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Applications of lipase

  • Review
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Lipases are endowed with a substrate specificity that surpasses that of any other known enzyme. This confers on these enzymes an application potential that is literally boundless. Lipases can be employed in the production of pharmaceuticals, cosmetics, leather, detergents, foods, perfumery, medical diagnostics, and other organic synthetic materials. This review attempts to present a comprehensive discussion on the present status of this unique group of enzymes in industry, as well as the actual potential. It represents an endeavor to provide a sincere answer to the question, “What can be done with this enzyme?” as well as, “Can lipase be utilized for this purpose?” It is intended that the manuscript will cover or at least mention all known applications, based on the exploitation of a particular type of reaction catalyzed by lipases. An attempt will be made to cover as large a number of references as possible, so as to further underline the importance and significance of lipase action for industry.

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References

  1. Kaufman, V.R., and N. Garti, Organic Reactions in Emulsions—Preparation of Glycerol and Polyglycerol Esters of Fatty Acids by Transesterification Reaction, J. Am. Oil Chem. Soc. 59:471–474 (1982).

    CAS  Google Scholar 

  2. Park, Y.K., G.M. Pastore, and M.M. DeAlmeida, Hydrolysis of Soyabean Oil by a Combined Lipase System, Ibid:252–254 (1988).

    Article  CAS  Google Scholar 

  3. Anonymous, Enzymes in the Fats and Oils Industry, Jap-Chem Week: 6–9 (January 9, 1981).

  4. Linfield, W.M., R.A. Barauskas, R. Sivieri, S. Serota, and R.W. Stevenson Sr., Enzymatic Fat Hydrolysis and Synthesis, J. Am. Oil Chem. Soc. 61:191–195 (1984).

    CAS  Google Scholar 

  5. Kosugi, Y., H. Suzuki, and T. Funada, Hydrolysis of Beef Tallow by Lipase from Pseudomonas species, Biotechnol. Bioeng., 31:349–356 (1988).

    Article  CAS  Google Scholar 

  6. Nielsen, T., Industrial Application Possibilities of Lipase, Fat Sci. Technol. 87:15–19 (1985).

    CAS  Google Scholar 

  7. Seitz, E.W., Industrial Applications of Microbial Lipases—A Review, J. Am. Oil Chem. Soc. 51:12–16 (1974).

    Article  PubMed  CAS  Google Scholar 

  8. Macrae, A.R., and R.C. Hammond, Present and Future Applications of Lipases, Biotechnol. Genetic Eng. Rev. 3:193–217 (1985).

    CAS  Google Scholar 

  9. Iwai, M., and Y. Tsujisaka, Fungal Lipase, in Lipases, edited by B. Borgstrom and H.L. Brockman, Elsevier, Amsterdam, 1984, pp. 443–469.

    Google Scholar 

  10. Macrae, A.R., Biotechnology in the Oils and Fats Industry, in Proceedings of the World Conference on Emerging Technologies in the Fats and Oils Industry, edited by A.R. Baldwin, American Oil Chemists’ Society, Champaign, 1986, pp. 7–13.

    Google Scholar 

  11. Yamane, T., Enzyme Technology of Lipids Industry: An Engineering Overview, J. Am. Oil Chem. Soc. 64:1657–1662 (1987).

    Article  CAS  Google Scholar 

  12. Gillis, A., Research Discovers New Roles for Lipases, Ibid.:846–850 (1988).

    Article  Google Scholar 

  13. Posorske, L.H., Industrial-Scale Application of Enzymes to the Fats and Oils Industry, Ibid.:1758–1760 (1984).

    Article  CAS  Google Scholar 

  14. Godfrey, T., and J. Reichelt, Industrial Applications, in Industrial Enzymology—Applications of Enzymes in Industry, The Nature Press, London, 1983, pp. 170–465.

    Google Scholar 

  15. Hoq, M.M., T. Yamane, S. Shimizu, T. Funada, and S. Ishida, Bioreactor for Enzymic Reaction of Fat and Fatty Acid Derivatives. III Continuous Hydrolysis of Olive Oil by Lipase in a Microporous Hydrophobic Membrane Reactor, J. Am. Oil Chem. Soc. 62:1016–1021 (1985).

    Article  CAS  Google Scholar 

  16. Stirton, A.J., Fat Splitting, Esterification and Interesterification, in Bailey’s Industrial Oil and Fat Products, edited by A.E. Bailey and D. Swern, John Wiley & Sons, New York, 1964, pp. 931–972.

    Google Scholar 

  17. Sonntag, N.O.V., Fat Splitting, J. Am. Oil Chem. Soc. 56:729A-732A (1979).

    CAS  Google Scholar 

  18. Stansby, M.E., Marine-Derived Fatty Acids of Fish Oils as Raw Material for Fatty Acids Manufacture, Ibid.:793A-796A (1979).

    CAS  Google Scholar 

  19. Mukherjee, K.-D., Plant Lipases and Their Application in Lipid Biotransformations, Prog. Lipid Res. 33:165–174 (1994).

    Article  PubMed  CAS  Google Scholar 

  20. Brahimi-Horn, M.C., M.L. Guglielmino, and L.G. Sparrow, Wax Esterase Activity in a Commercially-Available Source of Lipase for C. cylindracea, J. Biotechnol. 12:299–306 (1989).

    Article  CAS  Google Scholar 

  21. Christner, J., E. Pfeiderer, and T. Taeger, Enzyme-Aided Soaking Process for Skins and Hides, United Kingdom Patent 2,233665 (1991).

  22. Figurin, Y.V., I.S. Shestakova, T.F. Mironova, I.V. Shtein, and I.M. Arends, Method of Processing Hides and Skins, Union of the Soviet Socialists Republic Patent 1,567,634 (1990).

  23. Muthukumaran, N., and S.C. Dhar, Comparative Studies on the Degreasing of Skins Using Acid Lipase and Solvent with Reference to the Quality of Finished Leathers, Leather Sci. 29:417–424 (1982).

    CAS  Google Scholar 

  24. Bailey, J.E., and D.F. Ollis, Applied Enzyme Catalysis, in Biochemical Engineering Fundamentals, 2nd edn., McGraw-Hill, New York, 1986, pp. 157–227.

    Google Scholar 

  25. Tschocke, C., Enzymic Treatment of Fats in Wastewater Treatment Plants, Eau Ind., Nuisances 138:63–64 (1990).

    CAS  Google Scholar 

  26. Nagayama, M., New Developments of Textile Detergency by the Use of Enzymes. The Present Situation of the Application of Enzymes for Detergent, Senshobu Kogyo 37:453–462 (1989).

    CAS  Google Scholar 

  27. Andree, H., W.R. Mueller, and R.D. Schmid, Lipases as Detergent Components, J. Appl. Biochem. 2:218–229 (1980).

    CAS  Google Scholar 

  28. Gerhartz, W., Industrial Uses of Enzymes, in Enzymes in Industry—Production and Application, VCH, Weinheim, 1990, pp. 77–148.

    Google Scholar 

  29. Starace, C.A., Detergent Enzymes—Past, Present and Future, J. Am. Oil Chem. Soc. 60:1025–1027 (1983).

    CAS  Google Scholar 

  30. Umehara, K., Y. Masago, T. Mukaiyama, and O. Okumura, Behaviour of Alkaline Lipase on Detergency, Yukagaku 39:321–326 (1990).

    CAS  Google Scholar 

  31. Watanabe, T., K. Mukoyama, and K. Mizuno, High Bulk-Density Granular Detergent Containing Alkaline Lipase. Japanese Patent 2,178,397 (1990).

  32. Aaslyng, D., E. Gormsen, and H. Malmos, Mechanistic Studies of Proteases and Lipases for the Detergent Industry, J. Chem. Technol. Biotechnol. 50:321–330 (1991).

    CAS  Google Scholar 

  33. Haverkamp, T., J.A. Van der Gugten, and A. Johanna, Particulate Detergent Composition with High Bulk Density and Enzyme Activity and Their Use, European Patent 381,397 (1990).

    Google Scholar 

  34. Armstrong, G.D., Lipase-Containing Detergent Composition for Washing Fabrics, European Patent 373,850 (1990).

    Google Scholar 

  35. Adams, C.J., G.D. Armstrong, and A.T. Hight, Lipolytic Enzyme-Containing Granular Detergent Composition, European Patent 366,589 (1990).

    Google Scholar 

  36. Nishioka, M., K. Joko, and M. Takama, Lipase Manufacture with Candida for Use in Detergents, Japanese Patent 2,92,281 (1990).

  37. Minoguchi, M., and T. Muneyuki, Immobilization of Lipase on Polyacrylamide and Its Use in Detergents, Japanese Patent 1,285,188 (1989).

  38. Fujii, T., T. Tatara, and M. Minagawa, Studies on Application of Lipolytic Enzymes in Detergency. 1. Effect of Lipase from Candida cylindracea on Removal of Olive Oil from Cotton Fabrics, J. Am. Oil Chem. Soc. 63:796–799 (1986).

    Article  CAS  Google Scholar 

  39. El Sayed, M.Y., S.N. Lewis, S.A. Anderson, and R.J. Wiersema, Lipase and/or Cutinase Containing Surfactant Systems and Method Useful in Laundering, European Patent 399,681 (1990).

    Google Scholar 

  40. Satsuki, T., and T. Watanabe, Application of Lipase to Laundry Detergents, Bio Ind. 7:501–507 (1990).

    CAS  Google Scholar 

  41. Fukano, K., and S. Abe, Lipase-Containing Detergent Composition for Dishwashing Machines, Japanese Patent 2,77,498 (1990).

  42. Van Dijk, W.R., Enzyme Dishwashing and Rinsing Composition Containing Lipase, European Patent 343,136 (1989).

    Google Scholar 

  43. Nakamura, K., and T. Nasu, Enzyme-Containing Bleaching Composition, Japanese Patent 2,208,400 (1990).

  44. Abo, M., Method of Purifying Dry-Cleaning Solvent by Decomposing Liquid Contaminants with a Lipase, World Organization Patent 90 07,606 (1990).

  45. Kobayashi, H., Liquid Leather Cleaners, Japanese Patent 1,225,700 (1989).

  46. Bhatia, R.P., Contact Lens Cleaning Composition Containing an Enzyme and a Carboxylvinyl Polymer, United States Patent 4,921,630 (1990).

  47. Moriguchi, H., J. Hirata, and T. Watanabe, Microorganism-Based Agent for Treatment of Organic Wastes, Japanese Patent 2,105,899 (1990).

  48. Abo, M., H. Sakaguchi, H. Sato, M. Onishi, M. Hashida, S. Ikeda, and H. Orito, Dirt Removal from Domestic Animals with Enzyme, Japanese Patent 2,245,129 (1990).

  49. Novak, J., B. Kralova, K. Demnerova, K. Prochazka, Z. Vodrazka, J. Tolman, D. Rysova, J. Smidrkal, and V. Lopata, Enzyme Agent Based on Lipases and Oxidoreductases for Washing, Degreasing and Water Reconditioning, European Patent 355,228 (1990).

  50. Arnold, R.G., K.M. Shahani, and B.K. Dwivedi, Application of Lipolytic Enzymes to Flavor Development in Dairy Products, J. Dairy Sci. 58:1127–1143 (1975).

    CAS  Google Scholar 

  51. Margrove, R.F., and F.E. McDonough, To Promote Flavor in Cream Used to Improve Skim Milk Cheese, United States Patent 3,156,568 (1964).

  52. Colburn, J.T., Lipase-Treated Milk Fats in Production of Butter/Margarine Flavors, United States Patent 3,477,857 (1969).

  53. Nelson, J.H., Enzymatically Produced Flavors for Fatty Systems, J. Am. Oil Chem. Soc. 49:559–562 (1972).

    Article  CAS  Google Scholar 

  54. Nelson, J.H., R.G. Jensen, and R.E. Pitas, Pregastric Esterase and Other Oral Lipases—A Review, J. Dairy Sci. 60:327–362 (1977).

    PubMed  CAS  Google Scholar 

  55. Kosikowski, F.V., Flavor Development by Enzyme Preparation in Natural and Processed Cheddar Cheese, United States Patent 3,975,544 (1976).

  56. Kinsella J.E., and D.H. Hwang, Enzymes of Penicillium roqueforti Involved in the Biosynthesis of Cheese Flavors, Crit. Rev. Food Sci. Nutr. 8:192–228 (1976).

    Article  Google Scholar 

  57. Sood, V.K., and F.V. Kosikowski, Accelerated Cheddar Cheese Ripening by Added Microbial Enzymes, J. Dairy Sci. 62:1865–1872 (1979).

    Article  CAS  Google Scholar 

  58. Farahat, S.M., A.M. Rabie, and A.A. Faras, Evaluation of the Proteolytic and Lipolytic Activity of Different Penicillium roqueforti Strains, Food Chem. 36:169–180 (1990).

    Article  CAS  Google Scholar 

  59. Shay, L.K., T.J. Fisher, D.S. Banasiak, and E.H. Wegner, Enhancing the Flavor of Proteinaceous Products Derived from Microorganisms, European Patent 357,812 (1990).

    Google Scholar 

  60. Alford, J.A., D.A. Pierce, and W.L. Sulzbacher, Microbial Lipases and Their Potential Importance to the Meat Industry, Proc. Res. Conf. Advisory Council Res. Am. Inst. Found. Univ. Chicago 15:11–16 (1963).

    CAS  Google Scholar 

  61. Johnson, R.H., and E.A. Welch, Baked Goods Preservatives, United States Patent 3,368,903 (1964).

  62. Wiseman, A., Industrial Practice with Enzymes: Applications and Sources of Industrial Enzymes, in Handbook of Enzyme Biotechnology, edited by A. Wiseman, Ellis Horwood Ltd., Chichester, 1975, pp. 252–259.

    Google Scholar 

  63. Haas, G.J., and J.C. Lugay, Animal Food of Increased Palatability, United States Patent 3,857,968 (1974).

  64. Masuda, T., Digestive Agents Containing Amino Acid Hydrochlorides and Enzymes, Japanese Patent 1,238,538 (1989).

  65. Gwozdz, G.P., K. Zuobi, and T. Bravdo, Lipase-Catalyzed Preparation of Optically Active γ-Butyrolactones in Organic Solvents, J. Org. Chem. 55:3546–3552.

  66. Lott., J.A., and Lu, C.J., Lipase Isoforms and Amylase Isoenzymes—Assays and Application in the Diagnosis of Acute Pancreatitis, Clin. Chem. 37:361–368 (1991).

    PubMed  CAS  Google Scholar 

  67. Schnatz, J.D., J.W. Ormsby, and R.H. Williams, Lipoprotein Lipase Activity in Human Heart, Am. J. Physiol. 205:401–404 (1963).

    PubMed  CAS  Google Scholar 

  68. Karube, I., and K. Sode, Biosensors for Lipids, in Proceedings of World Conference on Biotechnology in the Fats and Oils Industry, edited by T.H. Applewhite, American Oil Chemists’ Society, Champaign, 1988, pp. 215–218.

    Google Scholar 

  69. Spohn, U., P. Miethe, and H. Voss, Conductometric Biosensor for Use in Organic Solvents, East Germany Patent 278,869 (1990).

  70. Iwai, M., Fundamentals and Use of Enzyme Lipase 7. Application of Lipase, Yushi 43:66–72 (1990).

    CAS  Google Scholar 

  71. Imamura, S., M. Takahashi, H. Misaki, and K. Matsuura, Method and Reagent Containing Lipases for Enzymatic Determination of Triglycerides, West Germany Patent 3,912,226 (1989).

  72. Kato, K., S. Nakamura, T. Sakugi, K. Kitai, K. Yone, J. Suzuki, and Y. Ichikawa. Tumor Necrosis Factor and Its Activators for the Treatment of Malignant Tumors, Japanese Patent 1,186,820 (1989).

  73. Mauvernay, R.Y., P. Laboreur, and M. Labrousse, Lipase Composition and Its Products, United States Patent 3,513,073 (1970).

  74. Saphir, J., Permanent Hair Waving, West Germany Patent 1,242,794 (1967).

  75. Berrobi, C., G. Manoussos, and S.A. Oreal, Cosmetic, Pharmaceutical Preparations Containing Lipase, Hyaluronidase and/or Thiomucase Enzymes, West Germany Patent 1,947,896 (1970).

  76. August, P., Lipase-Containing Defatting Creams, West Germany 2,064,940 (1972).

  77. Smythe, C.V., Microbiological Production of Enzymes and Their Industrial Application, Econ. Botany 5:126–144 (1951).

    CAS  Google Scholar 

  78. Hirashima, Y., A.A. Farooqui, E.J. Murphy, and L.A. Horrocks, Purification of Plasmalogens Using R. delemar Lipase and Naja naja naja Phospholipase A2. Lipids 25:344–348 (1990).

    Article  PubMed  CAS  Google Scholar 

  79. Sonnet, P.E., Lipase Selectivities, J. Am. Oil Chem. Soc. 65:900–904 (1988).

    Article  CAS  Google Scholar 

  80. Hills, M.J., I. Kiewitt, and K.D. Mukherjee, Enzymatic Fractionation of Fatty Acids: Enrichment of γ-linolenic Acid and Docosahexaenoic Acid. Selective Esterification Catalyzed by Lipase, Ibid.:561–564 (1990).

    Article  CAS  Google Scholar 

  81. Gavino, V.C., and G.R. Gavino, Adipose Hormone Sensitive Lipase Preferentially Releases Polyunsaturated Fatty Acids from Triglycerides, Lipids 27:950–954 (1992).

    Article  PubMed  CAS  Google Scholar 

  82. Alford, J.A., and J.L. Smith, Production of Microbial Lipases for the Study of Triglyceride Structure, J. Am. Oil Chem. Soc. 42:1038–1040 (1965).

    Article  PubMed  CAS  Google Scholar 

  83. Brockerhoff, H., and R.G. Jensen, Lipolytic Enzymes, Academic Press, New York, 1974.

    Google Scholar 

  84. Brockerhoff, H., Unsolved Problem of Triglyceride Analysis, Lipids 1:162–163.

  85. Jensen, R.G., J. Sampugna, and J.G. Quinn, Analysis of Some Triacid Triglyceride Mixtures, Ibid. 1:294–295.

  86. Fukuda, S., S. Hayashi, H. Ochiai, T. Iiizumi, and K. Nakamura, Improvers for Deinking of Wastepaper, Japanese Patent 2,229,290 (1990).

  87. Sharyo, M., and H. Sakaguchi, Deinking Used Paper with Incorporation of Lipase, Japanese Patent 2,160,984 (1990).

  88. Hagiwara, M., Y. Okamoto, and J. Shinoda, Deinking Agents for Offset-Printed Wastepaper, Japanese Patent 2,80,684 (1990).

  89. Ladner, W.E., and G.M. Whitesides, Lipase-Catalyzed Hydrolysis as a Route to Esters of Chiral Epoxyalcohols, J. Am. Chem. Soc. 106:7250–7251 (1984).

    Article  CAS  Google Scholar 

  90. Kirchner, G., M.P. Scollar, and A.M. Klibanov, Resolution of Racemic Mixtures via Lipase Catalysis in Organic Solvents, Ibid.:7072–7076 (1985).

    Article  CAS  Google Scholar 

  91. Matsumae, H., M. Furui, and T. Shibatani, Lipase-Catalyzed Asymmetric Hydrolysis of 3-Phenylglycidic Acid Ester, The Key Intermediate in the Synthesis of Diltiazem Hydrochloride, J. Ferment. Bioeng. 75:93–98 (1993).

    Article  CAS  Google Scholar 

  92. Roberts, S.M., Production of Man-Made Molecules Using Nature’s Catalysts, Kem-Kemi 16:250–251 (1989).

    CAS  Google Scholar 

  93. Foelsche, E., A. Hickel, H. Hoenig, and P. Seufer-Waserthal, Lipase-Catalyzed Resolution of Acyclic Aminoalcohol Precursors, J. Org. Chem. 55:1749–1753 (1990).

    Article  CAS  Google Scholar 

  94. Miyata, A., and H. Sato, Manufacture of Optically Active 2-Hydroxy 4-Phenylbutyrate Esters by Enzymatic Asymmetric Hydrolysis, Japanese Patent 1,225,499 (1989).

  95. Hoshino, T., T. Yamane, and S. Shimizu, Bioreactor for Enzymatic Reaction of Fat and Fatty Acid Derivatives. Part XII Selective Hydrolysis of Fish Oil by Lipase to Concentrate n-3 Polyunsaturated Fatty Acids (n-3 Pufa), Agric. Biol. Chem. 54:1459–1467 (1990).

    CAS  Google Scholar 

  96. Mbayhoudel, K., and L.C. Comeau, Selective Preparation of Petroselinic Acid from Fennel Oil by Enzymatic Hydrolysis, Rev. Fr. Corps Gras 36:427–431 (1989).

    CAS  Google Scholar 

  97. Liu, Q., X. Chang, K. Yue, and C. Wang, Refining Mulberry Silk with Protease and Lipase, Fangzhi Xuebao 10:116–119 (1989).

    CAS  Google Scholar 

  98. Sugawara, Y., E. Shionu, and S. Kaneuchi, Solid Mouth-Deodorant Containing Proteinase, Lipase and/or Bacteriolytic Enzyme, Japanese Patent 1,221,310 1989).

  99. Gandhi, N.N., S.B. Sawant, and J.B. Joshi, Studies on the Lipozyme-Catalyzed Synthesis of Butyl Laurate, Biotechnol. Bioeng. 46:1–12 (1995).

    Article  CAS  Google Scholar 

  100. Matos, J.R., J.B. West, and C.-H. Wong, Lipase-Catalyzed Synthesis of Peptides: Preparation of a Penicillin G Precursor and Other Peptides, Biotechnol. Lett. 9:233–236 (1987).

    Article  CAS  Google Scholar 

  101. Nagao, A., and M. Kito, Synthesis of O-acyl-l-homoserine by Lipase, J. Am. Oil Chem. Soc. 66:710–713 (1989).

    CAS  Google Scholar 

  102. Bistline R.G., Jr., A. Bilyk, and S.H. Feairheller, Lipase-Catalyzed Formation of Fatty Amides, Ibid.:95–98 (1991).

    CAS  Google Scholar 

  103. Godtfredsen, S.E., K. Ingvorsen, B. Yde, and O. Andresen, The Scope of Biocatalysts in Organic Chemical Processing, in Enzymes as Catalysts in Organic Synthesis, edited by M.P. Schneider, Reidel Publishing Co., Philadelphia, 1986, pp. 77–95.

    Google Scholar 

  104. Welsh, F.W., R.E. Williams, and K.H. Dawson, Lipase-Mediated Synthesis of Low Molecular Weight Flavor Esters, J. Food Sci. 55:1679–1682 (1990).

    Article  CAS  Google Scholar 

  105. Gandhi, N.N., S.B. Sawant, and J.B. Joshi, Specificity of a Lipase in Ester Synthesis: Effect of Alcohol, Biotechnol. Progr. 11:282–287 (1995).

    Article  CAS  Google Scholar 

  106. Arctander, S., Application of Esters, in Perfume Flavor Chemicals—Vol. I Weigner, Montclair, 1969, pp. 26–79.

    Google Scholar 

  107. Scott, D., Speciality Enzymes and Products for the Food Industry, in Biocatalysis in Agricultural Biotechnology, edited by J.R. Whitaker and P.E. Sonnet, ACS Symposium Series 389, Washington, DC, 1989, pp. 176–192.

  108. Okumura, S., M. Iwai, and Y. Tsujisaka, Synthesis of Various Kinds of Esters by Four Microbial Lipases, Biochim. Biophys. Acta 575:156–165 (1979).

    PubMed  CAS  Google Scholar 

  109. Tsujisaka, Y., S. Okumura, and M. Iwai, Glyceride Synthesis by Four Kinds of Microbial Lipases, Biochim. Biophys. Acta 489:415–422 (1977).

    PubMed  CAS  Google Scholar 

  110. Iwai, M., S. Okumura, and Y. Tsujisaka, Studies on Lipase, Part XV Synthesis of Terpene Alcohol Esters by Lipase, Agric. Biol. Chem. 44:2731–2732 (1980).

    CAS  Google Scholar 

  111. Miyamoto, A., A. Shigeta, Y. Tanaka, H. Oomura, K. Masui, M. Katada, M. Asahi, T. Komori, and T. Sukuki, Process for Preparation of Polyol Fatty Acid Esters Having Mixed Acid Groups for Cosmetics, European Patent 319,126 (1989).

    Google Scholar 

  112. Mittelbach, M., Lipase-Catalyzed Alcoholysis of Sunflower Oil, J. Am. Oil Chem. Soc. 67:168–170 (1990).

    Article  CAS  Google Scholar 

  113. Monot, G., F. Borzeix, M. Bardin, and J.-P. Vandecasteele, Enzymatic Esterification in Organic Media: The Role of Water and Organic Solvent in Kinetics and Yield of Butyl Butyrate Synthesis, Appl. Microbiol. Biotechnol. 35:759–765 (1991).

    Article  CAS  Google Scholar 

  114. Morrow, C.J., J.S. Wallace, G.M. Bybee, K.B. Reda and M.E. Williams, Biocatalytic Synthesis of Polyesters by Enzyme Catalyzed Transesterification in Organic Media, Mater. Res. Soc. Symp. Proc. 174:197–208 (1990).

    CAS  Google Scholar 

  115. Seino, H., T. Uchibori, T. Nishitani, and S. Inamasu, Enzymatic Synthesis of Carbohydrate Esters of Fatty Acids (I) Esterification of Sucrose, Glucose, Fructose and Sorbitol, J. Am. Oil Chem. Soc. 61:1761–1765 (1984).

    Article  CAS  Google Scholar 

  116. David, M.H.L., H.O.J. Lemmens, H. Gunther, and H.W. Roper, Surface-Active Acylated Alkylglycosides and Their Preparation by Esterification in Presence of an Enzyme, European Patent 334,498 (1989).

    Google Scholar 

  117. Ota, Y., and H. Machida, Manufacture of Sucrose Fatty Acid Esters with Lipase, Japanese Patent 2,60,591 (1990).

  118. Nagao, A., and M. Kito, Manufacture of O-Acylated Amino Acids as Emulsifying Agents for Foods, Japanese Patent 2,17,156 (1990).

  119. Adelhorst, K., F. Bjorkling, S.E. Godtfredsen, and O. Kirk, Enzyme-Catalyzed Preparation of 6-O-Acylglucopyranosides, Synthesis 2:112–115 (1990).

    Article  Google Scholar 

  120. Zaks, A., and A.T. Gross, Production of Monoglycerides by Enzymatic Transesterification, World Organization Patent 90,04,033 (1990).

  121. Antizak, T., A. Krystynowicz, and E. Galas, Biosynthesis and Applications of Lipases and Esterases in Ester Synthesis and Transformation of Acylglycerols, Kosmos 38:95–99 (1989).

    Google Scholar 

  122. Luck, T., and W. Bauer, Application of Immobilized Lipases for the Interesterification of Lipids, DECHEMA Biotech. Conf. 3:631–636 (1989).

    CAS  Google Scholar 

  123. Bauky, T., Lipase Application in Lipid Chemistry I Transesterification of Triglycerides, Elelmez Ip 44:15–20 (1990).

    Google Scholar 

  124. Mukherjee, K.D., Lipase-Catalyzed Reactions for Modification of Fats and Other Lipids, Biocatalysis 3:277–293 (1990).

    CAS  Google Scholar 

  125. Meusel, D., A. Muschter, M. Tuelsner, and W. Paul, Lipase-Catalyzed Exchange of Fatty Acids in the Manufacture of Shortenings, Lebensmittelindustrie 37:63–66 (1990).

    CAS  Google Scholar 

  126. Nakai, E., T. Nezu, K. Suzuki, and W. Matsumoto, Modification of Hydrogenated Oils with Lipase, Japanese Patent 3,30,686 (1991).

  127. Haumann, B.F., Food Technology, INFORM 4:1233–1235 (1993).

    Google Scholar 

  128. Servat, F., D. Montet, M. Pina, P. Galzy, A. Arnaud, H. Ledon, L. Marcou, and J. Graille, Synthesis of Fatty Hydroxamic Acids Catalyzed by the Lipase of Mucor miehei, J. Am. Oil Chem. Soc. 67:646–649 (1990).

    Article  CAS  Google Scholar 

  129. Cambou, B., and A.M. Klibanov, Comparison of Different Strategies for the Lipase-Catalyzed Preparative Resolution of Racemic Acids and Alcohols: Asymmetric Hydrolysis, Esterification and Transesterification, Biotechnol. Bioeng. 37:1004–1009 (1984).

    Google Scholar 

  130. Whitesides, G.M., and C.-H. Wong, Enzymes as Catalysts in Synthetic Organic Chemistry, Angew. Chem. Int. Ed. Engl. 24:617–718 (1985).

    Article  Google Scholar 

  131. Akiyama, A., M. Bednarski, M.-J. Kim, E.S. Simon, H. Waldmann, and G.M. Whitesides, Enzymes in Organic Synthesis, CHEMTECH 18:627–634 (1988).

    CAS  Google Scholar 

  132. Langrand, G., C. Triantaphylides, and J. Baratti, Lipase-Catalyzed Formation of Flavor Esters, Biotechnol. Lett. 10:549–554 (1988).

    Article  CAS  Google Scholar 

  133. Fukusaki, E., S. Senda, Y. Nakazono, H. Yuasa, and T. Omata, Lipase-Catalyzed Kinetic Resolution of 2,3-Epoxy-8-methyl-1-nonanol, the Key Intermediate in the Synthesis of the Gypsy Moth Hormone, J. Ferment. Bioeng. 73:280–283 (1992).

    Article  CAS  Google Scholar 

  134. Yamazaki, Y., and K. Hosono, Facile Resolution of Planar Chiral Organometallic Alcohols with Lipases in Organic Solvents, Tetrahedron Lett. 31:3895–3896 (1990).

    Article  CAS  Google Scholar 

  135. Yamamota, Y., and J. Oda, Application of Enzymatic Reactions to Asymmetric Synthesis Using Lipase, Kagaku, Zokan (Kyoto) 119:125–132 (1991).

    Google Scholar 

  136. Sugai, T., H. Kakeya, H. Yamada, K. Matsumoto, S. Ohsawa, N. Suzuki, and H. Ohta, Synthesis of Naturally Optically Active Products by the Aid of Lipases, Tennen Yuki Kagobutsu Toroukai Koen Yoshishu 32:563–570 (1990).

    CAS  Google Scholar 

  137. Xier, Z.F., and K. Sakai, Preparation of a Chiral Building Block Based on 1,3 syn-diol Using P. fluorescens Lipase and Its Application to the Synthesis of a Hunger Modulator, Chem. Pharm. Bull. 37:1650–1652 (1989).

    Google Scholar 

  138. Kitatsume, T., and S. Kokusho, Preparation of Optically Active Fluoride-Containing Polyesters by Enzymatic Esterification. Japanese Patent 2,40,343 (1990).

  139. Azuma, T., and M. Minamii, Manufacture of Optically Active Terphenyl Derivatives with Lipase, Japanese Patent 1,16,731 (1989).

  140. Bianchi, D., P. Costi, F. Francalonci, and W. Cabri, Enzymatic Separation of Optical Isomers of Racemic α-Alkyl Substituted Primary Alcohols, European Patent 328,125 (1989).

    Google Scholar 

  141. Macrae, A.R. Lipase-Catalyzed Interesterification of Oils and Fats, J. Am. Oil Chem. Soc. 60:291–294 (1983).

    Article  CAS  Google Scholar 

  142. Tajima, I., and A. Kurashige, Fats and Oils Modified with Lipase for Margarines and Shortenings, Japanese Patent 2,219,581 (1990).

  143. Richardson, G.H., Dairy Industry, in Enzymes in Food Processing, edited by G.H. Reed, Academic Press, New York, 1975, pp. 361–395.

    Google Scholar 

  144. Bloomer, S., P. Adlercreutz, and B. Mattiasson, Facile Synthesis of Fatty Acid Esters in High Yields, Enzyme Microb. Technol. 14:546–552 (1992).

    Article  CAS  Google Scholar 

  145. Chang, M.K., G. Abraham, and V.T. John, Production of Cocoa. Butter-Like Fat from Interesterification of Vegetable Oils, J. Am. Oil Chem. Soc. 67:832–834 (1990).

    Article  CAS  Google Scholar 

  146. Haelck, L., and F. Spener, Enzyme Functionalization for Alternate Applications of Natural Fats, DECHEMA Biotech. Conf. 3:113–116 (1989).

    Google Scholar 

  147. Macrae, A.R., Microbial Lipases as Catalysts for Interesterification of Oils, Biotechnol. Oils Fats Ind., AOCS Monogr. 11:189–198 (1984).

    CAS  Google Scholar 

  148. Zaks, A., and A.M. Klibanov, Enzymatic Catalysis in Organic Media, Science 224:1249–1251 (1984).

    Article  PubMed  CAS  ADS  Google Scholar 

  149. Gandhi, N.N., S.B. Sawant, J.B. Joshi, and D. Mukesh. Lipozyme Deactivation by Butanol and Temperature, Enzyme Microb. Technol. 17:373–380 (1995).

    Article  CAS  Google Scholar 

  150. Gandhi, N.N., Vijayalakshmi, V., S.B. Sawant, and J.B. Joshi, Studies in the Immobilization of the M. miehei Lipase on Ion Exchange Resins, Chem. Eng. J., in press (1996).

  151. Cowley, E., and J. Knights, Natural Flavors, in Food Flavorings, edited by P.R. Ashurst, Blackie, Glascow 1991, pp. 43–47.

    Google Scholar 

  152. Gillies, B., H. Yamazaki, and D.W. Armstrong, Natural Flavor Esters: Production by Candida cylindracea Lipase Adsorbed to Silica Gel, in Biocatalysis in Organic Media, edited by C. Laane, J. Tramper and M.D. Lilly, Elsevier, Amsterdam, 1987, pp. 227–232.

    Google Scholar 

  153. Tanigaki, M., M. Sakata, and H. Wada, Hydrolysis of Soybean Oil by Lipase with a Bioreactor Having Two Different Membranes, J. Ferment. Bioeng. 75:53–57 (1993).

    Article  CAS  Google Scholar 

  154. Slaughter, J.C., L.R. Weatherley, and A. Wilkinson, Electrically Enhances Enzymic Hydrolysis of Vegetable Oils Using Lipase from Candida rugosa, Enzyme Microb. Technol. 15:293–296 (1993).

    Article  CAS  Google Scholar 

  155. Hedstrom, G., M. Bucklund, and J.P. Slotte, Enantioselective Synthesis of Ibuprofen Esters in AOT/Isooctane Microemulsions by Candida cylindracea Lipase, Biotechnol. Bioeng. 42:618–624 (1993).

    Article  CAS  Google Scholar 

  156. Yang, D., and J.S. Rhee, Continuous Hydrolysis of Olive Oil by Immobilized Lipase in Organic Solvent, Ibid.:748–752 (1992).

    Article  CAS  Google Scholar 

  157. Pronk, W., M. Van Der Burgt, G. Boswinkel, and K. Van’t Riet, A Hybrid Membrane-Emulsion Reactor for the Enzymatic Hydrolysis of Lipids, J. Am. Oil Chem. Soc. 68:852–856 (1991).

    CAS  Google Scholar 

  158. Garcia, H.S., F.X. Malcata, C.G. Hill Jr., and C.H. Amundson, Use of Candida rugosa Immobilized in a Spiral Wound Membrane Reactor for the Hydrolysis of Milk Fat, Enzyme Microb. Technol. 14:535–545 (1992).

    Article  CAS  Google Scholar 

  159. Malcata, F.X., C.G. Hill Jr., and C.H. Amundson, Use of a Lipase Immobilized in a Membrane Reactor to Hydrolyze the Glycerides of Butteroil, Biotechnol. Bioeng. 38:853–868 (1991).

    Article  CAS  Google Scholar 

  160. Tanaka, Y., T. Funada, J. Hirano, and R. Hashizume, Triglyceride Specificity of Candida cylindracea Lipase: Effect of Docosahexaenoic Acid on Resistance of Triglyceride to Lipase, J. Am. Oil Chem. Soc. 70:1031–1034 (1993).

    Article  CAS  Google Scholar 

  161. Tsai, S.-W., G.-H. Wu, and C.-L. Chiang, Kinetics of Enzymatic Hydrolysis of Olive Oil in Biphasic Organic-Aqueous Systems, Biotechnol. Bioeng. 38:761–766 (1991).

    Article  CAS  Google Scholar 

  162. Dandik, L., and H.A. Aksoy, The Kinetics of Hydrolysis of Nigella sativa (Black Cumin) Seed Oil Catalyzed by Native Lipase in Ground Seed, J. Am. Oil Chem. Soc. 69:1239–1241 (1992).

    Article  CAS  Google Scholar 

  163. Chen, J.P., and K.-C. Chang, Lipase-Catalyzed Hydrolysis of Milk Fat in Lecithin Reverse Micelles, J. Ferment. Bioeng. 76:98–104 (1993).

    Article  CAS  Google Scholar 

  164. Martinez, O., A.-M. Wilhelm, and J.-P. Riba, Kinetic Study of an Enzymatic Liquid-Liquid Reaction: The Hydrolysis of Tributyrin by Candida cylindracea Lipase, J. Chem. Technol. Biotechnol. 53:373–378 (1992).

    CAS  Google Scholar 

  165. Haas, M.J., D.J. Cichowicz, J. Phillips, and R. Moreau, The Hydrolysis of Phosphatidylcholine by an Immobilized Lipase: Optimization of Hydrolysis in Organic Solvents, J. Am. Oil Chem. Soc. 70:111–117 (1993).

    Article  CAS  Google Scholar 

  166. Hayes, D.G., and R. Kleiman, 1,3-Specific Lipolysis of Lesquerella fendleri Oil by Immobilized and Reverse-Micellar Encapsulated Enzymes, Ibid.:1121–1127 (1993).

    Article  CAS  Google Scholar 

  167. Kim, M.K., and J.S. Rhee, Lipid Hydrolysis by Pseudomonas putida 3SK Cultured in Organic-Aqueous Two-Phase System, Enzyme Microb. Technol. 15:612–616 (1993).

    Article  CAS  Google Scholar 

  168. Tanaka, Y., J. Hirano, and T. Funada, Concentration of Docosahexaenoic Acid in Glycerides by Hydrolysis of Fish Oil with Candida cylindracea Lipase, J. Am. Oil Chem. Soc. 69:1210–1214 (1992).

    Article  CAS  Google Scholar 

  169. Miyake, Y., M. Ohkube, and M. Teramoto, Lipase-Catalyzed Hydrolysis of 2-Naphthyl Esters in Biphasic System, Biotechnol. Bioeng. 38:30–36 (1991).

    Article  CAS  Google Scholar 

  170. Junker, B.H., M. Bhupathy, and B.C. Buckland, Development of a Recovery and Recycle Process for a Pseudomonas Lipase Used for Large-Scale Enzymatic Synthesis, Ibid.:487–493 (1993).

    Article  CAS  Google Scholar 

  171. Sonnet, P.E., and M.W. Baillargeon, Methyl-Branched Octanoic Acids as Substrates for Lipase-Catalyzed Reactions, Lipids 26:295–300 (1991).

    Article  PubMed  CAS  Google Scholar 

  172. Wilcox, R.W., T. Thuren, P. Sisson, G.L. Kucera, and M. Waite, Hydrolysis of Neutral Substrates by Rat Hepatic Lipase, Ibid.:283–288 (1991).

    Article  PubMed  CAS  Google Scholar 

  173. Prazeres, D.M.F., F. Lemos, F.A.P. Garcia, and J.M.S. Cabral, Modelling Lipolysis in a Reversed Micellar System: Part I. Conventional Batch Reactor, Biotechnol. Bioeng. 42:759–764 (1993).

    Article  CAS  Google Scholar 

  174. Taylor, F., M.J. Kurantz, and J.C. Craig Jr., Kinetics of Continuous Hydrolysis of Tallow in a Multi-Layered Flat-Plate Immobilized-Lipase Reactor, J. Am. Oil Chem. Soc. 69:591–594 (1992).

    CAS  Google Scholar 

  175. Bilyk, A., R.G. Bistline Jr., M.J. Haas, and S.H. Feairheller, Lipase-Catalyzed Triglyceride Hydrolysis in Organic Solvent, Ibid.:320–323 (1991).

    CAS  Google Scholar 

  176. Virto, M.D., J.M. Lascaray, R. Solozabal, and M. De Renobales, Enzymic Hydrolysis of Animal Fats in Organic Solvents at Temperatures Below Their Melting Points, Ibid.:324–326 (1991).

    CAS  Google Scholar 

  177. Yadwad, V.B., O.P. Ward, and L.C. Noronha, Application of Lipase to Concentrate the Docosahexaenoic Acid (DHA) Fraction of Fish Oil, Biotechnol. Bioeng. 38:956–959 (1991).

    Article  CAS  Google Scholar 

  178. Guit, R.P.M., M. Kloosterman, G.W. Meindersma, M. Mayer, and E.M. Meijer, Lipase Kinetics: Hydrolysis of Triacetin by Lipase from Candida cylindracea in a Hollow-Fibre Membrane Reactor, Ibid.:727–732 (1991).

    CAS  Google Scholar 

  179. Rostrup-Nielsen, T., L.S. Pedersen, and J. Villadsen, Thermodynamics and Kinetics of Lipase Catalyzed Hydrolysis of Oleyl Oleate, J. Chem. Tech. Biotechnol. 48:467–482 (1990).

    CAS  Google Scholar 

  180. Shaw, J.-F., R.-C. Chang, F.F. Wang, and Y.J. Wang, Lipolytic Activities of a Lipase Immobilized on Six Selected Supporting Materials, Biotechnol. Bioeng. 35:132–137 (1990).

    Article  CAS  Google Scholar 

  181. Uemura, A., K. Nozaki, J-I. Yamashita, and M. Yasumoto, Regioselective Deprotection of 3′,5′-O-Acylated Nucleosides by Lipase and Esterase, Tetrahedron Lett. 30:3819–3820 (1989).

    Article  CAS  Google Scholar 

  182. Chen, J.-P., Enhancement of Enzymatic Hydrolysis Rate of Olive Oil in Water by Dimethyl β-Cyclodextrin, Biotechnol. Lett. 2:633–636 (1989).

    Article  Google Scholar 

  183. Holmberg, K., and E. Osterberg, Enzymatic Preparation of Monoglycerides in Microemulsions, J. Am. Oil Chem. Soc. 65:1544–1548 (1988).

    CAS  Google Scholar 

  184. Philippi, M.C., J.A. Jongejan, and J.A. Duine, Enantioselective Hydrolysis of Glycidol Esters: Analytical and Enzymatical Aspects, Proc. Fourth Eur. Congr. Biotech. 2:281–284 (1987).

    Google Scholar 

  185. Dahod, S.K., and P. Siuta-Mangano, Carbon Tetrachloride-Promoted Stereoselective Hydrolysis of Methyl-2-Chloropropionate by Lipase. Biotechnol. Bioeng. 30:995–999 (1987).

    Article  CAS  Google Scholar 

  186. Ishii, T., T. Mori, J. Chen, Y. Itoh, S. Shimura, K. Kirimura, and S. Usami, Ester Synthesis by a Crude Lipase of Rhizopus oligosporus in an Aqueous System. J. Ferment. Bioeng. 70:188–189 (1990).

    Article  CAS  Google Scholar 

  187. Lazar, G., A. Weiss, and R.D. Schmid, Synthesis of Esters by Lipases, in Proceedings of the World Conference on Emerging Technologies in the Fats and Oils Industry, edited by A.R. Baldwin, American Oil Chemists’ Society, Champaign, 1986, pp. 346–354.

    Google Scholar 

  188. Dordick, J.S., D.R. Patil, S. Parida, K. Ryu, and D.G. Rethswisch, Enzymatic Catalysis in Organic Media. Prospects for the Chemical Industry, in Catalysis of Organic Reactions, edited by W.E. Pascoe, Marcel Dekker, New York, 1992, pp. 267–292.

    Google Scholar 

  189. Pecnik, S., M. Habulin, and Z. Knez, Fatty Acid Ester Synthesis Catalyzed by Immobilized Lipase from Mucor miehei, Vestn. Slov. Kem. Drus. 38:287–301 (1991).

    CAS  Google Scholar 

  190. Gutman, A.L., K. Zuobi, and T. Bravdo, Lipase-Catalyzed Preparation of Optically Active γ-Butyrolactones in Organic Solvents, J. Org. Chem. 55:3546–3552 (1990).

    Article  CAS  Google Scholar 

  191. Rees, G.D., M.G. Nascimento, T.R.J. Jenta, and B.H. Robinson, Reverse-Enzyme Synthesis in Microemulsion-Based Organo-Gels, Biochim. Biophys. Acta 1073:493–501 (1991).

    PubMed  CAS  Google Scholar 

  192. Chulalaksananukul, W., J.S. Condoret, P. Delorme, and R.M. Willemot, Kinetic Study of Esterification by Immobilized Lipase in n-Hexane, FEBS Lett. 276:181–184 (1990).

    Article  PubMed  CAS  Google Scholar 

  193. Yamane, T., Y. Kojima, T. Ichiryu, M. Nagata, and S. Shimizu, Intramolecular Esterification by Lipase Powder in Microaqueous Benzene: Effect of Moisture Content, Biotechnol. Bioeng. 34:838–843 (1989).

    Article  CAS  Google Scholar 

  194. Ikeda, I., J. Tanaka, and K. Sukuki, Synthesis of Acrylic Esters by Lipase, Tetrahedron Lett. 32:6865–6866 (1991).

    Article  CAS  Google Scholar 

  195. Knez, Z., M. Leitgeb, D. Zavrsnik, and B. Lavric, Synthesis of Oleic Acid Esters with Immobilized Lipase, Fat Sci. Technol. 92:169–172 (1990).

    CAS  Google Scholar 

  196. Dumont, T., D. Barth, C. Corbier, G. Branlant, and M. Perrut, Enzymatic Reaction Kinetic: Comparison in an Organic Solvent and in Supercritical Carbon Dioxide, Biotechnol. Bioeng. 39:329–333 (1992).

    Article  Google Scholar 

  197. Carta, G., J.L. Gainer, and M.E. Gibson. Synthesis of Esters Using a Nylon-Immobilized Lipase in Batch and Continuous Reactors, Enzyme Microb. Technol. 14:904–910 (1992).

    Article  PubMed  CAS  Google Scholar 

  198. Miller, C., H. Austin, L. Posorske, and J. Gonzlez, Characteristics of an Immobilized Lipase for the Commercial Synthesis of Esters, J. Am. Oil Chem. Soc. 65:927–931 (1988).

    Article  CAS  Google Scholar 

  199. Kosugi, Y., H. Tanaka, N. Tomizuka, K. Akeboshi, Y. Matsufune, and S. Yoshikawa, Enzymic Manufacture of Sterol Fatty Acid Esters, Japanese Patent 1,218,593 (1989).

  200. Koshiro, A., Cholesterol Ester and Its Manufacture Using Microbial Lipase, Japanese Patent 62,296,894 (1987).

  201. Kokusho, S., A. Tsunoda, N. Shimizu, H. Machida, and S. Iwasaki, Fatty Acid Ester Manufacture by Alkaline Lipase in an Anhydrous System, Japanese Patent 62,107,791 (1987).

    Google Scholar 

  202. Gatfield, I.L., The Enzymatic Synthesis of Esters in Nonaqueous Systems, Ann. N.Y. Acad. Sci. 434:569–572 (1984).

    Article  CAS  Google Scholar 

  203. Mestri, S., and J.S. Pai, Synthesis of Isoamyl Butyrate by Lipase of Mucor miehei, PAFAI J. 16:24–30 (1994).

    CAS  Google Scholar 

  204. Baratti, J., G. Buono, H. Deleuze, G. Langrand, M. Secchi, and C. Triantaphylides, Enantioselective Synthesis of Fatty Acid Esters by Lipases, in Proceedings of the World Conference of Emerging Technologies in the Fats and Oils Industry edited by A.R. Baldwin, American Oil Chemists’ Society, Champaign, 1986, pp. 355–358.

    Google Scholar 

  205. Takahashi, K., Y. Saito, and Y. Inada, Lipases Made Active in Hydrophobic Media, J. Am. Oil Chem. Soc. 65:911–916 (1988).

    Article  CAS  Google Scholar 

  206. Gatfield, I., and T. Sand, Enzymic Production of Esters and Lactones, West Germany Patent 3,108,927 (1982).

  207. Nishio, T., and M. Kamimura, Manufacture of Fatty Acid Esters with Lipase from Pseudomonas Species, Japanese Patent 1,174,391 (1989).

  208. Bhirud, V.S., V.V.R. Subrahmanyam, and S.D. Vaidya, Influence of Reaction Media on Esterification Catalyzed by Mucor miehei Lipase, J. Oil Tech. Assocn. India 23:44–47 (1991).

    CAS  Google Scholar 

  209. Osada, K., K. Takahashi, and M. Hatano, Polyunsaturated Fatty Glyceride Syntheses by Microbial Lipases, J. Am. Oil Chem. Soc. 67:921–922 (1990).

    Article  CAS  Google Scholar 

  210. Omar, I.C., H. Saeki, N. Nishio, and S. Nagai, Synthesis of Acetone Glycerol Acyl Esters by Immobilized Lipase of Mucor miehei, Biotechnol. Lett. 11:161–166 (1989).

    Article  CAS  Google Scholar 

  211. Kim, S.M, and J.S. Rhee, Production of Medium-Chain Glycerides by Immobilized Lipase in a Solvent-Free System, J. Am. Oil Chem. Soc. 68:499–503 (1991).

    CAS  Google Scholar 

  212. Muthukumaran, N., and S.C. Dhar, Studies on Glyceride Synthesis by Rhizopus nodosus Acid Lipase, Leather Sci. 30:97–100 (1983).

    CAS  Google Scholar 

  213. Kiyono, H., T. Uchibori, M. Tsujita, Y. Nakao, I. Morita, and H. Nishitani, Polyglycerol Fatty Acid Esters by Enzymatic Esterification, Japanese Patent 61,187,795 (1986).

  214. Uemura, A., K. Nozaki, J. Yamashita, and M. Yasumoto, Lipase-Catalyzed Regioselective Acylation of Sugar Moieties of Nucleosides, Tetrahedron Lett. 30:3817–3818 (1989).

    Article  CAS  Google Scholar 

  215. Bjorkling, F., S. E. Godtfredsen, and O. Kirk, A Highly Selective Enzyme-Catalyzed Esterification of Simple Glucosides, J. Chem. Soc., Chem. Commun. 934–935 (1989).

  216. Fregapane, G., D.B. Sarney, and E.N. Vulfson, Enzymic Solvent-Free Synthesis of Sugar Acetal Fatty Acid Esters, Enzyme Microb. Technol. 13:796–800 (1991).

    Article  CAS  Google Scholar 

  217. Miyake, H., M. Hirano, H. Toda, and K. Kitano, Manufacture of Sugar Fatty Acid Ester Mixtures with Lipase, Japanese Patent 4,16,194 (1992).

  218. Kobori, J., and Y. Hirota, Esterification of Fatty Acids and Alcohols in Presence of Lipase, Japanese Patent 63,133,991 (1988).

  219. Mukesh, D., D. Sheth, A. Mokashi, J. Wagh, J.M. Tilak, A.A. Banerji, and K.R. Thakkar, Lipase-Catalyzed Esterification of Isosorbide and Sorbitol, Biotech. Lett. 15:1243–1246 (1993).

    CAS  Google Scholar 

  220. Li, Z.-Y., and O.P. Ward, Lipase-Catalyzed Esterification of Glycerol and n-3 Polyunsaturated Fatty Acid Concentrate in Organic Solvent, J. Am. Oil Chem. Soc. 70:745–748 (1993).

    Article  CAS  Google Scholar 

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Gandhi, N.N. Applications of lipase. J Amer Oil Chem Soc 74, 621–634 (1997). https://doi.org/10.1007/s11746-997-0194-x

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