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Synthesis of(S)-omeprazole catalyzed by soybean pod peroxidase in water-in-oil microemulsions:optimization and modeling
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  • Hui Tang,
  • yuanyuan zhang,
  • Yashan Deng,
  • depeng Li,
  • zhiyong Wang,
  • huiling Li,
  • xin Gao,
  • Fanye Wang
Hui Tang
Qingdao University of Science and Technology

Corresponding Author:943422042@qq.com

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yuanyuan zhang
Qingdao University of Science and Technology
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Yashan Deng
Qingdao University of Science and Technology
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depeng Li
Qingdao University of Science and Technology
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zhiyong Wang
Qingdao University of Science and Technology
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huiling Li
Qingdao University of Science and Technology
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xin Gao
Qingdao University of Science and Technology
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Fanye Wang
Qingdao University of Science and Technology
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Abstract

Response surface methodology(RSM)was used to optimize the oxidizing the omeprazole sulfide to(S)-omeprazole catalyzed by 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. The 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. With 5.44% of the average relative error, a kinetic model based on the mechanisms 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.