Bioreduction of substituted a-tetralones promoted by Daucus carota root

Ferraz, Helena M. C.; Bianco, Graziela G.; Bombonato, Fernanda I.; Andrade, Leandro H.; Porto, André Luiz Meleiro

doi:10.1590/s0100-40422008000400020

Cited by 14 publications

(4 citation statements)

References 40 publications

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“…In our laboratory we have researched the biocatalytic diversity of endophytic microorganisms (bacteria, yeast and fungi) in order to identify newer biocatalysts and also to enlighten the interesting phenomena of the stereoselective reduction of ketones by simple plants fragments. These type of enzymatic transformations were originally reported by Mironowicz [9] and Baldassarre [10] at the end of the XX century and several other reports have followed studying the scope and limitations of the reactions [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 90%

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

Coronel

Arce

Iglesias

et al. 2014

Journal of Molecular Catalysis B: Enzymatic

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Section: Introductionmentioning

confidence: 90%

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

Coronel

Arce

Iglesias

et al. 2014

Journal of Molecular Catalysis B: Enzymatic

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“…Similarly, Yadav et al reported that Daucus carota exhibited good performance in the asymmetric reduction of 1 to ( S )‐2 in terms of enantioselectivity (96% ee), but low conversion (70%) and yield (52%) 21 . 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 .…”

Section: Introductionmentioning

confidence: 89%

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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“…Different natural materials are used as solid support as well as catalysts in a large number of reactions promoting the formation of final products. Natural materials such as different plant parts such as fruits, root extracts [26][27][28][29][30][31][32], clays [33,34], zeolites [35,36] and enzymes [37,38] are used effectively in numerous chemical transformations.…”

Section: Introductionmentioning

confidence: 99%

Synergistic effect of natural chickpea leaf exudates acids in heterocyclization: a greener protocol for benzopyran synthesis

Mali¹,

Shinde²,

Damte³

et al. 2018

R. Soc. open sci.

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Without using any toxic or hazardous reagent, ligand, acid, transition metal catalyst, additives/promoters and organic solvent, green Knoevenagel condensation and tandem Knoevenagel–Michael reactions have been successfully carried out by using chickpea leaf exudates as a naturally sourced Bronsted acid type bio-catalyst. The reaction proceeds in neat chickpea leaf exudates at room temperature in aqueous conditions in very short reaction times, and therefore, it is an evergreen and environmentally sound alternative to the existing protocols for benzopyran synthesis. In comparison to the conventional methods, this synthetic pathway complies with several key requirements of green chemistry principles such as the utilization of biodegradable catalyst obtained from renewable feedstock, auxiliary aqueous conditions, along with waste prevention. The same protocol was also extended to the synthesis of 2H-xanthene-1,8-diones by condensation of aromatic aldehydes with dimedone achieving excellent yields. Thus, the reported protocol offers an attractive option because of its ecological safety, environmental acceptance, sustainability, low-cost straightforward work-up procedure and with excellent values of green chemistry metrics as compared with other reported methods.

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Bioreduction of substituted a-tetralones promoted by Daucus carota root

Cited by 14 publications

References 40 publications

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

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

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

Synergistic effect of natural chickpea leaf exudates acids in heterocyclization: a greener protocol for benzopyran synthesis

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