.; Ramírez-Palacios, C.; Wijma, H.J.; Marrink, S.J.; Janssen, D.B. Asymmetric Synthesis of Optically Pure Aliphatic Amines with an Engineered Robust ω-Transaminase. Catalysts 2020, 10, 1310. https://doi.org/10.3390/catal10111310

AMA Style

Dong L, Meng Q, Ramírez-Palacios C, Wijma HJ, Marrink SJ, Janssen DB. Asymmetric Synthesis of Optically Pure Aliphatic Amines with an Engineered Robust ω-Transaminase. Catalysts. 2020; 10(11):1310. https://doi.org/10.3390/catal10111310

Chicago/Turabian Style

Dong, Linhan, Qinglong Meng, Carlos Ramírez-Palacios, Hein J. Wijma, Siewert J. Marrink, and Dick B. Janssen. 2020. "Asymmetric Synthesis of Optically Pure Aliphatic Amines with an Engineered Robust ω-Transaminase" Catalysts 10, no. 11: 1310. https://doi.org/10.3390/catal10111310

APA Style

Dong, L., Meng, Q., Ramírez-Palacios, C., Wijma, H. J., Marrink, S. J., & Janssen, D. B. (2020). Asymmetric Synthesis of Optically Pure Aliphatic Amines with an Engineered Robust ω-Transaminase. Catalysts, 10(11), 1310. https://doi.org/10.3390/catal10111310

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