Enzymatic processes in alternative reaction media: a mini review

Authors

  • Mansour Ghaffari-Moghaddam University of Zabol
  • Hassan Eslahi University of Zabol
  • Yasar A. Aydin Istanbul Technical University
  • Didem Saloglu Yalova University

DOI:

https://doi.org/10.14440/jbm.2015.60

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.


References

Koch K, Van den Berg, RJF, Nieuwland PJ, Wijtmans R, Wubbolts MG, Schoemaker HE, Rutjes FPJT, Van Hest JCM (2008) Enzymatic synthesis of optically pure cyanohydrins in microchannels using a crude cell lysate. Chem Eng J 135: 89-92.

Teo EL, Chuah GK, Huguet ARJ, Jaenicke S, Pande G, Zhu Y (2004) Process intensification with biocatalysts: dynamic kinetic resolution and fluorous phase switch with continuous extraction. Catal Today 97: 263-270.

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.

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.

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.

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.

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.

Ogawa J, Shimizu S (1999) Microbial enzymes: new industrial applications from traditional screening methods. Trends in Biotechnol 17: 13–20.

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.

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.

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.

Reetz MT (2002) Lipases as practical biocatalysts. Curr Opin Chem Bio 6: 145–150.

Krishna SH (2002) Developments and trends in enzyme catalysis in nonconventional media. Biotechnol Adv 20: 239–267.

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.

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.

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.

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.

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.

Trusek-Holownia A, Noworyta A (2007) An integrated process: Ester synthesis in an enzymatic membrane reactor and water sorption. J Biotechnol 130: 47-56.

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.

Villeneuve P (2007) Lipases in lipophilization reactions. Biotechnol Adv 25: 515-536.

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.

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.

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.

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.

Klibanov AM (2003) Asymmetric enzymatic oxidoreductions in organic solvents. Curr Opin Biotechnol 14: 427-431.

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.

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.

Xu JC, Li WM, Zheng H, Lai YF, Zhang PF (2011) One-pot synthesis of tetrahydrochromene derivatives catalyzed by lipase. Tetrahedron 67: 9582-9587.

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.

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.

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.

Serdakowski AL, Dordick JS (2008) Enzyme activation for organic solvents made easy. Trends in Biotechnol. 26: 48–54.

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.

Jeng FY, Lin SC (2006) Characterization and application of PEGylated horseradish peroxidase for the synthesis of poly(2-naphthol). Process Biochem 4: 1566-1573.

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.

Doukyu N, Ogino H (2010) Organic solvent-tolerant enzymes. Biochem Eng J 48: 270-282.

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.

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.

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.

Ghanem A (2006) Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds. Tetrahedron 63: 1721-1754.

Kragl U, Eckstein M, Kaftzik N (2002) Enzyme catalysis in ionic liquids. Curr Opin Biotechnol 13: 565-571.

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.

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.

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.

Samayam IP, Schall CA (2010) Saccharification of ionic liquid pretreated biomass with commercial enzyme mixtures. Bioresour Technol 101: 3561-3566.

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.

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.

Cvjetko M, Vorkapic-Furac J, Znidarsic-Plazl P (2012) Isoamyl acetate synthesis in imidazolium-based ionic liquids using packed bed enzyme microreactor. Process Biochem 47: 1344-1350.

Kielbasinski P, Albrycht M, Luczak J, Mikolajczyk M (2002) Enzymatic reactions in ionic liquids: lipase-catalysed kinetic resolution of racemic, P-chiral hydroxymethanephosphinates and hydroxymethylphosphine oxides. Tetrahedron: Asym 13: 735-738.

Lai JQ, Hu ZL, Wang PW, Yang Z (2012) Enzymatic production of microalgal biodiesel in ionic liquid [BMIm][PF6]. Fuel 95: 329-333.

Goldfeder M, Fishman A (2014) Modulating enzyme activity using ionic liquids or surfactants. Appl Microbiol Biotechnol 98:545-554.

Bi Y-H, Duan Z-Q, Li X-Q, Wang Z-Y, Zhao X-R (2015) Introducing biobased ionic liquids as the nonaqueous media for enzymatic synthesis of phosphatidylserine. J Agric Food Chem 63:1558-1561.

Zhao H, Zhang C, Crittle TD (2013) Choline-based deep eutectic solvents for enzymatic preparation of biodiesel from soybean J Mol Catal B: Enzym 85–86: 243-247.

Huang Z-L, Wu B-P, Wen Q, Yang T-X, Yang Z (2014) Deep eutectic solvents can be viable enzyme activators and stabilizers. J Chem Technol Biotechnol 89:1975-1981.

Wu B-P, Wen Q, Xu H, Yang Z Insights into the impact of deep eutectic solvents on horseradish peroxidase: activity, stability and structure J Mol Catal B: Enzym 101:101-107.

Hayyan M, Hashim MA, Hayyan A, Al-Saadi MA, AlNashef IM, Mirghani MES, Saheed OK (2013) Are deep eutectic solvents benign or toxic? Chemosphere 90:2193-2195.

Liu Y, Chen D, Xu L, Yan Y (2012) Evaluation of structure and hydrolysis activity of Candida rugosa Lip7 in presence of sub-/super-critical CO2. Enzym Microb Technol 51: 354-358.

van den Broek LAM, Boeriu CG (2013) Enzymatic synthesis of oligo- and polysaccharide fatty acid esters. Carbohydr Polym 93: 65-72.

Jérôme C, Lecomte, P (2008) Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization. Adv Drug Deliv Rev 60: 1056-1076.

Yan JY, Yan YJ, Yang JK, Xu L, Liu Y (2009) Combined strategy for preparation of a bioimprinted Geotrichum sp. lipase biocatalyst effective in non-aqueous media. Process Biochem 44: 1128-1132.

Mesiano AJ, Beckman EJ, Russell AJ (1999) Supercritical biocatalysis. Chem Rev 99: 623-634.

Habulin M, Primozic M, Knez Z (2007) Supercritical fluids as solvents for enzymatic reactions. Acta Chim Slov 54: 667–677.

Hobbs HR, Thomas NR (2007) Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions. Chem Rev 107: 2786-2820.

Kamat SV, Beckman EJ, Russell A (1995) Enzyme activity in supercritical fluids. Crit Reviews Biotechnol 15: 41-71.

Matsuda T, Watanabe K, Harada T, Nakamura K (2004) Enzymatic reactions in supercritical CO2: carboxylation, asymmetric reduction and esterification. Catal Today 96: 103-111.

Shin MH, Cheong NY, Lee JH, Kim KH (2009) Transglucosylation of caffeic acid by a recombinant sucrose phosphorylase in aqueous buffer and aqueous-supercritical CO2 media. Food Chem. 115: 1028-1033.

Dolores M, Diaz R, Gómez JM, Díaz-Suelto B, García-Sanz A (2010) Enzymatic synthesis of short-chain esters in n-hexane and supercritical carbon dioxide: Effect of the acid chain length. Eng Life Sci 10:171-176.

Kmecz I, Simandi B, Poppe L, Juvanicz Z, Renner K, Bodai V, Toke ER, Csajagi C, Sawinsky J (2006) Lipase-catalyzed enantioselective acylation of 3-benzyloxypropane-1,2-diol in supercritical carbon dioxide. Biochem Eng J 28: 275-280.

Romero MD, Calvo L, Alba C, Habulin M, Primozic M, Knez Z (2005) Enzymatic synthesis of isoamyl acetate with immobilized Candida antarctica lipase in supercritical carbon dioxide. J Supercrit Fluids 33: 77-84.

Loeker FC, Duxbury CJ, Kumar R, Gao W, Gross RA, Howdle SM (2004) Enzyme-catalyzed ring-opening polymerization of ε-caprolactone in supercritical carbon dioxide. Macromol 37: 2450-2453.

Beier P, O’Hagan D (2002) Enantiomeric partitioning using fluorous biphase methodology for lipase-mediated (trans)esterifications. Chem Commun 1680-1681.

Saul S, Corr S, Micklefield J (2004) Biotransformations in Low-Boiling Hydrofluorocarbon Solvents. Angew Chem Int Ed 43: 5519-5523.

Hobbs HR, Kirke HM, Poliakoff M, Thomas NR (2007) Homogeneous biocatalysis in both fluorous biphasic and supercritical carbon dioxide systems. Angew Chem Int Ed 46: 7860-7863.

Panza JL, Russell AJ, Beckman, EJ (2002) Synthesis of fluorinated NAD as a soluble coenzyme for enzymatic chemistry in fluorous solvents and carbon dioxide. Tetrahedron 58: 4091-4104.

Jin JN, Lee SH, Lee SBJ (2003) Immobilization of lipase in a mesoporous reactor based on MCM-41. Mol Catal B: Enzym 26: 209-217.

Gomez JL, Bastida J, Máximo MF, Montiel MC, Murcia MD, Ortega S (2011) Solvent-free polyglycerol polyricinoleate synthesis mediated by lipase from Rhizopus arrhizus. Biochem Eng J 54: 111-116.

Yadav GD, Thorat PA (2012) Microwave assisted lipase catalyzed synthesis of isoamyl myristate in solvent-free system. J Mol Catal B: Enzym 83:17-22.

Kuperkar VV, Lade VG, Prakash A, Rathod VK (2014) Synthesis of isobutyl propionate using immobilized lipase in a solvent free system: Optimization and kinetic studies. J Mol Catal B: Enzym 99: 143-149.

Törnvall U, Orellana-Coca C, Hatti-Kaul R, Adlercreutz D (2007) Stability of immobilized Candida antarctica lipase B during chemo-enzymatic epoxidation of fatty acids. Enzym Microb Technol 40: 447-451.

Santos JC, Bueno T, Molgero da Ros PC, de Castro HF (2007) Lipase-catalyzed synthesis of butyl esters by direct esterification in solvent-free system J Chem Technol Biotechnol 82: 956-961.

Bezbradica D, Mijin D, Siler-Marinkovic S, Knezevic Z (2007) The effect of substrate polarity on the lipase-catalyzed synthesis of aroma esters in solvent-free systems. J Mol Catal B: Enzym 45: 97-101.

Sorour N, Karboune S, Saint-Louis R, Kermasha S (2012) Enzymatic synthesis of phenolic lipids in solvent-free medium using flaxseed oil and 3,4-dihydroxyphenyl acetic acid. Process Biochem 47: 1813–1819.

Bezbradica D, Mijin D, Siler-Marinkovic S, Knezevic Z (2006) The Candida rugosa lipase catalyzed synthesis of amyl isobutyrate in organic solvent and solvent-free system: A kinetic study. J Mol Catal B: Enzym 38: 11-16.

Sun J, Yu B, Curran P, Liu SQ (2012) Lipase-catalysed transesterification of coconut oil with fusel alcohols in a solvent-free system. Food Chem 134: 89-94.

Véras IC, Silva FAL, Ferrão-Gonzales AD, Moreau VH (2011) One-step enzymatic production of fatty acid ethyl ester from high-acidity waste feedstocks in solvent-free media. Bioresour Technol 102: 9653-9658.

Sun S, Song F, Bi Y, Yang G, Liu W (2012) Solvent-free enzymatic transesterification of ethyl ferulate and monostearin: Optimized by response surface methodology. J Biotechnol 164: 340-345.

Chaibakhsh N, Rahman MBA, Abd-Aziz S, Basri M, Salleh AB, Rahman RNZRA (2009) Optimized lipase-catalyzed synthesis of adipate ester in a solvent-free system. J Ind Microbiol Biotechnol 36: 1149-1155.

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Published

2015-09-02

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1.
Ghaffari-Moghaddam M, Eslahi H, Aydin YA, Saloglu D. Enzymatic processes in alternative reaction media: a mini review. J Biol Methods [Internet]. 2015Sep.2 [cited 2022Aug.11];2(3):e25. Available from: https://jbmethods.org/jbm/article/view/60

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