Diacylglycerols (DAG) were synthesised by lipase-catalysed esterification of glycerol with fatty acids from palm oil deodoriser distillate (PODD). Effects of reaction parameters such as reaction time, temperature, enzyme type, enzyme load, substrate mole ratio and water content were determined. The effect of molecular sieves as a water adsorbent was also studied. Rhizomucor mieheilipase (Lipozyme RM IM) was found to be most effective among the lipases screened for DAG production. The following conditions yielded 52% (w/w) DAG: 6h reaction time, 65 °C reaction temperature, 10% (w/w) Lipozyme RM IM, 2.5:1 fatty acid to glycerol molar ratio, and 30% (w/w) molecular sieves. DAG synthesis of 10.9% (w/w) was still observed at 10% (w/w) water content.
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References
1.
Bergqvist M.H.J. and Kaufmann P. (1993). A multivariate optimisation of triacylglycerol analysis by highperformance liquid chromatography . Lipids28: 667–675 .
2.
BjÖrkling F., Godtfredsen S.E. and Kirk O. (1991). The future impact of industrial lipases . Trends in Biotechnology9: 360–363 .
3.
Chulaksananukul W., Concoret J.S., Delorme P. and Willemot R.M. (1990). Kinetic study of esterification by immobilised lipase in n-hexane . FEBS Letters276: 181–184 .
4.
Fureby A.M., Tian L., Adlercreutz P. and Mattiasson B. (1997). Lipase-catalysed preparation of diglycerides . Enzyme Microbiology and Technology20: 198–206 .
5.
Garson-Aburbeh A., Poupaert J.H., Claesen M. and Dumont P. (1986). A lymphotrophic prodrug of L-Dopa: Synthesis, pharmacological properties, and pharmacokinetic behaviour of 1,3-dihexadecanoyl-2-[(S)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl] propane-1,2,3-triol . Journal of Medicinal Chemistry29: 687–691 .
6.
Garson-Aburbeh A., Poupaert J.H., Claesen M., Dumont P. and Atassi G. (1983). 1,3-Dipalmitoylglycerol ester of chlorambucil as lymphotrophic, orally administrable antineoplastic agent . Journal of Medicinal Chemistry26: 1200–1203 .
7.
Hirota Y., Kohori J. and Kawakara Y. (1989). Preparation of Diglycerides. European Patent EP 0 307 154.
8.
Lin J.-T., Woodruff C.L. and McKeon T.A. (1997). Nonaqueous reversed-phase high-performance liquid chro- matography of synthetic triacylglycerols and diacylglycerols . Journal of Chromatography A. 782: 41–48 .
9.
Malcata F.X., Reyes H.R., Garcia H.S., Hill C.G. and Admundson C.H. (1992). Kinetics and mechanisms of reactions catalyzed by immobilised lipases . Enzyme Microbiology and Technology14: 426–446 .
10.
Martinelle M. and Hult K. (1994). Kinetics of triglyceride lipases. In: Woodley, P. and Petersen S.B. (eds.), Lipases: Their Structure, Biochemistry and Application. Cambridge: Cambridge University Press , pp. 159–180.
11.
Murata M., Hara K. and Ide T. (1994). Alteration of diacylglycerols of the transport and fatty acid composition of lymph chylomicron in rats . Bioscience, Biotechnology and Biochemistry58: 1416–1419 .
12.
Murata M., Ide T. and Hara K. (1997). Reciprocal responses to dietary diacylglycerol of hepatic enzymes of fatty acid synthesis and oxidation in the rat . British Journal of Nutrition77: 107–121 .
13.
Nagao T., Watanabe H., Goto N., Onizawa K., Taguchi H., Matsuo N., Yasukawa T., Tsushima R., Shimasaki H. and Itakura I. (2000). Dietary diacylglycerol suppresses accumulation of body fat compared to triacylglycerol in men in a double-blind controlled trial . Journal of Nutrition130: 792–797 .
14.
Pastor E., Otero C. and Ballasteros A. (1995). Synthesis of mono- and dioleoylglycerols using immobilized lipase . Applied Biochemistry and Biotechnology50: 251–263 .
15.
Plou F.J., Barandiar·n M., Calvo M.V., Ballasteros A. and Pastor E. (1996). High-yield production of mono- and di-oleylglycerol by lipase-catalyzed hydrolysis of triolein . Enzyme Microbiology and Technology18: 66–71 .
16.
Saraiva-Concalves J.C., Razouk C., Poupaert J.H. and Dumont P. (1989). High-performance liquid chromatography of chlorambucil prodrugs structurally related to lipids in rat plasma . Journal of Chromatography494: 389–396 .
17.
SAS Institute Inc. (1989). SAS/STAT User’s Guide, 4th edn, Cary, NC: SAS .
18.
Shimizu S. (1987). Glycerolysis of Oil and Fat. Jap. Patent JP 62201591.
19.
van Deenen L.L.M. and de Haas G.H. (1963). The substrate specificity of phospholipase A . Biochim. Biophys. Acta70: 538–553 .
20.
Wehrli H.P. and Pomeranz Y. (1969). Synthesis of galactosyl glycerides and related lipids . Chemistry and Physics of Lipids3: 357–370 .
21.
Xu X. (2000). Production of specific-structured triacylglycerols by lipase-catalyzed reactions: a review . European Journal of Lipid Science and Technology102: 287–303 .
22.
Yamada Y., Shimizu M., Sugiura M. and Yamada N. (1999). Process for Producing Diglycerides. Int. Patent WO 99/09119.
23.
Yamane, T., Kang S.T., Kawahara K. and Koizumi Y. (1994). High-yield diacylglycerol formation by solidphase enzymatic glycerolysis of hydrogenated beef tallow . Journal of the American Oil Chemists’ Society71: 339–342 .
