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Lipase catalyzed reaction of L-ascorbic acid with cinnamic acid esters and substituted cinnamic acids |
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| Authors: | Yung-Hun Yang Takao Raku Eunjung Song Sung-Hee Park Dongwon Yoo Hyung-Yeon Park Byung-Gee Kim Hyung-Ju Kim Sang-Hyun Lee Hyung-Sup Kim Yutaka Tokiwa |
| Affiliation: | 1. Department of Microbial Engineering, College of Engineering, Konkuk University, Seoul, 143-701, Korea 2. New Energy and Industrial Technology Development Organization (NEDO), Ibaraki, 305-8566, Japan 3. School of Chemical and Biological Engineering, Bioengineering Institute and Institute of Molecular Biology and Genetics, Seoul National University, Seoul, 151-742, Korea 4. Bio-MAX Institute, Seoul National University, Seoul, 151-742, Korea 5. Department of Textile Engineering, College of Engineering, Konkuk University, Seoul, 143-701, Korea 6. National Institute of Advanced Industrial Science and Technology (AIST), Ibaraki, 305-8566, Japan |
| Abstract: | To perform the lipase-catalyzed synthesis of L-ascorbic acid derivatives from plant-based compounds such as cinnamic and ferulic acid under mild reaction conditions, the activities of immobilized Candida ntarctica lipase with different cinnamic acid esters and substituted cinnamic acids were compared. As a result, immobilized C. ntarctica lipase was found to prefer vinyl cinnamic acid to other esters such as allyl-, ethyl-, and isobutyl cinnamic acids as well as substituted cinnamic acids such as p-coumaric acid, caffeic acid, ferulic acid, and sinapic acid. Based on these results, large-scale synthesis of 6-O-cinnamyl-L-ascorbic acid ester was performed using immobilized C. ntarctica lipase in dry organic solvent, resulting in 68% yield (493 mg) as confirmed by 13C-NMR. |
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