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One-Pot Enzymatic–Chemical Cascade Route for Synthesizing Aromatic α-Hydroxy Ketones
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-02-16 , DOI: 10.1021/acscatal.0c04961 Lei Wang 1 , Wei Song 1, 2 , Binju Wang 3 , Yan Zhang 2 , Xin Xu 1 , Jing Wu 2 , Cong Gao 1 , Jia Liu 1 , Xiulai Chen 1 , Jinghua Chen 2 , Liming Liu 1
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-02-16 , DOI: 10.1021/acscatal.0c04961 Lei Wang 1 , Wei Song 1, 2 , Binju Wang 3 , Yan Zhang 2 , Xin Xu 1 , Jing Wu 2 , Cong Gao 1 , Jia Liu 1 , Xiulai Chen 1 , Jinghua Chen 2 , Liming Liu 1
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2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C–C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic–chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.
中文翻译：
一锅酶-化学级联途径合成芳族α-羟基酮
2-羟基苯乙酮（2-HAP）是生产一系列天然产物和药物的重要组成部分。但是，没有安全，有效和经济的2-HAP合成方法。在此，基于逆合成分析，设计了一种一锅法酶-化学级联途径来合成2-HAP。首先，利用计算模拟设计了自发的质子转移反应，该模拟使得能够从异构体2-羟基-2-苯基乙醛合成2-HAP。然后通过将非天然底物乙醛酸引入由热带假丝酵母催化的CC连接反应中，构建了2-羟基-2-苯基乙醛合成的路线。丙酮酸脱羧酶。该酶促化学级联途径的组装和优化产生了92.7％的最终收率。此外，引入立体特异性羰基还原酶以构建合成的应用平台，该平台能够将2-HAP进一步转化为（S）-和（R）-1-苯基-1,2-乙二醇。级联自发的化学和酶促反应以合成化学药品的方法，为深入了解合成其他有价值的化学药品的途径提供了见识。
更新日期：2021-03-05
中文翻译：
一锅酶-化学级联途径合成芳族α-羟基酮
2-羟基苯乙酮（2-HAP）是生产一系列天然产物和药物的重要组成部分。但是，没有安全，有效和经济的2-HAP合成方法。在此，基于逆合成分析，设计了一种一锅法酶-化学级联途径来合成2-HAP。首先，利用计算模拟设计了自发的质子转移反应，该模拟使得能够从异构体2-羟基-2-苯基乙醛合成2-HAP。然后通过将非天然底物乙醛酸引入由热带假丝酵母催化的CC连接反应中，构建了2-羟基-2-苯基乙醛合成的路线。丙酮酸脱羧酶。该酶促化学级联途径的组装和优化产生了92.7％的最终收率。此外，引入立体特异性羰基还原酶以构建合成的应用平台，该平台能够将2-HAP进一步转化为（S）-和（R）-1-苯基-1,2-乙二醇。级联自发的化学和酶促反应以合成化学药品的方法，为深入了解合成其他有价值的化学药品的途径提供了见识。
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