Quantitative enzymatic production of 1,6-diacyl fructofuranoses

Enzyme and Microbial Technology

Volumn 22, Issue 1, 1998, Pages 27-35

  Arcos, J A ^a   Bernabe M ^b   Otero, Cristina ^a,c  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Amphiphiles; Candida antarctica lipase; Emulsifiers; Food additives; Fructose; Lipases; Sugar

Indexed keywords

ACETONE; BIOSYNTHESIS; FATTY ACIDS; FOOD ADDITIVES; FRUCTOSE; ORGANIC SOLVENTS; SUGARS;

AMPHIPHILE COMPOUNDS; ENZYMATIC PRODUCTION; LIPASES;

ENZYMES;

ACETONE; ESTER; FOOD ADDITIVE; FRUCTOSE; SUGAR; TRIACYLGLYCEROL LIPASE;

ARTICLE; BIOSYNTHESIS; CANDIDA ALBICANS; CATALYST; CULTURE MEDIUM; ENZYME ACTIVITY; ESTERIFICATION; NONHUMAN; QUANTITATIVE ASSAY; REACTION TIME; TEMPERATURE;

EID: 17544385285     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(97)00100-2     Document Type: Article

References (36)

1. 1. Conley, A. J. and Kabara, J. J. Antimicrobial action of esters of polyhydric alcohols. Antimicrob. Agents Chemother. 1973, 4, 501-506
2. 2. Griffin, W. C. Classification of surface-active agents by "HLB". J. Soc. Cosmet. Chem. 1949, 1, 311-326
3. 3. Akoh, C. C. Synthesis of carbohydrate fatty acid polyesters. In: Carbohydrate Polyesters as Fat Substitutes (Akoh, C. C. and Swanson, B. G., Eds.). Marcel Deckker, NY, 1994, 9-35
4. 4. Osipow, L. I., Snell, F. D., York, W. C., and Finchler, A. Methods of preparation of fatty acid esters of sucrose. Ind. Eng. Chem. 1956, 48, 1459-1462
5. 5. Osipow, L. I. and Rosenblatt, W. Microemulsion process for the preparation of sucrose esters. J. Am. Oil Chem. Soc. 1967, 44, 307-309
6. 6. Kosaka, T. and Yamada, T. New plant and new applications of sucrose esters. In: Sucrochemistry (Hickson, J. L., Ed.). American Chemical Society, Washington, D.C, 1977, 84
7. 7. Feuge, R. O., Zeringue, Jr., H. J., Weiss, T. J., and Brown, M. Preparation of sucrose esters by interesterification. J. Am. Oil Chem. Soc. 1970, 47, 56-60
8. 8. Kea, S., Walker, C. E., Kline, E. US Patent n° 4,683,299; 1987
9. 9. Fregapane, G., Sarney, D. B., Greenberg, S. G., Knight, D. J., and Vulfson, E. N. Enzymatic synthesis of monosaccharide fatty acid esters and their comparison with conventional products. J. Am. Oil Chem. Soc. 1994, 71, 87-91
10. 10. Seino, H., Uchibori, T., Nishitani, T., and Inamusu, S. Enzymatic synthesis of carbohydrate esters of fatty acids (1): Esterification of sucrose, glucose, fructose, and sorbitol. J. Am. Chem. Oil Soc. 1984, 61, 1761-1765
11. 11. Therisod, M. and Klibanov, A. M. Facile enzymatic preparation of monoacylated sugars in pyridine. J. Am. Chem. Soc. 1986, 108, 5638-5640
12. 12. Riva, S., Chopineau, J., Kieboom, A. P. G., and Klibanov, A. M. Protease catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide. J. Am. Chem. Soc. 1988, 110, 584-589
13. 13. Therisod, M. and Klibanov, A. M. Regioselective acylation of secondary hydroxyl groups in sugars catalyzed by lipases in organic solvents. J. Am. Chem. Soc. 1987, 109, 3977-3981
14. 14. Björkling, F., Godtfredsen, S. E., and Kirk, O. A highly selective enzyme-catalysed esterification of simple glucosides. J. Chem. Soc. Chem. Commun. 1989, 14, 934-935
15. 15. Khaled, N., Montet, D., Farines, M., Pina, M., and Graille, J. Synthesis of sugar monoesters by biocatalysis. Oleagineux 1992, 47, 181-190
16. 16. Ku, M. A. and Hang, Y. D. Enzymatic synthesis of esters in organic medium with lipase from Byssochlamys fulva. Biotechnol. Lett. 1995, 17, 1081-1084
17. 17. Khaled, N., Montet, D., Pina, M., and Graille, J. Fructose oleate synthesis in a fixed catalyst bed reactor. Biotechnol. Lett. 1991, 13, 167-172
18. 18. Guillardeau, L., Montet, D., Khaled, N., Pina, M., and Graille, J. Fructose caprytate biosynthesis in a solvent-free medium. Tenside Surf. Det. 1992, 29, 342-344
19. 19. Ducruet, A., Giroux, A., Trani, M., and Lortie, R. Enzymatic preparation of biosurfactants from sugars or sugar alcohols and fatty acids in organic media under reduced pressure. Biotechnol. Bioeng. 1995, 48, 214-221
20. 20. Sin, Y. M., Chung, S. H., Park, J. Y., and Lee, T. H. Synthesis of biodegradable emulsifier using lipase in anhydrous pyridine. Biotechnol. Lett. 1996, 18, 689-694
21. 21. Macrae, A. R. Interesterification of fats and oils. In: Biocatalysts in Organic Synthesis (Tramper, J., Vand der Plas, H. C., and Lin Ko, P., Eds.). Elsevier, Amsterdam, 1985, 195-208
22. 22. Gerhartz, W. Industrial uses of enzymes. In: Enzymes in Industry (Gerhartz, W., Ed.). VCH Verlagsgesellschaft, Weinhetm, Germany, 1990, 89-91
23. 23. Arcos, J. A. and Otero, C. Enzyme, medium and reaction engineering to design a low-cost, selective production method for mono-and dioleoylglycerols. J. Am. Oil Chem. Soc. 1996, 73, 673-682
24. 24. Scheckermann, C., Schlotterbeck, A., Schmidt, M., Wray, V., and Lang, S. Enzymatic monoacylation of fructose by two procedures. Enzyme Microb. Technol. 1995, 17, 157-162
25. 25. Bock, K., Pedersen, C., and Pedersen, H. Adv. Carb. Chem. & Biochem. 1994, 42, 193-225
26. 26. Griffin, W. C. Classification of surface-active agents by "HLB". J. Soc. Cosmet. Chem. 1949, 1, 311-326
27. 27. Kirk, E. and Othmer, D. F., (Eds.). Encyclopedia of Chemical Technology Vol. 21. Wiley-Interscience, NY, 1976, 944
28. 28. Lauridsen, J. B. Food emulsifiers: surface activity, edibility, manufacture, composition and application. J. Am. Chem. Oil Soc. 1976, 53, 400-407
29. 29. Adlehorst, K., Bjorkling, F., Godtfresen, S. E., and Kirk, O. Enzyme catalysed preparation of 6-acylglucopyranosides. Synthesis 1990, 2, 112-115
30. 30. Fregapane, G., Sarney, D. B., and Vulfson, E. N. Enzymic solvent-free synthesis of sugar acetal fatty acid esters. Enzyme Microb. Technol. 1991, 13, 796-800
31. 31. Mutua, L. N. and Akoh, C. C. Synthesis of alkyl glycoside fatty acid esters in nonaqueous media by Candida sp. lipase. J. Am. Chem. Oil Soc. 1993, 70, 43-46
32. 32. Coulon, D., Girardin, M., Rovel, B., and Ghoul, M. Comparison of direct esterification and transesterification of fructose by Candida antarctica lipase. Biotechnol. Lett. 1995, 17, 183-186
33. 33. Arcos, J. A. and Otero, C. Spanish Patent n° 9,602,091; 1996
34. 34. Schlotterbeck, A., Lang, S., Wray, V., and Wagner, F. Lipase-catalyzed monoacylation of fructose. Biotechnol. Lett. 1993, 15, 61-64
35. 35. Oguntimein, G. B., Erdmann, H., and Schmid, R. D. Lipase catalysed synthesis of sugar ester in organic solvents. Biotechnol. Lett. 1993, 15, 175-180
36. 36. Ducret, A., Giroux, A., Trani, M., and Lortie, R. Characterization of enzymatically prepared biosurfactants. J. Am. Chem. Oil Soc. 1996, 73, 109-113