Construction and optimization of a biocatalytic route for the synthesis of neomenthylamine from menthone

Hui-Jue Zhu; Jiang Pan; Chun-Xiu Li; Fei-Fei Chen; Jian-He Xu

doi:10.1186/s40643-023-00693-w

Construction and optimization of a biocatalytic route for the synthesis of neomenthylamine from menthone

Bioresour Bioprocess. 2023 Nov 3;10(1):75. doi: 10.1186/s40643-023-00693-w.

Authors

Hui-Jue Zhu¹, Jiang Pan¹, Chun-Xiu Li¹, Fei-Fei Chen², Jian-He Xu³

Affiliations

¹ Laboratory of Biocatalysis and Synthetic Biotechnology, State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Centre for Biomanufacturing, College of Biotechnology, East China University of Science and Technology, Shanghai, 200237, People's Republic of China.
² Laboratory of Biocatalysis and Synthetic Biotechnology, State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Centre for Biomanufacturing, College of Biotechnology, East China University of Science and Technology, Shanghai, 200237, People's Republic of China. feifeichen@mail.ecust.edu.cn.
³ Laboratory of Biocatalysis and Synthetic Biotechnology, State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Centre for Biomanufacturing, College of Biotechnology, East China University of Science and Technology, Shanghai, 200237, People's Republic of China. jianhexu@ecust.edu.cn.

Abstract

(+)-Neomenthylamine is an important industrial precursor used to synthesize high value-added chemicals. Here, we report a novel biocatalytic route to synthesize (+)-neomenthylamine by amination of readily available (-)-menthone substrate using ω-transaminase. By screening a panel of ω-transaminases, an ω-transaminase from Vibrio fluvialis JS17 was identified with considerable amination activity to (-)-menthone, and then characterization of enzymatic properties was conducted for the enzyme. Under optimized conditions, 10 mM (-)-menthone was transformed in a mild aqueous phase with 4.7 mM product yielded in 24 h. The biocatalytic route using inexpensive starting materials (ketone substrate and amino donor) and mild reaction conditions represents an easy and green approach for (+)-neomenthylamine synthesis. This method underscores the potential of biocatalysts in the synthesis of unnatural terpenoid amine derivatives.

Keywords: (+)-N-Boc-Neomenthylamine; (+)-Neomenthylamine; Asymmetric synthesis; Biocatalysis; Transaminase.

Abstract

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