Bioreactors with immobilized lipases: state of the art.

This review attempts to provide an updated compilation of studies reported in the literature pertaining to reactors containing lipases in immobilized forms, in a way that helps the reader direct a bibliographic search and develop an integrated perspective of the subject. Highlights are given to industrial applications of lipases (including control and economic considerations), as well as to methods of immobilization and configurations of reactors in which lipases are used. Features associated with immobilized lipase kinetics such as enzyme activities, adsorption properties, optimum operating conditions, and estimates of the lumped parameters in classical kinetic formulations (Michaelis-Menten model for enzyme action and first-order model for enzyme decay) are presented in the text in a systematic tabular form.

[1]  L. Posorske,et al.  Characteristics of an immobilized lipase for the commercial synthesis of esters , 1988 .

[2]  D. Hayes,et al.  1,3-specific lipolysis ofLesquerella fendleri oil by immobilized and reverse-micellar encapsulated enzymes , 1993 .

[3]  C. W. Wang,et al.  Fractionation procedures for obtaining cocoa butter-like fat from enzymatically interesterified palm olein , 1992 .

[4]  T. Yamane,et al.  High-yield diacylglycerol formation by solid-phase enzymatic glycerolysis of hydrogenated beef tallow , 1994 .

[5]  Ž. Knez,et al.  The influence of water on the synthesis of n-butyl oleate by immobilizedMucor miehei lipase , 1990 .

[6]  P. Linko,et al.  Effect of enzymatic interesterification on the melting point of tallow-rapeseed oil (LEAR) mixture , 1992 .

[7]  O. Edholm,et al.  Molecular dynamics simulations of an enzyme surrounded by vacuum, water, or a hydrophobic solvent. , 1994, Biophysical journal.

[8]  T. Yamane,et al.  High-yield enzymatic glycerolysis of fats and oils , 1991 .

[9]  C. G. Smith,et al.  Enzymic Interesterification of fats: Immobilization and Immunogold Localization of Lipase on Ion-Exchange Resins , 1990 .

[10]  F. Thorsteinsson,et al.  The preparation of triglycerides highly enriched with ω-3 polyunsaturated fatty acids via lipase catalyzed interesterification , 1989 .

[11]  H. Fukuda,et al.  Feedforward/feedback control of interesterification of fats and oils using a microaqueous bioreactor , 1992 .

[13]  David F. Ollis,et al.  Biochemical Engineering Fundamentals , 1976 .

[14]  R. Furneaux,et al.  Near-quantitative production of fatty acid alkyl esters by lipase-catalyzed alcoholysis of fats and oils with adsorption of glycerol by silica gel , 1994 .

[15]  S. A. Barker,et al.  Immobilization of lipase from Candida cylindraceae and its use in the synthesis of menthol esters by transesterification. , 1990, Enzyme and microbial technology.

[16]  M. Haas,et al.  Enzymatic phosphatidylcholine hydrolysis in organic solvents: An examination of selected commercially available lipases , 1994 .

[17]  A. Ballesteros,et al.  Influence of the support on the reaction course of tributyrin hydrolysis catalyzed by soluble and immobilized lipases , 1990, Applied biochemistry and biotechnology.

[18]  A. Padt,et al.  Candida rugosa lipase stability during acylglycerol synthesis. , 1992 .

[19]  V. John,et al.  Production of cocoa butter-like fat from interesterification of vegetable oils , 1990 .

[20]  D. Thomas,et al.  Water activity as a key parameter of synthesis reactions: the example of lipase in biphasic (liquid/solid) media. , 1990, Enzyme and microbial technology.

[21]  F. Malcata,et al.  Hydrolysis of Butteroil by Immobilized Lipase Using a Hollow-Fiber Reactor: Part V. Effects of ph. , 1993 .

[22]  A. Kemppinen,et al.  Mass spectrometric identification of triacylglycerols of enzymatically modified butterfat separated on a polarizable phenylmethylsilicone column , 1993 .

[23]  J. Shaw,et al.  Production of propylene glycol fatty acid monoesters by lipase-catalyzed reactions in organic solvents , 1994 .

[24]  H. Maehr,et al.  Enzymic enhancement of n−3 fatty acid content in fish oils , 1994 .

[25]  M. Schneider,et al.  Enzymatic esterification of glycerol I. Lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols , 1992 .

[26]  R. Willemot,et al.  Kinetic study of esterification by immobilized lipase in n‐hexane , 1990, FEBS letters.

[27]  G. Robinson,et al.  An investigation into the factors influencing lipase-catalyzed intramolecular lactonization in microaqueous systems , 1994 .

[28]  F. Winkler,et al.  Structure of human pancreatic lipase , 1990, Nature.

[29]  A. Kemppinen,et al.  Fractionation of the triacylglycerols of lipase-modified butter oil , 1993 .

[30]  C. Wandrey,et al.  Pseudomonas fluorescens lipase adsorption and the kinetics of hydrolysis in a dynamic emulsion system. , 1994, Enzyme and microbial technology.

[31]  T. Yoshimoto,et al.  Ester synthesis in benzene by polyethylene glycol-modified lipase from Pseudomonas fragi 22.39B , 1988 .

[32]  P. Brodelius Industrial applications of immobilized biocatalysts , 1978 .

[33]  T. Kaimal,et al.  Modification of selected indian vegetable fats into cocoa butter substitutes by lipase-catalyzed ester interchange , 1991 .

[34]  R. Jacobi,et al.  [Stability and stabilization of enzymes]. , 1989, Die Pharmazie.

[35]  H. Murakami,et al.  Hydroxylation Reactions by Recombinant Yeast Cells Expressing P450 Monooxygenases a , 1990, Annals of the New York Academy of Sciences.

[36]  N. Nishio,et al.  Hydrolysis of Triglycerides by Immobilized Thermostable Lipase from Humicola lanuginosa , 1988 .

[37]  Michel Pina,et al.  Aptitude à la transestérification de quelques lipases régiosélectives 1-3. I: Détermination de l'activité spécifique de transestérification: comparaison entre interestérification et hydrolyse dans l'action des lipases , 1988 .

[38]  Jyh-Ping Chen,et al.  Enhancement of Release of Short-Chain Fatty Acids from Milk Fat with Immobilized Microbial Lipase , 1992 .

[39]  S. Godtfredsen,et al.  A highly selective enzyme-catalysed esterification of simple glucosides , 1989 .

[40]  Michel Pina,et al.  Interestérification catalysée par les lipases régio-sélectives 1,3 en milieu fondu: applications à l'huile de palme et à sa fraction concrète , 1989 .

[41]  Polymeric membranes for lipase immobilization , 1990 .

[42]  P. Luisi,et al.  Dependence of Lipase Activity on Water Content and Enzyme Concentration in Reverse Micelles , 1990 .

[43]  F. Malcata,et al.  Use of Candida rugosa lipase immobilized in a spiral wound membrane reactor for the hydrolysis of milkfat , 1992 .

[44]  J. Kurashige,et al.  MODIFICATION OF FATS AND OILS BY LIPASES , 1989 .

[45]  S. M. Kim,et al.  Production of medium-chain glycerides by immobilized lipase in a solvent-free system , 1991 .

[46]  J. Patton Immobilized pancreatic lipase and colipase for purification and binding studies , 1978, FEBS letters.

[47]  F. Wang,et al.  Lipolytic activities of a lipase immobilized on six selected supporting materials , 1990, Biotechnology and bioengineering.

[48]  O. Ward,et al.  Lipase-catalyzed esterification of glycerol and n-3 polyunsaturated fatty acid concentrate in organic solvent , 1993 .

[49]  E. Brown,et al.  Enzymatic interesterification of triolein with tripalmitin in canola lecithin-hexane reverse micelles , 1993 .

[50]  M. Lilly,et al.  Effect of solvent concentration on enzyme catalysed interesterification of fats , 1988 .

[51]  D. Thomas,et al.  Gas phase transesterification reactions catalyzed by lipolytic enzymes. , 1992, Biotechnology and bioengineering.

[52]  F. Malcata,et al.  Hydrolysis of butteroil by immobilized lipase using a hollow-fiber reactor: part VI. Multiresponse analyses of temperature and pH effects , 1993 .

[53]  S. Ghoshray,et al.  Enzymatic preparation of ricinoleic acid esters of long-chain monohydric alcohols and properties of the esters , 1992 .

[54]  T. Yamane,et al.  Kinetic Studies on the Interesterification of Oils and Fats Using Dried Cells of Fungus , 1988 .

[55]  K. Hult,et al.  TRANSESTERIFICATION WITH CANDIDA CYLINDRACEA LIPASE IN A BIPHASIC AQUEOUS-ORGANIC SYSTEM. DEPENDENCE OF THE ENANTIOMERIC RATIO AND THE REACTION RATE ON THE PROPORTIONS OF WATER AND CYCLOHEXANE , 1990 .

[56]  Yuquan Feng,et al.  Lipase catalysis in organic solvents , 1992 .

[57]  E. Gulari,et al.  Formation of polyol–fatty acid esters by lipases in reverse micellar media , 1992, Biotechnology and bioengineering.

[58]  M. Renobales,et al.  Hydrolysis of animal fats by immobilized Candida rugosa lipase , 1994 .

[59]  J. Cabral,et al.  Production of Ethyl Butyrate by Candida rugosa Lipase Immobilized in Polyurethane , 1991 .

[60]  K. Holmberg,et al.  Lipase Catalyzed Transesterification of Unsaturated Lipids in a Microemulsion , 1989 .

[61]  S. Tsai,et al.  Kinetics, mechanism, and time course analysis of lipase‐catalyzed hydrolysis of high concentration olive oil in AOT–isooctane reversed micelles , 1991, Biotechnology and bioengineering.

[62]  C. Akoh,et al.  Enzymatic synthesis of geranyl acetate inn-hexane withCandida antarctica lipases , 1994 .

[63]  B. Mattiasson,et al.  Triglyceride interesterification by lipases. 1. Cocoa butter equivalents from a fraction of palm oil , 1990 .

[64]  J. Whitaker Principles of Enzymology for the Food Sciences , 2018 .

[65]  Ö. Almarsson,et al.  Studies on the Positional Specificity of Lipase from Mucor miehei during Interesterification Reactions of Cod Liver Oil with n--3 Polyunsaturated Fatty Acid and Ethyl Ester Concentrates. , 1991 .

[66]  T. Kaimal,et al.  Modification of selected edible vegetable oils to high oleic oils by lipase-catalyzed ester interchange , 1991 .

[67]  L. Posorske,et al.  Process considerations of continuous fat modification with an immobilized lipase , 1988 .

[68]  Ž. Knez,et al.  Enzymatic fatty ester synthesis , 1992 .

[69]  K. Fujimoto,et al.  Influence of interesterification on the oxidative stability of marine oil triacylglycerols , 1994 .

[70]  B. Mattiasson,et al.  Lipase-catalyzed alcoholysis of triglycerides for the preparation of 2-monoglycerides , 1994 .

[71]  K. Hult,et al.  Hydrolysis and Esterification with Lipase from Candida Cylindracea. Influence of the Reaction Conditions and Acid Moiety on the Enantiomeric Excess , 1989 .

[72]  Ross E. Williams,et al.  LIPASE MEDIATED SYNTHESIS OF LOW MOLECULAR WEIGHT FLAVOR ESTERS , 1990 .

[73]  S. Barreiros,et al.  Lipase-catalyzed enantioselective esterification of glycidol in supercritical carbon dioxide , 1994 .

[74]  P. Linko,et al.  Enzymatic transesterification of rapeseed oil and lauric acid in a continuous reactor , 1993 .

[75]  F. Ergan,et al.  Lipase-catalyzed production of wax esters , 1991 .

[76]  S. Schwimmer Source book of food enzymology. , 1981 .

[77]  H. Tilbeurgh,et al.  Interfacial activation of the lipase–procolipase complex by mixed micelles revealed by X-ray crystallography , 1993, Nature.

[78]  P. Sonnet,et al.  Lipase Modified for Solubility in Organic Solvents , 1988, Annals of the New York Academy of Sciences.

[79]  K. Hult,et al.  S-ethyl thiooctanoate as acyl donor in lipase catalysed resolution of secondary alcohols , 1993 .

[80]  J. Kurashige,et al.  Enzymatic modification of canola/palm oil mixtures: Effects on the fluidity of the mixture , 1993 .

[81]  M. Reuss,et al.  A kinetic study of immobilized lipase catalysing the synthesis of isoamyl acetate by transesterification in n-hexane. , 1992, Enzyme and microbial technology.

[82]  Y. Inada,et al.  Lipase made active in hydrophobic media by coupling with polyethylene glycol , 1994 .

[83]  W. D. Murray,et al.  Enzyme and Whole Cell Production of Flavor and Fragrance Compounds a , 1988 .

[84]  B. Huge-Jensen,et al.  Studies on free and immobilized lipases fromMucor miehei , 1988 .

[85]  T. Yamane,et al.  Intramolecular esterification by lipase powder in microaqueous benzene: Factors affecting activity of pure enzyme , 1990, Biotechnology and bioengineering.

[86]  T. O. Larsen,et al.  Fatty Acid Specificity in Lipase-Catalyzed Synthesis of Glucoside Esters , 1992 .

[87]  H. Fukuda,et al.  Continuous interesterification of oils and fats using dried fungus immobilized in biomass support particles , 1991 .

[88]  B. Witholt,et al.  Interesterification of Milk Fat with Oleic Acid Catalyzed by Immobilized Rhizopus oryzae Lipase , 1994 .

[89]  G. Fregapane,et al.  Lipase-catalyzed synthesis of lysophospholipids in a continuous bioreactor , 1994 .

[90]  F. Young Biochemistry , 1955, The Indian Medical Gazette.

[91]  S. H. Feairheller,et al.  Enzymatic interesterification of tallow-sunflower oil mixtures , 1993 .

[92]  F. Ergan,et al.  Enzymatic Triglyceride Synthesis with Total Consumption of Concentrated Substrates , 1990 .

[93]  P. Halling,et al.  Lipases from different sources vary widely in dependence of catalytic activity on water activity. , 1992, Biochimica et biophysica acta.

[94]  K. D. Mukherjee,et al.  Enrichment of γ-linolenic acid from evening primrose oil and borage oilvia lipase-catalyzed hydrolysis , 1994 .

[95]  J. Shaw,et al.  Lipase-catalyzed oil hydrolysis in the absence of added emulsifier. , 1988, Biotechnology and bioengineering.

[96]  M. Hills,et al.  Enzymatic fractionation of fatty acids: Enrichment of γ-linolenic acid and docosahexaenoic acid by selective esterification catalyzed by lipases , 1990 .

[97]  C. Akoh,et al.  Effect of reaction parameters on SP435 lipase-catalyzed synthesis of citronellyl acetate in organic solvent , 1994 .

[98]  M. Rucka,et al.  Ultrafiltration membranes as carriers for lipase immobilization. , 1990, Enzyme and microbial technology.

[99]  J. Rhee,et al.  Immobilization of lipase for effective interesterification of fats and oils in organic solvent , 1993, Biotechnology and bioengineering.

[100]  I. Miller,et al.  On the adsorption of serum proteins on polymer membrane surfaces , 1973 .

[101]  C. Akoh,et al.  Synthesis of alkyl glycoside fatty acid esters: Effect of reaction parameters and the incorporation of n-3 polyunsaturated fatty acids , 1994 .

[102]  M. Gordon,et al.  Effect of phospholipids on enzyme-catalyzed transesterification of oils , 1991 .

[103]  D. Combes,et al.  Kinetics of geranyl acetate synthesis by lipase-catalysed transesterification in n-hexane , 1992 .

[104]  Y. Linko,et al.  Optimization of Enzymic Production of Oleic Acid , 1990 .

[105]  J. Hartsuck,et al.  Kinetics of acylglycerol sequential hydrolysis by human milk bile salt activated lipase and effect of taurocholate as fatty acid acceptor. , 1988, Biochemistry.

[106]  D. Thomas,et al.  The control of lipase-catalysed transesterification and esterification reaction rates. Effects of substrate polarity, water activity and water molecules on enzyme activity. , 1990, European journal of biochemistry.

[107]  J. Prausnitz,et al.  Kinetics of lipase-catalysed interesterification of triglycerides in cyclohexane , 1991 .

[108]  K. Poutanen,et al.  Applications of immobilized lipases to transesterification and esterification reactions in nonaqueous systems. , 1993, Enzyme and microbial technology.

[109]  F. Malcata,et al.  Hydrolysis of butteroil by immobilized lipase using a hollow‐fiber reactor: Part II. Uniresponse kinetic studies , 1992, Biotechnology and bioengineering.

[110]  R. Verger,et al.  Interfacial enzyme kinetics of lipolysis. , 1976, Annual review of biophysics and bioengineering.

[111]  F. Malcata,et al.  Hydrolysis of butteroil by immobilized lipase using a hollow‐fiber reactor: Part I. Lipase adsorption studies , 1992, Biotechnology and bioengineering.

[112]  C. Chiang,et al.  Mathematical modelling and simulation of a recycle dialysis membrane reactor in a reversed micellar system. , 2007 .

[113]  C. Brady,et al.  Lipase immobilized on a hydrophobic, microporous support for the hydrolysis of fats , 1988 .

[114]  B. Magnuson,et al.  Enzymatic Interesterification of Canola Oil , 1988 .

[115]  Frank Taylor,et al.  Scale-up of flat-plate reactors for enzymatic hydrolysis of fats and oils , 1991 .

[116]  P. V. Rao,et al.  Lipase catalyzed deacidification of high free fatty acid rice bran oil , 1992 .

[117]  F. Malcata,et al.  Use of a lipase immobilized in a membrane reactor to hydrolyze the glycerides of butteroil , 1991, Biotechnology and bioengineering.

[118]  P. Langholz,et al.  Application of a specificity ofMucor miehei lipase to concentrate docosahexaenoic acid (DHA) , 1989 .

[119]  G. Skjåk‐Braek,et al.  Alginate as immobilization matrix and stabilizing agent in a two-phase liquid system: application in lipase-catalysed reactions. , 1992, Enzyme and microbial technology.

[120]  O. Almarsson,et al.  The preparation of homogeneous triglycerides of eicosapentaenoic acid and docosahexaenoic acid by lipase , 1993 .

[121]  S. T. Kang,et al.  Characteristics of immobilized lipase‐catalyzed hydrolysis of olive oil of high concentration in reverse phase system , 1989, Biotechnology and bioengineering.

[122]  J. Tramper,et al.  Enzymic transesterification in near-critical carbon dioxide: Effect of pressure, Hildebrand solubility parameter and water content , 1992 .

[123]  T. Funada,et al.  Synthesis of docosahexaenoic acid-rich triglyceride with immobilizedChromobacterium viscosum lipase , 1994 .

[124]  Jyh-Ping Chen,et al.  Enzymatic hydrolysis of triglycerides by Rhizopus delemar immobilized on biomass support particles , 1992 .

[125]  A. Ballesteros,et al.  Hydrolysis and Synthesis of Butyrylglycerols by Lipases a , 1990 .

[126]  G. Vunjak‐Novakovic,et al.  Rhizopus arrhizus lipase-catalyzed interesterification of the midfraction of palm oil to a cocoa butter equivalent fat , 1993 .

[127]  M. Guisnet Heterogeneous catalysis and fine chemicals II : proceedings of the 2nd international symposium, Poitiers, October 2-5, 1990 , 1991 .

[128]  F. Kolisis,et al.  Lipase‐catalyzed Esterification of Fatty Acids in Nonionic Microemulsions a , 1990 .

[129]  C. H. Amundson,et al.  Partial Characterization of the Action of An A. niger Lipase on Butteroil Emulsions , 1991 .

[130]  C. Singh,et al.  Synthesis of mono- and diglycerides in water-in-oil microemulsions , 1994 .

[131]  Frank Taylor,et al.  Kinetics of continuous hydrolysis of tallow in a multi-layered flat-plate immobilized-lipase reactor , 1992 .

[132]  C. Hill,et al.  Kinetic modeling of interesterification reactions catalyzed by immobilized lipase , 1994, Biotechnology and bioengineering.

[133]  P. Kerkhof,et al.  The hydrolysis of triglycerides by immobilized lipase in a hydrophiiic membrane reactor , 1988, Biotechnology and bioengineering.

[134]  H. Tilbeurgh,et al.  Structure of the pancreatic lipase–procolipase complex , 1992, Nature.

[135]  L. Sarda,et al.  Action de la lipase pancréatique sur les esters en émulsion , 1958 .

[136]  C. G. Smith,et al.  Mass transfer effects in solvent‐free fat interesterification reactions: Influences on catalyst design , 1994, Biotechnology and bioengineering.

[137]  T. Yamane,et al.  Increasing n-3 polyunsaturated fatty acid content of fish oil by temperature control of lipase-catalyzed acidolysis , 1993 .

[138]  Y. Kosugi,et al.  Continual conversion of free fatty acid in rice bran oil to triacylglycerol by immobilized lipase , 1994 .

[139]  K. D. Mukherjee,et al.  γ-Linolenic acid concentrates from borage and evening primrose oil fatty acidsvia lipase-catalyzed esterification , 1994 .

[140]  R. Hartel,et al.  Evaluation of Milk Fat Fractionation and Modification Techniques for Creating Cocoa Butter Replacers , 1994 .

[141]  A. Padt,et al.  Enzymatic acylglycerol synthesis in a membrane bioreactor , 1990 .

[142]  K. Holmberg,et al.  Covalent immobilization of lipase in organic solvents , 1989, Biotechnology and bioengineering.

[143]  J. Cabral,et al.  Chromatographic and Membrane Processes in Biotechnology , 1991 .

[144]  Process integration involving lipase-catalyzed ester synthesis reactions , 1994 .