Triglyceride Interesterification by Lipases: 2. Reaction parameters for the reduction of trisaturated impurities and diglycerides in batch reactions

References

• Bloomer S., Adlercreutz P., Mattiasson B. Triglyceride interesterification by lipases. 1. Cocoa butter equivalents from a fraction of palm oil. J. Am. Oil Chem. Soc. 1990; 67: 519–524
   Web of Science ®Google Scholar
• Brady L., Brzozowski A. M., Derewenda Z. S., Dodson E., Dodson G., Tolley S., Turkenburg J. P., Christiansen L., Huge-Jensen B., Norskov L., Thim L., Menge U. A serine protease triad forms the catalytic centre of a triacylglycerol lipase. Nature 1990; 343: 767–770
   PubMed Web of Science ®Google Scholar
• Chapus C., Sémériva M., Bovier-Lapierre C., Desnuelle P. Mechanism of pancreatic lipase action. 1. Interfacial activation of pancreatic lipase. Biochemistry 1976; 15: 4980–4987
   PubMed Web of Science ®Google Scholar
• Crossley A., Freeman I. P., Hudson B. J. F., Pierce J. H. Acyl migration in diglyceridcs. J. Chem. Soc. 1959; 760–764
   Google Scholar
• Dziezak J. T. Ingredients for sweet success. Food Technology 1989; 43: 94–116
   Google Scholar
• Ergan F., Tvani M., André G. Solvent free triglyceride synthesis using LipozymeTM IM-20. Biotechnol. Letters 1988; 10: 629–634
   Web of Science ®Google Scholar
• Ergan F., Trani M., André G. Production of glycerides from glycerol and fatty acid by immobilized lipases in non-aqueous media. Biotechnol. Bioeng. 1990; 35: 195–200
   PubMed Web of Science ®Google Scholar
• Fischer E. Wanderung von Acyl bei den Glyceriden. Berichte iter Deutschen Chemischen Gesellschaft 1920; 53: 1621–1633
   Google Scholar
• Freeman I. P., Morton I. D. Acyl migration in diglyceridcs. J. Chem. Soc. (C)Org. 1966; 1710–1711
   Google Scholar
• Goderis H. L., Ampe G., Feyten M. P., Fouwé B. L., Guffens W. M., Van Cauwenbergh S. M., Tobback P. P. Lipase-catalyzcd ester exchange reactions in organic media with controlled humidity. Biotechnol. Bioeng. 1987; 30: 258–266
   PubMed Web of Science ®Google Scholar
• Greenspan L. Humidity fixed points of binary saturated aqueous solutions. J. Res. Nut. Bureau Stds. A Physics and Chemistry 1977; 81A: 89–96
   Google Scholar
• Haraldsson G. G. The lipase-catalyzed interestification of cod liver oil with n -3 polunsaturated fatty acid and ester concentrates. (Paper given at the 1990 AOCS annual convention in Baltimore). Inform 1990; 1: 305
   Google Scholar
• Harwood H. J., Thomas A. E., Scharoun J. E., Slutkin R. Composition of the equilibrium mixture of 1,2 and 1,3 distearin. Chem. and Ind. 1963; 651
   Google Scholar
• Holmberg K., Österberg E. Enzymatic transesterification of a triglyceride in microemuisions. Progr. Colloid and Polymer Sci. 1987; 74: 98–102
   Google Scholar
• Ikeda I., Gu X.-P., Miyamoto I., Okahara M. Preparation of 1,3-diacylglycerols and 1-alkyl-3-acylglycerols in the presence of quaternary ammonium salt. J. Am. Oil Chem. Soc. 1989; 66: 822–824
   Web of Science ®Google Scholar
• Ison A. P., Dunnill P., Lilly M. D. Enzymic interesterification of fats: Immobilization and immunogoid localization on ion-exchange resins. Biocatalysis 1990; 3: 329–342
   Google Scholar
• Jensen B. F., Eigtved P. Safety aspects of microbial enzyme technology, exemplified by the safety assessment of an immobilized lipase preparation, LipozymeTM. Food Biotechnology 1990; 4: 699–725
   Web of Science ®Google Scholar
• Jensen R. G., Pitas R. E. Synthesis of some acylglycerols and phosphoglycerides. Adv. Lipid Research 1976; 14: 213–247
   Google Scholar
• Jensen R. G., Galluzzo D. R., Bush V. R. Selectivity is an important characteristic of lipases (acylglycerol hydrolases). Biocatalysis 1990; 3: 307–316
   Google Scholar
• Kaimal T. N. B., Saroja M. Selective removal of linolenic acid from soybean oil by lipase-catalyzed interesterification at low temperature. Biotechnol. Letters 1988; 10: 337–340
   Web of Science ®Google Scholar
• Kalo P., Huotari H., Antila M. Pseudomonas fluorescens lipase-catalyzed interesterification of butter fat. Fat Sci. Techol. 1989; 91: 276–281
   Google Scholar
• Kang S. T., Rhee J. S. Effect of water on hydrolysis of olive oil by immobilized lipase in reverse phase system. Biotechnol. Letters 1988; 10: 341–346
   Google Scholar
• Kastle J. H., Loevenhart A. S. Concerning lipase, the fat-splitting enzyme, and the reversibility of its action. Amer. Chemical J. 1900; 24: 491–525
   Google Scholar
• Kodali D. R., Tercyak A., Fahey D. A., Small D. M. Acyl migration in 1,2-dipalmitoyl-sn-glycerol. Chem. and Phys. Lipids 1990; 52: 163–170
   PubMed Web of Science ®Google Scholar
• Van Lohuiven O. E., Verkade P. E. Migration of an acyl group in glycrol derivatives. 1. Migration of the acyl group in monoglycerides in acid medium. Recueil 1960; 79: 133–159
   Google Scholar
• Macrae A. R. Lipase-catalyzed interesterification of fats and oils. J. Am. Oil Chem. Soc. 1983a; 60: 243A–246A
   Web of Science ®Google Scholar
• Macrae A. R. Extracellular Microbial Lipases. Microbial Enzymes and Biotechnology, W. M. Fogart. Applied Science Publishers, London 1983b; 225–250
   Google Scholar
• Matsuo T., Sawamura N., Hashimoto Y., Hashida W. Producing a cocoa butter substitute by transesterification of fats and oils UK Patent Application. GB 2 035 359 A, 1979
   Google Scholar
• Mattson F. H., Volpenhein R. A. Synthesis and properties of glycerides. Lipid Research 1962; 3(3)281–296
   Google Scholar
• Moore H., Brench A. W., Macrae A. R. Symmetrical triglycerides. European Patent Application. EP 0199580 A2, Oct. 29 1986, 1986
   Google Scholar
• Mukherjee K. D. Lipase-catalyzed reactions for modification of fats and other lipids. Biocatalysis 1990; 3: 277–293
   Google Scholar
• Nakamura K., Yokomichi H., Okisaka K., Nishide T., Kawahara Y., Nomura S. Process for transesterifying fats. European Patent Application. EP 0 257 388 A2, March 2, 1988, 1988
   Google Scholar
• Nielsen T. Industrial application possibilities for lipase. Fat Sci. Technol. 1985; 87: 15–18
   Google Scholar
• Okumura S., Iwai M., Tsujisaka Y. The effect of reverse action on triglyceride hydrolysis by lipase. Agric. Biol. Chem. 1981; 45: 185–189
   Web of Science ®Google Scholar
• Pavlova L. V., Rachinskii F. Y. Rearrangements connected with the migration of acyl and certain other groups. Russian Chem. Reviews 1968; 37: 587–602
   Google Scholar
• Pease J. J. Confectionery fats from palm oil and lauric oil. J. Am. Oil Chem. Soc. 1985; 62: 426–430
   Web of Science ®Google Scholar
• Plüchthun A., Dennis E. A. Acyl and phosphoryl migration in lysophospholipids: importance in phospholipid synthesis and phospholipase specificity. Biochemistry 1982; 21: 1743–1750
   Google Scholar
• Podlaha O., Töregård B. A system for identification of triglycerides in reversed phase HPLC chromatograms based on equivalent carbon numbers. J. High Resolut. Chromatogr. Chromatogr. Commun. 1982; 5: 553–558
   Google Scholar
• Posorske L. H. Industrial-scale application of enzymes to the fats and oil industry. J. Am. Oil Chem. Soc. 1984; 61: 1758–1760
   Web of Science ®Google Scholar
• Posorske L. H., LeFebvre G. K., Miller C. A., Hansen T. T., Glenvig B. L. Process considerations of continuous fat modification with an immobilized lipase. J. Am. Oil Chem. Soc. 1988; 65: 922–926
   Web of Science ®Google Scholar
• Schuch R., Mukherjee K. D. Radiochemical methods for studying lipase-catalyzed interesterification of lipids. Zeit. für Naturforschung 1987; 42: 1285–1290
   Google Scholar
• Semeriva M., Chapus C., Bovier-Lapierre C., Desnuelle P. On the transient formation of an acetyl enzyme intermediate during the hydrolysis of p-nitrophenyl acetate by pancreatic lipase. Biochem. Biophys. Res. Commun. 1976; 58: 808–813
   Google Scholar
• Sémériva M., Desnuelle P. Pancreatic lipase and colipase. An example of heterogeneous biocatalysis. Adv. Enzymol. 1979; 48: 319–370
   PubMedGoogle Scholar
• Serdarevich B. Glyceride isomerizations in lipid chemistry. J. Am. Oil Chem. Soc. 1968; 44: 381–393
   Google Scholar
• Shukla V. K. S., Nielsen W., Batsberg W. A simple and direct procedure for the evaluation of triglyceride composition of cocoa butters by high performance liquid chromatography—a comparison with the existing TLC-GC method. Fat Sci. Technol. 1983; 82: 274–278
   Google Scholar
• Stevenson R. W., Luddy F. E., Rothbart H. L. Enzymatic acyl exchange to vary saturation in di- and triglycerides. J. Am. Oil Chem. Soc. 1979; 56: 676–680
   Google Scholar
• Svensson I., Adlercreutz P., Mattiasson B. Interesterification of phosphatidylcholine with lipases in organic media. Appl. Microbiol. Biotechnol. 1990; 33: 255–258
   PubMed Web of Science ®Google Scholar
• Tanaka T., Ono E., Ishihara M., Yamanaka S., Takinami K. Enzymatic acyl exchange of triglyceride in n-hexane. Agric. Biol. Chem. 1981; 45: 2387–2389
   Web of Science ®Google Scholar
• Wisdom R. A., Dunnill P., Lilly M. D. Enzymic interesterification of fats: Laboratory and pilot-scale studies with immobilized lipase from Rhizopus arrhizus. Biotechnol. Bioeng. 1987; 29: 1081–1085
   PubMedGoogle Scholar
• Yamane T. Enzyme technology for the lipids industry: An engineering overview. Proceedings of the World Conference on Biotechnology for the Fats and Oils Industry. 1988, T. H. Applewhite. Amer. Oil Chem. Soc., Champaigne, 17–22
   Google Scholar
• Yamane T., Kojima Y., Ichiryu T., Nagata M., Shimizu S. Intramolecular esterification by lipase powder in microaqueous benzene: Effect of moisture content. Biotechnol. Bioeng. 1989; 34: 838–843
   PubMed Web of Science ®Google Scholar
• Yokozeki K., Yamanaka S., Takinami K., Hirose Y., Tanaka A., Sonomoto K. Application of immobilized lipase to regio-specific interesterification of triglyceride in organic solvent. Eur. J. Appl. Microbiol. Biotechnol. 1982; 14: 1–5
   Google Scholar