Weeds as biocatalysts in the stereoselective synthesis of chiral phenylethanols used as key intermediates for pharmaceuticals

Bordón, Daniela L.; Villalba, Leonardo D.; Aimar, Mario L.; Cantero, Juan José; Vázquez, Ana María; Formica, Stella M.; Krapacher, Claudio R.; Rossi, L.

doi:10.1016/j.bcab.2015.08.001

Cited by 13 publications

(5 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In another study, (S)-2 was synthesized with 99% e. e., 42% conversion, and 12% yield using roots of Eodinarthrum horridum. 22 Although these results are satisfactory in terms of e. e., they are quite low in terms of conversion and yield.…”

Section: Introductionmentioning

confidence: 89%

“…Santhanam et al 21 described the synthesis of (S)‐2 with 82% e. e. and 78% yield using Vigna radiata biocatalyst. In another study, ( S )‐2 was synthesized with 99% e. e., 42% conversion, and 12% yield using roots of Eodinarthrum horridum 22 . Although these results are satisfactory in terms of e. e., they are quite low in terms of conversion and yield.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Şahin

2022

Chirality

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

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

Şahin

2022

Chirality

View full text Add to dashboard Cite

show abstract

“…(R,S)-1-Phenylethanol was chosen as a model substrate, since studies using this alcohol are widely reported in the literature. [20][21][22][23] Several variables were evaluated in the acylation reaction of (R,S)-1-phenylethanol with different acyl donors, such as the size of the alkyl chain added to the ester, the molar ratio, the effect of the solvent and the reutilization of the biocatalyst. The conversion, enantiomeric excesses and enantioselectivity of the lipases were evaluated.…”

Section: Resultsmentioning

confidence: 99%

Easy and Simple SiO2 Immobilization of Lipozyme CaLB-L: Its Use as a Catalyst in Acylation Reactions and Comparison with Other Lipases

Mittersteiner¹,

Machado²,

Jesus³

et al. 2016

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

In this study, lipase from Candida antarctica B (Lipozyme CaLB-L) was successfully immobilized on SiO 2 through adsorption and used to obtain (R)-(+)-esters derived from (R,S)-1-phenylethanol. The new immobilized enzyme was compared with commercially immobilized lipases (Novozyme 435, Lipozyme 435 and Pseudomonas cepacia (PSC-II and PSD-I)). Lipozyme CaLB-L adsorbed onto SiO 2 was found to be a good catalyst and, under optimal conditions, esters could be obtained with conversion 44%, enantiomeric excess of product (ee p ) > 99%, enantiomeric excess of substract (ee s ) 77% and enantiomeric ratio (E) > 200. The lipase maintained enantioselectivity under adverse conditions, such as in organic solvents, with an excess of substrate and at different temperatures. The immobilized lipase could be reused five times with no significant loss of the activity.

show abstract

“…In particular, Daucus carota root is a rich source of ketoreductase enzymes that catalyze the reduction of keto functionality 10 . Indeed, the plant whole cell enzymes offer several advantages such as bio‐compatible and versatile source for the reduction of different prochiral ketones with regio‐, enantio‐, stereoselectivity under mild reaction conditions 11,12 . Although previous methods reported the use of biocatalysis using whole cells microorganisms 6 for the reduction of heteroaryl ketones, these methods involve the use of expensive co‐factors like NADP or NAD.…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic enantioselective synthesis of cenobamate, an antiepileptic drug

Haritha,

Deepthi,

Gundamalla

et al. 2024

Chirality

View full text Add to dashboard Cite

A green and efficient process for the synthesis of cenobamate has been accomplished in 70% yield and >99% ee through the bio‐reduction of β‐ketotetrazole using Daucus carota whole plant cells. The corresponding β‐hydroxytetrazole was isolated in 60% yield and >98% ee. This is the first report on the biocatalytic reduction of β‐ketotetrazole using plant enzymes derived from D. carota root cells with excellent enantioselectivity.

show abstract

Weeds as biocatalysts in the stereoselective synthesis of chiral phenylethanols used as key intermediates for pharmaceuticals

Cited by 13 publications

References 42 publications

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

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

Easy and Simple SiO2 Immobilization of Lipozyme CaLB-L: Its Use as a Catalyst in Acylation Reactions and Comparison with Other Lipases

Biocatalytic enantioselective synthesis of cenobamate, an antiepileptic drug

Contact Info

Product

Resources

About