Glyceride synthesis in a solvent-free system

JAOCS, Journal of the American Oil Chemists' Society

Volumn 73, Issue 11, 1996, Pages 1489-1495

  Fureby, Anna Millqvist ^a,b   Adlercreutz, Patrick ^a   Mattiasson, Bo ^a  

^a CHEMICAL CENTER   (Sweden)

^b INSTITUTE OF FOOD RESEARCH   (United Kingdom)

Author keywords

Acyl donors; Glyceride synthesis; Lipase; Solvent free

Indexed keywords

CATALYSIS; COMPOSITION EFFECTS; ENZYMES; MASS TRANSFER; ORGANIC ACIDS; PRECIPITATION (CHEMICAL); SUBSTRATES; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; WATER;

CAPRIC ACIDS; LIPASES; SOLVENT FREE SYSTEM;

GLYCEROL;

EID: 0030291391     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02523515     Document Type: Article

References (37)

1. Young, F.V.K., C. Poot, E. Biernoth, N. Krog, N.G.J. Davidson, and F.D. Gunstone, in Lipid Handbook, 2nd edn., edited by F.D. Gunstone, J.L. Harwood, and F.B. Padley, Chapman & Hall, London, 1994, pp. 296-304.
2. Hernqvist, L., and K. Anjou, Diglycerides as a Stabilizer of the β′-Crystal Structure in Margarines and Fats, Fette Seifen Anstrichm. 85:64-66 (1983).
3. Garzon-Aburbeh, A., J.H. Poupaert, M. Claesen, P. Dumont, and G. Atassi, 1,3-Dipalmitoylglycerol Ester of Chlorambucil as Lymphotrophic, Orally Administrable Antineoplastic Agent, J. Med. Chem. 26:1200-1203 (1983).
4. Garzon-Aburbeh, A., J.H. Poupaert, M. Claesen, and P. Dumont, A Lymphotrophic Prodrug of L-Dopa: Synthesis, Pharmacological Properties and Pharmaco-Kinetic Behaviour of 1,3-Dihexadecanoyl-2-[(S)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl] propane-1,2,3-triol, Ibid. 29:687-691 (1986).
5. Saraiva Conçalves, J.C., C. Razouk, J.H. Poupaert, and P. Dumont, High Performance Liquid Chromatography of Chloram ucil Prodrugs Structurally Related to Lipids in Rat Plasma, J. Chromatogr. 494:389-396 (1989).
6. van Deenen, L.L. and G. de Haas, The Substrate Specificity of Phospholipase A, Biochim. Biophys. Acta 70:538-553 (1963).
7. Wehrli, H.P., and Y. Pomeranz, Synthesis of Galactosyl Glycerides and Related Lipids, Chem. Phys. Lipids 3:357-370 (1969).
8. Sonntag, N.O.V., Glycerolysis of Fats and Methyl Esters - Status, Review and Critique, J. Am. Oil Chem. Soc. 59:795A-780A (1982).
9. Zaks, A., and A.M. Klibanov, Enzyme-Catalyzed Processes in Organic Solvents, Proc. Natl. Acad. Sci. USA 82:3192-3196 (1985).
10. Bovara, R., G. Carrea, G. Ottolina, and S. Riva, Water Activity Does Not Influence the Enantioselectivity of Lipase PS and Lipoprotein Lipase in Organic Solvents, Biotechnol. Lett. 15:169-174 (1993).
11. Öhrner, N., M. Martinelle, A. Mattson, T. Norin, and K. Huit, Displacement of the Equilibrium in Lipase Catalysed Transesterification in Ethyl Octanoate by Continuous Evaporation of Ethanol, Ibid. 14:263-268 (1992).
12. Mukherjee, K.D., and I. Kiewitt, Preparation of Esters Resembling Natural Waxes by Lipase-Catalyzed Reactions, J. Agric. Food Chem. 36:1333-1336 (1988).
13. Trani, M., F. Ergan, and G. André, Lipase-Catalyzed Production of Wax Esters, J. Am. Oil Chem. Soc. 68:20-22 (1991).
14. Bloomer, S., P. Adlercreutz, and B. Mattiasson, Facile Synthesis of Fatty Acid Esters in High Yields, Enzyme Microb. Technol. 14:546-552 (1992).
15. Ergan, F., M. Trani, and G. André, Production of Glycerides from Glycerol and Fatty Acid by Immobilized Lipases in Non-Aqueous Media, Biotechnol. Bioeng. 35:195-200 (1990).
16. Ergan, F., and M. Trani, Effect of Lipase Specificity on Triglyceride Synthesis, Biotechnol. Lett. 13:19-24 (1991).
17. Weiss, A., Enzymatische Herstellung von festen Fettsäuremonoglyceriden, Fat Sci. Technol. 92:392 (1990).
18. 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).
19. Berger, M., K. Laumen, and M.P., Schneider, Enzymatic Esterification of Glycerol I. Lipase-Catalyzed Synthesis of Regioisomerically Pure 1,3-Diacylglycerols, Ibid. 69:955-960 (1992).
20. Berger, M., and M.P. Schneider, Enzymatic Esterification of Glycerol II. Lipase-Catalyzed Synthesis of Regioisomerically Pure 1(3)-rac-Monoacylglycerols, Ibid. 69:961-965 (1992).
21. Van der Padt, A., J.T.F. Keurentjes, J.J.W. Sewalt, E.M. Van Dam, L.J. Van Dorp, and K. Van't Riet, Enzymatic Synthesis of Monoglycerides in a Membrane Reactor with an In-Line Adsorption Column, Ibid. 69:748-754 (1992).
22. Ferreira-Dias, S., and M.M.R. da Fonseca, Production of Monoglycerides by Glycerolysis of Olive Oil with Immobilized Lipases: Effects of the Water Activity, Bioprocess Eng. 12:327-337 (1995).
23. Pastor, E., C. Otero, and A. Ballesteros, Enzymatic Preparation of Mono- and Distearin by Glycerolysis of Ethyl Stearate and Direct Esterification of Glycerol in the Presence of a Lipase from Candida antarctica (Novozym 435), Biocatalysis Biotrans. 12:147-157 (1995).
24. Zaks, A., and A.T. Gross, Production of Monoglycerides by Transesterification, WO (Patent Cooperation Treaty) 90/04033 (1990).
25. Mazur, A.W., G.D. Hiler, and M. El-Nokaly, Preparation of 2-Monoglycerides, in Microemulsions and Emulsions in Foods, Am. Chem. Soc. Symposium Series, edited by M. El-Nokaly and D. Cornell, American Chemical Society, Washington, DC, 1991, pp. 51-61.
26. Millqvist, A., P. Adlercreutz, and B. Mattiasson, Lipase-Catalyzed Alcoholysis of Triglycerides for the Preparation of 2-Monoglycerides, Enzyme Microb. Technol. 16:1042-1047 (1994).
27. Millqvist Fureby, A., P. Adlercreutz and B. Mattiasson, Preparation of Diglycerides by Lipase Catalysed Alcoholysis of Triglycerides, Ibid., in press.
28. Janssen, A.E.M., A. Van der Padt, H.M. Van Sonsbeck, and K. Van't Riet, The Effect of Organic Solvents on the Equilibrium Position of Enzymatic Acylglycerol Synthesis, Biotechnol. Bioeng. 41:95-103 (1993).
29. Bornscheuer, U.T., and T. Yamane, Fatty Acid Vinyl Esters as Acylating Agents: A New Method for the Enzymatic Synthesis of Monoacylglycerols, J. Am. Oil Chem. Soc. 72:193-197 (1995).
30. Kaga, H., and K. Faber, presented at European Symposium on Biocatalysis, Graz, Austria, 1993.
31. McNeill, G., S. Shimizu, and T. Yamane, Solid Phase Enzymatic Glycerolysis of Beef Tallow Resulting in a High Yield of Monoglyceride, J. Am. Oil Chem. Soc. 67:779-783 (1990).
32. Yamane, T., S. Tae Kang, K. Kawahara, and Y. Koizumi, High-Yield Diacylglycerol Formation by Solid-Phase Enzymatic Glycerolysis of Hydrogenated Beef Tallow, Ibid. 71:369-372 (1994).
33. Bloomer, S., Lipase-Catalyzed Lipid Modifications in Non-Aqueous Media. Ph.D. Thesis, Lund University, Lund, Sweden (1992).
34. Millqvist Fureby, A., C. Virto, P. Adlercreutz, and B. Mattiasson, Acyl Migration in 2-Monoolein, Biocatalysis Biotrans. in press.
35. Bloomer, S., P. Adlercreutz, and B. Mattiasson, Triglyceride Interesterification of Triglycerides. 2. Reaction Parameters for the Reduction of Trisaturated Impurities and Diglycerides in Batch Reactions, Biocatalysis 5:145-162 (1991).
36. Serdarevich, B., Glyceride Isomerization in Lipid Chemistry. J. Am. Oil Chem. Soc. 44:381-393 (1967).
37. Kodali, D.R., A. Tercyak, D.A. Fahey, and D.M. Small, Acyl Migration in 1,2-Dipalmitoyl-sn-Glycerol, Chem. Phys. Lipids 52:163-170 (1990).