Kinetic model of lipase-catalyzed conversion of ascorbic acid and oleic acid to liposoluble vitamin C ester

Biochemical Engineering Journal

Volumn 71, Issue , 2013, Pages 89-96

  Bezbradica, Dejan ^a   Stojanović, Marija ^a   Veličković, Dušan ^b   Dimitrijević, Aleksandra ^b   Carević, Milica ^a   Mihailović, Mladen ^a   Milosavić, Nenad ^b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Ascorbyl oleate; Candida antarctica; Kinetic parameters; Lipase; Production kinetics; Substrate inhibition

Indexed keywords

ASCORBIC ACIDS; ASCORBYL OLEATE; CANDIDA ANTARCTICA; ENZYME CONCENTRATIONS; ESTER HYDROLYSIS; ESTER SYNTHESIS; EXPERIMENTAL FACTORS; IMMOBILIZED LIPASE; KINETIC CONSTANT; KINETIC MODELS; KINETIC STUDY; L-ASCORBYL OLEATE; LIPASE-CATALYZED; PRODUCTION KINETICS; PROGRESS CURVES; REACTION MECHANISM; REACTION OPTIMIZATION; RESPONSE SURFACE METHODOLOGY; REVERSE REACTIONS; SUBSTRATE INHIBITION; VITAMIN C;

ACETONE; BIOSYNTHESIS; ESTERIFICATION; ESTERS; ISOMERS; KINETIC PARAMETERS; KINETIC THEORY; LIPASES; OLEIC ACID; ORGANIC ACIDS; RATE CONSTANTS; SUBSTRATES; UNSATURATED FATTY ACIDS; VITAMINS;

KINETICS;

ASCORBIC ACID; ESTER; OLEIC ACID; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VITAMIN C ESTER;

ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; HYDROLYSIS; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS; TEMPERATURE; WATER CONTENT;

CANDIDA ANTARCTICA;

EID: 84872407885     PISSN: 1369703X     EISSN: 1873295X     Source Type: Journal    
DOI: 10.1016/j.bej.2012.12.001     Document Type: Article

References (24)

1. Cao L., Fischer A., Bornscheuer U.T., Schmid R.D. Lipase-catalyzed solid phase preparation of sugar fatty acid esters. Biocatal. Biotransform. 1997, 14:269-283.
2. Yan Y., Bornscheuer U.T., Schmid R.D. Lipase-catalyzed synthesis of vitamin C fatty acid esters. Biotechnol. Lett. 1999, 21:1051-1054.
3. Wong C.H., Whitesides G.M. Enzyme in Synthetic Organic Chemistry 1994, Pergamon Press, Oxford.
4. Guillen M., Benaiges M.D., Valero F. Biosynthesis of ethyl butyrate by immobilized recombinant Rhyzopus oryzae lipase expressed in Pichia pastoris. Biochem. Eng. J. 2012, 65:1-9.
5. Karmee S.K. Biocatalytic synthesis of ascorbyl esters and their biotechnological applications. Appl. Microbiol. Biotechnol. 2009, 81:1013-1022.
6. Song Q.X., Zhao Y., Xu W.Q., Zhou W.Y., Wei D.Z. Enzymatic synthesis of l-ascorbyl linoleate in organic media. Bioprocess Biosyst. Eng. 2005, 28:211-215.
7. Song Q.X., Wei D.Z. Study of vitamin C ester synthesis by immobilized lipase from Candida sp. J. Mol. Catal. B: Enzym. 2002, 18:261-266.
8. Adamczak M., Bornscheuer U.T., Bednarski W. Synthesis of ascorbyl oleate by immobilized Candida antarctica lipases. Process Biochem. 2005, 40:3177-3180.
9. Adamczak M., Bornscheuer U.T. Improving ascorbyl oleate synthesis catalyzed by Candida antarctica lipase B in ionic liquids and water activity control by salt hydrates. Process Biochem. 2009, 44:257-261.
10. Hsieh H.J., Chen J.W., Giridhar R., Wu W.T. Synthesis of mixed esters of ascorbic acid using methyl esters of palm and soybean oils. Prep. Biochem. Biotechnol. 2005, 35:113-118.
11. Kuwabara K., Watanabe Y., Adachi S., Nakanishi K., Matsuno R. Synthesis of 6-O-unsaturated acyl l-ascorbates by immobilized lipases in acetone in the presence of molecular sieve. Biochem. Eng. J. 2003, 16:17-22.
12. Segel I.H. Enzyme Kinetic 1975, Wiley/Interscience, New York.
13. Garcia T., Coteron A., Martinez M., Aracil J. Kinetic modeling of esterification reactions catalyzed by immobilized lipases. Chem. Eng. Sci. 1996, 51:2841-2846.
14. Yadav G.D., Lathi P.S. Kinetics and Mechanism of synthesis of butyl isobutyrate over immobilized lipases. Biochem. Eng. J. 2003, 16:245-252.
15. Yadav G.D., Lathi P.S. Synthesis of citronellol laurate in organic media catalyzed by immobilized lipase: kinetic studies. J. Mol. Catal. B: Enzym. 2004, 27:113-119.
16. Garcia T., Sanchez N., Martinez M., Aracil J. Enzymatic synthesis of fatty esters. Part I. Kinetic approach. Enzyme Microb. Technol. 1999, 25:584-590.
17. Arcos J.A., Hill C.G., Otero C. Kinetics of the lipase-catalyzed synthesis of the glucose esters in acetone. Biotechnol. Bioeng. 2001, 73:104-110.
18. Janssen A.E.M., Sjursnes B.J., Vakurov A.V., Halling P.J. Kinetics of lipase-catalyzed esterification in organic media: correct model and solvent effects on parameters. Enzyme Microb. Technol. 1999, 24:463-470.
19. Bezbradica D., Mijin D., Šiler-Marinković S., Knežević Z. The Candida rugosa lipase catalyzed synthesis of amyl isobutyrate in organic solvent and solvent-free system: a kinetic study. J. Mol. Catal. B: Enzym. 2006, 38:11-16.
20. Knežević-Jugović Z., Bezbradica D., Jakovljević Ž., Branković-Dimitrijević S., Mijin D. Lipase catalyzed synthesis of flavor esters in non-aqueous media: optimization of the yield of pentyl 2-methylpropanoate by statistical analysis. J. Serb. Chem. Soc. 2008, 73:1139-1151.
21. Jiménez M.J., Esteban L., Robles A., Hita E., González P.A., Munío M.M., Molina E. Production of triacylglycerols rich in palmitic acid at sn-2 position by lipase-catalyzed acidolysis. Biochem. Eng. J. 2010, 51:172-179.
22. Pleiss J., Fischer M., Schmid R.D. Anatomy of lipase binding sites: the scissile fatty acid binding site. Chem. Phys. Lipids 1998, 93:67-80.
23. Viklund F., Alander J., Hult K. Antioxidative properties and enzymatic synthesis of ascorbyl FA esters. J. Am. Oil Chem. Soc. 2003, 80:795-799.
24. Paiva A.L., Balcao V.M., Malcata F.X. Kinetics and mechanisms of reactions catalyzed by immobilized lipases. Enzyme Microb. Technol. 2000, 27:187-204.