Evaluation of factors influencing the enantioselective enzymatic esterification of lactic acid in ionic liquid

Bioprocess and Biosystems Engineering

Volumn 35, Issue 4, 2012, Pages 625-635

  Findrik, Zvjezdana ^a   Németh, Gergely ^b   Gubicza, László ^b   Vasić Rački, Durda ^a   Bélafi Bakó, Katalin ^b  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b UNIVERSITY OF PANNONIA   (Hungary)

Author keywords

Conversion; Enantioselectivity; Experimental plan; Lipase; Optimization

Indexed keywords

CANDIDA ANTARCTICA B; DESIGN-EXPERT; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; ENZYMATIC ESTERIFICATION; ETHYL LACTATE; EXPERIMENTAL DATA; EXPERIMENTAL PLAN; INITIAL CONDITIONS; MASS RATIO; MOLAR EXCESS; NOVOZYME 435; STATISTICAL PROCESSING; VARIABLE RANGE;

ENANTIOMERS; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; ETHANOL; IONIC LIQUIDS; LIPASES; MATHEMATICAL MODELS; OPTIMIZATION; SHIP CONVERSION;

LACTIC ACID;

ALCOHOL; FUNGAL ENZYME; IONIC LIQUID; LACTIC ACID; TRIACYLGLYCEROL LIPASE;

ARTICLE; BATCH REACTOR; CANDIDA ANTARCTICA; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME MECHANISM; ENZYME MODIFICATION; ESTERIFICATION; MATHEMATICAL MODEL; NONHUMAN; PRIORITY JOURNAL; PROCESS OPTIMIZATION; TEMPERATURE SENSITIVITY; WATER CONTENT;

CANDIDA; COMBINATORIAL CHEMISTRY TECHNIQUES; COMPUTER SIMULATION; ESTERIFICATION; ETHANOL; IONIC LIQUIDS; LACTIC ACID; LIPASE; MODELS, CHEMICAL;

CANDIDA ANTARCTICA;

EID: 84861481431     PISSN: 16157591     EISSN: 16157605     Source Type: Journal    
DOI: 10.1007/s00449-011-0645-5     Document Type: Article

References (43)

1. Jaeger KE, Schneidinger B, Rosenau F, Werner M, Lang D, Dijkstra BW, Schimossek K, Zonta A, Reetz MT (1997) Bacterial lipases for biotechnological applications. J Mol Cat B Enzym 3:3-12 (Pubitemid 27276898)
2. Theil F (1995) Lipase-supported synthesis of biologically active compounds. Chem Rev 95:2203-2227
3. Kakasi-Zsurka S, Todea A, But A, Paul C, Boeriu CG, Davidescu C, Nagy L, Kuki A, Keki S, Peter F (2011) Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone. J Mol Cat B Enzym 71:22-28
4. Jaeger KE, Eggert T (2002) Lipases for biotechnology. Cur Opin Biotechnol 13:390-397
5. Turner NJ (2003) Controlling chirality. Cur Opin Biotechnol 14:401-406
6. Berglund P (2001) Controlling lipase enantioselectivity for organic synthesis. Biomol Eng 18:13-22
7. Chang CS, Su CC, Zhuang JR, Tsai SW (2004) Enhancement of enantioselectivity on the synthesis of (S)-naproxen morpholinoalkyl ester prodrugs in organic solvents using isopropanol-dried immobilized lipase. J Mol Cat B Enzym 30:151-157
8. Bhandarkar SV, Neau SH (2000) Lipase-catalyzed enantioselective esterification of flurbiprofen with n-butanol. Eur J Biotechnol 3(2):1-7
9. Bornscheuer UT (2002) Methods to increase enantioselectivity of lipases and esterases. Cur Opin Biotechnol 13:543-547
10. Engström K, Nyhlén J, Sandström AG, Bäckvall JE (2010) Directed evolution of an enantioselective lipase with broad substrate scope for hydrolysis of α-substituted esters. J Am Chem Soc 132:7038-7042
11. Liebeton K, Zonta A, Schimossek K, Nardini M, Lang D, Dijkstra BW, Reetz MT, Jaeger KE (2000) Directed evolution of an enantioselective lipase. Chem Biol 7:709-718
12. Lang DA, Dijkstra BW (1998) Structural investigations of the regio- and enantioselectivity of lipases. Chem Phys Lipids 93:115-122 (Pubitemid 28383210)
13. Köhler J, Wünsch B (2007) The allosteric modulation of lipases and it possible biological relevance. Theor Biol Med Model 4:34-54
14. Hæffner F, Norin T, Hult K (1998) Molecular modeling of the enantioselectivity in lipase catalyzed transesterification reactions. Biophys J 74:1251-1262 (Pubitemid 28108535)
15. Overbeeke PLA, Orrenius SC, Jongejan JA, Duine JA (1998) Enthalpic and entropic contributions to lipase enantioselectivity. Chem Phys Lipids 93:81-93 (Pubitemid 28383207)
16. Weuster-Botz D (2000) Experimental design for fermentation media development: Statistical design or global random search? J Biosci Bioeng 90:473-483
17. 2 system using factorial experimental design. Chem Eng J 150:476-484
18. Design-Expert® software, Version 6 User's Guide, Stat-Ease, 2000l
19. Yuan Y, Bai S, Sun Y (2006) Comparison of lipase-catalyzed enantioselective esterification of (±)-menthol in ionic liquids and organic solvent. Food Chem 97:324-330 (Pubitemid 41829610)
20. Ulbert O, Fráter T, Bélafi-Bakó K, Gubicza L (2004) Enhanced enantioselectivity of Candida rugosa lipase in ionic liquids as compared to organic solvents. J Mol Cat B Enzym 31:39-45 (Pubitemid 39297068)
21. Eckstein M, Sesing M, Kragl U, Adlercreutz P (2002) Enhanced enantioselectivity of lipase from Pseudomonas sp. at high temperatures and fixed water activity in the ionic liquid 1-butyl-3-methyl bis((trifluoromethyl) sulfonyl)amide. Biotechnol Lett 24:867-872
22. Sheldon RA, Lau RM, Sorgedrager MJ, Van Rantwijk F, Seddon KR (2002) Biocatalysis in ionic liquid. Green Chem 4:147-151
23. Habulin M, Knez Ž (2009) Optimization of (R, S)-1-phenylethanol kinetic resolution over Candida antarctica lipase B in ionic liquid. J Mol Cat B Enzym 58:24-28
24. De Diego T, Lozano P, Abad MA, Steffensky K, Vaultier M, Iborra JL (2009) On the nature of ionic liquids and their effects on lipases that catalyze ester synthesis. J Biotechnol 140:234-241
25. Bousquet MP, Willemot RM, Monsan P, Boures E (1999) Lipase-catalyzed α-butylglucoside lactate synthesis in organic solvent for dermo-cosmetic application. J Biotechnol 68:61-69 (Pubitemid 29073435)
26. Kiran KR, Divakar S (2001) Lipase catalyzed synthesis of organic acid esters of lactic acid in non-aqueous media. J Biotechnol 87:109-121 (Pubitemid 32241094)
27. Jovanović O, Pajin B (2004) Influence of lactic acid ester on chocolate quality. Trends Food Sci Technol 15:128-136 (Pubitemid 38300184)
28. Delgado P, Sanz MT, Beltran S (2007) Kinetic study for esterification of lactic acid with ethanol and hydrolysis of ethyl lactate using an ion-exchange resin catalyst. Chem Eng J 126:111-118 (Pubitemid 46205362)
29. Pereira CAM, Zabka M, Silva VMTM, Rodrigues AE (2009) A novel process for the ethyl lactate synthesis in a simulated moving bed reactor (SMBR). Chem Eng Sci 64:3301-3310
30. Gao J, Zhao XM, Zhou LY, Huang ZH (2007) Investigation of ethyl lactate reactive distillation process. Chem Eng Res Design 85:525-529 (Pubitemid 46672016)
31. Ohara H, Onogi A, Yamamoto M, Kobayashi S (2010) Lipase-catalyzed oligomerization and hydrolysis of alkyl lactates: direct evidence in the catalysis mechanism that enantioselection is governed by a deacylation step. Biomacromolecules 11:2008-2015
32. Data R, Henry M (2006) Lactic acid: recent advances in products, processes and technologies - a review. J Chem Technol Biotechnol 81:1119-1129
33. Inaba C, Maekawa K, Morisaka H, Kuroda K, Ueda M (2009) Efficient synthesis of enantiomeric ethyl lactate by Candida antarctica lipase B (CALB)-displaying yeasts. Appl Microbiol Biotechnol 83:859-864
34. Chahal SP (1990) Lactic acid, Ullman's Encyclopedia of Industrial Chemistry vol A15, VCH Verlagsgesellschaft, Weincheim
35. Troupe RA, Dimilla E (1957) Kinetics of the ethyl alcohol-lactic acid reaction. Ind Eng Chem 49:847-855
36. Kramer M, Cruz JC, Pfromm PH, Rezac ME, Czermak P (2010) Enantioselective transesterification by Candida antarctica lipase B immobilized on fumed silica. J Biotechnol 150:80-86
37. Major B, Németh G, Bélafi-Bakó K, Gubicza L (2010) Unique role of water content in enzymatic synthesis of ethyl lactate using ionic liquid as a solvent. Chem Pap 64(2):261-264
38. Chen CS, Wu SH, Girdaukas G, Sih CJ (1987) Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems. J Am Chem Soc 109:2812-2817
39. Hult K, Norin T (1992) Enantioselectivity of some lipases: Control and prediction. Pure Appl Chem 64(8):1129-1134
40. Bovara R, Carrea G, Ottolina G, Riva S (1993) Water activity does not influence the enantioselectivity of lipase PS and lipoprotein lipase in organic solvents. Biotechnol Lett 15:169-174 (Pubitemid 23092487)
41. Wehtje E, Costes D, Adlercreutz P (1993) Enantioselectivity of lipases: effects of water activity. J Mol Cat B Enzym 3:221-230
42. Persson M, Costes D, Wehtje E, Adlercreutz P (2002) Effect of solvent, water activity and temperature on lipase and hydroxynitrile lyase enantioselectivity. Enzyme Microb Technol 30:916-923 (Pubitemid 34655415)
43. Montgomery DC (2001) Design and analysis of experiments. Wiley, New York