Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime

Demidova, Yu. S.; Mozhaitsev, E. S.; Суслов, Е. В.; Nefedov, Andrey A.; Saraev, Аndrey А.; Волчо, К. П.; Salakhutdinov, N. F.; Simakov, Andrey; Simakova, Irina L.; Murzin, Dmitry Yu.

doi:10.1016/j.apcata.2020.117799

Cited by 3 publications

(2 citation statements)

References 69 publications

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“…In recent reports, hydrogenation of menthone oxime to amines via gold catalysts has excellent yields in high temperature. The drawback of this system is the expensive costs of gold nanoparticles (Demidova et al 2020).…”

Section: Introductionmentioning

confidence: 99%

Construction and Optimization of a Biocatalytic Route for Menthone Amination

Zhu

Jia

et al. 2023

Preprint

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(+)-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. All raw materials were cheap and by-products were easily removed. This method underscores the potential of biocatalysts in the synthesis of unnatural terpenoid amine derivatives.

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Section: Introductionmentioning

confidence: 99%

Construction and Optimization of a Biocatalytic Route for Menthone Amination

Zhu

Jia

et al. 2023

Preprint

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“…In recent reports, hydrogenation of menthone oxime to amines via gold catalysts could afford excellent yields at 100 °C. The drawbacks of this system are the high cost of gold nanoparticles and use of high temperature (Demidova et al 2020 ).…”

Section: Introductionmentioning

confidence: 99%

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

Zhu,

Pan,

et al. 2023

Bioresour. Bioprocess.

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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. Graphical Abstract

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