Optimization of Synthesis of (S)-Omeprazole Catalyzed by Soybean Pod Peroxidase in Water-in-Oil Microemulsions Using RSM

Tang Hui; Zhang Yuanyuan; Deng YashanDu ShanshanLi DepengWang ZhiyongLi HuilingGao XinWang Fanye

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Optimization of Synthesis of (S)-Omeprazole Catalyzed by Soybean Pod Peroxidase in Water-in-Oil Microemulsions Using RSM

机译：Optimization of Synthesis of (S)-Omeprazole Catalyzed by Soybean Pod Peroxidase in Water-in-Oil Microemulsions Using RSM

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Abstract Response surface methodology (RSM) was used to optimize the oxidizing the omeprazole sulfide to (S)-omeprazole catalyzed by environmentally friendly catalyst soybean pod peroxidase (SPP) in cetyltrimethylammonium bromide (CTAB)/isooctane/n-butyl alcohol/water water-in-oil microemulsions. With the initial concentration of SPP of 3200 U ml?1, the conversion of the omeprazole sulfide, the (S)-omeprazole yield and ee were 93.75%, 91.56% and 96.08%, respectively, under the optimal conditions: Wo of 15.85, the concentration of H2O2 of 22.44?mM and reaction temperature of 49.68?°C, respectively. The proposed mechanism of asymmetric sulfoxidations catalyzed by SPP involves three concomitant mechanisms as follows: (1) a two-electron reduction of SPP-I, (2) a single-electron transfer to SPP-I and (3) nonenzymatic reactions. Based on the proposed mechanism which is reasonable and can express the oxidations, the reaction system includes five enzymatic and two nonenzymatic reactions. With 5.44% of the average relative error, a kinetic model based on the mechanisms fitting observed data very well was established, and the SPP-catalyzed reactions including both the two-electron reduction and the single-electron transfer mechanisms obey ping-pong mechanism with substrate and product inhibition, while nonenzymatic reactions follow a power law. This study has also demonstrated the feasibility of SPP as a substitute with low cost, excellent enantioselectivity and better thermal stability.Graphic Abstract

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《Catalysis Letters》 |2022年第3期|720-731|共12页
作者
Tang Hui; Zhang Yuanyuan; Deng YashanDu ShanshanLi DepengWang ZhiyongLi HuilingGao XinWang Fanye;
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Qingdao University of Science and Technology;

Rheinischen Friedrich -Wilhelms-Universität Bonn Gerhard-Domagk-Str;

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正文语种英语
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Soybean pod peroxidase; Response surface optimization; Water-in-oil microemulsion; Asymmetric sulfoxidation; Chiral sulfoxides;

Optimization of Synthesis of (S)-Omeprazole Catalyzed by Soybean Pod Peroxidase in Water-in-Oil Microemulsions Using RSM

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