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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References
Davies, M. B., J. Austin, and D. A. Partridge (1991) Vitamine C: Its chemistry and biochemistry. Mol. Microbiol. 30: 895–903.
Kang, H. H. and S. G. Oh (2003) Synthesis of L-ascorbic acid derivative including 3-aminopropane phosphoric acid as a novel whitening agent. Bull Kor. Chem. Soc. 24: 1169–1171.
Lee, J. S., J. W. Kim, S. H. Han, I. S. Chang, H. H. Kang, O. S. Lee, S. G. Oh, and K. D. Suh (2004) The stabilization of L-ascorbic acid in aqueous solution and water-in-oil-in-water double emulsion by controlling pH and electrolyte concentration. J. Cosmet. Sci. 55: 1–12.
Austria, R., A. Semenzato, and A. Bettero (1997) Stability of vitamin C derivatives in solution and topical formulations. J. Pharm. Biomed. Anal. 15: 795–801.
Streicher, H., B. Ostersehlt, and H. Westenfelder (2002) Cosmetic and pharmaceutical preparations comprising ascorbic acid derivatives. US Patent 6,346,254.
Tabak, M., R. Armon, G. Rosenblat, E. Stermer, and I. Neeman (2003) Diverse effects of ascorbic acid and palmitoyl ascorbate on Helicobacter pylori survival and growth. FEMS Microbiol. Lett. 224: 247–253.
Vanholme, R., K. Morreel, J. Ralph, and W. Boerjan (2008) Lignin engineering. Curr. Opin. Plant Biol. 11: 278–285.
Kikuzaki, H., M. Hisamoto, K. Hirose, K. Akiyama, and H. Taniguchi (2002) Antioxidant properties of ferulic acid and its related compounds. J. Agric. Food Chem. 50: 2161–2168.
Otto, R. T., U. T. Bornscheuer, H. Scheib, J. Pleiss, C. Syldatk, and R. D. Schmid (1998) Lipase-catalyzed esterification of unusual substrates: Synthesis of glucuronic acid and ascorbic acid (vitamin C) esters. Biotechnol. Lett. 20: 1091–1094.
Humphreys, J. M. and C. Chapple (2002) Rewriting the lignin roadmap. Curr. Opin. Plant Biol. 5: 224–229.
Boudet, A. M., S. Kajita, J. Grima-Pettenati, and D. Goffner (2003) Lignins and lignocellulosics: A better control of synthesis for new and improved uses. Trends Plant Sci. 8: 576–581.
Degn, P. and W. Zimmermann (2001) Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica. Biotechnol. Bioeng. 74: 483–491.
Raku, T. and Y. Tokiwa (2003) Chemoenzymatic synthesis of fucose-or rhamnose-branched polymer. Maromol. Biosci. 3: 151–156.
Vijayakumar, G. R., K. Lohith, B. R. Somashekar, and S. Divakar (2004) Lipase catalyzed synthesis of L-alanyl, L-leucyl and Lphenylalanyl esters of D-glucose using unprotected amino acids. Biotechnol. Lett. 26: 1323–1328.
Arcos, J. A., M. Bernabe, and C. Otero (1998) Quantitative enzymatic production of 6-O-acylglucose esters. Biotechnol. Bioeng. 57: 505–509.
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Yang, YH., Raku, T., Song, E. et al. Lipase catalyzed reaction of L-ascorbic acid with cinnamic acid esters and substituted cinnamic acids. Biotechnol Bioproc E 17, 50–54 (2012). https://doi.org/10.1007/s12257-011-0071-1
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DOI: https://doi.org/10.1007/s12257-011-0071-1