Enzymatic synthesis of poly(ε-caprolactone): Thermal properties, recovery, and reuse of lipase B from Candida antarctica immobilized on macroporous acrylic resin particles

Polymer Bulletin

Volumn 70, Issue 5, 2013, Pages 1543-1552

  Poojari, Yadagiri ^a   Beemat, Jaspreet S ^b   Clarson, Stephen J ^b  

^a OHIO STATE UNIVERSITY   (United States)

^b University of Cincinnati   (United States)

Author keywords

Candida antarctica lipase B; Enzyme recycle; Poly( caprolactone); Thermal stability

Indexed keywords

CANDIDA; ISOMERS; POLYDISPERSITY; RECOVERY; RESINS; THERMODYNAMIC PROPERTIES; THERMODYNAMIC STABILITY; YEAST;

CANDIDA ANTARCTICA LIPASE B; CAPROLACTONE; LIPASE B FROM CANDIDA ANTARCTICA; MECHANICAL AGITATION; POLY (EPSILONCAPROLACTONE); POLY(E-CAPROLACTONE); POLYDISPERSITY INDICES; WEIGHT-AVERAGE MOLECULAR WEIGHT;

ENZYME IMMOBILIZATION;

EID: 84884346452     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-013-0916-1     Document Type: Article

References (27)

1. Brady L, Brzozowski AM, Derewenda ZS, Dodson E, Dodson G, Tolley S, Turkenburg JP, Christiansen L, Huge-Jensen B, Norskov L, Thim L, Menge U (1990) A serine protease triad forms the catalytic centre of a triacylglycerol lipase. Nature 43:767-770
2. Mateo C, Palomo JM, Fernandez-Lorente G, Guisán JM, Fernandez-Lafuente R (2007) Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb Technol 40:1451-1463
3. Salis A, Meloni D, Ligas S, Casula MF, Monduzzi M, Solinas V, Dumitriu E (2005) Physical and chemical adsorption of Mucor javanicus lipase on SBA-15 mesoporous silica. Synthesis, structural characterization, and activity performance. Langmuir 21:5511-5516
4. David AE, Wang NS, Yang VC, Yang AJ (2006) Chemically surface modified gel (CSMG): an excellent enzyme-immobilization matrix for industrial processes. J Biotechnol 125:395-407
5. Knezevic Z, Milosavic N, Bezbradica D, Jakovljevic Z, Prodanovic R (2006) Immobilization of lipase from Candida rugosa on Eupergit-C supports by covalent attachment. Biochem Eng J 30:269-278
6. Ragheb AM, Brook MA, Hrynyk M (2005) Highly active, lipase silicone elastomers. Biomaterials 26:1653-1664
7. Chen B, Hu J, Miller EM, Xie W, Cai M, Gross RA (2008) Candida antarctica lipase B chemically immobilized on epoxy-activated micro-and nanobeads: catalysts for polyester synthesis. Biomacromolecules 9:463-471
8. Luckarift HR, Spain JC, Naik RR, Stone MO (2004) Enzyme immobilization in a biomimetic silica support. Nat Biotechnol 22:211-213
9. Reetz MT, Zonta A, Simpelkamp J (1996) Efficient immobilization of lipases by entrapment in hydrophobic sol-gel materials. Biotechnol Bioeng 49:527-534
10. Bishwabhusan S, Brandstadt KF, Lane TH, Gross RA (2005) ''Sweet silicones'': biocatalytic reactions to form organosilicon carbohydrate macromers. Org Lett 18:3857-3860
11. Moris F, Gotor V (1993) A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction. J Org Chem 58:653-660
12. Bertinotti A, Carrea G, Ottolina G, Riva S (1994) Regioselective esterification of polyhydroxylated steroids by Candida antarctica lipase B. Tetrahedron 50:13165-13172
13. Hansen TV, Waagen V, Partli V, Anthosen HW, Anthosen T (1995) Co-solvent enhancement of enantioselectivity in lipase-catalysed hydrolysis of racemic esters. A process for production of homochiral C-3 building blocks using lipase B from Candida antarctica. Tetrahedron Asymmetry 6:499-504
14. Frykman H, Ohmer N, Norin T, Hult K (1993) S-ethyl thiooctanoate as acyl donor in lipase catalysed resolution of secondary alcohols. Tetrahedron Lett 34:1367-1370
15. Arroyo M, Sinisterra J (1994) High enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized lipase from Candida antarctica: a mechanistic approach. J Org Chem 59:4410-4417
16. Gross RA, Kumar A, Kalra B (2001) Polymer synthesis by in vitro enzyme catalysis. Chem Rev 101:2097-2124
17. Poojari Y, Palsule AS, Cai M, Clarson SJ, Gross RA (2008) Synthesis of organosiloxane copolymers using enzymatic polyesterification. Eur Polym J 44:4139-4145
18. Poojari Y, Clarson SJ (2009) Lipase catalyzed synthesis of poly(e-caprolactone)-poly(dimethylsiloxane)-poly(e-caprolactone) triblock copolymers. Silicon 1:165-172
19. Poojari Y, Clarson SJ (2009) Lipase catalyzed synthesis of silicone polyesters. Chem Comm 6834-6835
20. Poojari Y, Clarson SJ (2010) Lipase catalyzed synthesis and thermal properties of poly(dimethylsiloxane)-poly(ethylene glycol) amphiphilic block copolymers. J Inorg Organomet Polym 20:46-52
21. Mei Y, Miller L, Gao W, Gross RA (2003) Imaging the distribution and secondary structure of immobilized enzymes using infrared microspectroscopy. Biomacromolecules 4:70-74
22. Zaks A, Klibnov AM (1985) Enzyme-catalyzed processes in organic solvents. Proc Natl Acad Sci 82:3192-3196
23. Wong C-H (1989) Enzymatic catalysts in organic synthesis. Science 244:1145-1152
24. Kumar A, Gross RA (2000) Candida antartica lipase B catalyzed polycaprolactone synthesis: effects of organic media and temperature. Biomacromolecules 1:133-138
25. Namekawa S, Suda S, Uyama H, Kobayashi S (1999) Lipase-catalyzed ring-opening polymerization of lactones to polyesters and its mechanistic aspects. Int J Biol Macromol 25:145-151
26. Kobayashi S, Uyama H, Namekawa S (1995) Enzymatic ring-opening polymerization of lactones to polyesters by lipase catalyst: unusually high reactivity of macrolides. Bull Chem Soc Jpn 68:56-61
27. Wiemann LO, Nieguth R, Eckstein M, Naumann M, Thum O, Ansorge-Schumacher MB (2009) Composite particles of novozyme 435 and silicone: advancing technical applicability of macroporous enzyme carriers. ChemCatChem 1:455-462