Asymmetric Bio-oxidation Using Resting Cells of Rhodococcus rhodochrous ATCC 4276 Mutant QZ-3 for Preparation of (S)-Omeprazole in a Chloroform–Water Biphasic System Using Response Surface Methodology

Zhang, Yuanyuan; Lv, Kuiying; Deng, Yashan; Li, Huiling; Wang, Zhiyong; Li, Depeng; Gao, Xin; Wang, Fanye

doi:10.1007/s10562-021-03531-w

Cited by 2 publications

(4 citation statements)

References 56 publications

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“…The product was obtained at a yield of 92.9 % and an excellent enantiomeric excess (>99 %) with no byproduct formation under optimized conditions (Scheme 4). These results indicated higher bio‐oxidation activity and substrate tolerance compared to the wild‐type strain [90] …”

Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 86%

“…[82b,89] More recently, Zhang et al performed a study describing the asymmetric sulfoxidation of omeprazole sulfide for the preparation of S-omeprazole using a mutant strain of R. rhodochrous ATCC 4276. [90] The S-enantiomer of omeprazole sulfoxide, an anti-ulcer drug, exerts a therapeutic effect better than that of racemates. [25a,91] The mutant strain was constructed via complex mutagenesis induced by using 0.025 mole/L NaNO 2 and UV irradiation.…”

Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 99%

“…These results indicated higher bio-oxidation activity and substrate tolerance compared to the wild-type strain. [90] Remarkably, Streptomyces species also have significant roles in bioconversion processes for the production of drug varieties, as recently reviewed, focusing on innovative approaches for improved production. [92] To state an example of the chiral transformation of drugs, a depolymerase from S. exfoliatus immobilized as cross-linked enzyme aggregates hydrolyzed poly-R-3-hydroxybutyrate to the chiral R-3-hydroxybutyric acid.…”

Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 99%

“… Asymmetric sulfoxidation of omeprazole to S ‐omeprazole sulfoxide using the resting cells of QZ‐3 of R. rhodochrous ATCC 4276 in a chloroform‐water biphasic system, modified from Zhang et al [90] …”

Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 99%

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Actinobacteria as Microbial Cell Factories and Biocatalysts in The Synthesis of Chiral Intermediates and Bioactive Molecules; Insights and Applications

Salama,

Mostafa,

Husseiny

et al. 2024

Chemistry & Biodiversity

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Actinobacteria are one of the most intriguing bacterial phyla in terms of chemical diversity and bioactivities of their reported biomolecules and natural products, including various types of chiral molecules. Actinobacterial genera such as Detzia, Mycobacterium, and Streptomyces are among the microbial sources targeted for selective reactions such as asymmetric biocatalysis catalyzed by whole cells or enzymes induced in their cell niche. Remarkably, stereoselective reactions catalyzed by actinobacterial whole cells or their enzymes include stereoselective oxidation, stereoselective reduction, kinetic resolution, asymmetric hydrolysis, and selective transamination, among others. Species of actinobacteria function with high chemo‐, regio‐, and enantio‐selectivity under benign conditions, which could help current industrial processing. Numerous selective enzymes were either isolated from actinobacteria or expressed from actinobacteria in other microbes and hence exploited in the production of pure organic compounds difficult to obtain chemically. In addition, different species of actinobacteria, especially Streptomyces species, function as natural producers of chiral molecules of therapeutic importance. Herein, we discuss some of the most outstanding contributions of actinobacteria to asymmetric biocatalysis, which are important in the organic and/or pharmaceutical industries. In addition, we highlight the role of actinobacteria as microbial cell factories for chiral natural products with insights into their various biological potentialities.

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Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 86%

Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 99%

Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 99%

Section: Actinobacteria As a Source Of Biocatalysts In Chiral Drug Sy...mentioning

confidence: 99%

See 2 more Smart Citations

Actinobacteria as Microbial Cell Factories and Biocatalysts in The Synthesis of Chiral Intermediates and Bioactive Molecules; Insights and Applications

Salama,

Mostafa,

Husseiny

et al. 2024

Chemistry & Biodiversity

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

et al. 2021

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Asymmetric Bio-oxidation Using Resting Cells of Rhodococcus rhodochrous ATCC 4276 Mutant QZ-3 for Preparation of (S)-Omeprazole in a Chloroform–Water Biphasic System Using Response Surface Methodology

Cited by 2 publications

References 56 publications

Actinobacteria as Microbial Cell Factories and Biocatalysts in The Synthesis of Chiral Intermediates and Bioactive Molecules; Insights and Applications

Actinobacteria as Microbial Cell Factories and Biocatalysts in The Synthesis of Chiral Intermediates and Bioactive Molecules; Insights and Applications

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

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