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

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

Biocatalysis / (+)-Neomenthylamine / Transaminase / Asymmetric synthesis / (+)-N-Boc-Neomenthylamine

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Funding

National Key Research and Development Program of China(2019YFA0905000)

National Natural Science Foundation of China(21871085)

Fundamental Research Funds for the Central Universities(222201714026)