Mechanistic investigations of lipase-catalyzed degradation of polycarbonate in organic solvents

Enzyme and Microbial Technology

Volumn 48, Issue 1, 2011, Pages 71-79

  Artham, Trishul ^a   Mohanalakshmi, N ^a   Paragi Vedanthi, Padma Priya ^a   Doble, Mukesh ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Biodegradation; Bisphenol A; Lipases; Molecular dynamics; Organic solvents; Polycarbonate

Indexed keywords

CANDIDA; CHLORINE COMPOUNDS; DEGRADATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GEL PERMEATION CHROMATOGRAPHY; LIPASES; MOLECULAR DYNAMICS; ORGANIC SOLVENTS; PHENOLS; POLYCARBONATES; YEAST;

BIS-PHENOL A; CANDIDA ANTARCTICA; DEGRADATION MECHANISM; DEGRADATION PRODUCTS; ENGINEERING THERMOPLASTICS; MECHANISTIC ASPECTS; NOVEL METHODOLOGY; POLY(BISPHENOL A CARBONATE);

BIODEGRADATION;

4,4' ISOPROPYLIDENEDIPHENOL; ASPARTIC ACID; CHLOROFORM; GLUTAMIC ACID; HISTONE; ORGANIC SOLVENT; PHENOL DERIVATIVE; POLY (BISPHENOL A CARBONATE); POLYCARBONATE; SERINE; TETRAHYDROFURAN; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIODEGRADATION; CANDIDA ANTARCTICA; CANDIDA RUGOSA; CATALYSIS; CHEMICAL BOND; CONTROLLED STUDY; DEGRADATION; GEL PERMEATION CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MISCIBILITY; MOLECULAR DYNAMICS; NONHUMAN; PANCREAS; SWINE;

CANDIDA ANTARCTICA; CANDIDA RUGOSA; SUS;

EID: 78149416149     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2010.09.011     Document Type: Article

References (40)

1. Beale A. Reengineering resins-polycarbonate and polyamide. 24th Annual World Petrochemicals Coference 2009.
2. Watanabe M., Matsuo Y., Matsushita T., Inomata H., Miyake T., Hironaka K. Chemical recycling of polycarbonate in high pressure high temperature steam at 573K. Polym Degrad Stab 2009, 94:2157-2162.
3. Artham T., Doble M. Fouling and degradation of polycarbonate in seawater: field and lab studies. J Polym Environ 2009, 17:170-180.
4. Artham T., Doble M. Biodegradation of physicochemically treated polycarbonate by fungi. Biomacromolecules 2010, 11:20-28.
5. Calil M., Gaboardi F., Bardi M., Rezende M., Rosa D. Enzymatic degradation of poly (e{open}-caprolactone) and cellulose acetate blends by lipase and α-amylase. Polym Test 2007, 26:257-261.
6. Suyama T., Tokiwa Y. Enzymatic degradation of an aliphatic polycarbonate, poly(tetramethylene carbonate). Enzyme Microb Technol 1997, 20:122-126.
7. Sivalingam G., Madras G. Dynamics of lipase catalyzed enzymatic degradation of poly(bisphenol-A carbonate). J Appl Polym Sci 2004, 91:2391-2396.
8. Cambou B., Klibanov A. Preparative production of optically active esters and alcohols using esterase-catalyzed stereospecific transesterification in organic media. J Am Chem Soc 1984, 106:2687-2692.
9. Kobayashi S., Uyama H., Takamoto T. Lipase-catalyzed degradation of polyesters in organic solvents. A new methodology of polymer recycling using enzyme as catalyst. Biomacromolecules 2000, 1:3-5.
10. Takamoto T., Shirasaka H., Uyama H., Kobayashi S. Lipase-catalyzed hydrolytic degradation of polyurethane in organic solvent. Chem Lett 2001, 30:492-493.
11. Abramowicz D.A., Keese C.R. Enzymatic transesterifications of carbonates in water-restricted environments. Biotechnol Bioeng 1989, 33:149-156.
12. Pencreac'h G., Baratti J.C. Hydrolysis of p-nitrophenyl palmitate in n-heptane by the Pseudomonas cepacia lipase: a simple test for the determination of lipase activity in organic media. Enzyme Microb Technol 1996, 18:417-422.
13. Grochulski P., Bouthillier F., Kazlauskas R., Serreqi A., Schrag J., Ziomek E., et al. Analogs of reaction intermediates identify a unique substrate binding site in Candida rugosa lipase. Biochemistry 1994, 33:3594-3600.
14. Uppenberg J., Oehrner N., Norin M., Hult K., Kleywegt G., Patkar S., et al. Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols. Biochemistry 1995, 34:16838-16851.
15. Hermoso J., Pignol D., Kerfelec B., Crenon I., Chapus C., Fontecilla-Camps J. Lipase activation by nonionic detergents. J Biol Chem 1996, 271:18007-18016.
16. Berman H., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., et al. The protein data bank. Nucleic Acids Res 2000, 28:235-242.
17. Bendler J. Conformational origin of glassy-state relaxation and ductility in aromatic polycarbonates. Comput Theor Polym Sci 1998, 8:83-92.
18. Dybal J., Schmidt P., Baldrian J., Kratochvil J. Ordered structures in polycarbonate studied by infrared and Raman spectroscopy. Wide-angle X-ray scattering, and differential scanning calorimetry. Macromolecules 1998, 31:6611-6619.
19. VEGA SUPER CLUSTER, http://hpce.iitm.ac.in/website/Vega.html.
20. Berendsen H.J.C., van der Spoel D., Van Drunen R. GROMACS: a message-passing parallel molecular dynamics implementation. Comput Phys Commun 1995, 91:43-56.
21. Lindahl E., Hess B., van der Spoel D. GROMACS 3.0: a package for molecular simulation and trajectory analysis. J Mol Model 2001, 7:306-317.
22. Hess B., Bekker H., Berendsen H., Fraaije J. LINCS: a linear constraint solver for molecular simulations. J Comput Chem 1997, 18:1463-1472.
23. Morris G., Goodsell D., Halliday R., Huey R., Hart W., Belew R., et al. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998, 19:1639-1662.
24. Huey R., Morris G., Olson A., Goodsell D. A semiempirical free energy force field with charge-based desolvation. J Comput Chem 2007, 28:1145-1152.
25. Wallace A.C., Laskowski R.A., Thornton J.M. LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Protein Eng 1995, 8:127-134.
26. Gorman L.A., Dordick J.S. Organic solvents strip water off enzymes. Biotechnol Bioeng 1992, 39:392-397.
27. Jang B.N., Wilkie C.A. The thermal degradation of bisphenol A polycarbonate in air. Thermochim Acta 2005, 426:73-84.
28. Heymans N. FT i.r. investigation of structural modification of polycarbonate during thermodynamical treatments. Polymer 1997, 38:3435-3440.
29. Bair H.E., Falcone D.R., Hellman M.Y., Johnson G.E., Kelleher P.G. Hydrolysis of polycarbonate to yield BPA. J Appl Polym Sci 1981, 26:1777-1786.
30. Heymans N., Dequenne B. Relationship between conformation and enthalpy or volume relaxation in polycarbonate. Polymer 2001, 42:5337-5342.
31. Schmidt P., Dybal J., Turska E., Kulczycki A. Conformational structure of bisphenol A polycarbonate studied by infra-red spectroscopy. Polymer 1991, 32:1862-1866.
32. Okajima S., Kondo R., Toshima K., Matsumura S. Lipase-catalyzed transformation of poly(butylene adipate) and poly(butylene succinate) into repolymerizable cyclic oligomers. Biomacromolecules 2003, 4:1514-1519.
33. Nerin C., Fernandez C., Domeno C., Salafranca J. Determination of potential migrants in polycarbonate containers used for microwave ovens by high-performance liquid chromatography with ultraviolet and fluorescence detection. J Agric Food Chem 2003, 51:5647-5653.
34. Okamoto M. DVD substrate application for polycarbonate end-capped with 4-α-cumylphenol. J Appl Polym Sci 2003, 88:404-406.
35. Trodler P, Pleiss J. Modeling structure and flexibility of Candida antarctica lipase B in organic solvents. BMC Struct Biol 2008, 8:9.
36. Grunwald P., Hansen K., Remus M. Enhanced heat stability of enzymes in apolar organic solvents. Indian J Chem 1993, 32 B:70-72.
37. Broos J., Visser A., Engbersen J., Verboom W, van Hoek A, Reinhoudt D Flexibility of enzymes suspended in organic solvents probed by time-resolved fluorescence anisotropy. Evidence that enzyme activity and enantioselectivity are directly related to enzyme flexibility. J Am Chem Soc 1995, 117:12657-12663.
38. Rao H.V., Peter J.H., Alan D.P., Alasdair R.M. Relationship between water activity and catalytic activity of lipases in organic media. Eur J Biochem 1994, 222:461-466.
39. Hedstrom L. Serine protease mechanism and specificity. Chem Rev 2002, 102:4501.
40. Monecke P., Friedemann R., Naumann S., Csuk R. Molecular modelling studies on the catalytic mechanism of Candida rugosa lipase. J Mol Model 1998, 4:395-404.