Tyrosinase-catalysed grafting of food-grade gallates to chitosan: Surface properties of novel functional coatings

Packaging Technology and Science

Volumn 21, Issue 6, 2008, Pages 317-328

  Vartiainen, Jari ^a   Rättö, Marjaana ^a   Lantto, Raija ^a   Nättinen, Kalle ^a   Hurme, Eero ^a  

^a VTT TECHNICAL RESEARCH CENTRE OF FINLAND   (Finland)

Author keywords

Antimicrobial activity; Chitosan; Gallate; Packaging; Plasma; Tyrosinase

Indexed keywords

CHITIN; CHITOSAN; COATINGS; ETHANOL; FLOCCULATION; GRAFTING (CHEMICAL); OXYGEN; PACKAGING MATERIALS; PLASMA APPLICATIONS; PLASMAS; POLYPROPYLENES; POLYSACCHARIDES; PROTECTIVE COATINGS; SURFACE CHEMISTRY; SURFACE PROPERTIES; SURFACE TENSION; SURFACE TREATMENT; SURFACES; WATER VAPOR;

AMINO GROUPS; ANTIMICROBIAL ACTIVITIES; ANTIMICROBIAL ACTIVITY; BACTERIA CELLS; BARRIER LAYERS; BIAXIALLY ORIENTED POLYPROPYLENES; BOPP FILMS; CARBOXYL GROUPS; CHITOSAN COATINGS; CHITOSAN SOLUTIONS; DIRECT CONTACTS; DRY CONDITIONS; ENZYME TYROSINASES; FUNCTIONAL COATINGS; GALLATE; GRAFTING; HUMIDITY CONDITIONS; HYDROPHOBIC; LISTERIA INNOCUA; LOGARITHMIC REDUCTIONS; LOGARITHMIC UNITS; OCTYL GALLATE; PAPER SUBSTRATES; PLASMA ACTIVATIONS; PLASMA TREATMENTS; S. AUREUS; STAPHYLOCOCCUS AUREUS; SURFACE ENERGIES; TRANSMISSION RATES; TYROSINASE; WATER VAPOURS;

AMINES;

BACTERIA (MICROORGANISMS); LISTERIA INNOCUA; NEGIBACTERIA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 55049112734     PISSN: 08943214     EISSN: 10991522     Source Type: Journal    
DOI: 10.1002/pts.813     Document Type: Article

References (36)

1. Rijk R, van Beest M, de Kruijf N et al Active and intelligent packaging systems and the legislative aspects. Food Packag. Bull. 2002; 10(9&10): 2-10.
2. Kubo I, Xiao P, Fujita K. Antifungal activity of octyl gallate: structural criteria and mode of action. Bioorg. Med. Chem. Lett. 2001; 11: 347-350.
3. Fujita K, Kubo I. Antifungal activity of octyl gallate. Int. J. Food Microbiol. 2002; 79: 193-201.
4. Shibata H, Kondo K, Katsuyama R et al. Alkyl gallates, intensifiers of β-lactam susceptibility in methicillin-resistant staphylococcus aureus. Antimicrob. Agents Chemother. 2005; 49(2): 549-555.
5. Kubo I, Kinst-Hori I, Nihei K-I et al. Tyrosinase inhibitors from galls of Rhus javanica leaves and their effects on insects. Z. Naturforsch. 2003; 58c: 719-725.
6. Kahn V, Ben Shalom N, Zakin V. Effect of benzenesulfinic acid on the oxidation of 0-dihydroxy and trihydroxyphenols by mushroom tyrosinase. J. Food Biochem. 1999; 23(3): 263-281.
7. Kahn V, Zakin V. Effect of kojic acid on the oxidation of trihydroxyphenols by mushroom tyrosinase. J. Food Biochem. 1995; 18(6): 427-443.
8. Yalpani M, Johnson F, Robinson LE. Antimicrobial activity of some chitosan derivatives. In Advances in Chitin and Chitosan, Brine CJ, Sandford PA, Zikakis JP (eds). Elsevier Applied Science: London, UK, 1992; 543-555.
9. Muzzarelli RAA, Muzzarelli C. Reactivity of quinones towards chitosan. Trends Glycosci. Glycotechnol. 2002; 14(78): 223-229.
10. Halaouli S, Asther M, Sigoillot JC, Hamdi M, Lomascolo L. Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications. J. Appl. Microbiol. 2006; 100: 219-232.
11. Lenhart JL, Chaubal MV, Payne GF, Barbari TA. Enzymatic modification of chitosan by tyrosinase. In Enzymes in Polymer Synthesis, Gross RA, Kaplan DL, Swift G (eds). American Chemical Society Symposium Series 684: Washington, DC, 1998; 188-198.
12. Aberg CM, Chen T, Olumide A, Raghavan SR, Payne GF. Enzymatic grafting of peptides from casein hydrolysate to chitosan. Potential for valueadded byproducts from food-processing wastes. J. Agric. Food Chem. 2004; 52(4): 788-793.
13. Chen T, Small D, Wu L-Q et al Nature-inspired creation of protein-polysaccharide conjugate and its subsequent assembly onto a patterned surface. Langmuir 2003; 19: 9382-9386.
14. Freddi G, Anghileri A, Sampaio S et al. Tyrosinase-catalyzed modification of Bombyx mori silk fibroin: grafting of chitosan under heterogeneous reaction conditions. J. Biotechnol. 2006; 125(2): 281-294.
15. Sampaio S, Taddei P, Monti P, Buchert J, Freddi G. Enzymatic grafting of chitosan onto Bombyx mori silk fibroin: kinetic and IR vibrational studies. J. Biotechnol. 2005; 116: 21-33.
16. Anghileri A, Lantto R, Kruus K, Arosio C, Freddi G. Tyrosinase-catalyzed grafting of sericin peptides onto chitosan and production of protein-polysaccharide bioconjugates. J. Biotechnol. 2007; 127(3): 508-519.
17. Payne GF, Chen T, Embree HD, Brown EM, Taylor MM. Enzyme-catalyzed gel-formation of gelatin and chitosan. Potential for in situ applications. Biomacromolecules 2003; 24: 2831-2841.
18. Shao L, Kumar G, Lenhart JL, Smith PJ, Payne GF. Enzymatic modification of the synthetic polymer polyhydrostyrene. Enzyme Microb. Technol 1999; 25: 660-668.
19. Wang G, Xu JJ, Ye LH, Zhu JJ, Chen HY. Highly sensitive sensors based on the immobilization of tyrosinase in chitosan. Bioelectrochemistry 2002; 57(1): 33-38.
20. Abdullah J, Ahmad M, Karuppiah N, Heng L-Y, Sidek H. Immobilization of tyrosinase in chitosan film for an optical detection of phenol. Sens. Actuators, B 2006; 114(2): 604-609.
21. Payne GF, Sun W-Q, Sohrabi A. Tyrosinase reaction/chitosan adsorption for selectively removing phenols from aqueous mixtures. Biotechnol. Bioeng. 1992; 40: 1011-1018.
22. Payne GF, Sun W-Q. Tyrosinase reaction and subsequent chitosan adsorption for selective removal of a contaminant from a fermentation recycle stream. Appl. Environ. Microbiol. 1994; 60(2): 397-401.
23. Sun W-Q, Payne GF. Tyrosinase-containing chitosan gels: a combined catalyst and sorbent for selective phenol removal. Biotechnol Bioeng. 1996; 51: 79-86.
24. Bevilaqua JV, Cammarota MC, Freire DMG, Sant'Anna Jr GL. Phenol removal through combined biological and enzymatic treatments. Braz. J. Chem. Eng. 2002; 19(2): 151-158.
25. Ensuncho L, Alvarez-Cuenca M, Legge RL. Removal of aqueous phenol using immobilized enzymes in a bench- and pilot-scale three-phase fluidized bed reactor. Bioprocess Biosyst. Eng. 2005; 27: 185-191.
26. Wu LQ, Chen T, Wallace KK, Vazquez-Duhalt R, Payne GF. Coupling of gas phenols to chitosan using tyrosinase. Biotechnol. Bioeng. 2001; 76(4): 325-332.
27. Mattinen M, Lantto R, Selinheimo E, Kruus K, Buchert J. Oxidation of peptides and proteins by Trichoderma and Agaricus tyrosinases. J. Biotechnol. 2008; 133: 395-402.
28. Selinheimo E, Saloheimo M, Ahola E et al. Production and characterization of a secreted, C-terminally processed tyrosinase from the filamentous fungus Trichoderma reesei. FEBS J. 2006; 273: 4322-4335.
29. Kubo I, Chen QX, Nihei K. Molecular design of anti-browning agents: antioxidative tyrosinase inhibitors. Food Chem. 2003; 81: 241-247.
30. Kubo I. Molecular design of antioxidative and antimicrobial agents. Chemtech 1999; 11: 37-42.
31. Tanford C. The Hydrophobic Effect: Formation of Micelles and Biological Membranes. Wiley: New York, 1980.
32. Kumar G, Bristow JF, Smith PJ, Payne GF. Enzymatic gelation of the natural polymer chitosan. Polymer 2000; 41: 2157-2168.
33. Cao W, Cheng M, Ao Q et al. Physical, mechanical and degradation properties, and schwann cell affinity of cross-linked chitosan films. J. Biomater. Sci. Polym. Ed. 2005; 16(6): 791-807.
34. Vartiainen J, Rättö M, Tapper U, Paulussen S, Hurme E. Surface modification or atmospheric plasma activated BOPP by immobilizing chitosan. Polym. Bull. 2005; 54(4&5): 343-352.
35. Payne GF, Vachoud L, Chen T, Govar CJ. Grafting renewable chemicals to functionalize chitosan. Polym. Prepr. 2000; 41(2): 1870.
36. Liu L, Li Y, Zhang W, Zhang G, Fang Y. Homogeneous graft copolymerization of chitosan with methyl methacrylate by γ-irradiation via a phthaloylchitosan intermediate. Polym. Int. 2004; 53: 1491-1494.