Enzymatic processes in alternative reaction media: a mini review
Main Article Content
Keywords
aqueous solvents, biocatalysts, enzymatic reactions, green solvents
Abstract
Biocatalysis is a growing field in the production of fine chemicals and will most probably increase its share in the future. Enzymatic reactions are carried out under mild conditions, i.e., non-toxic solvents, low temperature and pressure, which eliminates most environmental drawbacks associated with conventional production methods. The superiority of chemo-, regio- and enantioselectivity of enzymes exhibit significant advantages over conventional catalysts for production of fine chemicals, flavors, fragrances, agrochemicals and pharmaceuticals. Enzymes can function both in aqueous and non-aqueous solvents. As a result of the growing scientific and industrial interest towards green chemistry, green solvent systems, which are mainly water, supercritical fluids, ionic liquids, fluorinated solvents, and solvent-free systems have become more popular in biocatalysis. However, the activity and selectivity of an enzyme is heavily dependent on solvent properties. In this review, various green solvents were classified and some of their influential features on enzyme activity were discussed.
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References
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3. Mateo C, Palomo JM, Fernandez-Lorente G, Guisan JM, Fernandez-Lafuente R (2007) Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzym Microb Technol 40: 1451-1463.
4. Solano DM, Hoyos P, Hernaiz MJ, Alcantara AR, Sanchez-Montero JM (2012) Industrial biotransformations in the synthesis of building blocks leading to enantiopure drugs. Bioresour Technol 115: 196-207.
5. Ghaffari Moghaddam M, Ahmad FBH, Basri M, Abdul Rahman MB (2010) Artificial neural network modeling studies to predict the yield of enzymatic synthesis of betulinic acid ester. Electron J Biotechnol 13: 3-4.
6. Ghaffari Moghaddam M, Ahmad FBH, Basri M, Abdul Rahman MB (2010) Lipase-catalyzed esterification of betulinic acid using phthalic anhydride in organic solvent media: Study of Reaction Parameters. J Appl Sci 10: 337-342.
7. Quiroga E, Priolo N, Obregon D, Marchese J, Barberis S (2008) Peptide synthesis in aqueous–organic media catalyzed by proteases from latex of Araujia hortorum (Asclepiadaceae) fruits. Biochem Eng J 39: 115-120.
8. Ogawa J, Shimizu S (1999) Microbial enzymes: new industrial applications from traditional screening methods. Trends in Biotechnol 17: 13–20.
9. Bousquet MP, Willemot RM, Monsan P, Boures E (1998) Production, purification, and characterization of thermostable α-transglucosidase from Talaromyces duponti–application to α–alkylglucoside synthesis. Enzym Microb Technol 23: 83–90.
10. Cramer JF, Dueholm MS, Nielsen SB, Pedersen DS, Wimmer R, Pedersen LH (2007) Controlling the degree of esterification in lipase catalysed synthesis of xylitol fatty acid esters Enzym Microb Technol 41: 346–352.
11. Ratzka J, Lauterbach L, Lenz O, Ansorge-Schumacher MB (2012) Stabilisation of the NAD+-reducing soluble [NiFe]-hydrogenase from Ralstonia eutropha H16 through modification with methoxy-poly(ethylene) glycol. J Mol Catal B: Enzym 74: 219-223.
12. Reetz MT (2002) Lipases as practical biocatalysts. Curr Opin Chem Bio 6: 145–150.
13. Krishna SH (2002) Developments and trends in enzyme catalysis in nonconventional media. Biotechnol Adv 20: 239–267.
14. Dhake KP, Deshmukhi KM, Patil YP, Singhal RS, Bhanage BM (2011) Improved activity and stability of Rhizopus oryzae lipase via immobilization for citronellol ester synthesis in supercritical carbon dioxide. J Biotechnol 156: 46–51.
15. Capello C, Fischer U, Hungerbühler K (2007) What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem 9: 927-934.
16. Bódalo A, Bastida J, Máximo MF, Montiel MC, Murcia MD, Ortega S (2009) Influence of the operating conditions on lipase-catalysed synthesis of ricinoleic acid estolides in solvent-free systems. Biochem Eng 44: 214-219.
17. Llerena-Suster CR, José C, Collins SE, Briand LE, Morcelle SR (2012) Investigation of the structure and proteolytic activity of papain in aqueous miscible organic media. Process Biochem 47: 47–56.
18. Yadav GD, Lathi PS (2006) Intensification of enzymatic synthesis of propylene glycol monolaurate from 1,2-propanediol and lauric acid under microwave irradiation: Kinetics of forward and reverse reactions. Enzym Microb Technol 38: 814-820.
19. Trusek-Holownia A, Noworyta A (2007) An integrated process: Ester synthesis in an enzymatic membrane reactor and water sorption. J Biotechnol 130: 47-56.
20. Vossenberg P, Beeftink HH, Nuijens T, Quaedflieg PJLM, Cohen Stuart MA, Tramper J (2012) Performance of Alcalase formulations in near dry organic media: Effect of enzyme hydration on dipeptide synthesis. J Mol Catal B: Enzym 78: 24–31.
21. Villeneuve P (2007) Lipases in lipophilization reactions. Biotechnol Adv 25: 515-536.
22. Vossenberg P, Beeftinka HH, Nuijens T, Cohen Stuart MA, Tramper J (2012) Selecting optimal conditions for Alcalase CLEA-OM for synthesis of dipeptides in organic media. J Mol Catal B: Enzym 75: 43-49.
23. Yang K, Wang YJ (2004) Lipase-catalyzed transesterification in aqueous medium under thermodynamic and kinetic control using carboxymethyl cellulose acetylation as the model reaction. Enzym Microb Technol 35: 223-231.
24. Knuttel T, Meyer H, Scheper T (2005) Synthesis, test and application of chirale fluorescence substrates to evaluate enzymatic processes in different reaction media. Enzym Microb Technol 37: 673-686.
25. Borchert S, Burda E, Schatz J, Hummel W, Groger H (2012) Combination of a Suzuki cross-coupling reaction using a water-soluble palladium catalyst with an asymmetric enzymatic reduction towards a one-pot process in aqueous medium at room temperature. J Mol Catal B: Enzym 84: 89- 93.
26. Klibanov AM (2003) Asymmetric enzymatic oxidoreductions in organic solvents. Curr Opin Biotechnol 14: 427-431.
27. Knuttel T, Meyer H, Scheper T (2006) The application of two-dimensional fluorescence spectroscopy for the on-line evaluation of modified enzymatic enantioselectivities in organic solvents by forming substrate salts. Enzym Microb Technol 39: 607-611.
28. Konieczny S, Fik CP, Averesch NLH, Tiller JC (2012) Organosoluble enzyme conjugates with poly(2-oxazoline)s via pyromellitic acid dianhydride. J Biotechnol 159: 195-203.
29. Xu JC, Li WM, Zheng H, Lai YF, Zhang PF (2011) One-pot synthesis of tetrahydrochromene derivatives catalyzed by lipase. Tetrahedron 67: 9582-9587.
30. Abdul Rahman MB, Tajudin SM, Hussein MZ, Zalih RN, Rahman RA, Salleh AB, Basri M (2005) Application of natural kaolin as support for the immobilization of lipase from Candida rugosa as biocatalsyt for effective esterification. Clay Sci 29: 111-116.
31. Liu B, Qian X, Wu Q, Lin X (2008) Two lipase-catalyzed sequential synthesis of drug derivatives in organic media. Enzym Microb Technol 43: 375-380.
32. Park OJ, Holland HL, Khan JA, Vulfson EN (2000) Production of flavour ketones in aqueous-organic two-phase systems by using free and microencapsulated fungal spores as biocatalysts. Enzym Microb Technol 26: 235–242.
33. Serdakowski AL, Dordick JS (2008) Enzyme activation for organic solvents made easy. Trends in Biotechnol. 26: 48–54.
34. Mine Y, Fukunaga K, Itoh K, Yoshimoto M, Nakao K, Sugimura T (2003) Enhanced enzyme activity and enantioselectivity of lipases in organic solvents by crown ethers and cyclodextrins. J Biosci Bioeng 95: 441-447.
35. Jeng FY, Lin SC (2006) Characterization and application of PEGylated horseradish peroxidase for the synthesis of poly(2-naphthol). Process Biochem 4: 1566-1573.
36. Ozturk TK, Kilinc A (2010) Immobilization of lipase in organic solvent in the presence of fatty acid additives. J Mol Catal B: Enzym. 67: 214-218.
37. Doukyu N, Ogino H (2010) Organic solvent-tolerant enzymes. Biochem Eng J 48: 270-282.
38. Sirotkin VA (2005) Effect of dioxane on the structure and hydration-dehydration of chymotrypsin as measured by FTIR spectroscopy. Biochim Biophys Acta 1750: 17-29.
39. Szabo A, Kotorman M, Laczko I, Simon LM (2009) Improved stability and catalytic activity of chemically modified papain in aqueous organic solvents. Process Biochem 44: 199-204.
40. Milasinovic N, Knezevic-Jugovic Z, Jakovljevic Z, Filipovic J, Krusic MK (2012) Synthesis of n-amyl isobutyrate catalyzed by Candida rugosa lipase immobilized into poly(N-isopropylacrylamide-co-itaconic acid) hydrogels. Chem Eng J 181–182: 614-623.
41. Ghanem A (2006) Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds. Tetrahedron 63: 1721-1754.
42. Kragl U, Eckstein M, Kaftzik N (2002) Enzyme catalysis in ionic liquids. Curr Opin Biotechnol 13: 565-571.
43. Naushad M, Al Othman ZA, Khan AB, Ali M (2012) Effect of ionic liquid on activity, stability, and structure of enzymes: A review. Int J Biol Macromol 51: 555-560.
44. Thomas MF, Li LL, Handley-Pendleton JM, van der Lelie D, Dunn JJ, Wishart JF (2011) Enzyme activity in dialkyl phosphate ionic liquids. Bioresour Technol 102, 11200–11203.
45. Fernandez-Fernandez M, Moldes D, Dominguez A, Sanroman MA, Tavares APM, Rodriguez O, Macedo EA (2014) Stability and kinetic behavior of immobilized laccase from Myceliophthora thermophila in the presence of the ionic liquid 1-ethyl-3-methylimidazolium ethylsulfate. Biotechnol Prog 30: 790-796.
46. Samayam IP, Schall CA (2010) Saccharification of ionic liquid pretreated biomass with commercial enzyme mixtures. Bioresour Technol 101: 3561-3566.
47. Adamczak M, Bornscheuer UT (2009) Improving ascorbyl oleate synthesis catalyzed by Candida antarctica lipase B in ionic liquids and water activity control by salt hydrates. Process Biochem 44: 257-261.
48. Kim M, Choi MY, Lee JK, Ahn Y (2003) Enzymatic selective acylation of glycosides in ionic liquids: significantly enhanced reactivity and regioselectivity. J Mol Catal B: Enzym 26: 115-118.
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Sep 2, 2015
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Ghaffari-Moghaddam M, Eslahi H, Aydin YA, Saloglu D. Enzymatic processes in alternative reaction media: a mini review. J Biol Methods [Internet]. 2015 Sep. 2 [cited 2024 Apr. 24];2(3):e25. Available from: https://jbmethods.org/index.php/jbm/article/view/60
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