Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Świzdor, Alina; Janeczko, Tomasz; Dmochowska-Gładysz, Jadwiga

doi:10.1007/s10295-010-0759-9

Cited by 10 publications

(4 citation statements)

References 47 publications

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“…The conversion of aromatic aldehydes and aromatic-aliphatic ketones such as acetophenones and acetylpyridines is not, to our knowledge, common in a single biocatalyst. Nevertheless, the filamentous fungus Didymosphaeria igniaria KCH 6670 was reported to carry out the asymmetric reductions of prochiral aromatic-aliphatic ketones, including acetonaphthones, acetophenones, and acetylpyridines, to mainly the corresponding ( S )-alcohols [ 47 ]. In the present study, the cells converted nonetheless 2.8-fold more benzaldehyde than any of the other substrates ( Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

Process Development for Benzyl Alcohol Production by Whole-Cell Biocatalysis in Stirred and Packed Bed Reactors

Rodrigues

Carvalho

2022

Microorganisms

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The ocean is an excellent source for new biocatalysts due to the tremendous genetic diversity of marine microorganisms, and it may contribute to the development of sustainable industrial processes. A marine bacterium was isolated and selected for the conversion of benzaldehyde to benzyl alcohol, which is an important chemical employed as a precursor for producing esters for cosmetics and other industries. Enzymatic production routes are of interest for sustainable processes. To overcome benzaldehyde low water solubility, DMSO was used as a biocompatible cosolvent up to a concentration of 10% (v/v). A two-phase system with n-hexane, n-heptane, or n-hexadecane as organic phase allowed at least a 44% higher relative conversion of benzaldehyde than the aqueous system, and allowed higher initial substrate concentrations. Cell performance decreased with increasing product concentration but immobilization of cells in alginate improved four-fold the robustness of the biocatalyst: free and immobilized cells were inhibited at concentrations of benzyl alcohol of 5 and 20 mM, respectively. Scaling up to a 100 mL stirred reactor, using a fed-batch approach, enabled a 1.5-fold increase in benzyl alcohol productivity when compared with batch mode. However, product accumulation in the reactor hindered the conversion. The use of a continuous flow reactor packed with immobilized cells enabled a 9.5-fold increase in productivity when compared with the fed-batch stirred reactor system.

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Section: Resultsmentioning

confidence: 99%

Process Development for Benzyl Alcohol Production by Whole-Cell Biocatalysis in Stirred and Packed Bed Reactors

Rodrigues

Carvalho

2022

Microorganisms

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“…In our previous studies on enantiospecific reduction of α-tetralone ( 1 ) and β-tetralone ( 3 ), the biotransformations in Fusarium culmorum [16] and Didymosphaeria igniaria KCh 6670 [17] cultures were presented. The obtained results prompted us to test another group of available microorganisms.…”

Section: Resultsmentioning

confidence: 99%

“…Only a few manuscripts have so far reported concurrent percentage variations of two enantiomers of alcohols formed during reduction of pro-chiral ketones [16, 17]. …”

Section: Resultsmentioning

confidence: 99%

Enantioselective Dynamic Process Reduction of α- and β-Tetralone and Stereoinversion of Resulting Alcohols in a Selected Strain Culture

et al. 2012

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α-Tetralone and β-tetralone were subjected to biotransformation by 14 fungal strains. Enantiomeric purity of the products depended on the reaction time. 3-Day transformation of α-tetralone in Absidia cylindrospora culture gave S-(+)-1,2,3,4-tetrahydro-1-naftol of 92 % ee, whereas longer biotransformation time resulted in decrease of ee value. 3-Day transformation of β-tetralone by the same strain gave predominantly S-(−)-1,2,3,4-tetrahydro-2-naftol, whereas after 9 days of the reaction, the R-enantiomer with 85 % ee was isolated. Transformation of β-tetralone by Chaetomium sp. KCh 6651 gave pure (S)-(−)-1,2,3,4-tetrahydro-2-naftol in high yield at the concentration of 1 g/l. In this process, a non-selective carbonyl reduction was observed, followed by a selective oxidation of the R-alcohol.

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“…In another study performed with D. carota cell biocatalyst, it was reported that ( S )‐2 was obtained with 88% conversion and 95% ee 22 . In another study in the literature, it was reported that in the presence of Didymosphaeria igniaria whole‐cell biocatalyst, the asymmetric reduction of 1 to ( S )‐2 was achieved with 71% yield and 78% ee 23 . In a study conducted with whole cells of the fungus Fusarium culmorum , it was reported that ( S )‐2 was fabricated with 53% conversion and 45% ee 24 .…”

Section: Introductionmentioning

confidence: 97%

Biocatalytic asymmetric synthesis of (R)‐1‐tetralol using Lactobacillus paracasei BD101

Kalay

Şahin

2021

Chirality

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Asymmetric bioreduction of ketones is a fundamental process in the production of organic molecules. Compounds containing tetralone rings are found in the structure of many biologically active and pharmaceutical molecules. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of Lactobacillus paracasei BD101 was investigated as whole-cell biocatalyst in the enantioselective reduction of 1-tetralone (1). In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. (R)-1-tetralol ((R)-2), which can be used to treat disorder such as obsessive compulsive, posttraumatic stress, premenstrual dysphoric, and social anxiety, was manufactured in enantiopure form, high yield and gram-scale, using whole-cell biocatalysts of L. paracasei BD101. The 7.04 g of (R)-2 was obtained in optically pure form with 95% yield. Also, to our knowledge, this is the first report on production of (R)-2 using whole-cell biocatalyst in excellent yield, conversion, enantiopure form and gram scale. This is a clean, eco-friendly and cheap method for the synthesis of (R)-2 compared with chemical catalyst.

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Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Cited by 10 publications

References 47 publications

Process Development for Benzyl Alcohol Production by Whole-Cell Biocatalysis in Stirred and Packed Bed Reactors

Process Development for Benzyl Alcohol Production by Whole-Cell Biocatalysis in Stirred and Packed Bed Reactors

Enantioselective Dynamic Process Reduction of α- and β-Tetralone and Stereoinversion of Resulting Alcohols in a Selected Strain Culture

Biocatalytic asymmetric synthesis of (R)‐1‐tetralol using Lactobacillus paracasei BD101

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