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- Title
Redox cascade reaction for kinetic resolution of racemic α-methylbenzylamine and biosynthesis of α-phenylethanol.
- Authors
Liu, Jinbin; Wang, Minyang; Liang, Chen; Deng, Huaxiang; Yu, Xiaohong
- Abstract
Chiral α-methylbenzylamine and α-phenylethanol are important building blocks for the industrial production of optically active drugs, bioactive compounds. Methods for the simultaneous synthesis of chiral α-methylbenzylamine and α-phenylethanol remain rare. Herein, a biocatalytic redox cascade reaction composed of ω-transaminase, aldo–keto reductase, and glutamate dehydrogenase for chiral α-methylbenzylamine and α-phenylethanol synthesis from racemic α-methylbenzylamine was constructed. A novel ω-transaminase and two different chiral aldo–keto reductases were demonstrated in the cascade reaction. The cosubstrate and redox equivalents were regenerated simultaneously by glutamate dehydrogenase. Using the approach, (R)-α-phenylethanol, (S)-α-phenylethanol, and (R)-α-methylbenzylamine were prepared with excellent stereoselectivity (ee > 99.7%). Furthermore, semi-preparative-scale biotransformation of racemic α-methylbenzylamine was conducted. The production of (R)-α-phenylethanol reached 26.05 mM at 24 h, and the production of (S)-α-phenylethanol reached 25.44 mM at 32 h. Taken together, a novel idea was proposed for the efficient and green synthesis of chiral α-methylbenzylamine and α-phenylethanol, which had great potential for industrial application. Key points: • Excellent stereoselectivity chiral α-methylbenzylamine and α-phenylethanol were synthesized. • A novel ω-transaminase demonstrated the catalysis toward (S)-α-methylbenzylamine. • Two novel aldo–keto reductases demonstrated the conversion toward acetophenone.
- Subjects
OXIDATION-reduction reaction; ALDO-keto reductases; KINETIC resolution; GLUTAMATE dehydrogenase; BIOSYNTHESIS; INDUSTRIAL capacity
- Publication
Applied Microbiology & Biotechnology, 2023, Vol 107, Issue 1, p125
- ISSN
0175-7598
- Publication type
Article
- DOI
10.1007/s00253-022-12299-x