Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents
Sugar fatty acid esters (SFAEs) are biocompatible nonionic surfactants with broad applications in food, cosmetic, and pharmaceutical industries. They can be synthesized enzymatically with many advantages over their chemical synthesis. In this study, SFAE synthesis was investigated by using two react...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2016-09-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/21/10/1294 |
| _version_ | 1811301992064090112 |
|---|---|
| author | Kai-Hua Zhao Yu-Zheng Cai Xiao-Sheng Lin Jun Xiong Peter J. Halling Zhen Yang |
| author_facet | Kai-Hua Zhao Yu-Zheng Cai Xiao-Sheng Lin Jun Xiong Peter J. Halling Zhen Yang |
| author_sort | Kai-Hua Zhao |
| collection | DOAJ |
| description | Sugar fatty acid esters (SFAEs) are biocompatible nonionic surfactants with broad applications in food, cosmetic, and pharmaceutical industries. They can be synthesized enzymatically with many advantages over their chemical synthesis. In this study, SFAE synthesis was investigated by using two reactions: (1) transesterification of glucose with fatty acid vinyl esters and (2) esterification of methyl glucoside with fatty acids, catalyzed by Lipozyme TLIM and Novozym 435 respectively. Fourteen ionic liquids (ILs) and 14 deep eutectic solvents (DESs) were screened as solvents, and the bisolvent system composed of 1-hexyl-3-methylimidazolium trifluoromethylsulfonate ([HMIm][TfO]) and 2-methyl-2-butanol (2M2B) was the best for both reactions, yielding optimal productivities (769.6 and 397.5 µmol/h/g, respectively) which are superior to those reported in the literature. Impacts of different reaction conditions were studied for both reactions. Response surface methodology (RSM) was employed to optimize the transesterification reaction. Results also demonstrated that as co-substrate, methyl glucoside yielded higher conversions than glucose, and that conversions increased with an increase in the chain length of the fatty acid moieties. DESs were poor solvents for the above reactions presumably due to their high viscosity and high polarity. |
| first_indexed | 2024-04-13T07:19:59Z |
| format | Article |
| id | doaj.art-2ce28bfa45e74b8f910024de7e7208e9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T07:19:59Z |
| publishDate | 2016-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2ce28bfa45e74b8f910024de7e7208e92022-12-22T02:56:38ZengMDPI AGMolecules1420-30492016-09-012110129410.3390/molecules21101294molecules21101294Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic SolventsKai-Hua Zhao0Yu-Zheng Cai1Xiao-Sheng Lin2Jun Xiong3Peter J. Halling4Zhen Yang5College of Life Sciences and Oceanography, Shenzhen Key Laboratory of Microbial Genetic Engineering, Shenzhen University, Shenzhen 518060, Guangdong, ChinaCollege of Life Sciences and oceanography, Shenzhen Key Laboratory of Marine Bioresources and Ecology, Shenzhen University, Shenzhen 518060, Guangdong, ChinaCollege of Life Sciences and Oceanography, Shenzhen Key Laboratory of Microbial Genetic Engineering, Shenzhen University, Shenzhen 518060, Guangdong, ChinaCollege of Life Sciences and oceanography, Shenzhen Key Laboratory of Marine Bioresources and Ecology, Shenzhen University, Shenzhen 518060, Guangdong, ChinaWestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, Glasgow G1 1XL, UKCollege of Life Sciences and Oceanography, Shenzhen Key Laboratory of Microbial Genetic Engineering, Shenzhen University, Shenzhen 518060, Guangdong, ChinaSugar fatty acid esters (SFAEs) are biocompatible nonionic surfactants with broad applications in food, cosmetic, and pharmaceutical industries. They can be synthesized enzymatically with many advantages over their chemical synthesis. In this study, SFAE synthesis was investigated by using two reactions: (1) transesterification of glucose with fatty acid vinyl esters and (2) esterification of methyl glucoside with fatty acids, catalyzed by Lipozyme TLIM and Novozym 435 respectively. Fourteen ionic liquids (ILs) and 14 deep eutectic solvents (DESs) were screened as solvents, and the bisolvent system composed of 1-hexyl-3-methylimidazolium trifluoromethylsulfonate ([HMIm][TfO]) and 2-methyl-2-butanol (2M2B) was the best for both reactions, yielding optimal productivities (769.6 and 397.5 µmol/h/g, respectively) which are superior to those reported in the literature. Impacts of different reaction conditions were studied for both reactions. Response surface methodology (RSM) was employed to optimize the transesterification reaction. Results also demonstrated that as co-substrate, methyl glucoside yielded higher conversions than glucose, and that conversions increased with an increase in the chain length of the fatty acid moieties. DESs were poor solvents for the above reactions presumably due to their high viscosity and high polarity.http://www.mdpi.com/1420-3049/21/10/1294sugar fatty acid estersionic liquidsdeep eutectic solventslipasealkyl glucosideesterificationtransesterification |
| spellingShingle | Kai-Hua Zhao Yu-Zheng Cai Xiao-Sheng Lin Jun Xiong Peter J. Halling Zhen Yang Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents Molecules sugar fatty acid esters ionic liquids deep eutectic solvents lipase alkyl glucoside esterification transesterification |
| title | Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents |
| title_full | Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents |
| title_fullStr | Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents |
| title_full_unstemmed | Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents |
| title_short | Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents |
| title_sort | enzymatic synthesis of glucose based fatty acid esters in bisolvent systems containing ionic liquids or deep eutectic solvents |
| topic | sugar fatty acid esters ionic liquids deep eutectic solvents lipase alkyl glucoside esterification transesterification |
| url | http://www.mdpi.com/1420-3049/21/10/1294 |
| work_keys_str_mv | AT kaihuazhao enzymaticsynthesisofglucosebasedfattyacidestersinbisolventsystemscontainingionicliquidsordeepeutecticsolvents AT yuzhengcai enzymaticsynthesisofglucosebasedfattyacidestersinbisolventsystemscontainingionicliquidsordeepeutecticsolvents AT xiaoshenglin enzymaticsynthesisofglucosebasedfattyacidestersinbisolventsystemscontainingionicliquidsordeepeutecticsolvents AT junxiong enzymaticsynthesisofglucosebasedfattyacidestersinbisolventsystemscontainingionicliquidsordeepeutecticsolvents AT peterjhalling enzymaticsynthesisofglucosebasedfattyacidestersinbisolventsystemscontainingionicliquidsordeepeutecticsolvents AT zhenyang enzymaticsynthesisofglucosebasedfattyacidestersinbisolventsystemscontainingionicliquidsordeepeutecticsolvents |