Enzymatic synthesis and anti-oxidative activities of plant oil-based ascorbyl esters in 2-methyltetrahydrofuran-containing mixtures

References

• Adamczak M, Bornscheuer UT, Bednarski W. 2005. Synthesis of ascorbyloleate by immobilized Candida antarctica lipases. Process Biochem 40:3177–3180.
   Web of Science ®Google Scholar
• Antonucci V, Coleman J, Ferry JB, Johnson N, Mathe M, Scott JP, Xu J. 2011. Toxicological assessment of 2-methyltetrahydrofuran and cyclopentyl methyl ether in support of their use in pharmaceutical chemical process development. Org Process Res Dev 15:939–941.
   Web of Science ®Google Scholar
• Burham H, Rasheed RAGA, Noor NM, Badruddin S, Sidek H. 2009. Enzymatic synthesis of palm-based ascorbyl esters. J Mol Catal B: Enzym 58:153–157.
   Web of Science ®Google Scholar
• Chen ZG, Zhang DN, Han YB. 2013. Lipase-catalyzed acylation of lily polysaccharide in ionic liquid-containing systems. Process Biochem 48:620–624.
   Web of Science ®Google Scholar
• Costa ICR, Sutili FK, da Silva GVV, Leite SGF, Miranda LSM, de Souza ROMA. 2014. Lipase catalyzed ascorbyl palmitate synthesis under microwave irradiation. J Mol Catal B: Enzym 102:127–131.
   Web of Science ®Google Scholar
• Ferrer M, Cruces MA, Bernabe M, Ballesteros A, Plou FJ. 1999. Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures. Biotechnol Bioeng 65:10–16.
   PubMed Web of Science ®Google Scholar
• Gao WL, Li N, Zong MH. 2013. Enzymatic regioselective acylation of nucleosides in biomass-derived 2-methyltetrahydrofuran: kinetic study and enzyme substrate recognition. J Biotechnol 164:91–96.
   PubMed Web of Science ®Google Scholar
• Gao WL, Liu H, Li N, Zong MH. 2012. Regioselective enzymatic undecylenoylation of 8-chloroadenosine and its analogs with biomass-based 2-methyltetrahydrofuran as solvent. Bioresour Technol 118:82–88.
   PubMed Web of Science ®Google Scholar
• Geilen FMA, Engendahl B, Harwardt A, Marquardt W, Klankermayer J, Leitner W. 2010. Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system. Angew Chem Int Ed 49:5510–5514.
   PubMed Web of Science ®Google Scholar
• Gu Y, Jerome F. 2013. Bio-based solvents: an emerging generation of fluids for the design of eco-efficient processes in catalysis and organic chemistry. Chem Soc Rev 42:9550–9570.
   PubMed Web of Science ®Google Scholar
• Haynes WM. 2011–2012. 16. Health and safety information. Octanol-water partition coefficients. In: Haynes WM, editor. CRC handbook of chemistry and physics. Boca Raton (FL): CRC Press. p. 42–46.
   Google Scholar
• Hu YD, Qin YZ, Li N, Zong MH. 2014. Highly efficient enzymatic synthesis of an ascorbyl unsaturated fatty acid ester with ecofriendly biomass-derived 2-methyltetrahydrofuran as co-solvent. Biotechnol Prog 30:1005–1011.
   PubMed Web of Science ®Google Scholar
• Jiang X-J, Hu Y, Jiang L, Zou B, Song P, Huang H. 2013. Optimization of enzymatic synthesis of L-ascorbyl palmitate by solvent engineering and statistical experimental designs. Biotechnol Bioprocess Eng 18:350–357.
   Web of Science ®Google Scholar
• Karmee SK. 2009. Biocatalytic synthesis of ascorbyl esters and their biotechnological applications. Appl Microbiol Biotechnol 81:1013–1022.
   PubMed Web of Science ®Google Scholar
• Karmee SK. 2011. The synthesis, properties, and applications of ascorbyl esters. Lipid Technol 23:227–229.
   Google Scholar
• Karmee SK. 2012. A two-step chemo-enzymatic method for the synthesis of fatty acid ascorbyl esters. J Oil Palm Res 24:1518–1523.
   Web of Science ®Google Scholar
• Klibanov AM. 1997. Why are enzymes less active in organic solvents than in water? Trends Biotechnol 15:97–101.
   PubMed Web of Science ®Google Scholar
• Klibanov AM. 2001. Improving enzymes by using them in organic solvents. Nature 409:241–246.
   PubMed Web of Science ®Google Scholar
• Laane C, Boeren S, Vos K, Veeger C. 1987. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30:81–87.
   PubMed Web of Science ®Google Scholar
• Lerin LA, Richetti A, Dallago R, Treichel H, Mazutti MA, Oliveira JV, Antunes OA, Oestreicher EG, de Oliveira D. 2012. Enzymatic synthesis of ascorbyl palmitate in organic solvents: process optimization and kinetic evaluation. Food Bioprocess Technol 5:1068–1076.
   Web of Science ®Google Scholar
• Li N, Ma D, Zong MH. 2008. Enhancing the activity and regioselectivity of lipases for 3’-benzoylation of floxuridine and its analogs by using ionic liquid-containing systems. J Biotechnol 133:103–109.
   PubMed Web of Science ®Google Scholar
• Li N, Smith TJ, Zong MH. 2010. Biocatalytic transformation of nucleoside derivatives. Biotechnol Adv 28:348–366.
   PubMed Web of Science ®Google Scholar
• Li XF, Lu ZH, Zhao GL, Wu H, Yu YG. 2012. A facile whole-cell biocatalytic approach to regioselective synthesis of monoacylated 1-β-D-arabinofuranosylcytosine: influence of organic solvents. Bioresour Technol 114:6–11.
   PubMed Web of Science ®Google Scholar
• Martínez-Montero S, Fernández S, Sanghvi YS, Gotor V, Ferrero M. 2012. CAL-B-catalyzed acylation of nucleosides and role of the sugar conformation: an improved understanding of the enzyme-substrate recognition. Eur J Org Chem 2012:5483–5490.
   Web of Science ®Google Scholar
• Moreno-Pereza S, Filice M, Guisana JM, Fernandez-Lorente G. 2013. Synthesis of ascorbyl oleate by transesterification of olive oil with ascorbic acid in polar organic media catalyzed by immobilized lipases. Chem Phys Lipids 174:48–54.
   PubMed Web of Science ®Google Scholar
• Pace V, Hoyos P, Castoldi L, María PDd, Alcántara AR. 2012. 2-Methyl-tetrahydrofuran (2-MeTHF): a biomass-derived solvent with broad application in organic chemistry. ChemSusChem 5:1369–1379.
   PubMed Web of Science ®Google Scholar
• Reyes-Duarte D, Lopez-Cortes N, Torres P, Comelles F, Parra J, Peña S, Ugidos A, Ballesteros A, Plou F. 2011. Synthesis and properties of ascorbyl esters catalyzed by Lipozyme TL IM using triglycerides as acyl donors. J Am Oil Chem Soc 88:57–64.
   Web of Science ®Google Scholar
• Santibanez L, Wilson L, Illanes A. 2014. Synthesis of ascorbyl palmitate with immobilized lipase from Pseudomonas stutzeri. J Am Oil Chem Soc 91:405–410.
   Web of Science ®Google Scholar
• Schuler P. 1990. Natural antioxidants exploited commercially. In: Hudson B, editor. Food antioxidants. London: Elsevier. p. 99–170.
   Google Scholar
• Simeo Y, Sinisterra JV, Alcantara AR. 2009. Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF. Green Chem 11:855–862.
   Web of Science ®Google Scholar
• Viklund F, Alander J, Hult K. 2003. Antioxidative properties and enzymatic synthesis of ascorbyl FA esters. J Am Oil Chem Soc 80:795–799.
   Web of Science ®Google Scholar
• Villeneuve P. 2007. Lipases in lipophilization reactions. Biotechnol Adv 25:515–536.
   PubMed Web of Science ®Google Scholar
• Watanabe Y, Kuwabara K, Adachi S, Nakanishi K, Matsuno R. 2003. Production of saturated acyl L-ascorbate by immobilized lipase using a continuous stirred tank reactor. J Agric Food Chem 51:4628–4632.
   PubMed Web of Science ®Google Scholar
• Yan Y, Bornscheuer U, Schmid R. 1999. Lipase-catalyzed synthesis of vitamin C fatty acid esters. Biotechnol Lett 21:1051–1054.
   Web of Science ®Google Scholar
• Yang K, Wang YJ. 2004. Lipase-catalyzed transesterification in aqueous medium under thermodynamic and kinetic control using carboxymethyl cellulose acetylation as the model reaction. Enzyme Microb Technol 35:223–231.
   Web of Science ®Google Scholar
• Yang Z, Huang ZL. 2012. Enzymatic synthesis of sugar fatty acid esters in ionic liquids. Catal Sci Technol 2:1767–1775.
   Web of Science ®Google Scholar
• Zhang DH, Li C, Xie LL, Yuwen LX. 2013. Enzymatic synthesis of L-ascorbyl laurate in DMSO-acetone mixed solvent. Ind Eng Chem Res 52:11875–11879.
   Web of Science ®Google Scholar
• Zhao H, Liu J, Lv F, Ye R, Bie X, Zhang C, Lu Z. 2014. Enzymatic synthesis of lard-based ascorbyl esters in a packed-bed reactor: optimization by response surface methodology and evaluation of antioxidant properties. LWT – Food Sci Technol 57:393–399.
   Web of Science ®Google Scholar
• Zhao H, Zhang Y, Lu F, Bie X, Lu Z, Ning H. 2011. Optimized enzymatic synthesis of ascorbyl esters from lard using Novozym 435 in co-solvent mixtures. J Mol Catal B: Enzym 69:107–111.
   Web of Science ®Google Scholar