Effect of different reaction parameters on the lipase-catalyzed selective acylation of polyhydroxylated natural compounds in ionic liquids |
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| Institution: | 1. Laboratory of Biotechnology, Department of Biological Applications and Technologies, University of Ioannina, University Campus, 45110 Ioannina, Greece;2. Biotechnology Laboratory, Chemical Engineering Department, National Technical University of Athens, 5 Iroon Polytechniou Str., Zografou Campus, 15700 Athens, Greece;1. Department of Food Science and Technology, Kaunas University of Technology, Radvilenu Str. 19, LT-50254 Kaunas, Lithuania;2. Department of Food Quality and Safety, Lithuanian University of Health Sciences, Veterinary Academy, Tilzes Str. 18, LT-47181 Kaunas, Lithuania;1. Department of Chemical and Biological Engineering, Korea University, 145, Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea;2. Department of Biotechnology, Sangmyung University, 20, Hongjimun 2-Gil, Jongno-Gu, Seoul 03016, Republic of Korea;3. Department of Interdisciplinary Bio-Micro System Technology, College of Engineering, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea;4. Plant Biomass Utilization Research Unit, Department of Botany, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;1. Center for Urban Energy Research, Korea Institute of Science and Technology, Hwarang-ro 14-gil 5, Seongbuk-gu, Seoul, 02792, Republic of Korea;2. Department of Interdisciplinary Bio-Micro System Technology, College of Engineering, Korea University, 145 Anam-ro 5, Seongbuk-gu, Seoul, 02841, Republic of Korea;3. Environmental Radioactivity Assessment Team, Korea Atomic Energy Research Institute, 989-111 Daedeok-daero, Yuseong-gu, Daejeon, 34057, Republic of Korea;4. Department of Chemical and Biological Engineering, College of Engineering, Korea University, 145 Anam-ro 5, Seongbuk-gu, Seoul, 02841, Republic of Korea;1. School of Food Science and Engineering, South China University of Technology, Wushan Road 381, Guangzhou 510640, China;2. State Key Laboratory of Pulp and Papermaking Engineering, South China University of Technology, Wushan Road 381, Guangzhou 510640, China;1. College of Food Science and Engineering, South China University of Technology, Wushan Road 381, Guangzhou, Guangdong 510640, China;2. College of Light Industry and Food Technology, Zhongkai University of Agriculture and Engineering, Dongsha Street 24, Guangzhou, Guangdong 510225, China;3. State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Wushan Road 381, Guangzhou, Guangdong 510640, China |
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| Abstract: | The effect of various reaction parameters on the enzymatic acylation of plant polyhydroxylated compounds, including phenolic and flavonoid glucosides (salicin, helicin, esculin and naringin), was investigated in imidazolium-based ionic liquids (1-butyl-3-methylimidazolium tetrafluoroborate bmim]BF4 and 1-butyl-3-methylimidazolium hexafluorophosphate bmim]PF6), using immobilized lipase B from Candida antarctica. The conversion yield, the regioselectivity and the reaction rate of the biocatalytic process strongly depended on the ionic liquid used, their water content, the incubation temperature, as well as the solubility and the concentration of substrates. For most glucosides tested, one major product (monoacylated derivative) was detected as a result of the acylation of the primary hydroxyl group of glucose moiety. The acylation rate and the regioselectivity of the process are higher in bmim]BF4, where the solubility of all glucosides is significantly higher than in bmim]PF6 or acetone. Response surface methodology (RSM) based on a five level-three variable central composite circumscribed design, was employed to evaluate the interactive effect of the molar ratio of substrates (MR), the initial concentration of glucoside (N) and the reaction time (RT), as well as for their optimization in bmim]BF4. At the optimal reaction conditions the maximum acylation yield was 87%. The amount of monoacylated derivatives produced in a single-step biocatalytic process reached values up to 31.6 g/l which is considerably higher than those reported for organic media. |
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