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从薄荷酮合成新薄荷胺的生物催化途径的构建与优化。

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

作者信息

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

机构信息

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.

出版信息

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

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.

摘要

(+)-新薄荷胺是用于合成高附加值化学品的重要工业前体。在此,我们报道了一种通过使用ω-转氨酶对易得的(-)-薄荷酮底物进行胺化反应来合成(+)-新薄荷胺的新型生物催化路线。通过筛选一系列ω-转氨酶,鉴定出一株来自河流弧菌JS17的ω-转氨酶对(-)-薄荷酮具有相当高的胺化活性,然后对该酶进行了酶学性质表征。在优化条件下,10 mM的(-)-薄荷酮在温和的水相中进行转化,24小时内产生了4.7 mM的产物。该生物催化路线使用廉价的起始原料(酮底物和氨基供体)以及温和的反应条件,是一种用于合成(+)-新薄荷胺的简便且绿色的方法。该方法突出了生物催化剂在合成非天然萜类胺衍生物方面的潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11d4/10992614/66d25e4b39cc/40643_2023_693_Sch1_HTML.jpg

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