Enzymatic Synthesis of Sugar-Derived Biosurfactants Using Multifunctional Ionic Liquids

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Project Summary Fatty acid sugar esters are a type of nonionic glycolipid surfactants and can be made from renewable biomaterials (saccharides and fatty acids). These biosurfactants are non-toxic, tasteless, odorless, nonirritant, and biodegradable with broad applications in pharmaceuticals, detergents and cleaners, cosmetics, and the food industry. As a timely application, these biosurfactants could control the spread of coronavirus-2 (SARS- CoV-2) by disrupting viral membrane, serving as handwashing and cleaning agents, and targeting and relieving the symptoms after infection. Enzymatic synthesis can lead to regioselective biosurfactants, but is hampered by a lack of reaction systems that can dissolve both polar sugar molecules and non-polar fatty acids/fatty acid esters. The long-term goal is to mentor and guide a team of undergraduates to develop a general methodology for efficient synthesis of glycolipid-type biosurfactants. The main objective of this proposal is for students to synthesize functionalized ionic solvents, called ionic liquids (ILs), that are lipase- compatible and can dissolve sugars and fatty acids/fatty acid esters, and conduct enzymatic preparation of sugar fatty acid esters in ionic media. The central hypothesis is that ionic liquids can be functionalized to afford high substrate dissolution and high lipase activity at the same time to promote efficient synthesis of glycolipid-type biosurfactants. To achieve this objective, three Specific Aims are proposed: Specific Aim 1: Design “water-like” multifunctional ILs that can dissolve sugars and are compatible with lipases. Specific Aim 2: Synthesize mono- and disaccharide fatty acid esters via enzymatic (trans)esterifications in functionalized ionic solvents. Specific Aim 3: Prepare oligo- and polysaccharide fatty acid esters via enzymatic transesterification in functionalized ionic solvents. This research is innovative and significant because the synergistic combination of substrate-dissolving ILs and their high compatibility with enzymes will enable students to create a general methodology for enzymatic synthesis of biosurfactants. The primary impact of this project will be working with a predominantly undergraduate student research team to develop an efficient preparation of a variety of sugar-based biosurfactants that have broad applications in the pharmaceutical industry. The project will involve the significant participation of undergraduate students in all stages of the research, including implementation of research plans and analysis of findings. These research experiences will develop undergraduate student research competencies, thereby preparing them for careers in biomedical research and/or graduate studies, while additionally strengthening the research environment at the University of Northern Colorado. The main objective of this proposal is consistent with the NIH mission to develop efficient reaction systems to produce biosurfactants with major uses in pharmaceuticals and, particularly in controlling the spread of Covid-19 in the current pandemic, and AREA priorities to provide biomedical research experiences for undergraduates and enhance the institutional research environment.