Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Ramos-Martín, Jesús; Khiari, Oussama; Alcántara, Andrés R.; Sánchez-Montero, J.M.

doi:10.20944/preprints202008.0352.v1

2020

DOI: 10.20944/preprints202008.0352.v1

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Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Jesús Ramos-Martín¹,

Oussama Khiari²,

Andrés R. Alcántara³

et al.

Abstract: Keywords: Geobacillus thermocatenolatus; lipases; ethanolysis; ionic liquids; kinetic resolution; mandelic acid.

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Cited by 3 publications

References 66 publications

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On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

et al. 2023

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In this paper, we describe the effectiveness of the combination between an organic solvent system mixture with orthoformates with different chain sizes from one to four carbon atoms. These orthoesters have been used as a “water trapper/alcohol releaser molecule” to reach a notable improvement in enantioselectivity and enantiomeric excess of our target compound, (S)-2-(4-isobutylphenyl)propanoic acid (ibuprofen eutomer), during the enzymatic kinetic resolution of rac-ibuprofen using immobilized lipase B of Candida antarctica as a biocatalyst. At the same time, one of the great problems of biocatalysis in organic media has been solved by eliminating excess water in the medium that allows the reversibility of the reaction. Following the optimization of the reaction conditions, an increase in enantiomeric excess and enantioselectivity was reached by using these acyl donors in the presence of a cosolvent.

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On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

et al. 2023

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The Application of Two-Phase Catalytic System in Enantioselective Separation of Racemic (R,S)-1-Phenylethanol

et al. 2023

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Kinetic resolution is one of the methods which allows obtaining enantiomerically pure compounds. In the study presented herein, enantioselective biotransformations of (R,S)-1-phenylethanol were performed with the use of various catalytic systems containing ionic liquids and n-heptane or toluene as a reaction medium, vinyl acetate or isopropenyl acetate as an acetylating agent, and lipases from Burkholderia cepacia or Candida rugosa. The conducted studies proved that the use of Burkholderia cepacia lipase, vinyl acetate, and n-heptane with [EMIM][BF4] allows obtaining enantiomerically pure 1-phenylethyl acetate, with the enantiomeric excess of products eep = 98.9%, conversion c = 40.1%, and high value of enantioselectivity E > 200. Additionally, the use of ionic liquids allowed us to reuse enzyme in 5 reaction cycles, ensuring the high operational stability of the protein.

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Bio-Approach for Obtaining Enantiomerically Pure Clopidogrel with the Use of Ionic Liquids

Chałupka

Sikora

Ziegler-Borowska

et al. 2023

IJMS

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Clopidogrel is a chiral compound widely used as an antiplatelet medication that lowers the risk of blood clots, strokes, and heart attacks. The main aim of the study presented herein was to obtain (S)-clopidogrel, which is commercially available in treatments, via the kinetic resolution of racemic clopidogrel carboxylic acid with the use of lipase from Candida rugosa and a two-phase reaction medium containing an ionic liquid. For this purpose, the enantioselective biotransformation of clopidogrel carboxylic acid and chiral chromatographic separation with the use of a UPLC-MS/MS system were optimized. The best kinetic resolution parameters were obtained by using a catalytic system containing lipase from Candida rugosa OF as a biocatalyst, cyclohexane and [EMIM][BF4] as a two-phase reaction medium, and methanol as an acyl acceptor. The enantiomeric excess of the product was eep = 94.21% ± 1.07 and the conversion was c = 49.60% ± 0.57%, whereas the enantioselectivity was E = 113.40 ± 1.29. The performed study proved the possibility of obtaining (S)-clopidogrel with the use of lipase as a biocatalyst and a two-phase reaction medium containing an ionic liquid, which is in parallel with green chemistry methodology and does not require environmentally harmful conditions.

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Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Abstract: Keywords: Geobacillus thermocatenolatus; lipases; ethanolysis; ionic liquids; kinetic resolution; mandelic acid.

Cited by 3 publications

References 66 publications

On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

The Application of Two-Phase Catalytic System in Enantioselective Separation of Racemic (R,S)-1-Phenylethanol

Bio-Approach for Obtaining Enantiomerically Pure Clopidogrel with the Use of Ionic Liquids

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