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. 2021 May 7;26(9):2759.
doi: 10.3390/molecules26092759.

Lipase-Catalyzed Production of Sorbitol Laurate in a "2-in-1" Deep Eutectic System: Factors Affecting the Synthesis and Scalability

André Delavault  1 , Oleksandra Opochenska  1 , Laura Laneque  1 , Hannah Soergel  2 , Claudia Muhle-Goll  2 , Katrin Ochsenreither  1 , Christoph Syldatk  1
Affiliations

Lipase-Catalyzed Production of Sorbitol Laurate in a "2-in-1" Deep Eutectic System: Factors Affecting the Synthesis and Scalability

André Delavault et al. Molecules. .

Abstract

Surfactants, such as glycolipids, are specialty compounds that can be encountered daily in cleaning agents, pharmaceuticals or even in food. Due to their wide range of applications and, more notably, their presence in hygiene products, the demand is continuously increasing worldwide. The established chemical synthesis of glycolipids presents several disadvantages, such as lack of specificity and selectivity. Moreover, the solubility of polyols, such as sugars or sugar alcohols, in organic solvents is rather low. The enzymatic synthesis of these compounds is, however, possible in nearly water-free media using inexpensive and renewable building blocks. Using lipases, ester formation can be achieved under mild conditions. We propose, herein, a "2-in-1" system that overcomes solubility problems, as a Deep Eutectic System (DES) made of sorbitol and choline chloride replaces either a purely organic or aqueous medium. For the first time, 16 commercially available lipase formulations were compared, and the factors affecting the conversion were investigated to optimize this process, owing to a newly developed High-Performance Liquid Chromatography-Evaporative Light Scattering Detector (HPLC-ELSD) method for quantification. Thus, using 50 g/L of lipase formulation Novozym 435® at 50 °C, the optimized synthesis of sorbitol laurate (SL) allowed to achieve 28% molar conversion of 0.5 M of vinyl laurate to its sugar alcohol monoester when the DES contained 5 wt.% water. After 48h, the de novo synthesized glycolipid was separated from the media by liquid-liquid extraction, purified by flash-chromatography and characterized thoroughly by one- and two-dimensional Nuclear Magnetic Resonance (NMR) experiments combined to Mass Spectrometry (MS). In completion, we provide initial proof of scalability for this process. Using a 2.5 L stirred tank reactor (STR) allowed a batch production reaching 25 g/L in a highly viscous two-phase system.

Keywords: biosynthesis; ester; glycolipid; optimization; sugar alcohol; unconventional media.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure A1
Figure A1
Extracted NMR signals of (A) C4H and (B) C3H of the sorbitol.
Figure 1
Figure 1
Lipase-catalyzed transesterification reaction between D-sorbitol and vinyl laurate. Evaporation of highly volatile acetaldehyde makes the conversion irreversible. S: Sorbitol; CC: Choline Chloride; mR: molar Ratio.
Figure 2
Figure 2
Comparison of SL conversion yields calculated from 0.5 M vinyl laurate. A triplicate was done for each screened commercially available formulation after 48 h at 50 °C. a–f show statistically significant differences (p < 0.05).
Figure 3
Figure 3
Time course of the reaction under unoptimized conditions: 0.5 M of vinyl laurate, 20 mg of Novozym 435® and 1.5 mL of Sorbit DES as solvent (sorbitol/choline chloride, 1:1, mR, 5 wt.% water) at 50 °C.
Figure 4
Figure 4
Novozym 435®-catalyzed transesterification of sorbitol and vinyl laurate in “2-in-1” Sorbit deep eutectic system: Effect of enzyme dosage (A); vinyl laurate concentration (B); water content in the media (C) on the titer after 48 h. a–d show statistically significant differences, at a 0.05 significance level, of the mean values obtained from three independent experiments ran under each condition.
Figure 5
Figure 5
Time course of SL production (g/L): STR with 3-bladed spiral propeller versus tube in orbital shaking.
Figure 6
Figure 6
Flowsheet and picture illustrating the visibly homogenized lipase-catalyzed production of sugar alcohol monoesters using a stirred-tank reactor.
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