Chapter 4 Cutinases:. Properties and Industrial Applications

Advances in Applied Microbiology

Volumn 66, Issue , 2009, Pages 77-95

  Pio, Tatiana Fontes ^a   Macedo, Gabriela Alves ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLESTERASE; CUTINASE; POLYMER;

BIOREMEDIATION; BIOTECHNOLOGY; CHEMISTRY; ECOSYSTEM RESTORATION; ENZYMOLOGY; ESTERIFICATION; FOOD HANDLING; FUNGUS; METABOLISM; METHODOLOGY; REVIEW; TEXTILE INDUSTRY;

BIODEGRADATION, ENVIRONMENTAL; BIOTECHNOLOGY; CARBOXYLIC ESTER HYDROLASES; ENVIRONMENTAL REMEDIATION; ESTERIFICATION; FOOD TECHNOLOGY; FUNGI; POLYMERS; TEXTILE INDUSTRY;

EID: 59349095484     PISSN: 00652164     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2164(08)00804-6     Document Type: Review

References (91)

1. Ahmed J.I. Trans"-fixed?. Food Sci. Technol. Today 9 (1995) 228-231
2. Alisch M., Feuerhack A., Blosfeld A., Andreaus J., and Zimmermann W. Polyethylene terephthalate fibers by esterases from actinomycete isolate. Biocatal. Biotransform. 22 (2004) 347-352
3. Andersen A., Svendsen A., Vind J., Lassen S.F., Hjort C., Borch K., and Patkar S.A. Studies of ferulic acid esterase activity in fungal lipases and cutinases. Colloids Surf. 26 (2002) 47-55
4. Ballesteros A., Bornscheuer U., Capewell A., Combes D., Condoret J.S., König K., Kolisis F.N., Marty A., Menge U., Scheper T., Stamatis H., and Xenakis A. Enzymes in non-conventional phases. Biocatal. Biotransform. 13 (1995) 1-42
5. Barlas M.E. Toxicological assessment of biodegraded malathion in albino mice. Bull. Environ. Contam. Toxicol. 57 (1996) 705-712
6. Barros D.P.C., Fonseca L.P., and Cabral J.M.S. Cutinase-catalyzed biosynthesis of short chain alkyl esters. J. Biotechnol. 131 (2007) 109-110
7. Bastioli C. Starch-polymer composites. In: Scott G., and Gilead D. (Eds). Degradable Polymers, Principles and Applications (1995), Chapman & Hall, London 112-133
8. Borreguero I., Carvalho C.M.L., Cabral J.M.S., Sinisterra J.V., and Alcántara A.R. Enantioselective properties of Fusarium solani pisi cutinase on transesterification of acyclic diols: Activity and stability evaluation. J. Mol. Catal. B: Enzym. 11 (2001) 613-622
9. Breccia J.D., Krook M., Ohlin M., and Hatti-Kaul R. The search for a peptide ligand targeting the lipolytic enzyme cutinase. Enzyme Microb. Technol. 33 (2003) 244
10. Brenda: The Comprehensive Enzyme Information System. Assessed online as. http://www.brenda-enzymes.info
11. Campbell M.K. Bioquímica. 3rd ed. (2000), Artmed Editora Ltda, Porto Alegre
12. Canadian Patents Database. Assessed online as. http://patents.ic.gc.ca
13. Carvalho C.M.L., Aires-Barros M.R., and Cabral J.M.S. Cutinase: From molecular level to bioprocess development. Biotechnol. Bioeng. 60 (1999) 17-34
14. Carvalho C.M.L., Aires-Barros M.R., and Cabral J.M.S. Kinetics of cutinase catalyzed transesterification in AOT reversed micelles: Modeling of a batch stirred tank reactor. J. Biotechnol. 81 (2000) 1-13
15. Carvalho P.O., Calafatti S.A., Marassi M., Silva D.M., Contesini F.J., Bizaco R., and Macedo G.A. Potencial de biocatálise enantiosseletiva de lipases microbianas. Quim. Nova 28 (2005) 614-621
16. Carvalho C.M.L., Serralheiro M.L.M., Cabral J.M.S., and Aires-Barros M.R. Application of factorial design to the study of transesterification reactions using cutinase in AOT-reversed micelles. Enzyme Microb. Technol. 21 (1997) 117-123
17. Casey J., and Macrae A. Biotechnology and the oleochemical industry. Inform. 3 (1992) 203-207
18. Castro H.F., Mendes A.A., Santos J.C., and Aguiar C.L. Modificação de óleos e gorduras por biotransformação. Quim. Nova. 27 (2004) 146-156
19. Castro H.F., Oliveira P.C., and Pereira E.B. Evaluation of different approaches for lipase catalyzed synthesis of citronellyl acetate. Biotechnol Lett. 19 (1997) 229-232
20. Chambers W.H. Organophosphorous compounds: An overview. In: Chambers J.E., and Levi P.E. (Eds). Organophosphates, Chemistry, Fate, and Effects (1992), Academic Press, San Diego 3-17
21. Chang B.V., Yang C.M., Cheng C.H., and Yuan S.Y. Biodegradation of phthalate esters by two bacteria strains. Chemosphere 55 (2004) 533-538
22. Claon P.A., and Akoh C.C. Effect of reaction parameters on SP435 lipase-catalyzed synthesis of citronellyl acetate in organic solvent. Enzyme Microb. Technol. 16 (1994) 835-838
23. Clauss J. Interesterificação de Óleo de Palma. Óleos & Grãos 5 (1996) 31-37
24. Creveld L.D., Meijberg W., Berendsen H.J.C., and Pepermans H.A.M. SDS studies of Fusarium solani pisi cutinase: Consequences for stability in the presence of surfactants. Biophys. Chem. 92 (2001) 61-75
25. Croteau R. Fragrance and Flavor Substances. (1980), D&PS Verlag, Germany
26. Dalla-Vecchia R., Nascimento M.G., and Soudi V. Aplicações sintéticas de lipases imobilizadas em polímeros. Quím. Nova. 27 (2004) 623-630
27. Degani O., Gepstein S., and Dosoretz C.G. Potential use of cutinase in enzymatic scouring cotton fiber cuticle. Appl. Biochem. Biotechnol. 102 (2002) 277-289
28. Doi Y. Microbial Polyesters. (1990), VCH Publishers, New York
29. Egmond M.R., and De Vlieg J. Fusarium solani pisi Cutinase. Biochem. 82 (2000) 1015-1021
30. Espinoza M.C.F., and Villeneuve P. Phenolic Acids Enzymatic Lipophilization. J. Agric. Food Chem. 53 (2005) 2779-2787
31. European Patent Office. Assessed online as. http://www.ep.espacenet.com/?locale=en_ep
32. Faber K. Biotransformations in Organic Chemistry. 4th ed. (2000), Springer-Verlag, New York
33. Ferreira B.S., Calado C.R.C., Keulen F., Fonseca L.P., Cabral J.M.S., and Fonseca M.M.R. Recombinant Saccharomyces cerevisiae strain triggers acetate production to fuel biosynthetic pathways. J. Biotechnol. 109 (2004) 159-167
34. Fett W.F., Gerard H.C., Moreau R.A., Osman S.F., and Jones L.E. Screening of nonfilamentous bacteria for production of cutin-degrading enzymes. Appl. Environ. Microbiol. 58 (1992) 2123-2130
35. Filipsen J.A.C., Appel A.C.M., Van Der Hidjen H.T.W.M., and Verrips C.T. Mechanism of removal of immobilized triacylglycerol by lipolytic enzymes in a sequential laundry wash process. Enzyme Microb. Technol. 23 (1998) 274-280
36. Fischer-Colbrie G., Heumann S., Liebminger S., Almansa E., Cavaco-Paulo A., and Gubitz G.M. New enzymes with potential for pet surface modification. Biocatal. Biotransform. 22 (2004) 341-346
37. Galloway T., and Handy R. Immunotoxicity of organophosphorus pesticides. Ecotoxicology 12 (2003) 345-363
38. Gandhi N.N. Applications of lipases. J. Am. Oil Chem. Soc. 74 (1997) 621-633
39. Garcia S., Vidinha P., Arvana H., Silva M.D.R.G., Ferreira M.O., Cabral J.M.S., Macedo E.A., Harper N., and Barreiros S.J. Cutinase activity in supercritical and organic media: Water activity, solvatation and acid-base effects. Supercrit. Fluids. 35 (2005) 62-69
40. Gonçalves L.A.G. Óleos e Grãos 5 (1996) 27
41. Gonçalves A.M., Schacht E., Matthjis G., Aires-Barros M.R., Cabral J.M.S., and Gil M.H. Stability studies of a recombinant cutinase immobilized to dextran and derivatized silica supports. Enzyme Microb. Technol. 24 (1999) 60-66
42. Gunstone F.D. What else besides commodity oils and fats?. Fett-Lipid 101 (1999) 124-130
43. Hammond E.G., and Glatz B.A. In: Kling R.D., and Cheetham P.S.J. (Eds). Food Biotechnology Vol. 2 (1988), Elsevier, Amsterdam 173-217
44. Hills G. Industrial use of lipases to produce fatty acid esters. Eur. J. Lipid Sci. Technol. 105 (2003) 601-607
45. Hunsen M., Azim A., Mang H., Wallner S.R., Ronkvist A., Xie W., and Gross R. A cutinase with polyester synthesis activity. Macromolecules 40 (2007) 148-150
46. Indeerjeet K., Mathur R.P., Tandon S.N., and Prem D. Identification of metabolites of malathion in plants, water and soil by CG-MS. Biomed. Chromatogr. 11 (1997) 352-355
47. John V.T., and Abraham G. Lipase catalysis and its applications. In: Dodrick J.S. (Ed). Biocatalysis for Industry (1991), Plenum Press, New York 193-217
48. Karra-Chaabouni M., Pulvin S., Touraud D., and Thomas D. Enzymatic synthesis of geraniol esters in a solvent-free system by lipases. Biotechnol. Lett. 18 (1996) 1083-1088
49. Kavlock R., Boekelheide K., Chapin R., Cunningham M., Faustman E., Foster P., Golub M., and Henderson R. NTP center for the evaluation of risks to human reproduction: phtalates expert panel report on the reproductive and developmental toxicity of di-it n-hexyl phthalate. Reprod. Toxicol. 16 (2002) 709-719
50. Kerry N.L., and Abbey M. Red wine and fractionated phenolic compounds prepared from red wine inhibit low density lipoprotein oxidation in vitro. Atherosclerosis 135 (1997) 93-102
51. Klibanov A.M. Enzymatic catalysis in anhydrous organic solvents. Trends Biochem. Sci. 14 (1989) 141-144
52. Klibanov A.M. Improving enzymes by using them in organic solvents. Nature 409 (2001) 241-246
53. Kolattukudy P.E. Cutinases from fungi and pollen. In: Borgstrom B., and Brockman T. (Eds). Lipases (1984), Elsevier Publishing, Amsterdam 471-504
54. Krishina S.H. Developments and trends in enzyme catalysis in nonconventional media. Biotechnol. Adv. 20 (2002) 239-267
55. Larsson K.M., Adlercreutz P., and Mattiasson B. Enzymatic catalysis in microemulsions: Enzyme reuse and product recovery. Biotechnol. Bioeng. 36 (1990) 135-141
56. Leal M.C.M.R., Cammarota M.C., Freire D.M.G., and Sant'Anna Jr. G.L. Hydrolytic enzymes as coadjuvants in the anaerobic treatment of dairy wastewaters. Braz. J. Chem. Eng. 19 (2002) 175-180
57. Lie E., and Molin G. In: Martin A.M. (Ed). Bioconversion of Waste Materials to Industrial Products (1991), Elsevier Applied Science, New York
58. Lima J.R., and Nassu R.T. Substitutos de Gorduras em Alimentos: Características e Aplicações. Quim. Nova. 19 (1996) 127-134
59. Longo M.A., and Sanromán M.A. Production of food aroma compounds: Microbial and enzymatic methodologies. Food Technol. Biotechnol. 44 (2006) 335-353
60. Macedo G.A., and Pio T.F. A rapid screening method for cutinase producing microorganisms. Braz. J. Microbiol. 36 (2005) 388-394
61. Mannesse M.L.M., Cox R.C., Koops B.C., Verheij H.M., Haas G.H., Egmond M., Van Der Hijden H.T.W., and Vlieg J. Cutinase from Fusarium solani pisi hydrolyzing triglyceride analogues. Effect of acyl chain length and position in the substrate molecule on activity and enantioselectivity. Biochemistry 34 (1995) 6400-6407
62. Masse L., Kennedy K.J., and Chou S. Testing of alkaline and enzymatic pretreatment for fat particles in slaughterhouses wastewater. Bioresour. Technol. 77 (2001) 145-155
63. Masson W., Loftsson T., and Haraldsson G.G. Marine lipids for products, soft compounds and other pharmaceutical applications. Pharmacies. 55 (2000) 172-177
64. Matamá T., Silva C., O'Neill A., Casal M., Soares C., Gubitz G.M., and Cavaco-Paulo A. Improving synthetic fibers with enzymes. 3rd. International Conference on Textile Biotechnology (abstract 5) (2004)
65. Mayer J.M., and Kaplin D.L. Biodegradable materials: Balancing degradability and performance. Trends Polym. Sci. 2 (1994) 227-235
66. Melo E.P., Costa S.M.B., Cabral J.M.S., Fojan P., and Petersen S.B. Cutinase-AOT interactions in reverse micelles: The effect of 1-hexanol. Chem. Phys. Lipids 124 (2003) 37-47
67. Muderhwa J., Pina M., and Graille J. Aptitude à la transesterification de quelques lipases regioselectives 1-3. J. Oléagineux. 43 (1988) 385-392
68. Mueller R.J. Biological degradation of synthetic polyesters-Enzymes as potential catalysists for polyester recycling. Process Biochem. 41 (2006) 2124-2128
69. Mukherjee K.D. Lipase-catalyzed reactions for modification of fats and other lipids. Biocatalysis. 3 (1990) 277-293
70. Murphy C.A., Cameron J.A., Huang S.J., and Vinopal R.T. Fusarium polycaprolactone depolimerase is cutinase. Appl. Environ. Microbiol. 62 (1996) 456-460
71. Pandey A., Benjamin S., Soccol C.R., Nigam P., Krieger N., and Soccol V.T. The realm of microbial lipases in biotechnology. Biotechnol. Appl. Biochem. 29 (1999) 119-131
72. Paques F.W., and Macedo G.A. Lipases de látex vegetais: propriedades e aplicações industriais. Quím. Nova. 29 (2006) 93-99
73. Petersen S.B., Johnson P.H., Fojan P., Petersen E.I., Petersen M.T.N., Hansen S., Ishak R.J., and Hough R.J. Protein engineering the surface of enzymes. J. Biotechnol. 66 (1998) 11-26
74. Pio T.F., and Macedo G.A. Optimizing the production of cutinase by Fusarium oxysporum using response surface methodology. J. Ind. Microbiol. Biotechnol. 10 (2007) 101-111
75. Regado M.A., Cristóvão B.M., Moutinho C.G., Balcão V.M., Aires-Barros R., Ferreira J.P.M., and Malcata F.X. Flavour development via lipolysis of milk fat: Changes in free fatty acid pool. Int. J. Food Sci. Technol. 42 (2007) 961-968
76. Sebastião M.J., Cabral J.M.S., and Aires-Barros M.R. Synthesis of fatty acid esters by a recombinant cutinase in reversed micelles. Biotechnol. Bioeng. 42 (1993) 326-332
77. Silva F.A.M., Borges F., Guimarães C., Lima J.L.F.C., Matos C., and Reis S. Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J. Agric. Food Chem. 48 (2000) 2122-2126
78. Silva C.M., Carneiro F., O'Neill A., Fonseca L.P., Cabral J.M.S., Guebitz G., and Cavaco-Paulo A. Cutinase-A new tool for biodegradation of synthetic fibers. J. Polym. Sci. 43 (2005) 2448-2450
79. Soares C.M., Teixeira V.H., and Baptista A.M. Protein structure and dynamics in no aqueous solvents: Insights from molecular dynamics simulation studies. Biophys. J. 84 (2003) 1628-1641
80. Stamatis H., Kolisis F.N., and Xenakis A. Enantiomeric selectivity of a lipase from Penicillium simplicissimum in the esterification of menthol in microemulsions. Biotechnol. Lett. 15 (1993) 471-476
81. Stamatis H., Sereti V., and Kolisis F.M. Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants. J. Am. Oil Chem. Soc. 12 (1999) 1505-1510
82. Sung H.H., Kao W.Y., and Su Y.J. Effects and toxicity of phthalate esters to haemocytes of giant fresh water prawn, Macrobacillum rosenbergii. Aquat. Toxicol. 64 (2003) 25-37
83. Ternström T., Svendsen A., Akke M., and Adlercreutz P. Unfolding and inactivation of cutinases by AOT and guanidine hydrochloride. Biochim. Biophys. Acta. 1748 (2005) 74-83
84. Vandamme E.J., and Soetaert W. Bioflavours and fragrances via fermentation and biocatalysis. J. Chem. Technol. Biotechnol. 77 (2002) 1323-1332
85. Vertommen M.A.M.E., Nierstrasz V.A., Van Der Veer M., and Warmoeskerken M.M.C.G. Enzymatic surface modification of poly(ethylene terephtalate). J. Biotechnol. 120 (2005) 376-386
86. Villeneuve P., Muderwha J.M., Graille J., and Hass M.J. Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biologic approach. J. Mol. Catal. B: Enzym. 4 (2000) 113-148
87. Walz I., and Schwack W. Cutinase inhibition by means of insecticidal organophosphates and Carbamates. Eur. Food Res. Technol. 225 (2007) 593-601
88. Walz I., and Schwack W. Cutinase inhibition by means of insecticidal organophosphates and Carbamates Part 2: Screening of representative insecticides on cutinase activity. Eur. Food Res. Technol. 226 (2008) 1135-1143
89. Welsh W.W., Murray W.D., and Williams R.E. Microbiological and enzymatic production of flavor and fragance chemicals. Crit. Rev. Biotechnol. 9 (1989) 105-169
90. Willis W.M., and Maragoni A.G. Biotechnology & genetic engineering reviews. Biotechnol. Genetic Eng. Rev. 16 (1999) 141-175
91. Yoon M., Kellis J., and Poulouse A.J. Enzymatic modification of polyester. AATCC 2 (2002) 33-36