Candida antarctica Lipase B as Catalyst for Cyclic Esters Synthesis, Their Polymerization and Degradation of Aliphatic Polyesters

Journal of Polymers and the Environment - Tập 26 - Trang 396-407 - 2017
Anna Kundys1, Ewa Białecka-Florjańczyk1, Agata Fabiszewska1, Jolanta Małajowicz1
1Department of Chemistry, Faculty of Food Sciences, Warsaw University of Life Sciences (SGGW), Warsaw, Poland

Tóm tắt

Candida antarctica: lipase B (CALB) is the most widely studied enzyme, due to its high selectivity and catalytic activity in organic and polymer synthesis. To avoid organometallic catalysts in the synthesis of biodegradable polyesters, the enzymatic ring-opening polymerization of cyclic esters can be carried out with CALB as a biocatalyst. This paper reviews selected examples of the application of lipases in polymer chemistry covering the synthesis of cyclic ester monomers, linear and star oligomers, as well as well-defined high molar mass polymers with improved mechanical properties. It is shown that by the selection of appropriate conditions of temperature and solvent assortment, CALB effectively catalyzes the polymerization of large size lactones obtaining polyesters with Mn up to 80 kg mol−1. The chemical structure and main applications of described materials are also discussed. As the polymer recycling is an important topic from environmental point of view, we also described the potential applications of CALB in degradation process of aliphatic polyesters.

Tài liệu tham khảo

Gupta R, Kumari A, Syal P, Singh Y (2015) Progr Lipid Res 57:40–54 Uyama H, Kobayashi S (2006) Adv Polym Sci 194:133–158 Taresco V, Creasey RG, Kennon J, Mantovani G, Alexander C, Burley JC, Garnett MC (2016) Polymer 89:41–49 Albertsson AC, Varma IK, Srivasta RK (2009) Polyesters from large lactones In: Dubois P, Coulembier O, Raquez JM (eds) Handbook of ring-opening polymerization, Wiley, Belgium, p 287–306 Numata K, Srivastava RK, Finne-Wistrand A, Albertsson AC, Doi Y, Abe H (2007) Biomacromolecules 8:3115–3125 Malberg S, Finne-Wistrand A, Albertsson AC (2010) Polymer 51(23):5318–5322 Duchiron SW, Pollet E, Givry S, Avérous L (2015) RSC Adv 5:84627–84635 Barrera-Rivera KA, Flores-Carreón A, Martínez-Richa A (2008) J Appl Polym Sci 109:708–719 Henderson LA, Svirkin YY, Gross RA (1996) Macromolecules 29(24):7759–7766 Cao H, Han H, Li G, Yang J, Zhang L, Yang Y, Fang X, Li Q (2012) Int J Mol Sci 13:12232–12241 Ma J, Li Q, Song B, Liu D, Zheng B, Zhang Z, Feng Y (2009) J Mol Catal B 56(2–3):151–157 Ates Z, Thornton PD, Heise A (2011) Polym Chem 2:309–312 Öztürk Düskünkorur H, Bégué A, Pollet E, Phalip V, Güvenilir Y, Avérous L (2015) J Mol Catal B 115: 20–28 Treichel H, de Oliveira D, Mazutti MA, Di Luccio M, Oliveira JV (2010) Food Bioprocess Technol 3(2):182–196 Domínguez de María P, Carboni-Oerlemans C, Tuin B, Bargeman G, van der Meer A, van Gemert R (2005) J Mol Catal B 37(1–6):36–46 Uppenberg J, Patkar S, Bergfors T, Jones TA (1994) J Mol Biol 235(2):790–792 Strzelczyk P, Bujacz GD, Kiełbasiński P, Błaszczyk J (2016) Acta Biochim Pol 63(1):103–109 Li C, Tan T, Zhang H, Feng W (2010) J Biol Chem 285(37):28434–28441 Pleiss J, Fischer M, Peiker M, Thiele C, Schmid RD (2000) J Mol Catal B 10(5):491–508 Martinelle M, Holmquist M, Hult K (1995) Biochim Biophys Acta 1258(3):272–276 Lund IT, Bøckmann PL, Jacobsen EE (2016) Tetrahedron. doi:10.1016/j.tet.2016.02.018 Mouada AM, Taupin D, Lehr L, Yvergnaux F, Porto AL (2016) J Mol Catal B 126:64–68 Ravelo M, Fuente E, Blanco A, Ladero M, García-Ochoa F (2015) Biochem Eng J 101:228–236 Hasegawa S, Azuma M, Takahashi K (2008) J Chem Technol Biotechnol 83:1503–1510 Idris A, Bukhari A (2012) Biotechnol Adv 30:550–563 Mateo C, Palomo JM, Fernandez-Lorente G, Guisan JM, Fernandez-Lafuente R (2007) Enzyme Microb Technol 40:1451–1463 Mei Y, Kumar A, Gross RA (2002) Macromolecules 35(14):5444–5448 Kataoka M, Miyakawa T, Shimizu S, Tanokura M (2016) Appl Microbiol Biotechnol 100:5747–5757 Yang Y, Yu Y, Zhang Y, Liu C, Shi W, Li Q (2011) Process Biochem 46:1900–1908 Kobayashi S (2010) Proc Jpn Acad Ser B Phys Biol Sci 86:338–365 De Miranda AS, Miranda LSM, de Souza ROMA (2015) Biotechnol Adv 33:372–393 Shimotori Y, Nakahachi Y, Inoue K, Miyakoshi T (2007) Flavour Fragr J 22:421–429 Shimotori Y, Sekine K, Miyakoshi T (2007) Flavour Fragr J 22:531–539 Zhang P, Iding H, Cedilote M, Brunner S, Williamson T, Cleary TP (2009) Tetrahedron 20:305–312 Jeon BW, Lee J, Kim HS, Cho DH, Lee H, Chang R, Kim YH (2013) J Biotechnol 168:201–207 Sayed M, Gaber Y, Bornadel A, Pyo SH (2016) Biotechnol Prog 32(1):83–88 Morén AK, Kumar A, Stenhagen G, Holmberg HK (2003) J Dispers Sci Technol 24(1):79–87 Kobayashi S (2006) Macromol Symp 240:178–185 Kaihara S, Fisher JP, Matsumura S (2009) Macromol Biosci 9:613–621 Kumar A, Gross RA (2000) Biomacromolecules 1:133–138 Todea A, Badea V, Nagy L, Kéki S, Boeriu CG, Péter F (2014) Acta Biochim Pol 61(2):205–210 Arumugasamy SK, Ahmad Z (2011) Asia-Pac J Chem Eng 6(3):398–405 Kikuchi H, Uyama H, Kobayashi S (2000) Macromolecules 33(24):8971–8975 Focarete MF, Scandola M, Kumar A, Gross RA (2001) J Polym Sci Part B 39:1721–1729 Yang Y, Ge Y, Zhao H, Shi W, Li Q (2011) Biocatal Biotransform 29(6):337–343 Loeker FC, Duxbury CJ, Kumar R, Gao W, Gross RA, Howdle SM (2004) Macromolecules 37(7):2450–2453 Takamoto T, Uyama H, Kobayashi S (2001) e-Polymers 4:1–6 Gorke JT, Okrasa K, Louwagie A, Kazlauskas RJ, Srienc F (2007) J Biotechnol 132(3):306–313 Piotrowska U, Sobczak M, Oledzka E, Combes C (2016) J Appl Polym Sci. doi:10.1002/APP.43728 Wu C, Zhang Z, Chen C, He F, Zhuo R (2013) Biotechnol Lett 35(10):1623–1630 Inprakhon P, Panlawan P, Pongtharankul T, Marie E, Wiemann LO, Durand A, Sieberb V (2014) Colloids Surf B 113:254–260 He F, Li S, Vert M, Zhuo R (2003) Polymer 44:5145–5151 Matsumura S, Suzuki Y, Tsukada K, Toshima K (1998) Macromolecules 31:6444–6449 He F, Li S, Garreau H, Vert M, Zhuo R (2005) Polymer 46:12682–12688 Shoda S, Uyama H, Kadokawa J, Kimura S, Kobayashi S (2016) Chem Rev 116:2307–2413 Matsumura M, Mabuchi K, Toshima K (1998) Macromol Symp 130(1):285–304 Zhou J, Wang W, Thurecht KJ, Villarroya S, Howdle SM (2006) Macromolecules 39:7302–7305 Hæffner F, Norin T, Hult K (1998) Biophys J 74:1251–1262 Kadokawa J, Kobayashi S (2010) Curr Opin Chem Biol 14:145–153 Hans M, Keul H, Moeller M (2009) Macromol Biosci 9:239–247 Sobczak M (2012) J Appl Polym Sci 125:3602–3609 Bonduelle C, Martin-Vaca B, Bourissou D (2009) Biomacromolecules 10:3069–3073 Kobayashi S, Takeya K, Sudu S, Uyama H (1998) Macromol Chem Phys 199:1729–1736 Cordova A, Iversen T, Hult K, Martinelle M (1998) Polymer 39(25):6519–6524 Poojari Y, Beemat JS, Clarson SJ (2013) Polym Bull 70:1543–1552 Wu WX, Qu L, Liu BY, Zhang WW, Wang N, Yu XQ (2015) Polymer 59:187–193 Hans M, Keul H, Moeller M (2008) Biomacromolecules 9:2954–2962 Poojari Y, Clarson SJ (2009) Silicon 1:165–172 Dai S, Li Z (2008) Biomacromolecules 9:1883–1893 Beyazkilic Z, Lligadas G, Ronda JC, Galià M, Cádiz V (2014) Macromol Chem Phys 215:2248–2259 Yang Y, Zhang J, Wu D, Xing Z, Zhou Y, Shi W, Li Q (2014) Biotech Adv 32:642–651 Kobayashi S, Makino A (2009) Chem Rev 109:5288–5353 Zhang J, Shi H, Wu D, Xing Z, Zhang A, Yang Y, Li Q (2014) Process Biochem 49:797–806 De Geus M, Peeters J, Wolffs M, Hermans T, Palmans ARA, Koning CE, Heise A (2005) Macromolecules 38:4220–4225 Zhang B, Li Y, Wang W, Wang J, Chen X (2011) Polym Bull 67(8):1507–1518 Thurecht KJ, Gregory AM, Villarroya S, Zhou J, Heise A, Howdle SM (2006) Chem Commun 42:4383–4385 Xiao Y, Coulembier O, Koning CE, Heise A, Dubois P (2009) Chem Commun 18:2472–2474 Xue L, Dai S, Li Z (2009) Macromolecules 42:964–972 Skaria S, Smet M, Frey H (2002) Macromol Rapid Commun 23:292–296 Ursu M, Frey H, Neuner I, Thomann R, Rusu M (2004) Rom Rep Phys 56(3):445–452 Kundys A, Plichta A, Florjańczyk F, Zychewicz A, Lisowska P, Parzuchowski P, Wawrzyńska E (2016) Polym Int 65(8):927–937 Ai P, Chen L, Hu D, Chen Y, Li D, Zhang B, Sha K, Wang J (2006) Chin Sci Bull 51(22):2706–2709 Hans M, Keul H, Heise A, Moeller M (2007) Macromolecules 40:8872–8880 Herrera-Kao W, Cervantes-Uc JM, Lara-Ceniceros T, Aguilar-Vega M (2015) Polym Bull 72:441–452 Takwa M, Xiao Y, Simpson N, Malmström E, Hult K, Koning CE, Heise A, Martinelle M (2008) Biomacromolecules 9:704–710 Korzhikov VA, Gusevskaya KV, Litvinchuk EN, Vlakh EG, Tennikova TB (2013) Int J Polym Sci. doi:10.1155/2013/476748 Takwa M, Simpson N, Malmström E, Hult K, Martinelle M (2006) Macromol Rapid Commun 27:1932–1936 Kumar A, Garg K, Gross RA (2001) Macromolecules 34:3527–3533 Veld MAJ, Fransson L, Palmans ARA, Meijer EW, Hult K (2009) Chem Bio Chem 10:1330–1334 Mee L, Helmich F, De Bruijn R, Vekemans JAJM, Palmans ARA, Meijer EW (2006) Macromolecules 39:5021–5027 Uyama H, Kikuchi H, Takeya K, Kobayashi S (1996) Acta Polym 47:357–360 Uyama H, Takeya K, Hoshi N, Kobayashi S (1995) Macromolecules 28(21):7046–7050 Namekawa S, Uyama H, Kobayashi S (1998) Proc Jpn Acad Ser B 74:65–68 Cai J, Hsiao BS, Gross RA (2009) Polym Int 58:944–953 Kumar A, Kalra B, Dekhterman A, Gross RA (2000) Macromolecules 33:6303–6309 De Geus M, Meulen I, Goderis B, Van Hecke K, Dorschu M, Van der Werff H, Koning CE, Heise A (2010) Polym Chem 1:525–533 Jiang Z, Azim H, Gross RA (2007) Biomacromolecules 8:2262–2269 Banerjee A, Chatterjee K, Madras G (2014) Polym Degrad Stab 110:284–289 Srivastava RK, Albertsson AC (2005) J Polym Sci A 43:4206–4216 Manzini B, Hodge P, Ben-Haida A (2010) Polym Chem 1:339–346 Eubeler JP, Bernhard M, Knepper TP (2010) Trends Anal Chem 29(1):84–100 Lucas N, Bienaime C, Belloy C, Queneudec M, Silvestre F, Nava-Saucedo JE (2008) Chemosphere 73(4):429–442 Takahashi Y, Okajima S, Toshima K, Matsumura S (2004) Macromol Biosci 4:346–353 Okajima S, Kondo R, Toshima K, Matsumura S (2003) Biomacromolecules 4:1514–1519 Osanai Y, Toshima K, Matsumura S (2004) Macromol Biosci 4:936–942 Osanai Y, Toshima K, Yoshie N, Inoue Y, Matsumura S (2002) Macromol Biosci 2:88–94 Matsumura S (2002) Japanese Patent JP2002017384 A Shimokawa K, Kato M, Matsumura S (2011) Macromol Chem Phys 212:150–158 Kobayashi S, Uyama H, Takamoto T (2000) Biomacromolecules 1:3–5 Osanai Y, Toshima K, Matsumura S (2003) Green Chem 5:567–570 Matsumura S, Harai S, Toshima K (2001) Macromol Rapid Commun 22:215–218 Jbilou F, Dole P, Degraeve P, Ladavière C, Joly C (2015) Eur Polym J 68:207–215 Kim DY, Rhee YH (2003) Appl Microbiol Biotechnol 61:300–308 Liu F, Yang J, Fan Z, Li S, Kasperczyk J, Dobrzynski P (2012) J Biomater Sci 23:1355–1368 Yang J, Tian W, Li Q, Li Y, Cao A (2004) Biomacromolecules 5:2258–2268 Ganesh M, Dave RN, L’Amoreaux W, Gross RA (2009) Macromolecules 42:6836–6839 Ganesh M, Gross RA (2012) Polymer 53:3454–3461 Khan A, Sharma SK, Kumar A, Watterson AC, Kumar J, Parmar VS (2014) Chem Sus Chem 7:379–390 Liu J, Jiang Z, Zhang S, Liu C, Gross RA, Kyriakides TR, Saltzman WM (2011) Biomaterials 32(27):6646–6654 Liu J, Jiang Z, Zhang S, Saltzman WM (2009) Biomaterials 30(29):5707–5719 Liu J, Qiu Z, Wang S, Zhou L, Zhang S (2010) Biomed Mater 5(6):065002 Stebbins ND, Yu W, Uhrich KE (2015) Macromol Biosci 15(8):1115–1124