Expanding the toolbox for enantioselective sulfide oxidations: Streptomyces strains as biocatalysts

Mascotti, María Laura; Palazzolo, Martín A.; Lewkowicz, Elizabeth Sandra; Kurina-Sanz, Marcela

doi:10.1016/j.bcab.2013.08.003

Cited by 8 publications

(14 citation statements)

References 28 publications

(29 reference statements)

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“…However, it was reported that Streptomyces hiroshimensis exhibited lower conversion of cyclohexyl methyl sulde and its enantioselectivity dropped upon using IPA 2% (v/ v) as a co-solvent. 17 Moreover, some Baeyer-Villiger monooxygenases may exhibit lower yields and enantioselectivity when IPA is added. 32 In another study, it was indicated that among different co-solvents tested with the fungus Aspergillus japonicus, IPA had the ability to enhance the chemo-and enantioselective sulfoxidation reaction.…”

Section: Effect Of Addition Of a Co-solventmentioning

confidence: 99%

“…12,13 However, as reported earlier, the ability of enantioselective oxidation of organic suldes was only studied in a limited number of Actinobacteria. 9, [14][15][16][17] Enantioenriched phenyl methyl sulfoxide (PMS) could be produced by various biotechnological approaches. These approaches include the use of isolated enzymes or biotransformation in microbial cultures using whole cells either of native hosts or recombinant systems.…”

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: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0

et al. 2020

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“…However, in the oxidation reaction of N-Boc derivative of l-4-S-morpholine-2-carboxylic acid, ery high conversion (above 90%) was observed with a high diasteroisomeric excess (above 95%) at he same time. It is worth noticing that strains of B. caledonica and B. bassiana [30] oxidized the ubstrate to compound, which is the intermediate compound in the synthesis of chondrine (Scheme ). However, in the oxidation reaction of N-Boc derivative of l-4-S-morpholine-2-carboxylic acid, very high conversion (above 90%) was observed with a high diasteroisomeric excess (above 95%) at the same time.…”

Section: Fungus and Yeastmentioning

confidence: 99%

“…After this time, the oxidation of cyclohexylmethyl sulfide to the R-isomer was also observed. Ultimately after 48 h, 55% R-cyclohexylmethyl sulfoxide with 55% ee was obtained [30].…”

Section: Substrate Yield (%) Sulfoxide Configuration De (%)mentioning

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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“…To assay their biocatalytic performances, bacterial and fungal strains were employed both as resting and growing cells, following similar procedures as described by Mascotti et al [22,23]. Standard biotransformation conditions were set as follows.…”

Section: Culture Conditions and Microbial Screeningmentioning

confidence: 99%

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Palazzolo

Mascotti

Lewkowicz

et al. 2015

Journal of Industrial Microbiology and Biotechnology

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Aromatic carboxylic acids are readily obtained from lignin in biomass processing facilities. However, efficient technologies for lignin valorization are missing. In this work, a microbial screening was conducted to find versatile biocatalysts capable of transforming several benzoic acids structurally related to lignin, employing vanillic acid as model substrate. The wild-type Aspergillus flavus growing cells exhibited exquisite selectivity towards the oxidative decarboxylation product, 2-methoxybenzene-1,4-diol. Interestingly, when assaying a set of structurally related substrates, the biocatalyst displayed the oxidative removal of the carboxyl moiety or its reduction to the primary alcohol whether electron withdrawing or donating groups were present in the aromatic ring, respectively. Additionally, A. flavus proved to be highly tolerant to vanillic acid increasing concentrations (up to 8 g/L), demonstrating its potential application in chemical synthesis. A. flavus growing cells were found to be efficient biotechnological tools to perform self-sufficient, structure-dependent redox reactions. To the best of our knowledge, this is the first report of a biocatalyst exhibiting opposite redox transformations of the carboxylic acid moiety in benzoic acid derivatives, namely oxidative decarboxylation and carboxyl reduction, in a structure-dependent fashion.

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Expanding the toolbox for enantioselective sulfide oxidations: Streptomyces strains as biocatalysts

Cited by 8 publications

References 28 publications

Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0

Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0

Biotechnological Methods of Sulfoxidation: Yesterday, Today, Tomorrow

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

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