Preparation of chiral phenylethanols using various vegetables grown in Algeria

Bennamane, Manhel; Razi, Samra; Zeror, Saoussen; Aribi‐Zouioueche, Louisa

doi:10.1016/j.bcab.2018.02.003

Cited by 12 publications

(10 citation statements)

References 34 publications

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“…After 25 days, they obtained only 26% alcohol. In turn, in a work by Bennamane et al [21], indan-1-one was reduced by Zingiber officinale and Citrus reticulata with a higher yield (36% and 43%, respectively) but lower stereoselectivity (26% S-(+) and 95% S-(+), respectively). Reactions were carried out with the aid of the crushed flesh of the above-mentioned plants suspended in a phosphate buffer of the appropriate pH.…”

Section: Biocatalystmentioning

confidence: 99%

“…In 2018, Bennamane et al [21] published a paper where the authors biotransformed indan-1-one by Zingiber officinale and Citrus reticulata. In addition, the ability of carrot to stereoselectivly reduce prochiral ketones has been very well documented in the literature (also in our team's research).…”

Section: Reduction Of Indan-1-one Using the Plant Enzymatic Systemmentioning

confidence: 99%

“…Plant biocatalysts have been applied primarily in the reduction of ketones. [8][9][10][11][19][20][21][22][23][24][25]. Biooxidation of alcohols has been described much less [8,[12][13][14][15]22].…”

Section: Introductionmentioning

confidence: 99%

“…In turn, PT285 and PT2877 are second-generation inhibitors of the hypoxia-inducible factor 2α (HIF-2α) and the key oncogenic driver in renal carcinoma [33]. Based on the literature data [21,[34][35][36][37], only a few biocatalytic methods have been employed to obtain the indan-1-ol enantiomers. Nevertheless, kinetic resolution of indan-1-ol has been elegantly performed using sequential combinations of lipase-catalyzed resolution and Mitsunobu inversion [37].…”

Section: Introductionmentioning

confidence: 99%

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Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

et al. 2019

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The main purpose of this work was to discover the way to obtain pure enantiomers of indan-1-ol. The subject of the study was the ability of the plant enzyme system to reduce the carbonyl group of indan-1-one, as well as to oxidize the hydroxyl group of racemic indan-1-ol. Locally available fruit and vegetables were selected for stereoselective biotransformation. During the reduction, mainly alcohol of the S-(+)-configuration with a high enantiomeric excess (ee = 99%) was obtained. The opposite enantiomer was obtained in bioreduction with the apple and parsley. Racemic indan-1-ol was oxidized by all catalysts. The best result was obtained for the Jerusalem artichoke: Over 50% conversion was observed after 1 h, and the enantiomeric excess of unreacted R-(–)-indan1-ol was 100%.

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Section: Biocatalystmentioning

confidence: 99%

Section: Reduction Of Indan-1-one Using the Plant Enzymatic Systemmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

et al. 2019

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“…Among the used cell and roots cultures, carrots seem to be very efficient for asymmetric reduction of prochiral ketones, not only in the form of crushed pulp [11,12,13,14,15,16,17,18,19,20,21,22] but also cell [17,23,24,25,26] and hairy roots cultures [27]. Based on literature date, [11,28,29,30,31] only few biocatalytic methods were used to obtain indan-1-ol enantiomers. The information presented above encouraged us to attempt research into the transformation of indan-1-one and indan-1-ol in carrot cell culture.…”

Section: Introductionmentioning

confidence: 99%

Plant-Mediated Enantioselective Transformation of Indan-1-one and Indan-1-ol. Part 2

et al. 2019

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The main purpose of this publication was to obtain the S-enantiomer of indan-1-ol with high enantiomeric excess and satisfactory yield. In our research, we used carrot callus cultures (Daucus carota L.), whereby the enzymatic system reduced indan-1-one and oxidized indan-1-ol. During the reaction of reduction, after five days, we received over 50% conversion, with the enantiomeric excess of the formed S-alcohol above 99%. In turn, during the oxidation of racemic indan-1-ol after 15 days, 36.7% of alcohol with an enantiomeric excess 57.4% S(+) remained in the reaction mixture. In addition, our research confirmed that the reactions of reduction and oxidation are competing reactions during the transformation of indan-1-ol and indan-1-one in carrot callus cultures.

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Gram‐scale synthesis of (S)‐1‐(thiophen‐2‐yl)ethanol in high enantiomeric purity under Enterococcus faecium BY48 biocatalysts

Şahin

2022

Chirality

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Sulfur‐containing chiral heterocyclic secondary alcohols are relevant intermediates in the preparation of enantiomerically pure compounds endowed with biological activity. In this report, we evaluated the reductive potential of different lactic acid bacteria as whole‐cell biocatalysts of the enantioselective reduction of 1‐(thiophen‐2‐yl)ethanone (1). Enterococcus faecium BY48, isolated from boza, a cereal‐based fermented beverage, was found to be the best biocatalyst in our initial investigations. Using whole‐cell preparations of E. faecium BY48, we then systematically analyzed the reaction parameters (pH, incubation period, agitation speed, and temperature) to optimize the yield, the enantiomeric excess (e. e.), and the conversion leading to (S)‐1‐(thiophen‐2‐yl)ethanol [(S)‐2]. The target derivative, which is a precursor in the synthesis of biologically active chiral compounds, was obtained in enantiomerically pure form, gram‐scale amounts, and high yield. This is also the first report that the manufacture of (S)‐2 in excellent conversion, yield, enantiopure form, and gram scale used whole‐cell biocatalyst. This whole‐cell E. faecium BY48 biocatalyzed reaction is a clean, environmentally friendly, and cost‐effective process, representing a valuable alternative to chemical catalysis or previously reported biocatalytic procedures in the preparation of (S)‐2.

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Preparation of chiral phenylethanols using various vegetables grown in Algeria

Cited by 12 publications

References 34 publications

Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

Plant-Mediated Enantioselective Transformation of Indan-1-one and Indan-1-ol. Part 2

Gram‐scale synthesis of (S)‐1‐(thiophen‐2‐yl)ethanol in high enantiomeric purity under Enterococcus faecium BY48 biocatalysts

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