Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability
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...
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| Format: | Article |
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MDPI AG
2021-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/9/2759 |
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| author | André Delavault Oleksandra Opochenska Laura Laneque Hannah Soergel Claudia Muhle-Goll Katrin Ochsenreither Christoph Syldatk |
| author_facet | André Delavault Oleksandra Opochenska Laura Laneque Hannah Soergel Claudia Muhle-Goll Katrin Ochsenreither Christoph Syldatk |
| author_sort | André Delavault |
| collection | DOAJ |
| description | 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<sup>®</sup> 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 <i>de novo</i> 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. |
| first_indexed | 2024-03-10T11:38:55Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:38:55Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d08159e5d5cd47d6806d79a38df9176d2023-11-21T18:42:33ZengMDPI AGMolecules1420-30492021-05-01269275910.3390/molecules26092759Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and ScalabilityAndré Delavault0Oleksandra Opochenska1Laura Laneque2Hannah Soergel3Claudia Muhle-Goll4Katrin Ochsenreither5Christoph Syldatk6Technical Biology, Institute of Process Engineering in Life Sciences II, Karlsruhe Institute of Technology, 76131 Karlsruhe, GermanyTechnical Biology, Institute of Process Engineering in Life Sciences II, Karlsruhe Institute of Technology, 76131 Karlsruhe, GermanyTechnical Biology, Institute of Process Engineering in Life Sciences II, Karlsruhe Institute of Technology, 76131 Karlsruhe, GermanyInstitute for Biological Interfaces 4 and Institute of Organic Chemistry, Karlsruhe Institute of Technology, 76021 Karlsruhe, GermanyInstitute for Biological Interfaces 4 and Institute of Organic Chemistry, Karlsruhe Institute of Technology, 76021 Karlsruhe, GermanyTechnical Biology, Institute of Process Engineering in Life Sciences II, Karlsruhe Institute of Technology, 76131 Karlsruhe, GermanyTechnical Biology, Institute of Process Engineering in Life Sciences II, Karlsruhe Institute of Technology, 76131 Karlsruhe, GermanySurfactants, 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<sup>®</sup> 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 <i>de novo</i> 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.https://www.mdpi.com/1420-3049/26/9/2759glycolipidsugar alcoholesterbiosynthesisoptimizationunconventional media |
| spellingShingle | André Delavault Oleksandra Opochenska Laura Laneque Hannah Soergel Claudia Muhle-Goll Katrin Ochsenreither Christoph Syldatk Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability Molecules glycolipid sugar alcohol ester biosynthesis optimization unconventional media |
| title | Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability |
| title_full | Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability |
| title_fullStr | Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability |
| title_full_unstemmed | Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability |
| title_short | Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability |
| title_sort | lipase catalyzed production of sorbitol laurate in a 2 in 1 deep eutectic system factors affecting the synthesis and scalability |
| topic | glycolipid sugar alcohol ester biosynthesis optimization unconventional media |
| url | https://www.mdpi.com/1420-3049/26/9/2759 |
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