Stereoselective oxidation of sulfides to optically active sulfoxides with resting cells of Pseudomonas monteilii CCTCC M2013683

Chen, Yongzheng; Zhuo, Junrui; Zheng, Daijun; Sheng, Tian; Li, Zhi

doi:10.1016/j.molcatb.2014.05.004

Cited by 26 publications

(28 citation statements)

References 31 publications

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“…Our research focused on the enzymatic oxidation reactions, including high regio‐ and stereo‐selective biocatalytic asymmetric sulfoxidation, and have developed a stereoselective oxidation method to synthesize optically active sulfoxides with resting cells of Pseudomonas monteilii CCTCC M2013683 . In this study, we tried to identify and heterogeneously express nine potential P450s and five redox partners genes from P. lavamentivorans DS‐1.…”

Section: Figurementioning

confidence: 99%

Biocatalytical Asymmetric Sulfoxidation by Identifying Cytochrome P450 from Parvibaculum Lavamentivorans DS‐1

Tang

Cui

et al. 2018

ChemCatChem

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Cytochrome P450 monooxygenases (P450s) catalyzed asymmetric sulfoxidation represents a green route for the synthesis of valuable enantiopure sulfoxides, which are potentially interesting synthons in synthetic and pharmaceutical chemistry. Here the potential P450 and redox partner genes from Parvibaculum lavamentivorans DS‐1 are screened and co‐expressed in Escherichia coli host to construct twenty recombinant P450 strains. By testing the whole‐cell biooxidation of thioanisole, P450PL2 (CYP278A4) and P450PL7 (CYP108G3) are identified with excellent S enantioselectivity while P450PL1 (CYP111B1) and P450PL9 (CYP153A26) exhibit the complementary R enantioselectivity. Asymmetric sulfoxidation of sulfides 1 a–1 m is further investigated using the recombinant E. coli strain P450PL2‐2 based on the optimal conditions, producing the corresponding enantioenriched sulfoxides with up to 82 % isolated yield and 99 % ee.

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Section: Figurementioning

confidence: 99%

Biocatalytical Asymmetric Sulfoxidation by Identifying Cytochrome P450 from Parvibaculum Lavamentivorans DS‐1

Tang

Cui

et al. 2018

ChemCatChem

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“…In our previous report, a bacterial strain was isolated from soil samples and named P. monteilii CCTCC M2013683 (Chen et al. ). When cultured with M9‐toluene medium, the whole‐cell bacteria could catalyze asymmetric oxidation of sulfides to chiral sulfoxides with 54–99% yields in 63–99% ee (Chen et al.…”

Section: Resultsmentioning

confidence: 99%

“…When cultured with M9‐toluene medium, the whole‐cell bacteria could catalyze asymmetric oxidation of sulfides to chiral sulfoxides with 54–99% yields in 63–99% ee (Chen et al. ). Moreover, the oxidation activity of this bacteria cell was activated when toluene was the only carbon and energy source (Chen et al.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, the oxidation activity of this bacteria cell was activated when toluene was the only carbon and energy source (Chen et al. ). When cultured under other carbon sources, like in LB medium with or without toluene, this bacterial strain exhibit less than 5% conversion (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Procedures of biocatalysis in this study were performed as previously reported (Chen et al. b; Zheng et al. ).…”

Section: Methodsmentioning

confidence: 99%

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RNA‐seq transcriptome analysis of a Pseudomonas strain with diversified catalytic properties growth under different culture medium

et al. 2016

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Biocatalysis is an emerging strategy for the production of enantio‐pure organic molecules. However, lacking of commercially available enzymes restricts the widespread application of biocatalysis. In this study, we report a Pseudomonas strain which exhibited versatile oxidation activity to synthesize chiral sulfoxides when growing under M9‐toluene medium and reduction activity to synthesize chiral alcohols when on Luria‐Bertani (LB) medium, respectively. Further comparative transcriptome analysis on samples from these two cultural conditions has identified 1038 differentially expressed genes (DEG). Gene Ontology (GO) enrichment and KEGG pathways analysis demonstrate significant changes in protein synthesis, energy metabolism, and biosynthesis of metabolites when cells cultured under different conditions. We have identified eight candidate enzymes from this bacterial which may have the potential to be used for synthesis of chiral alcohol and sulfoxide chemicals. This work provides insights into the mechanism of diversity in catalytic properties of this Pseudomonas strain growth with different cultural conditions, as well as candidate enzymes for further biocatalysis of enantiomerically pure molecules and pharmaceuticals.

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Unconventional Biocatalytic Approaches to the Synthesis of Chiral Sulfoxides

et al. 2020

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Sulfoxides are a class of organic compounds that find wide application in medicinal and organic chemistry. Several biocatalytic approaches have been developed to synthesise enantioenriched sulfoxides, mainly by exploiting oxidative enzymes. Recently, the use of reductive enzymes such as Msr and Dms has emerged as a new, alternative method to obtain enantiopure sulfoxides from racemic mixtures. In parallel, novel oxidative approaches, employing nonclassical solvents such as ionic liquids (ILs) and deep eutectic solvents (DESs), have been developed as greener and more sustainable biocatalytic synthetic pathways. This minireview aims highlights the recent advances made in the biocatalytic synthesis of enantioenriched sulfoxides by employing such unconventional approaches.

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Stereoselective oxidation of sulfides to optically active sulfoxides with resting cells of Pseudomonas monteilii CCTCC M2013683

Cited by 26 publications

References 31 publications

Biocatalytical Asymmetric Sulfoxidation by Identifying Cytochrome P450 from Parvibaculum Lavamentivorans DS‐1

Biocatalytical Asymmetric Sulfoxidation by Identifying Cytochrome P450 from Parvibaculum Lavamentivorans DS‐1

RNA‐seq transcriptome analysis of a Pseudomonas strain with diversified catalytic properties growth under different culture medium

Unconventional Biocatalytic Approaches to the Synthesis of Chiral Sulfoxides

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