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Biocatalyzed Vinyl Laurate Transesterification in Natural Deep Eutectic Solvents

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Abstract

Purpose

Natural deep eutectic solvents (NADES) represent a green alternative to conventional organic solvents as reaction medium, offering more benign properties. To efficiently design NADES for biocatalysis, a better understanding of their effect on these reactions is needed. We hypothesize that this effect can be described by separately considering (1) the solvent interactions with the substrates, (2) the solvent viscosities and (3) the enzyme stability in NADES.

Methods

We investigated the effect of substrate solvation and viscosity on the reaction rate; and the stability of the enzyme in NADES. To this end, we monitored the conversion over time of the transesterification of vinyl laurate with 1-butanol by the lipase enzyme Candida antarctica B in NADES of different compounds and molar ratios.

Results

The initial reaction rate is higher in most NADES (varying between 1.14 and 15.07 \(\mu mol\;min^{-1}\;mg^{-1}\)) than in the reference n-hexane (4.0 \(\mu mol\;min^{-1}\;mg^{-1}\))), but no clear relationship between viscosity and initial reaction rate was found. The increased reaction rate is most likely related to the solvation of the substrate due to a change in the activation energy of the reaction or a change in the conformation of the substrate. The enzyme retained part of its activity after the first 2 h of reaction (on average 20 % of the substrate reacted in the 2-24 h period). Enzyme incubation in ethylene glycol-based NADES resulted in a reduced reaction rate (15.07 vs. 3.34 \(\mu mol\;min^{-1}\;mg^{-1}\)), but this may also be due to slow dissolution of the substrate.

Conclusions

The effect of viscosity seems to be marginal next to the effect of solvation and possible enzyme-NADES interaction. The enzyme retains some of its activity during the 24-hour measurements, but the enzyme incubation experiments did not yield accurate, comparable values.

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Data Availibility

The data sets generated and/or analyzed in the current study are available from the corresponding author upon reasonable request.

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Funding

This study was funded by University of Antwerp (Grant Number: BOF DOCPRO3 40005).

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Authors and Affiliations

  1. iPRACS research group, University of Antwerp, Groenenborgerlaan 171, 2020, Antwerp, Belgium

    Attila Kovács, Nathalie Janssens, Miguel Mielants & Pieter Billen

  2. BioWAVE research group, University of Antwerp, Groenenborgerlaan 171, 2020, Antwerp, Belgium

    Iris Cornet

  3. PLASMANT research group, University of Antwerp, Universiteitsplein 1, 2610, Wilrijk, Belgium

    Erik C. Neyts

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  1. Attila Kovács
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Contributions

AK and PB conceived and designed research. AK, NJ and MM conducted experiments and analyzed the results. AK wrote the original manuscript. PB, IC and EN reviewed and edited the manuscript. PB and IC acquired funding. PB, IC and EN supervised the research. All authors read and approved the manuscript.

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Correspondence to Attila Kovács.

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Kovács, A., Janssens, N., Mielants, M. et al. Biocatalyzed Vinyl Laurate Transesterification in Natural Deep Eutectic Solvents. Waste Biomass Valor 15, 2807–2818 (2024). https://doi.org/10.1007/s12649-023-02331-0

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