Chemoenzymatic synthesis of fluoxetine precursors. Reduction of β-substituted propiophenones

Coronel, Camila; Arce, Gabriel; Iglesias, César; Noguera, Cynthia Magallanes; Bonnecarrère, Paula Rodriguez; Giordano, Sonia Rodríguez; González, David

doi:10.1016/j.molcatb.2014.01.022

Cited by 10 publications

(5 citation statements)

References 39 publications

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“…Therefore, the reaction efficiency of the biocatalytic reduction of CPE in the presence of [ChCl][U] were clearly superior to that in [ChCl][U]-free aqueous system. To our knowledge, the results presented here were better than those reported previously in other similar studies. , …”

Section: Resultscontrasting

confidence: 68%

“…To our knowledge, the results presented here were better than those reported previously in other similar studies. 8,30 Operational Stability of the Immobilized Cells in [ChCl][U]-based Reaction System. To estimate the reusability of the immobilized cells, the reuse of the cells was investigated in the [ChCl][U]-containing reaction system under the optimized reaction conditions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Enhancing Asymmetric Reduction of 3-Chloropropiophenone with Immobilized Acetobacter sp. CCTCC M209061 Cells by Using Deep Eutectic Solvents as Cosolvents

et al. 2015

ACS Sustainable Chem. Eng.

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Use of deep eutectic solvents (DESs) to improve biocatalytic asymmetric reduction of 3-chloropropiophenone to (S)-3-chloro-1-phenylpropanol catalyzed by whole-cell of Acetobacter sp. CCTCC M209061 was successfully performed. The cells immobilized on PVA-sodium sulfate exhibited markedly enhanced stability. Diverse DESs as co-solvents manifested significantly different influences on the reaction. Among them, the DES choline chloride/urea ([ChCl][U]) showed the best biocompatibility and moderately increased the cell member permeability, as demonstrated by MAR and flow cytometry assays, and consequently gave the best results. For the bioreduction conducted in the [ChCl][U]-containing system, the optimum [ChCl][U] content, substrate concentration, glucose concentration, pH and temperature were 5% (v/v), 10.0 mmol/L, 60 mmol/L, 5.5 and 30 °C, respectively. Under the optimized conditions, the obtained yield and product e.e. were 82.3% and above 99.0% at a reaction time of 6 h, respectively, and the productivity was 1.37 mmol/L/h. The efficient whole-cell biocatalytic process proved to be feasible on a 500-mL preparative scale. Moreover, the combination of water-immiscible ionic liquid C 4 MIM·PF 6 with [ChCl][U] in a biphasic system further enhanced substrate concentration (16.0 mmol/L), product yield (93.3%) and productivity (1.87 mmol/L/h) significantly, showing to be very promising for biocatalytic synthesis of (S)-3-chloro-1-phenylpropanol with immobilized Acetobacter sp. CCTCC M209061 cells.Acetobacter sp. CCTCC M209061, isolated from Chinese kefir grains by our group, was used as an efficient biocatalyst for highly enantioselective anti-Prelog reduction of prochiral ketones. 11Over the last several years, deep eutectic solvents (DESs) have been considered as another promising alternative to conventional ionic liquids (ILs) as green solvents. 12, 13 DESs are eutectic mixtures composed of two or three cheap and safe components which could associate with each other through hydrogen bond interactions. 14 These solvents not only share the similar characteristics with ILs such as low vapor pressure, non-flammability, thermal stability, but also have some special virtues including relatively low cost, good sustainability, biocompatibility and biodegradability. 15,16 Most importantly, the formation of these solvents is very simple and needs no further purification steps. Up to now, there appears to be some researches related to the applications of DESs as co-solvents in biocatalytic reactions, especially in enzyme-catalyzed reactions. [17][18][19] However, few accounts were published about whole-cell biocatalysis in a In the present study, we attempted for the first time to use various DESs as co-solvents in aqueous system to improve the biocatalytic asymmetric reduction of CPE with immobilized Acetobacter sp. CCTCC M209061 cells (Scheme 1). The biocompatibility of these DESs with the cells and their effects on the cell member integrity were investigated systematically as well as several influential factors on the react...

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Section: Resultscontrasting

confidence: 68%

Section: ■ Results and Discussionmentioning

confidence: 99%

Enhancing Asymmetric Reduction of 3-Chloropropiophenone with Immobilized Acetobacter sp. CCTCC M209061 Cells by Using Deep Eutectic Solvents as Cosolvents

et al. 2015

ACS Sustainable Chem. Eng.

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“…In addition, the immobilization of Candida antarctica enzyme onto a macroporous acrylic resin displayed intriguing biocatalytic performance toward the preparation of dichloropropyl acrylates from dichloropropyl dodecanoates via transesterification reactions [158]. In many industrial processes, these isolates have been utilized severally in the bioreduction of ketones, e.g., acetophenone [159], propiophenones [160] cocktail of ketones [161], etc. to alcohol under ambient conditions and increased product yield.…”

Section: Biocatalystsmentioning

confidence: 99%

Production and Functionalities of Specialized Metabolites from Different Organic Sources

et al. 2022

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Medicinal plants are rich sources of specialized metabolites that are of great importance to plants, animals, and humans. The usefulness of active biological compounds cuts across different fields, such as agriculture, forestry, food processing and packaging, biofuels, biocatalysts, and environmental remediation. In recent years, research has shifted toward the use of microbes, especially endophytes (bacteria, fungi, and viruses), and the combination of these organisms with other alternatives to optimize the production and regulation of these compounds. This review reinforces the production of specialized metabolites, especially by plants and microorganisms, and the effectiveness of microorganisms in increasing the production/concentration of these compounds in plants. The study also highlights the functions of these compounds in plants and their applications in various fields. New research areas that should be explored to produce and regulate these compounds, especially in plants and microbes, have been identified. Methods involving molecular studies are yet to be fully explored, and next-generation sequencing possesses an interesting and reliable approach.

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“…However, interestingly, the reaction catalyzed by DABCO furnished an unexpected 1,4-disubstituted-1,2,3-triazole 10a via a [3 + 2]-cycloaddition of the in situ generated enone 2a and the azide 3a , followed by aromatization . Formation of enones from β-azidoketones, which occurs via a retro-Michael process, is rare, since azide is a poor leaving group …”

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confidence: 99%

Organocatalytic β-Azidation of Enones Initiated by an Electron-Donor–Acceptor Complex

Shirke

Ramasastry

2017

Org. Lett.

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An operationally straightforward organocatalytic β-azidation of α,β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones via the formation of an electron-donor-acceptor complex. The application of this protocol is demonstrated through one-step elaborations leading to the synthesis of unprecedented classes of 1,2,3-triazoles.

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Chemoenzymatic synthesis of fluoxetine precursors. Reduction of β-substituted propiophenones

Cited by 10 publications

References 39 publications

Enhancing Asymmetric Reduction of 3-Chloropropiophenone with Immobilized Acetobacter sp. CCTCC M209061 Cells by Using Deep Eutectic Solvents as Cosolvents

Enhancing Asymmetric Reduction of 3-Chloropropiophenone with Immobilized Acetobacter sp. CCTCC M209061 Cells by Using Deep Eutectic Solvents as Cosolvents

Production and Functionalities of Specialized Metabolites from Different Organic Sources

Organocatalytic β-Azidation of Enones Initiated by an Electron-Donor–Acceptor Complex

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