Abstract
Regioisomerically pure 1,3-sn-diacylglycerols are conveniently prepared in high yields (>80%) and in large quantities by enzymatic esterification of glycerol in the presence of various 1,3-selective lipases(Chromobacterium viscosum, Rhizopus delemar, Rhizomucor miehei) and a variety of different acyl donors like free fatty acids, fatty acid alkyl esters and vinyl esters. All reactions are carried out in aprotic organic solvents of low water content, namelyn-hexane, diethyl ether or tBuOMe. The creation of an artificial interphase between the solvent-immiscible hydrophilic glycerol and the hydrophobic reaction media by the adsorption of glycerol onto a solid support prior to use was essential for the success of these transformations. The effects of reaction conditions and the regioselectivities of the lipases on the product yields are described in detail.
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References
Wehrli, H.P., and Y. Pomeranz,Chem. Phys. Lipids 3:357 (1969).
Van Deenen, L.L.M., and G.H. De Haas,Biochim. Biophys. Acta 70:538 (1963).
Kumar, R., and J.D. Billimoria,J. Pharm. Pharmacol. 30:754 (1978).
Paris, G.Y., D.G. Cimon, D.L. Garmaise, L. Swett, J.W. Carter and P.Y. Young,Eur. J. Med. Chem. 17:193 (1980).
Jacob, J.N., G.W. Hesse and V.E. Shashoua,J. Med. Chem. 30:1573 (1987).
Jacob, J.N., G.W. Hesse and V.E. Shashoua,:733 (1990).
Garzon-Aburbeh, A., J.H. Poupaert, M. Claesen, P. Dumont and G. Atassi,:1200 (1983).
Saraiva Goncalves, J.C., C. Razzouk, J.H. Poupaert and P. Dumont,J. Chromatogr. 494:389 (1989).
Garzon-Aburbeh, A., J.H. Poupaert, M. Claesen and P. Dumont,J. Med. Chem. 29:687 (1986).
Mantelli, S., P. Speiser and H. Hauser,Chem. Phys. Lipids 37:329 (1985).
Kido, H., N. Fukusen, K. Ishidoh and N. Katunuma,Biochem. Biophys. Res. Commun. 138:275 (1986).
Siegel, D.P., J. Banschbach, D. Alford, H. Ellens, L.J. Lis, P.J. Quinn, P.L. Yeagle and J. Bentz,Biochemistry 28:3703 (1989).
Swern, D., inBailey’s Industrial Oil and Fat Products, Vol. 1, Wiley Interscience, New York, 1979, p. 3.
Pratt, C.D., and W.W. Hays,Food Eng. 24:109 (1952).
Ikeda, I., X.P. Gu, I. Mijamoto and M. Okahara,J. Am. Oil Chem. Soc. 66:822 (1989).
Bentley, P.H., and W. McCrae,J. Org. Chem. 35:2082 (1970).
Mattson, F.H., and R.A. Volpenheim,J. Lipids Res. 3:281 (1962).
Howe, R.J., and T. Malkin,J. Chem. Soc., 2663 (1951).
Osada, K., K. Takahashi and M. Hatano,J. Am. Oil Chem. Soc. 67:921 (1990).
Zaks, A.,:484 (1989).
Holmberg, K., and E. Osterberg,:1544 (1988).
Berger, M., and M.P. Schneider,Biotechnol. Lett. 13:333 (1991).
Schneider, M., K. Laumen, D. Breitgoff, D. Wullbrandt, M. Schlingmann and R. Keller, European Patent No. 254,243 (1987).
Eigtved, P., T.T. Hansen and C.A. Miller, inProceedings of the World Conference on Biotechnology for the Fats and Oils Industry, edited by T. Applewhite, American Oil Chemists’ Society, Champaign, 1987, p. 134.
Rabiller, C., and F. Maze,Magnetic Resonance in Chemistry 27:582 (1989).
Schuch, R., and K. Mukherjee,Appl. Microbiol. Biotechnol. 30:332 (1989).
Riva, M., A. Daghetta and M. Galli,Riv. Ital. Sost. Grasse 58:432 (1981).
Kodali, D.R., A. Tercyak, D.A. Fahey and D.M. Small,Chem. Phys. Lipids 52:163 (1990).
Iwai, M., inLipases, edited by B. Borgström and H.L. Brockmann, Elsevier Science Publishers, Amsterdam, 1984, p. 416.
Yamane, T., inProceedings of the World Conference on Biotechnology for the Fats and Oils Industry, edited by T. Applewhite, American Oil Chemists’ Society, Champaign, 1987, p. 17.
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Berger, M., Laumen, K. & Schneider, M.P. Enzymatic esterification of glycerol I. Lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols. J Am Oil Chem Soc 69, 955–960 (1992). https://doi.org/10.1007/BF02541057
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DOI: https://doi.org/10.1007/BF02541057