Fast synthesis of 1,3-DAG by Lecitase® Ultra-catalyzed esterification in solvent-free system

European Journal of Lipid Science and Technology

Volumn 113, Issue 8, 2011, Pages 973-979

  Liu, Ning ^a   Wang, Yong ^a,b   Zhao, Qiangzhong ^a   Zhang, Qingli ^a   Zhao, Mouming ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b JINAN UNIVERSITY   (China)

Author keywords

1,3 DAG; Esterification; Lecitase Ultra; Reaction conditions; Solvent free system

Indexed keywords

INSECTIVORA;

EID: 80051690019     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201000507     Document Type: Article

References (32)

1. Fureby, A. M., Tian, L., Adlercreutz, P., Mattiasson, B., Preparation of diglycerides by lipase-catalyzed alcoholysis of triglycerides. Enzyme Microb. Technol. 1997, 20, 198-206.
2. Taguchi, H., Watanabe, H., Onizawa, K., Nagao T., et al., Double-blind controlled study on the effects of dietary diacylglycerol on postprandial serum and chylomicron triacylglycerol responses in healthy humans. J. Am. Coll. Nutr. 2000, 19, 789-796.
3. Nagao, T., Watanabe, H., Goto, N., Onizawa K., et al., Dietary diacylglycerol suppresses accumulation of body fat compared to triacylglycerol in men in a double-blind controlled trial. J. Nutr. 2000, 130, 792-797.
4. Murase, T., Mizuno, T., Omachi, T., Onizawa K., et al., Dietary diacylglycerol suppresses high fat and high sucrose diet-induced body fat accumulation in C57BL/6J mice. J. Lipid Res. 2001, 42, 372-378.
5. Reyes, G., Yasunaga, K., Rothenstein, E., Karmally W., et al., Effects of a 1, 3-diacylglycerol oil-enriched diet on postprandial lipemia in people with insulin resistance. J. Lipid Res. 2008, 49, 670-678.
6. Guanti, G., Banfi, L., Basso, A., Bevilacqua E., et al., Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG). Tetrahedron: Asymmetry 2004, 15, 2889-2892.
7. Villeneuve, P., Muderhawa, J. M., Graille, J., Haas, M. J., Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J. Mol. Catal. B: Enzym. 2000, 9, 113-148.
8. Blasi, F., Cossignani, L., Simonetti, M. S., Damiani, P., Biocatalysed synthesis of sn-1, 3-diacylglycerol oil from extra virgin olive oil. Enzyme Microb. Technol. 2007, 41, 727-732.
9. Cheong, L. Z., Tan, C. P., Long, K., Yusoff M. S. A., et al., Production of a diacylglycerol-enriched palm olein using lipase-catalyzed partial hydrolysis: Optimization using response surface methodology. Food Chem. 2007, 105, 1614-1622.
10. Rosu, R., Yasui, M., Iwasaki, Y., Yamane, T., Enzymatic synthesis of symmetrical 1, 3-diacylglycerols by direct esterification of glycerol in solvent-free system. JAOCS 1999, 76, 839-843.
11. Weber, N., Mukherjee, K. D., Solvent-free lipase-catalyzed preparation of diacylglycerols. J. Agric. Food Chem. 2004, 52, 5347-5353.
12. Yang, T., Zhang, H., Mu, H., Sinclair, A. J., Xu, X., Diacylglycerols from butterfat: Production by glycerolysis and short-path distillation and analysis of physical properties. JAOCS 2004, 81, 979-987.
13. Yesiloglu, Y., Kilic, I., Lipase-catalyzed esterification of glycerol and oleic acid. JAOCS 2004, 81, 281-284.
14. Kwon, S. J., Han, J. J., Rhee, J. S., Production and in situ separation of mono- or diacylglycerol catalyzed by lipases in n-hexane. Enzyme Microb. Technol. 1995, 17, 700-704.
15. Duan, Z. Q., Du, W., Liu, D. H., Novozym 435-catalyzed 1, 3-diacylglycerol preparation via esterification in t-butanol system. Process Biochem. 2010, 45, 1923-1927.
16. Fregolente, P. B. L., Fregolente, L. V., Pinto, G. M. F., Batistella B. C., et al., Monoglycerides and diglycerides synthesis in a solvent-free system by lipase-catalyzed glycerolysis. Appl. Biochem. Biotechnol. 2008, 146, 165-172.
17. Fernandez-Lorente, G., Filice, M., Terreni, M., Guisan J. M., et al., Lecitase® Ultra as regioselective biocatalyst in the hydrolysis of fully protected carbohydrates strong modulation by using different immobilization protocols. J. Mol. Catal. B: Enzym. 2008, 51, 110-117.
18. Sheelu, G., Kavitha, G., Fadnavis, N. W., Efficient immobilization of Lecitase in gelatin hydrogel and degumming of rice bran oil using a spinning basket reactor. JAOCS 2008, 85, 739-748.
19. Yang, B., Wang, Y. H., Yang, J. G., Optimization of enzymatic degumming process for rapeseed oil. JAOCS 2006, 83, 653-658.
20. 1-catalyzed synthesis of phospholipids enriched in n-3 polyunsaturated fatty acid residues. Enzyme Microb. Technol. 2007, 40, 1130-1135.
21. 1 (Lecitase Ultra). Food Chem. 2010, 121, 1066-1072.
22. 1-catalyzed partial hydrolysis. Eur. J. Lipid Sci. Technol. 2009, 111, 652-662.
23. Mishra, M. K., Kumaraguru, T., Sheelu, G., Fadnavis, N. W., Lipase activity of Lecitase® Ultra: Characterization and applications in enantioselective reactions. Tetrahedron: Asymmetry 2009, 20, 2854-2860.
24. Kuo, S. J., Parkin, K. L., Solvent polarity influences product selectivity of lipase-mediated esterification reactions in microaqueous media. JAOCS 1996, 73, 1427-1433.
25. Duan, Z. Q., Du, W., Liu, D. H., The solvent influence on the positional selectivity of Novozym 435 during 1, 3-diolein synthesis by esterification. Bioresour. Technol. 2010, 101, 2568-2571.
26. Zhong, N., Li, L., Xu, X., Cheong L., et al., An efficient binary solvent mixture for monoacylglycerol synthesis by enzymatic glycerolysis. JAOCS 2009, 86, 783-789.
27. Monot, F., Borzeix, F., Bardin, M., Vandecasteele, J. P., Enzymatic esterification in organic media: Role of water and organic solvent in kinetics and yield of butyl butyrate synthesis. Appl. Microbiol. Biotechnol. 1991, 35, 759-765.
28. Watanabe, T., Shimizu, M., Sugiura, M., Sato M., et al., Optimization of reaction conditions for the production of DAG using immobilized 1, 3-regiospecific lipase Lipozyme RM IM. JAOCS 2003, 80, 1201-1207.
29. Szelag, H., Zwierzykowski, W., The application of molecular distillation to obtain high concentration of monoglycerides. Fette Seifen Anstrichmittel 1983, 85, 443-446.
30. Batistella, C. B., Wolf-Maciel, M. R., Recovery of carotenoids from palm oil by molecular distillation. Comput. Chem. Eng. 1998, 22, S53- S60.
31. Fregolente, P. B. L., Pinto, G. M. F., Wolf-Maciel, M. R., Filho, R. M., Monoglyceride and diglyceride production through lipase-catalyzed glycerolysis and molecular distillation. Appl. Biochem. Biotechnol. 2010, 160, 1879-1887.
32. Xu, X., Jacobsen, C., Nielsen, N. S., Heinrich, M. T., Zhou, D., Purification and deodorization of structured lipids by short path distillation. Eur. J. Lipid Sci. Technol. 2002, 104, 745-755.