Enantioselective oxidation of sulfides to sulfoxides by Gordonia terrae IEGM 136 and Rhodococcus rhodochrous IEGM 66

Elkin, Andrey A.; Kylosova, T.I.; Гришко, В. В.; Ившина, И. Б.

doi:10.1016/j.molcatb.2012.12.001

Cited by 20 publications

(12 citation statements)

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“…Enantioselective oxidation of aromatic suldes was reported earlier using whole-cells of some Actinobacteria including Rhodococcus species and Gordonia terrae IEGM. 9,15 Although the free growing cells of these bacteria achieved high yields, they did not exhibit satisfactory enantioselectivities (<95%) as shown in Table 2. Remarkably, one of the Rhodococcus strains produced the (S)-sulfoxide with >99% ee aer reaction conditions were optimized.…”

Section: Effect Of Addition Of a Co-solventmentioning

confidence: 98%

“…[6][7][8] However, it was indicated that bacteria belonging to the genus Gordonia, Rhodococcus and Pseudomonas possess fairly high activity and enantioselectivity for a large number of suldes. 3,[9][10][11] Actinobacteria have been exploited successfully in the search for novel biocatalysts. 12,13 However, as reported earlier, the ability of enantioselective oxidation of organic suldes was only studied in a limited number of Actinobacteria.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0

et al. 2020

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Section: Effect Of Addition Of a Co-solventmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0

et al. 2020

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“…Later, Elkin and his group [ 56 ] optimized the conditions for the oxidation of methyl phenyl sulfide ( 94 ) by the application of the bacteria Rhodococcus rhodochrous IEGM 66 and Gordonia terrae IEGM 136, studying the effects of pH of the culture medium, sulfide concentration, temperature and aeration regimes. In a 50 mg scale reaction, the selected biocatalysts were highly active toward methyl phenyl sulfide and its analogs ethyl phenyl, methyl p -tolyl, and benzyl methyl sulfides, reaching yields between 64–100% and enantiomeric excess ranging from 54% to 95%.…”

Section: Oxidation Of Sulfidesmentioning

confidence: 99%

Whole Cells as Biocatalysts in Organic Transformations

et al. 2018

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Currently, the power and usefulness of biocatalysis in organic synthesis is undeniable, mainly due to the very high enantiomeric excess reached using enzymes, in an attempt to emulate natural processes. However, the use of isolated enzymes has some significant drawbacks, the most important of which is cost. The use of whole cells has emerged as a useful strategy with several advantages over isolated enzymes; for this reason, modern research in this field is increasing, and various reports have been published recently. This review surveys the most recent developments in the enantioselective reduction of carbon-carbon double bonds and prochiral ketones and the oxidation of prochiral sulfides using whole cells as biocatalytic systems.

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“…The catalytic bio-oxidation reactions can also be catalyzed using bacterial strains. Previous research [32,33] has shown that this process occurs in bacteria, as in the case of fungi, and can be catalyzed using P450 or dibenzothiophene monooxygenases [34].…”

Section: Bacteriamentioning

confidence: 99%

Biotechnological Methods of Sulfoxidation: Yesterday, Today, Tomorrow

2018

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The production of chiral sulphoxides is an important part of the chemical industry since they have been used not only as pharmaceuticals and pesticides, but also as catalysts or functional materials. The main purpose of this review is to present biotechnological methods for the oxidation of sulfides. The work consists of two parts. In the first part, examples of biosyntransformation of prochiral sulfides using whole cells of bacteria and fungi are discussed. They have more historical significance due to the low predictability of positive results in relation to the workload. In the second part, the main enzymes responsible for sulfoxidation have been characterized such as chloroperoxidase, dioxygenases, cytochrome flavin-dependent monooxygenases, and P450 monooxygenases. Particular emphasis has been placed on the huge variety of cytochrome P450 monooxygenases, and flavin-dependent monooxygenases, which allows for pure sulfoxides enantiomers effectively to be obtained. In the summary, further directions of research on the optimization of enzymatic sulfoxidation are indicated.

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Enantioselective oxidation of sulfides to sulfoxides by Gordonia terrae IEGM 136 and Rhodococcus rhodochrous IEGM 66

Cited by 20 publications

References 20 publications

Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0

Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0

Whole Cells as Biocatalysts in Organic Transformations

Biotechnological Methods of Sulfoxidation: Yesterday, Today, Tomorrow

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