Abstract
Synthesis of polyesters via enzymatic polymerization is described comprehensively in up-to-dated review manner, in which the polymerization is of polycondensation type using hydrolases mainly lipase as catalyst. First, characteristics of lipase catalysis are discussed: catalyst nature for green polymer chemistry including the catalysis mechanism, immobilization of lipases, role of surfactants for lipase catalysis, and so forth. Then, the lipase-catalyzed polycondensation synthesis of polyesters is argued according to the types of polymerization reactions: via dehydration of α- and ω-oxyacids and of dicarboxylic acids, via transesterification using carboxylic acid esters, and via ring-opening addition-condensation polymerization using cyclic anhydrides or cyclic esters as a monomer component. Other polymers like polyamides, polyamines, polycarbonates, and sulfur-containing polymers were synthesized by lipase catalyst. These reaction results indicate that lipase catalysts induce various polycondensation reactions to produce a variety of new polyesters. Further, protease which catalyzes primarily the peptide bond cleavage and bond formation catalyzed also the polyester production via polycondensation.
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References
Kobayashi S, Shoda S, Uyama H (1995) Enzymatic polymerization and oligomerization. Adv Polym Sci 121:1–30
Kobayashi S, Shoda S, Uyama H (1996) Enzymatic polymerization. In: Salamone JC (ed) Polymeric materials encyclopedia. CRC Press Inc, Boca Raton, pp 2102–2107
Kobayashi S, Shoda S, Uyama H (1997) Enzymatic catalysis. In: Kobayashi S (ed) Catalysis in precision polymerization. John Wiley & Sons, Chichester, pp 417–441
Kobayashi S (1999) Enzymatic polymerization: A new method of polymer synthesis. J Polym Sci Polym Chem 37:3041–3056
Kobayashi S, Uyama H (1999) Biocatalytical routes to polymers. In: Schlueter AD (ed) Material science and technology-synthesis of polymers, vol 54. Wiley-VCH, Weinheim, pp 549–569
Kobayashi S, Uyama H, Ohmae M (2001) Enzymatic polymerization for precision polymer synthesis. Bull Chem Soc Jpn 74:613–635
Gross RA, Kumar A, Kalra B (2001) Polymer synthesis by in vitro enzyme catalysis. Chem Rev 101:2097–2124
Kobayashi S, Uyama H, Kimura S (2001) Enzymatic polymerization. Chem Rev 101:3793–3818
Kobayashi S, Uyama H (2001) In vitro biosynthesis of polyesters. In: Babel WSA (ed) Advances in biochemical engineering/biotechnology, Biopolyesters, vol 71. Springer, Heidelberg, pp 241–262
Kobayashi S, Uyama H (2002) Enzymatic polymerization to polyesters. In: Doi Y, Steinbüchel A (eds) Handbook of biopolymers, polyesters I, vol 3a. Wiley-VCH, pp 373–400
Kobayashi S, Uyama H (2003) Enzymatic polymerization. In: Kroschwitz JI (ed) Encyclopedia of polymer science and technology, 3rd edn. Wiley, New York, pp 328–364
Cheng HN, Gross RA (eds) (2005) Polymer biocatalysis and biomaterials, ACS symposium series, vol 900. American Chemical Society, Washington, DC
Kobayashi S, Ritter H, Kaplan D (eds) (2006) Enzyme-catalyzed synthesis of polymers, Advances in polymer science, vol 194. Springer, Berlin
Kobayashi S (2009) Recent developments in lipase-catalyzed synthesis of polyesters. Macromol Rapid Commun 30:237–266
Kobayashi S, Makino A (2009) Enzymatic polymer synthesis: an opportunity for green polymer chemistry. Chem Rev 109:5288–5353
Kobayashi S (2010) Lipase-catalyzed polyester synthesis – a green polymer chemistry. Proc Jpn Acad, Ser B 86:338–365
Cheng HN, Gross RA (eds) (2010) Green polymer chemistry: biocatalysis and biomaterials, ACS symposium series, vol 1043. American Chemical Society, Washington, DC
Loos K (ed) (2011) Biocatalysis in polymer chemistry. Wiley-VCH, Weinheim
Kobayashi S (2012) Enzymatic polymerization. In: Matyjaszewski K, Moeller M (eds) Polymer science: a comprehensive reference, vol 5. Elsevier, Amsterdam, pp 217–237
Kobayashi S (2013) Green polymer chemistry: recent developments. Adv Polym Sci 262:141–166
Kobayashi S (2014) Enzymatic polymerization. In: Seidel A (ed) Encyclopedia of polymer science and technology, 4th edn. Wiley, Hoboken, pp 221–292
Cheng HN, Gross RA, Smith PB (eds) (2015) Green polymer chemistry: Biobased materials and biocatalysis, ACS symposium series, vol 1192. American Chemical Society, Washington, DC
Shoda S, Kobayashi A, Kobayashi S (2015) Production of polymers by white biotechnology. In: Coelho MAZ, Ribeiro BD (eds) White biotechnology for sustainable chemistry. Royal Society of Chemistry, Cambridge, pp 274–309
Kobayashi S (2015) Enzymatic ring-opening polymerization and polycondensation for the green synthesis of polyesters. Polym Adv Technol 26:677–686
Shoda S, Uyama H, Kadokawa J et al (2016) Enzymes as green catalysts for precision macromolecular synthesis. Chem Rev 116:2307–2413
Kumar A, Khan A, Malhotra S et al (2016) Synthesis of macromolecular systems via lipase catalyzed biocatalytic reactions: applications and future perspectives. Chem Soc Rev 45:6855–6887
Jiang Y, Loos K (2016) Enzymatic synthesis of biobased polyesters and polyamides. Polymers 8:243–296
Douka A, Vouyiouka S, Papaspyridi L-M et al (2018) A review on enzymatic polymerization to produce polycondensation polymers: the case of aliphatic polyesters, polyamides and polyesteramides. Prog Polym Sci 79:1–25
Kobayashi S (2017) Green polymer chemistry: new methods of polymer synthesis using renewable starting materials. Struc Chem 28:461–474
Okumura S, Iwai M, Tominaga Y (1984) Synthesis of ester oligomer by Aspergillius-niger lipase. Agric Biol Chem 48:2805–2808
Ajima A, Yoshimoto T, Takahashi K et al (1985) Polymerization of 10-hydroxydecanoic acid in benzene with polyethylene glycol-modified lipase. Biotechnol Lett 7:303–306
Enzyme nomenclature 1992: recommendations of the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology on the nomenclature and classification of enzymes (1992). Published for the International Union of Biochemistry and Molecular Biology by Academic Press, San Diego
Sym EA (1936) A method for enzymic ester synthesis. Enzymologia 1:156–160
Jones JB (1986) Enzymes in organic-synthesis. Tetrahedron 42:3351–3403
Klibanov AM (1990) Asymmetric transformations catalyzed by enzymes in organic-solvents. Acc Chem Res 23:114–120
Wong CH, Whitesides GMP (1994) Enzymes in synthetic organic chemistry. Pergamon, Oxford
Uyama H, Kobayashi S (1993) Enzymatic ring-opening polymerization of lactones catalyzed by lipase. Chem Lett 22:1149–1150
Uyama H, Takeya K, Kobayashi S (1993) Synthesis of polyesters by enzymatic ring-opening copolymerization using lipase catalyst. Proc Jpn Acad, Ser B 69:203–207
Knani D, Gutman AL, Kohn DH (1993) Enzymatic polyesterification in organic media-enzyme-catalyzed synthesis of linear polyesters. I. Condensation polymerization of linear hydroxyesters. II. Ring-opening polymerization of ε-caprolactone. J Polym Sci Polym Chem 31:1221–1232
Uyama H, Takeya K, Hoshi N et al (1995) Lipase-catalyzed ring-opening polymerization of 12-dodecanolide. Macromolecules 28:7046–7050
Foresti ML, Ferreira ML (2004) Synthesis of polycaprolactone using free/supported enzymatic and non-enzymatic catalysts. Macromol Rapid Commun 25:2025–2028
Uppenberg J, Hansen MT, Patkar S et al (1994) Sequence, crystal-structure determination and refinement of 2 crystal forms of lipase B from Candida antarctica. Structure 2:293–308
Gotor-Fernández V, Busto E, Gotor V (2006) Candida antarctica lipase B: An ideal biocatalyst for the preparation of nitrogenated organic compounds. Adv Syn Catal 348:797–812
Hsieh Y-L, Wang Y, Chen H (2005) Enzyme immobilization onto ultrahigh specific surface cellulose fibers via amphiphilic (PEG) spacers and electrolyte (PAA) grafts. In: Polymer biocatalysis and biomaterials, ACS symposium series, vol 900. American Chemical Society, Washington, DC, pp 63–79
Cheng HN, Gross RA (2002) Biocatalysis in polymer science: an overview. In: Biocatalysis in polymer science, ACS symposium series, vol 840. American Chemical Society, Washington, DC, pp 1–32
Cantone S, Ferrario V, Corici L et al (2013) Efficient immobilisation of industrial biocatalysts: criteria and constraints for the selection of organic polymeric carriers and immobilisation methods. Chem Soc Rev 42:6262–6276
Widhyahrini K, Handayani N, Wahyuningrum D et al (2017) The microwave-assisted synthesis of polyethersulfone (pes) as a matrix in immobilization of Candida antarctica lipase B (Cal-B). Bull Chem Res Eng Cat 12:343–350
Takahashl K, Saito Y, Inada Y (1988) Lipase made active in hydrophobic media. J Am Oil Chem Soc 65:911
Kodera Y, Sakurai K, Satoh Y et al (1998) Regioselective deacetylation of peracetylated monosaccharide derivatives by polyethylene glycol-modified lipase for the oligosaccharide synthesis. Biotechnol Lett 20:177–180
Yang Z, Domach M, Auger R et al (1996) Polyethylene glycol-induced stabilization of subtilisin. Enzym Microb Technol 18:82–89
Ohya Y, Sugitou T, Ouchi T (1995) Polycondensation of α-hydroxy acids by enzymes of peg-modified enzymes in organic media. J Macromol Sci-Pure Appl Chem A32:179–190
Miletic N, Vukovic Z, Nastasovic A et al (2009) Macroporous poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate) resins-versatile immobilization supports for biocatalysts. J Mol Catal B Enzym 56:196–201
Liu T, Liu Y, Wang X et al (2011) Improving catalytic performance of Burkholderia cepacia lipase immobilized on macroporous resin NKA. J Mol Catal B Enzym 71:45–50
Valério A, Nicoletti G, Cipolatti EP et al (2015) Kinetic Study of Candida antarctica Lipase B immobilization using poly(methyl methacrylate) nanoparticles obtained by miniemulsion polymerization as support. Appl Biochem Biotechnol 175:2961–2971
Sawada S, Akiyoshi K (2010) Nano-encapsulation of lipase by self-assembled nanogels: Induction of high enzyme activity and thermal stabilization. Macromol Biosci 10:353–358
Nishimura T, Sasaki Y, Akiyoshi K (2017) Cancer therapy: Biotransporting self-assembled nanofactories using polymer vesicles with molecular permeability for enzyme prodrug cancer therapy. Adv Mater 29:1702406
LeDuc PR, Wong MS, Ferreira PM et al (2007) Towards an in vivo biologically inspired nanofactory. Nat Nanotechnol 2:3–7
Omay D (2014) Immobilization of lipase onto a photo-crosslinked polymer network: characterization and polymerization applications. Biocatal Biotransformation 32:132–140
Ye P, Xu Z-K, Wu J et al (2006) Nanofibrous membranes containing reactive groups: electrospinning from poly(acrylonitrile-co-maleic acid) for lipase immobilization. Macromolecules 39:1041–1045
Talbert JN, Wang L-S, Duncan B et al (2014) Immobilization and stabilization of lipase (CALB) through hierarchical interfacial assembly. Biomacromolecules 15:3915–3922
Marciello M, Bolivar JM, Filice M et al (2013) Preparation of lipase-coated, stabilized, hydrophobic magnetic particles for reversible conjugation of biomacromolecules. Biomacromolecules 14:602–607
Bellusci M, Francolini I, Martinelli A et al (2012) Lipase immobilization on differently functionalized vinyl-based amphiphilic polymers: influence of phase segregation on the enzyme hydrolytic activity. Biomacromolecules 13:805–813
Mathesh M, Luan B, Akanbi TO et al (2016) Opening lids: Modulation of lipase immobilization by graphene oxides. ACS Catal 6:4760–4768
Nakamura I, Yoneda H, Maeda T et al (2005) Enzymatic polymerization behavior using cellulose-binding domain deficient endoglucanase II. Macromol Biosci 5:623–628
Kobayashi S, Kashiwa K, Kawasaki T et al (1991) Novel method for polysaccharide synthesis using an enzyme – the 1st in vitro synthesis of cellulose via a nonbiosynthetic path utilizing cellulase as catalyst. J Am Chem Soc 113:3079–3084
Fernández-Lorente G, Palomo JM, Mateo C et al (2006) Glutaraldehyde cross-linking of lipases adsorbed on aminated supports in the presence of detergents leads to improved performance. Biomacromolecules 7:2610–2615
Mogensen JE, Sehgal P, Otzen DE (2005) Activation, inhibition, and destabilization of Thermomyces lanuginosus lipase by detergents. Biochemistry 44:1719–1730
Kiran KR, Divakar S (2003) Lipase-catalysed polymerization of lactic acid and its film forming properties. World J Microb Biot 19:859–865
Inkinen S, Hakkarainen M, Albertsson A-C et al (2011) From lactic acid to poly(lactic acid) (PLA): characterization and analysis of PLA and its precursors. Biomacromolecules 12:523–532
Ishimoto K, Arimoto M, Ohara H et al (2009) Biobased polymer system: miniemulsion of poly(alkyl methacrylate-graft-lactic acid)s. Biomacromolecules 10:2719–2723
Ishimoto K, Arimoto M, Okuda T et al (2012) Biobased polymers: synthesis of graft copolymers and comb polymers using lactic acid macromonomer and properties of the product polymers. Biomacromolecules 13:3757–3768
Ohara H, Onogi A, Yamamoto M et al (2010) Lipase-catalyzed oligomerization and hydrolysis of alkyl lactates: direct evidence in the catalysis mechanism that enantioselection is governed by a deacylation step. Biomacromolecules 11:2008–2015
Ohara H, Nishioka E, Yamaguchi S et al (2011) Protease-catalyzed oligomerization and hydrolysis of alkyl lactates involving L-enantioselective deacylation step. Biomacromolecules 12:3833–3837
Ohara H, Yamamoto M, Onogi A et al (2011) Optical resolution of n-butyl D- and L-lactates using immobilized lipase catalyst. J Biosci Bioeng 111:19–21
Kobayashi S, Uyama H, Suda S et al (1997) Dehydration polymerization in aqueous medium catalyzed by lipase. Chem Lett:105–105
Suda S, Uyama H, Kobayashi S (1999) Dehydration polycondensation in water for synthesis of polyesters by lipase catalyst. Proc Jpn Acad, Ser B 75:201–206
Matsumura S, Takahashi J (1986) Enzymatic-synthesis of functional oligomers. 1. Lipase catalyzed polymerization of hydroxy-acids. Makromol Chem Rapid Commun 7:369–373
Ebata H, Toshima K, Matsumura S (2007) Lipase-catalyzed synthesis and curing of high-molecular-weight polyricinoleate. Macromol Biosci 7:798–803
Noll O, Ritter H (1996) Enzymes in polymer chemistry, 9. Polymerizable oligoesters from cholic acid via lipase catalyzed condensation reactions. Macromol Rapid Commun 17:553–557
Mahapatro A, Kumar A, Gross RA (2004) Mild, solvent-free ω-hydroxy acid polycondensations catalyzed by Candida antarctica lipase B. Biomacromolecules 5:62–68
Feder D, Gross RA (2010) Exploring chain length selectivity in HiC-catalyzed polycondensation reactions. Biomacromolecules 11:690–697
O’Hagan D, Zaidi NA (1994) Enzyme-catalyzed condensation polymerization of 11-hydroxyundecanoic acid with lipase from Candida-cylindracea. Polymer 35:3576–3578
Olsson A, Lindstrom M, Iversen T (2007) Lipase-catalyzed synthesis of an epoxy-functionalized polyester from the suberin monomer cis-9,10-epoxy-18-hydroxyoctadecanoic acid. Biomacromolecules 8:757–760
Dong H, Wang HD, Cao SG et al (1998) Lipase-catalyzed polymerization of lactones and linear hydroxyesters. Biotechnol Lett 20:905–908
Veld MAJ, Palmans ARA, Meijer EW (2007) Selective polymerization of functional monomers with Novozym 435. J Polym Sci Polym Chem 45:5968–5978
Noll O, Ritter H (1997) New side-chain poly(methacryl-rotaxanes) bearing cyclodextrins as non-covalently anchored ring components. Chemoenzymatic synthesis and degradation. Macromol Rapid Commun 18:53–58
Ebata H, Toshima K, Matsumura S (2008) Lipase-catalyzed synthesis and properties of poly[(12-hydroxydodecanoate)-co-(12-hydroxystearate)] directed towards novel green and sustainable elastomers. Macromol Biosci 8:38–45
O’Hagan D, Parker AH (1998) Enzyme mediated polyester synthesis with the lipase from Candida rugosa – preparation of an enantiomerically enriched polymer from an A-B monomer. Polym Bull 41:519–524
Knani D, Kohn DH (1993) Enzymatic polyesterification in organic media. II. Enzyme-catalyzed synthesis of lateral-substituted aliphatic polyesters and copolyesters. J Polym Sci Polym Chem 31:2887–2897
Kanca U, Van Buijtenen J, Van As BAC et al (2008) Iterative tandem catalysis of racemic AB monomers. J Polym Sci Polym Chem 46:2721–2733
Miao SD, Zhang SP, Su ZG et al (2008) Chemoenzymatic synthesis of oleic acid-based polyesters for use as highly stable biomaterials. J Polym Sci Polym Chem 46:4243–4248
Binns F, Roberts SM, Taylor A et al (1993) Enzymatic polymerization of an unactivated diol diacid system. J Chem Soc-Perkin Trans 1:899–904
Wang ZL, Hiltunen K, Orava P et al (1996) Lipase-catalyzed polyester synthesis. J Macromol Sci-Pure Appl Chem A33:599–612
Linko YY, Wang ZL, Seppälä J (1995) Lipase-catalyzed linear aliphatic polyester synthesis in organic-solvent. Enzym Microb Technol 17:506–511
Linko YY, Seppälä J (1996) Producing high molecular weight biodegradable polyesters. ChemTech 26:25–31
Uyama H, Inada K, Kobayashi S (1998) Enzymatic polymerization of dicarboxylic acid and glycol to polyester in solvent-free system. Chem Lett:1285–1286
Uyama H, Inada K, Kobayashi S (2000) Lipase-catalyzed synthesis of aliphatic polyesters by polycondensation of dicarboxylic acids and glycols in solvent-free system. Polym J 32:440–443
Binns F, Harffey P, Roberts SM et al (1998) Studies of lipase-catalyzed polyesterification of an unactivated diacid/diol system. J Polym Sci Polym Chem 36:2069–2079
Mahapatro A, Kalra B, Kumar A et al (2003) Lipase-catalyzed polycondensations: effect of substrates and solvent on chain formation, dispersity, and end-group structure. Biomacromolecules 4:544–551
Kubisa P (2005) Ionic liquids in the synthesis and modification of polymers. J Polym Sci Polym Chem 43:4675–4683
Uyama H, Takamoto T, Kobayashi S (2002) Enzymatic synthesis of polyesters in ionic liquids. Polym J 34:94–96
Chen B, Hu J, Miller EM et al (2008) Candida antarctica lipase B chemically immobilized on epoxy-activated micro- and nanobeads: catalysts for polyester synthesis. Biomacromolecules 9:463–471
Binns F, Harffey P, Roberts SM et al (1999) Studies leading to the large scale synthesis of polyesters using enzymes. J Chem Soc-Perkin Trans 1:2671–2676
Korupp C, Weberskirch R, Muller JJ et al (2010) Scaleup of lipase-catalyzed polyester synthesis. Org Process Res Dev 14:1118–1124
Yao D-H, Li G-J, Kuila T et al (2011) Lipase-catalyzed synthesis and characterization of biodegradable polyester containing L-malic acid unit in solvent system. J Appl Polym Sci 120:1114–1120
Vouyiouka SN, Topakas E, Katsini A et al (2013) A green route for the preparation of aliphatic polyesters via lipase-catalyzed prepolymerization and low-temperature postpolymerization. Macromol Mater Eng 298:679–689
Kumar A, Kulshrestha AS, Gao W et al (2003) Versatile route to polyol polyesters by lipase catalysis. Macromolecules 36:8219–8221
Fu HY, Kulshrestha AS, Gao W et al (2003) Physical characterization of sorbitol or glycerol containing aliphatic copolyesters synthesized by lipase-catalyzed polymerization. Macromolecules 36:9804–9808
Kulshrestha AS, Gao W, Gross RA (2005) Glycerol copolyesters: control of branching and molecular weight using a lipase catalyst. Macromolecules 38:3193–3204
Kulshrestha AS, Gao W, Fu HY et al (2007) Synthesis and characterization of branched polymers from lipase-catalyzed trimethylolpropane copolymerizations. Biomacromolecules 8:1794–1801
Zhang Y-R, Spinella S, Xie W et al (2013) Polymeric triglyceride analogs prepared by enzyme-catalyzed condensation polymerization. Eur Polym J 49:793–803
Hu J, Gao W, Kulshrestha A et al (2006) “Sweet polyesters”: lipase-catalyzed condensation – polymerizations of alditols. Macromolecules 39:6789–6792
Hunsen M, Azim A, Mang H et al (2007) A cutinase with polyester synthesis activity. Macromolecules 40:148–150
Yang YX, Lu WH, Zhang XY et al (2010) Two-step biocatalytic route to biobased functional polyesters from ω-carboxy fatty acids and diols. Biomacromolecules 11:259–268
Kanelli M, Douka A, Vouyiouka S et al (2014) Production of biodegradable polyesters via enzymatic polymerization and solid state finishing. J Appl Polym Sci 131. https://doi.org/10.1002/app.40820
Habeych DI, Juhl PB, Pleiss J et al (2011) Biocatalytic synthesis of polyesters from sugar-based building blocks using immobilized Candida antarctica lipase B. J Mol Catal B Enzym 71:1–9
Barrett DG, Merkel TJ, Luft JC et al (2010) One-step syntheses of photocurable polyesters based on a renewable resource. Macromolecules 43:9660–9667
Yang YX, Lu WH, Cai JL et al (2011) Poly(oleic diacid-co-glycerol): comparison of polymer structure resulting from chemical and lipase catalysis. Macromolecules 44:1977–1985
Nguyen H, Löf D, Hvilsted S et al (2016) Highly branched bio-based unsaturated polyesters by enzymatic polymerization. Polymers 8:363. https://doi.org/10.3390/polym8100363
Pellis A, Guarneri A, Brandauer M et al (2016) Exploring mild enzymatic sustainable routes for the synthesis of bio-degradable aromatic-aliphatic oligoesters. Biotechnol J 11:642–647
Uyama H, Wada S, Kobayashi S (1999) Synthesis of aliphatic polyester by insertion of glycols into polyanhydrides using lipase catalyst. Chem Lett 28:893–894
Wallace JS, Morrow CJ (1989) Biocatalytic synthesis of polymers -synthesis of an optically-active, epoxy-substituted polyester by lipase-catalyzed polymerization. J Polym Sci Polym Chem 27:2553–2567
Japu C, de Ilarduya AM, Alla A et al (2015) Copolyesters made from 1,4-butanediol, sebacic acid, and D-glucose by melt and enzymatic polycondensation. Biomacromolecules 16:868–879
Pellis A, Ferrario V, Zartl B et al (2016) Enlarging the tools for efficient enzymatic polycondensation: structural and catalytic features of cutinase 1 from Thermobifida cellulosilytica. Cat Sci Technol 6:3430–3442
Pellis A, Guebitz GM, Farmer TJ (2016) On the effect of microwave energy on lipase-catalyzed polycondensation reactions. Molecules 21:1245. https://doi.org/10.3390/molecules21091245
Wang HY, Zhang WW, Wang N et al (2010) Biocatalytic synthesis and in vitro release of biodegradable linear polyesters with pendant ketoprofen. Biomacromolecules 11:3290–3293
Wang H-Y, Zhou Y-J, Wang Z et al (2011) Enzyme-catalyzed synthesis of a novel thermosensitive polyester with pendant ketoprofen. Macromol Biosci 11:595–599
Berkane C, Mezoul G, Lalot T et al (1997) Lipase-catalyzed polyester synthesis in organic medium. Study of ring-chain equilibrium. Macromolecules 30:7729–7734
Jacobson H, Stockmayer WH (1950) Intermolecular reaction in polycondensations. 1. The theory of linear systems. J Chem Phys 18:1600–1606
Lavalette A, Lalot T, Brigodiot M et al (2002) Lipase-catalyzed synthesis of a pure macrocyclic polyester from dimethyl terephthalate and diethylene glycol. Biomacromolecules 3:225–228
Ciulik C, Safari M, Martínez de Ilarduya A et al (2017) Poly(butylene succinate-ran-ε-caprolactone) copolyesters: enzymatic synthesis and crystalline isodimorphic character. Eur Polym J 95:795–808
Warwel S, Demes C, Steinke G (2001) Polyesters by lipase-catalyzed polycondensation of unsaturated and epoxidized long-chain α,ω-dicarboxylic acid methyl esters with diols. J Polym Sci Polym Chem 39:1601–1609
Azim H, Dekhterman A, Jiang ZZ et al (2006) Candida antarctica lipase B-catalyzed synthesis of poly(butylene succinate): shorter chain building blocks also work. Biomacromolecules 7:3093–3097
Marcilla R, de Geus M, Mecerreyes D et al (2006) Enzymatic polyester synthesis in ionic liquids. Eur Polym J 42:1215–1221
Chaudhary AK, Beckman EJ, Russell AJ (1995) Rational control of polymer molecular-weight and dispersity during enzyme-catalyzed polyester synthesis in supercritical fluids. J Am Chem Soc 117:3728–3733
Linko YY, Wang ZL, Seppälä J (1994) Lipase-catalyzed synthesis of poly(1,4-butanediol succinate) in organic-solvent. Biocatalysis 8:269–282
Wallace JS, Morrow CJ (1989) Biocatalytic synthesis of polymers. 2. Preparation of [AA-BB]X polyesters by porcine pancreatic lipase catalyzed transesterification in anhydrous, low polarity organic solvents. J Polym Sci Polym Chem 27:3271–3284
Brazwell EM, Filos DY, Morrow CJ (1995) Biocatalytic synthesis of polymers. 3. Formation of a high-molecular-weight polyester through limitation of hydrolysis by enzyme-bound water and through equilibrium control. J Polym Sci Polym Chem 33:89–95
Hilker I, Rabani G, Verzijl GKM et al (2006) Chiral polyesters by dynamic kinetic resolution polymerization. Angew Chem Int Ed 45:2130–2132
Uyama H, Kobayashi S (1994) Lipase-catalyzed polymerization of divinyl adipate with glycols to polyesters. Chem Lett:1687–1690
Uyama H, Yaguchi S, Kobayashi S (1999) Lipase-catalyzed polycondensation of dicarboxylic acid-divinyl esters and glycols to aliphatic polyesters. J Polym Sci Polym Chem 37:2737–2745
Taresco V, Creasey RG, Kennon J et al (2016) Variation in structure and properties of poly(glycerol adipate) via control of chain branching during enzymatic synthesis. Polymer 89:41–49
Chaudhary AK, Beckman EJ, Russell AJ (1997) Biocatalytic polyester synthesis: analysis of the evolution of molecular weight and end group functionality. Biotechnol Bioeng 55:227–239
Kline BJ, Lele SS, Lenart PJ et al (2000) Use of a batch-stirred reactor to rationally tailor biocatalytic polytransesterification. Biotechnol Bioeng 67:424–434
Naolou T, Busse K, Kressler J (2010) Synthesis of well-defined graft copolymers by combination of enzymatic polycondensation and “click” chemistry. Biomacromolecules 11:3660–3667
Kim DY, Dordick JS (2001) Combinatorial array-based enzymatic polyester synthesis. Biotechnol Bioeng 76:200–206
Takamoto T, Uyama H, Kobayashi S (2001) Lipase-catalyzed synthesis of aliphatic polyesters in supercritical carbon dioxide. E-Polymers 4:1–6
Uyama H, Yaguchi S, Kobayashi S (1999) Enzymatic synthesis of aromatic polyesters by lipase-catalyzed polymerization of dicarboxylic acid divinyl esters and glycols. Polym J 31:380–383
Rodney RL, Allinson BT, Beckman EJ et al (1999) Enzyme-catalyzed polycondensation reactions for the synthesis of aromatic polycarbonates and polyesters. Biotechnol Bioeng 65:485–489
Barrett DG, Yousaf MN (2008) Preparation of a class of versatile, chemoselective, and amorphous polyketoesters. Biomacromolecules 9:2029–2035
Frampton MB, Subczynska I, Zelisko PM (2010) Biocatalytic synthesis of silicone polyesters. Biomacromolecules 11:1818–1825
Jiang Y, Woortman AJJ, van EGORA et al (2013) Enzyme-catalyzed synthesis of unsaturated aliphatic polyesters based on green monomers from renewable resources. Biomol Ther 3:461–480
Liu W, Wang F, Tan T et al (2013) Lipase-catalyzed synthesis and characterization of polymers by cyclodextrin as support architecture. Carbohydr Polym 92:633–640
Zhao X, Bansode SR, Ribeiro A et al (2016) Ultrasound enhances lipase-catalyzed synthesis of poly (ethylene glutarate). Ultrason Sonochem 31:506–511
Tomke PD, Zhao X, Chiplunkar PP et al (2017) Lipase-ultrasound assisted synthesis of polyesters. Ultrason Sonochem 38:496–502
Takamoto T, Kerep P, Uyama H et al (2001) Lipase-catalyzed transesterification of polyesters to ester copolymers. Macromol Biosci 1:223–227
Debuissy T, Pollet E, Avérous L (2016) Enzymatic synthesis of a bio-based copolyester from poly(butylene succinate) and poly((R)-3-hydroxybutyrate): study of reaction parameters on the transesterification rate. Biomacromolecules 17:4054–4063
Debuissy T, Pollet E, Avérous L (2017) Enzymatic synthesis of biobased poly(1,4-butylene succinate-ran-2,3-butylene succinate) copolyesters and characterization. Influence of 1,4- and 2,3-butanediol contents. Eur Polym J 93:103–115
Debuissy T, Pollet E, Avérous L (2017) Lipase-catalyzed synthesis of biobased and biodegradable aliphatic copolyesters from short building blocks. Effect of the monomer length. Eur Polym J 97:328–337
Jiang Y, Woortman AJJ, Alberda van Ekenstein GOR et al (2014) Enzymatic synthesis of biobased polyesters using 2,5-bis(hydroxymethyl)furan as the building block. Biomacromolecules 15:2482–2493
Jiang Y, Woortman AJJ, Alberda van Ekenstein GOR et al (2015) A biocatalytic approach towards sustainable furanic–aliphatic polyesters. Polym Chem 6:5198–5211
Papageorgiou GZ, Papageorgiou DG, Terzopoulou Z et al (2016) Production of bio-based 2,5-furan dicarboxylate polyesters: recent progress and critical aspects in their synthesis and thermal properties. Eur Polym J 83:202–229
Juais D, Naves AF, Li C et al (2010) Isosorbide polyesters from enzymatic catalysis. Macromolecules 43:10315–10319
Kato M, Toshima K, Matsumura S (2009) Direct enzymatic synthesis of a polyester with free pendant mercapto groups. Biomacromolecules 10:366–373
Tanaka A, Kohri M, Takiguchi T et al (2012) Enzymatic synthesis of reversibly crosslinkable polyesters with pendant mercapto groups. Polym Degrad Stab 97:1415–1422
Gustini L, Lavilla C, Janssen WWTJ et al (2016) Green and selective polycondensation methods toward linear sorbitol-based polyesters: enzymatic versus organic and metal-based catalysis. ChemSusChem 9:2250–2260
Gustini L, Finzel L, Lavilla C et al (2016) Understanding the limitations of the solvent-free enzymatic synthesis of sorbitol-containing polyesters. ACS Sustain Chem Eng 4:2259–2268
Kline BJ, Beckman EJ, Russell AJ (1998) One-step biocatalytic synthesis of linear polyesters with pendant hydroxyl groups. J Am Chem Soc 120:9475–9480
Uyama H, Inada K, Kobayashi S (2001) Regioselectivity control in lipase-catalyzed polymerization of divinyl sebacate and triols. Macromol Biosci 1:40–44
Uyama H, Klegraf E, Wada S et al (2000) Regioselective polymerization of sorbitol and divinyl sebacate using lipase catalyst. Chem Lett:800–801
Tsujimoto T, Uyama H, Kobayashi S (2001) Enzymatic synthesis of cross-linkable polyesters from renewable resources. Biomacromolecules 2:29–31
Tsujimoto T, Uyama H, Kobayashi S (2002) Enzymatic synthesis and curing of biodegradable crosslinkable polyesters. Macromol Biosci 2:329–335
Uyama H, Kuwabara M, Tsujimoto T et al (2003) Enzymatic synthesis and curing of biodegradable epoxide-containing polyesters from renewable resources. Biomacromolecules 4:211–215
Torron S, Semlitsch S, Martinelle M et al (2016) Biocatalytic synthesis of epoxy resins from fatty acids as a versatile route for the formation of polymer thermosets with tunable properties. Biomacromolecules 17:4003–4010
Yang Z, Zhang XF, Luo XG et al (2013) Enzymatic synthesis of poly(butylene-co-sebacate-co-glycolate) copolyesters and evaluation of the copolymer nanoparticles as biodegradable carriers for doxorubicin delivery. Macromolecules 46:1743–1753
Naves AF, Fernandes HTC, Immich APS et al (2013) Enzymatic syntheses of unsaturated polyesters based on isosorbide and isomannide. J Polym Sci Polym Chem 51:3881–3891
Kumari M, Gupta S, Achazi K et al (2015) Dendronized multifunctional amphiphilic polymers as efficient nanocarriers for biomedical applications. Macromol Rapid Commun 36:254–261
Kumar S, Achazi K, Licha K et al (2017) Chemo-enzymatic synthesis of dendronized polymers for cyanine dye encapsulation. Adv Polym Technol. https://doi.org/10.1002/adv.21839
Kobayashi S, Uyama H (1993) Enzymatic polymerization of cyclic acid anhydrides and glycols by a lipase catalyst. Makromol Chem Rapid Commun 14:841–844
Uyama H, Wada S, Fukui T et al (2003) Lipase-catalyzed synthesis of polyesters from anhydride derivatives involving dehydration. Biochem Eng J 16:145–152
Yamaguchi S, Tanha M, Hult A et al (2014) Green polymer chemistry: lipase-catalyzed synthesis of bio-based reactive polyesters employing itaconic anhydride as a renewable monomer. Polym J 46:2–13
Namekawa S, Uyama H, Kobayashi S (2000) Enzymatic synthesis of polyesters from lactones, dicarboxylic acid divinyl esters, and glycols through combination of ring-opening polymerization and polycondensation. Biomacromolecules 1:335–338
Jiang ZZ (2008) Lipase-catalyzed synthesis of aliphatic polyesters via copolymerization of lactone, dialkyl diester, and diol. Biomacromolecules 9:3246–3251
Jiang Z, Zhang J (2013) Lipase-catalyzed synthesis of aliphatic polyesters via copolymerization of lactide with diesters and diols. Polymer 54:6105–6113
Mazzocchetti L, Scandola M, Jiang ZZ (2009) Enzymatic synthesis and structural and thermal properties of poly(ω-pentadecalactone-co-butylene-co-succinate). Macromolecules 42:7811–7819
Eriksson M, Fogelstrom L, Hult K et al (2009) Enzymatic one-pot route to telechelic polypentadecalactone epoxide: synthesis, uv curing, and characterization. Biomacromolecules 10:3108–3113
Nie W-C, Dang H-C, Wang X-L et al (2017) One-step enzymatic synthesis of poly(p-dioxanone-co-butylene-co-succinate) copolyesters with well-defined structure and enhanced degradability. Polymer 111:107–114
Qian X, Wang J, Li Y et al (2014) Two enzyme cooperatively catalyzed tandem polymerization for the synthesis of polyester containing chiral (R)- or (S)-ibuprofen pendants. Macromol Rapid Commun 35:1788–1794
Gu Q-M, Maslanka WW, Cheng HN (2008) Enzyme-catalyzed polyamides and their derivatives. In: Polymer biocatalysis and biomaterials II, ACS symposium series, vol 999. American Chemical Society, Washington, DC, pp 309–319
Stavila E, van Ekenstein GORA, Loos K (2013) Enzyme-catalyzed synthesis of aliphatic-aromatic oligoamides. Biomacromolecules 14:1600–1606
Jiang Y, Maniar D, Woortman AJJ et al (2015) Enzymatic polymerization of furan-2,5-dicarboxylic acid-based furanic-aliphatic polyamides as sustainable alternatives to polyphthalamides. Biomacromolecules 16:3674–3685
Jiang Y, Maniar D, Woortman AJJ et al (2016) Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides: enzymatic polymerization kinetics, effect of diamine chain length and thermal properties. RSC Adv 6:67941–67953
Steunenberg P, Uiterweerd M, Sijm M et al (2013) Enzyme-catalyzed polymerization of β-alanine esters, a sustainable route towards the formation of poly-β-alanine. Curr Org Chem 17:682–690
Zhang Y, Xia B, Li Y et al (2016) Solvent-free lipase-catalyzed synthesis: unique properties of enantiopure D- and L- polyaspartates and their complexation. Biomacromolecules 17:362–370
Totsingan F, Centore R, Gross RA (2017) CAL-B catalyzed regioselective bulk polymerization of L-aspartic acid diethyl ester to α-linked polypeptides. Chem Commun 53:4030–4033
Kato M, Toshima K, Matsumura S (2005) Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid. Biomacromolecules 6:2275–2280
Kato M, Toshima K, Matsumura S (2006) Enzyme-catalyzed preparation of aliphatic polythioester by direct polycondensation of diacid diester and dithiol. Macromol Rapid Commun 27:605–610
Iwata S, Toshima K, Matsumura S (2003) Enzyme-catalyzed preparation of aliphatic polyesters containing thioester linkages. Macromol Rapid Commun 24:467–471
Wu W-X, Yang X-L, Liu B-Y et al (2016) Lipase-catalyzed synthesis of oxidation-responsive poly(ethylene glycol)-b-poly(β-thioether ester) amphiphilic block copolymers. RSC Adv 6:11870–11879
Finnveden M, Nameer S, Johansson M et al (2016) One-component thiol-alkene functional oligoester resins utilizing lipase catalysis. Macromol Chem Phys 217:1335–1341
Jiang ZZ, Liu C, Xie WC et al (2007) Controlled lipase-catalyzed synthesis of poly(hexamethylene carbonate). Macromolecules 40:7934–7943
Rodney RL, Stagno JL, Beckman EJ et al (1999) Enzymatic synthesis of carbonate monomers and polycarbonates. Biotechnol Bioeng 62:259–266
Matsumura S, Harai S, Toshima K (2000) Lipase-catalyzed polymerization of diethyl carbonate and diol to aliphatic poly(alkylene carbonate). Macromol Chem Phys 201:1632–1639
Jiang ZZ, Liu C, Gross RA (2008) Lipase-catalyzed synthesis of aliphatic poly(carbonate-co-esters). Macromolecules 41:4671–4680
Jiang ZZ (2011) Lipase-catalyzed copolymerization of dialkyl carbonate with 1,4-butanediol and ω-pentadecalactone: Synthesis of poly-(ω-pentadecalactone-co-butylene-co-carbonate). Biomacromolecules 12:1912–1919
Liu C, Jiang ZZ, Decatur J et al (2011) Chain growth and branch structure formation during lipase-catalyzed synthesis of aliphatic polycarbonate polyols. Macromolecules 44:1471–1479
Hedstrom L (2002) Serine protease mechanism and specificity. Chem Rev 102:4501–4523
Patil DR, Rethwisch DG, Dordick JS (1991) Enzymatic-synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media. Biotechnol Bioeng 37:639–646
Park HG, Chang HN, Dordick JS (1994) Enzymatic-synthesis of various aromatic polyesters in anhydrous organic-solvents. Biocatalysis 11:263–271
Kawai F, Nakadai K, Nishioka E et al (2011) Different enantioselectivity of two types of poly(lactic acid) depolymerases toward poly(L-lactic acid) and poly(D-lactic acid). Polym Degrad Stabil 96:1342–1348
Wilmouth RC, Clifton IJ, Robinson CV et al (1997) Structure of a specific acyl-enzyme complex formed between β-casomorphin-7 and Porcine pancreatic elastase. Nat Struct Biol 4:456–462
Ollis DL, Cheah E, Cygler M et al (1992) The α/β-hydrolase fold. Protein Eng 5:197–211
Borén L, Martín-Matute B, Xu Y et al (2006) (S)-selective kinetic resolution and chemoenzymatic dynamic kinetic resolution of secondary alcohols. Chem Eur J 12:225–232
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Kobayashi, S., Uyama, H. (2019). Synthesis of Polyesters I: Hydrolase as Catalyst for Polycondensation (Condensation Polymerization). In: Kobayashi, S., Uyama, H., Kadokawa, Ji. (eds) Enzymatic Polymerization towards Green Polymer Chemistry. Green Chemistry and Sustainable Technology. Springer, Singapore. https://doi.org/10.1007/978-981-13-3813-7_5
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