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通过多酶级联反应将（-）-柠檬烯区域特异性C-H胺化合成（-）-紫苏胺。

Regiospecific C-H amination of (-)-limonene into (-)-perillamine by multi-enzymatic cascade reactions.

作者信息

Ge Yue, Huang Zheng-Yu, Pan Jiang, Li Chun-Xiu, Zheng Gao-Wei, 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. 2022 Aug 26;9(1):88. doi: 10.1186/s40643-022-00571-x.

DOI:10.1186/s40643-022-00571-x
PMID:38647597
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10992285/
Abstract

BACKGROUND

(-)-Limonene, one of cyclic monoterpenes, is an important renewable compound used widely as a key building block for the synthesis of new biologically active molecules and fine chemicals. (-)-Perillamine, as derived from (-)-limonene, is a highly useful synthon for constructing more complicated and functionally relevant chemicals.

AIM

We aimed to report a more sustainable and more efficient method for the regiospecific C-H amination of (-)-limonene into (-)-perillamine.

RESULTS

Here, we report an artificial penta-enzymatic cascade system for the transformation of the cheap and easily available (-)-limonene into (-)-perillamine for the first time. This system is composed of cytochrome P450 monooxygenase, alcohol dehydrogenase and w-transaminase for the main reactions, as well as formate dehydrogenase and NADH oxidase for cofactor recycling. After optimization of the multi-enzymatic cascade system, 10 mM (-)-limonene was smoothly converted into 5.4 mM (-)-perillamine in a one-pot two-step biotransformation, indicating the feasibility of multi-enzymatic C7-regiospecific amination of the inert C-H bond of (-)-limonene. This method represents a concise and efficient route for the biocatalytic synthesis of derivatives from similar natural products.

摘要

背景

（-）-柠檬烯是环状单萜之一，是一种重要的可再生化合物，被广泛用作合成新型生物活性分子和精细化学品的关键构建单元。（-）-紫苏胺由（-）-柠檬烯衍生而来，是构建更复杂且功能相关化学品的非常有用的合成子。

目的

我们旨在报道一种更可持续、更高效的方法，将（-）-柠檬烯区域特异性C-H胺化转化为（-）-紫苏胺。

结果

在此，我们首次报道了一种人工五酶级联系统，用于将廉价易得的（-）-柠檬烯转化为（-）-紫苏胺。该系统由细胞色素P450单加氧酶、醇脱氢酶和ω-转氨酶进行主要反应，以及甲酸脱氢酶和NADH氧化酶进行辅因子循环。对多酶级联系统进行优化后，在一锅两步生物转化中，10 mM（-）-柠檬烯顺利转化为5.4 mM（-）-紫苏胺，表明对（-）-柠檬烯惰性C-H键进行多酶C7区域特异性胺化的可行性。该方法代表了一种从类似天然产物生物催化合成衍生物的简洁高效途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/1f83dbeba3c2/40643_2022_571_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/b13876b30dc2/40643_2022_571_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/7e86182b3f50/40643_2022_571_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/70c727e38660/40643_2022_571_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/1f83dbeba3c2/40643_2022_571_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/b13876b30dc2/40643_2022_571_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/7e86182b3f50/40643_2022_571_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/70c727e38660/40643_2022_571_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2478/10992285/1f83dbeba3c2/40643_2022_571_Fig3_HTML.jpg

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7
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9
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