Lipase catalyzed reaction of L-ascorbic acid with cinnamic acid esters and substituted cinnamic acids

• Published in: Biotechnology and bioprocess engineering 2012, 17(1), , pp.50-54
• Main Authors: Yang, Y.H., Konkuk University, Seoul, Republic of Korea, Raku, Takao, New Energy and Industrial Technology Development Organization, Ibaraki, Japan, Song, E.J., Seoul National University, Seoul, Republic of Korea, Park, S.H., Seoul National University, Seoul, Republic of Korea, Yoo, D.W., Seoul National University, Seoul, Republic of Korea, Park, H.Y., Seoul National University, Seoul, Republic of Korea, Kim, B.G., Seoul National University, Seoul, Republic of Korea, Kim, H.J., Konkuk University, Seoul, Republic of Korea, Lee, S.H., Konkuk University, Seoul, Republic of Korea, Kim, H.S., Konkuk University, Seoul, Republic of Korea, Tokiwa, Yutaka, National Institute of Advanced Industrial Science and Technology, Ibaraki, Japan
• Format: Article
• Language: English
• Subjects: 6-O-cinnamyl-L-ascorbic acid; Antioxidants; Ascorbic acid; ascorbic cinnamic acid ester; Bioengineering; Biosynthesis; Biotechnology; Caffeic acid; Candida; Candida ntarctica; Chemistry; Chemistry and Materials Science; Cinnamic acid; Cosmetics; Engineering; Engineering schools; enzymatic synthesis; Enzymes; Esters; Ferulic acid; Food irradiation; Industrial and Production Engineering; Oxidative stress; p-Coumaric acid; Particle size; Research Paper; sinapic acid; Solvents; Studies; TRIACILGLICEROL LIPASA; TRIACYLGLYCEROL LIPASE; vinyl cinnamic acid; Vitamin C; 생물공학
• ISSN: 1226-8372; 1976-3816
• DOI: 10.1007/s12257-011-0071-1

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.