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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Yerko FredesZaida Cabrera

Abstract

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% (v/v) 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% (v/v) as reaction medium at pH 7 and 30 °C were used. Under such conditions, the R-monoester was produced with an enantiomeric purity of 99%. Novozym 435 was more stable in ChCl:urea/phosphate buffer 50% (v/v) 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.

References

Aug 29, 2003·Current Opinion in Biotechnology·Nicholas J Turner
Apr 30, 2011·Chemical Reviews·Eduardo García-UrdialesVicente Gotor
Feb 2, 2017·Beilstein Journal of Organic Chemistry·Davide BrennaVito Capriati
Aug 11, 2017·Bioresources and Bioprocessing·Pei XuWen-Yong Lou

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Citations

Sep 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Carolina TufiñoLorena Wilson
Sep 25, 2021·Chembiochem : a European Journal of Chemical Biology·Martin PengKersten S Rabe

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