Lipase-Catalyzed Cellulose Acetylation in Aqueous and Organic Media

Biotechnology Progress

Volumn 19, Issue 6, 2003, Pages 1664-1671

  Yang, Kui ^a,b   Wang, Ya Jane ^a  

^a UNIVERSITY OF ARKANSAS   (United States)

^b TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; CATALYSIS; CELLULOSE; ENZYMES; SCREENING; SUBSTRATES;

REACTION MEDIA;

BIOTECHNOLOGY;

ACETYLATION; CARBOXYMETHYLCELLULOSE; CATALYSIS; ENZYME ACTIVATION; LIPASE; ORGANIC CHEMICALS; SOLVENTS; SUBSTRATE SPECIFICITY; WATER;

ASPERGILLUS; ASPERGILLUS NIGER;

EID: 0346152856     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp0341388     Document Type: Article

References (55)

1. Treece, L. C.; Johnson, G. I. Cellulose Acetate. Chem. Ind. 1993, 49, 241-156.
2. Sereti, V.; Stamatis, H.; Pappas, C.; Polissiou, M.; Kolisis, F. N. Enzymatic Acylation of Hydroxypropyl Cellulose in Organic Media and Determination of Ester Formation by Diffuse Reflectance Infrared Fourier Transform (DRIFT) Spectroscopy. Biotechnol. Bioeng. 2001, 72, 495-500.
3. Kuo, C. M.; Bogan, R. T. Process for the Manufacture of Cellulose Acetate. U.S. Patent 5, 608, 050, 1997.
4. Saikia, C. N.; Ali, F.; Goswami, T.; Ghosh, A. C. Esterification of High α-Cellulose Extracted from Hibiscus cannabinus. Ind. Crops Prod. 1995, 4, 233-239.
5. Saikia, C. N.; Tosh, B. N.; Goswami, T.; Ghosh, A. C. Preparation of Different Molecular Weight Fractions of Cellulose and Characterization of Homogeneously Acetylated Fractions. Indian J. Chem. Technol. 1996, 3, 333-337.
6. Tosh, B.; Saikia, C. N. Homogeneous Esterification of Fractionated Cellulose in Dimethylsulfoxide/Paraformaldehyde Solvent System: Characterization of Esterified Products. Trends Carbohydr. Chem. 1999, 4, 55-67.
7. Marson, G. A.; El Seoud, O. A. A Novel, Efficient Procedure for Acylation of Cellulose under Homogeneous Solution Conditions. J. Appl. Polym. Sci. 1999, 74, 1355-1360.
8. El Seoud, O. A.; Marson, G. A.; Ciacco, G. T.; Frollini, E. An Efficient, One-Pot Acylation of Cellulose under Homogeneous Reaction Conditions. Macromol. Chem. Phys. 2000, 201, 882-889.
9. Koeller, K. M.; Wong, C. H. Enzymes for Chemical Synthesis. Nature 2001, 409, 232-240.
10. Cui, W.; Winter, W. T.; Tanenbaum, S. W.; Nakas, J. P. Purification and Characterization of an Intracellular Carboxylesterases from Arthrobacter viscosus NRRL B-1973. Enzyme Microb. Technol. 1999, 24, 200-208.
11. Klibanov, A. M. Improving Enzymes by Using Them in Organic Solvents. Nature 2001, 409, 241-246.
12. Klibanov, A. M. Asymmetric Transformations Catalyzed by Enzymes in Organic Solvents. Acc. Chem. Res. 1990, 23, 114-120.
13. Cruces, M. A.; Otero, C.; Bernabe, M.; Martin-Lomas, M.; Ballesteros, A. Enzymatic Preparation of Acylated Sucroses. Ann. N. Y. Acad. Sci. 1992, 672, 436-443.
14. Sharma, A.; Chattopadhyay, S. Lipase-Catalyzed Acetylation of Carbohydrates. Biotechnol. Lett. 1993, 15, 1145-1146.
15. Rich, J. O.; Bedell, B. A.; Dordick, J. S. Controlling Enzyme-Catalyzed Regioselectivity in Sugar Ester Synthesis. Biotechnol. Bioeng. 1995, 45, 426-434.
16. Koskinen, A. M. P.; Klibanov, A. M. Enzymatic Reactions in Organic Media; Blackie Academic & Professional: Glasgow, Scotland, 1996.
17. MacManus, D. A.; Vulfson, E. N. Reversal of Regioselectivity in the Enzymatic Acylation of Secondary Hydroxyl Groups Mediated by Organic Solvents. Enzyme Microb. Technol. 1997, 20, 225-228.
18. Degn, P.; Zimmermann, W. Optimization of Carbohydrate Fatty Acid Ester Synthesis in Organic Media by a Lipase from Candida antarctica. Biotechnol. Bioeng. 2001, 74, 483-491.
19. Donnelly, M. J. In vitro Enzymatic Synthesis of Polymers Containing Saccharides, Lignins, Proteins or Related Compounds: A Review. Polym. Int. 1998, 47, 257-266.
20. Akkara, J. A.; Ayyagari, S. R.; Bruno, F. F. Enzymatic Synthesis and Modification of Polymers in Nonaqueous Solvents. Trends Biotechnol. 1999, 17, 67-73.
21. Xie, J.; Hsieh, Y. L. Enzyme-Catalyzed Transesterification of Vinyl Esters on Cellulose Solids. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1931-1939.
22. Sereti, V.; Stamatis, H.; Koukios, E. G.; Kolisis, F. N. Enzymatic Acylation of Cellulose Acetate in Organic Media. J. Biotechnol. 1998, 66, 219-223.
23. Schmid, A.; Dordick, J. S.; Hauer, B.; Kiener, A.; Wubbolts, M.; Witholt, B. Industrial Biocatalysis Today and Tomorrow. Nature 2001, 409, 258-268.
24. Johnson, D. C.; Nicholson, M. D.; Haigh, F. C. Dimethyl Sulfoxide/Paraformaldehyde: A Nondegrading Solvent for Cellulose. Appl. Polym. Symp. 1976, 28, 931-943.
25. Dubois, M.; Gilles, K. A.; Hamilton, J. K.; Rebers, P. A.; Smith, F. Colorimetric Method for Determination of Sugars and Related Substances. Anal. Chem. 1956, 28, 350-356.
26. McComb, E. A.; McCready, R. M. Determination of Acetyl in Pectin and in Acetylated Carbohydrate Polymers. Anal. Chem. 1957, 29, 819-821.
27. D-871 Degree of Acetylation. AnnualBook of ASTM Standards; American Society for Testing and Materials: Philadelphia, PA, 1970; Vol. 15, pp 272-290.
28. Bornscheuer, U. T.; Kazlauskas, R. J. Hydrolyases in Organic Synthesis, Regio-and Stereoselective Biotransformations; Wiley-VCH: New York, 1999.
29. Chang, R. C.; Chou, S. J.; Shaw, J. F. Synthesis of Fatty Acid Esters by Recombinant Staphylocossus epidermidia Lipases in Aqueous Environment. J. Agric. Food Chem. 2001, 49, 2619-2622.
30. Patel, R. N.; Banerjee, A.; Nanduri, V. Enzymatic Acetylation of 10-Deacetylbaccatin III to Baccatin III by C-10 Deacetylase from Nocardioides luteus SC 13913. Enzyme Microb. Technol. 2000, 27, 371-375.
31. Stephen, A. M. Food Polysaccharides and Their Applications; Dekker: New York, 1995; pp 139-148.
32. Fan, L. T.; Lee, Y. H.; Beardmore, D. H. The Influence of Major Structural Features of Cellulose on Rate of Enzymatic Hydrolysis. Biotechnol. Bioeng. 1981, 23, 419-424.
33. Koukios, E. G.; Pastou, A.; Koullas, D. P.; Sereti, V.; Stamatis, H.; Kolisis, F. New Green Products from Cellulosics. In Biomass, a Growth Opportunity in Green Energy and Value-Added Products; Elservier Science: Oxford, U.K., 1999; pp 641-647.
34. Zhuang, J. M. Pressure Pretreatment for Improving the Acetylation of Cellulose. U.S. Patent 5, 371, 207, 1994.
35. Zheng, Y.; Lin, H. M.; Tsao, G. T. Pretreatment for Cellulose Hydrolysis by Carbon Dioxide Explosion. Biotechnol. Prog. 1998, 14, 890-896.
36. Gama, F. M.; Carvalho, M. G.; Figueiredo, M. M.; Mota, M. Comparative Study of Cellulose Fragmentation by Enzymes and Ultrasound. Enzyme Microb. Technol. 1997, 20, 12-17.
37. Mahinpour, R.; Sarbolouki, M. N. Enhancing Enzymatic Hydrolysis of Cellulose by Ultrasonic Pretreatment. Iran. J. Chem. Chem. Eng. 1998, 17, 8-13.
38. Helle, S. S.; Duff, S. J. B.; Cooper, D. G. Effect of Surfactants on Cellulose Hydrolysis. Biotechnol. Bioeng. 1993, 42, 611-617.
39. Kaar, W. E.; Holtzapple, M. T. Benefits from Tween during Enzymic Hydrolysis of Corn Stover. Biotechnol. Bioeng. 1998, 59, 419-427.
40. Bell, G.; Halling, P. J.; Moore, B. D.; Partridge, J.; Rees, D. G. Biocatalyst Behaviour in Low-Water Systems. Trends Biotechnol. 1995, 13, 468-473.
41. Shimizu, Y.; Nakayama, A.; Hayashi, J. Acylation of Cellulose with Carboxylate Salts. Cellulose Chem. Technol. 1991, 23, 275-281.
42. Klibanov, A. M. Why Are Enzymes Less Active in Organic Solvents Than in Water? Trends Biotechnol. 1997, 15, 97-101.
43. Carrea, G.; Riva, S. Properties and Synthetic Applications of Enzymes in Organic Solvents. Angew Chem., Int. Ed. 2000, 39, 2226-2254.
44. Almarsson, O.; Klibanov, A. M. Remarkable Activation of Enzymes in Nonaqueous Media by Denaturing Organic Cosolvents. Biotechnol. Bioeng. 1996, 49, 87-92.
45. Ferrer, M.; Cruces, M. A.; Bernabé, M.; Ballesteros, A.; Plou, F. J. Lipase-Catalyzed Regioselective Acylation of Sucrose in Two-Solvent Mixtures. Biotechnol. Bioeng. 1999, 65, 10-16.
46. Therisod, M.; Klibanov, A. M. Facile Enzymatic Preparation of Monoacylated Sugars in Pyridine. J. Am. Chem. Soc. 1996, 108, 5638-5640.
47. Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. Protease-Catalyzed Regioselective Esterification of Sugars and Related Compounds in Anhydrous Dimethylformamide. J. Am. Chem. Soc. 1988, 110, 584-589.
48. Griebenow, K.; Klibanov, A. M. Can Conformational Changes Be Responsible for Solvent and Excipient Effects on the Catalytic Behavior of Subtilisin Carlsberg in Organic Solvents. Biotechnol. Bioeng. 1995, 53, 351-362.
49. Kwon, O. H.; Imanishi, Y.; Ito, Y. Catalytic Activity and Conformation of Chemically Modified Subtilisin Carlsberg in Organic Media. Biotechnol. Bioeng. 1999, 66, 265-270.
50. Laane, C.; Boeren, S.; Vos, K.; Veeger, C. Roles for Optimization of Biocatalysis in Organic Solvents. Biotechnol. Bioeng. 1987, 30, 81-87.
51. Okahata, Y.; Mori, T. Lipid-Coated Enzymes as Efficient Catalysts in Organic Media. Trends Biotechnol. 1997, 15, 50-54.
52. Huang, S. Y.; Chang, H. L. Kinetic Study on the Esterification of Geraniol and Acetic Acid in Organic Solvents Using Surfactant-Coated Lipase. J. Chem. Technol. Biotechnol. 1999, 74, 183-187.
53. Kamiya, N.; Kasagi, H. I.; Inoue, M.; Kusunoki, K. Enantioselective Recognition Mechanism of Secondary Alcohol by Surfactant-Coated Lipases in Nonaqueous Media. Biotechnol. Bioeng. 1999, 65, 227-232.
54. Alston, M. J.; Freedman, R. B. A Comparison of Lipase-Catalysed Ester and Lactone Synthesis in Low-Water Systems: Analysis of Optimum Water Activity. Biotechnol. Bioeng. 2002, 77, 641-650.
55. Alston, M. J.; Freedman, R. B. The Water-Dependence of the Catalytic Activity of Bilirubin Oxidase Suspensions in Low-Water Systems. Biotechnol. Bioeng. 2002, 77, 651-657.