Advances in the field of the synthesis of amino derivatives of terpenoids

Козлов, Н. Г.

doi:10.1007/bf00577177

Cited by 7 publications

(7 citation statements)

References 47 publications

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“…Currently, all the synthetic pathways of (+)-neomenthylamine rely on chemical methods with terpenoids initial reactants such as (−)-menthone (Wallach 1891;Kozlov et al 1981;Kozlov 1982;Schopohl et al 2003). A conventional way was to convert (−)-menthone by reductive amination under Leuckart-Wallach conditions (Kitamura et al 2002), which could obtain all the neomenthylamines isomers.…”

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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“…Currently, all the synthetic pathways of (+)-neomenthylamine rely on chemical methods with terpenoid initial reactants such as (−)-menthone (Wallach 1891 ; Kozlov et al 1981 ; Kozlov 1982 ). A conventional way was to convert (−)-menthone by reductive amination under Leuckart–Wallach conditions (Kitamura et al 2002 ), which could obtain all the neomenthylamines isomers.…”

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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“…Different terpene oximes are widely used as starting compounds and intermediates to obtain important heterocycles, nitriles, amines and carbonyl compounds [3]. Reduction of menthone oxime leads to formation of menthylamine [4] (Figure 1), which is of great practical interest due to its wide application for synthesis of catalysts for chiral phasetransfer [5] and a range of chiral reactions, including hydrosilylation [6,7,8], Michael addition [9,10], asymmetric epoxidation [11,12] and Henry reactions [13]. Moreover, menthylamine is applied for synthesis of the stationary phase for high performance column chromatography [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

“…Menthylamine can be produced from menthone via a multistep reductive amination under Leuckart-Wallach conditions (a thermally driven reaction) or from menthone oxime under Bouveault-Blanc conditions using absolute ethanol and sodium metal and via hydrogenation using a transition metal catalyst [4,17,18]. In particular, menthone oxime was reduced using platinum black in glacial acetic acid and Raney nickel in methanol [4,18]. These approaches resulted in menthylamine formation as a diastereomeric mixture, with the total yield of amine reaching 40-60%.…”

Section: Introductionmentioning

confidence: 99%