Increased Selectivity of Novozym 435 in the Asymmetric Hydrolysis of a Substrate with High Hydrophobicity Through the Use of Deep Eutectic Solvents and High Substrate Concentrations

Increased Selectivity of Novozym 435 in the Asymmetric Hydrolysis of a Substrate with High Hydrophobicity Through the Use of Deep Eutectic Solvents and High Substrate Concentrations

The effects of the reaction medium and substrate concentration were studied on the selectivity of Novozym 435 using the asymmetric hydrolysis of dimethyl-3-phenylglutarate as a model reaction. Results show that the use of choline chloride ChCl:urea/phosphate buffer 50% ( ) as a reaction medium incre...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 24; no. 4; p. 792
Main Authors: Fredes, Yerko, Chamorro, Lesly, Cabrera, Zaida
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 22-02-2019
MDPI
Subjects:
Asymmetric synthesis
Asymmetry
Catalysts
Commercialization
deep eutectic solvents
dimethyl-3-phenylglutarate
Enzymes
Format
Glycerol
hydrophobic substrates
Hydrophobicity
Isomers
Novozym 435
Optical isomers
Organic chemistry
Pharmaceutical industry
Physiological responses
Productivity
Selectivity
Solvents
Substrates
Urea
hydrophobic substrates
asymmetric synthesis
dimethyl-3-phenylglutarate
Novozym 435
deep eutectic solvents
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Summary:The effects of the reaction medium and substrate concentration were studied on the selectivity of Novozym 435 using the asymmetric hydrolysis of dimethyl-3-phenylglutarate as a model reaction. Results show that the use of choline chloride ChCl:urea/phosphate buffer 50% ( ) as a reaction medium increased the selectivity of Novozym 435 by 16% (e.e = 88%) with respect to the one in 100% phosphate buffer (e.e = 76%). Best results were obtained when high substrate concentrations (well above the solubility limit, 27-fold) and ChCl:urea/phosphate buffer 50% ( ) as reaction medium at pH 7 and 30 °C were used. Under such conditions, the -monoester was produced with an enantiomeric purity of 99%. Novozym 435 was more stable in ChCl:urea/phosphate buffer 50% ( ) than in phosphate buffer, retaining a 50% of its initial activity after 27 h of incubation at pH 7 and 40 °C. Results suggest that the use of deep eutectic solvents (ChCl:urea/phosphate buffer) in an heterogeneous reaction system (high substrate concentration) is a viable and promising strategy for the synthesis of chiral drugs from highly hydrophobic substrates.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24040792