Next Article in Journal
Effects of Epigallocatechin Gallate on the Stability of Epicatechin in a Photolytic Process
Previous Article in Journal
Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies
Previous Article in Special Issue
Isolation, Characterisation, and Lipase Production of a Cold-Adapted Bacterial Strain Pseudomonas sp. LSK25 Isolated from Signy Island, Antarctica
Article Menu
Issue 4 (February-2) cover image

Export Article

Open AccessFeature PaperArticle

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

School of Biochemical Engineering, Pontificia Universidad Católica de Valparaíso; Avda. Brasil 2085 Valparaíso, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Jose M. Palomo
Molecules 2019, 24(4), 792; https://doi.org/10.3390/molecules24040792
Received: 14 January 2019 / Revised: 10 February 2019 / Accepted: 14 February 2019 / Published: 22 February 2019
(This article belongs to the Special Issue Biomolecular Catalysts)
  |  
PDF [829 KB, uploaded 25 February 2019]
  |     |  

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. View Full-Text
Keywords: asymmetric synthesis; Novozym 435; deep eutectic solvents; dimethyl-3-phenylglutarate; hydrophobic substrates asymmetric synthesis; Novozym 435; deep eutectic solvents; dimethyl-3-phenylglutarate; hydrophobic substrates
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

Fredes, Y.; Chamorro, L.; Cabrera, Z. 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 2019, 24, 792.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top