Enzymatic ring‐opening polymerization of ε‐caprolactone by a new lipase from <i>Yarrowia lipolytica</i>

Barrera-Rivera, Karla A.; Flores-Carreón, Arturo; Martínez‐Richa, Antonio

doi:10.1002/app.28116

Cited by 38 publications

(16 citation statements)

References 27 publications

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“…The poly-merization was carried out at 60 °C for 24 h to produce poly(ɛ-CL) of M n ranged of 300–9,000, which is a telechelic polymer having OH group at one end and CO 2 H group at the other. 61) …”

Section: Ring-opening Polymerization Of Cyclic Ester (Lactone) Monomersmentioning

confidence: 99%

Lipase-catalyzed polyester synthesis - A green polymer chemistry

Kobayashi

2010

Proc. Jpn. Acad., Ser. B

163

110

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This article is a short comprehensive review describing in vitro polyester synthesis catalyzed by a hydrolysis enzyme of lipase, most of which has been developed for these two decades. Polyesters are prepared by repeated ester bond-formation reactions; they include two major modes, ring-opening polymerization (ROP) of cyclic monomers such as cyclic esters (lactones) and condensation polymerization via the reaction between a carboxylic acid or its ester group and an alcohol group. Polyester synthesis is, therefore, a reaction in reverse way of in vivo lipase catalysis of ester bond-cleavage with hydrolysis. The lipase-catalyzed polymerizations show very high chemo-, regio-, and enantio-selectivities and involve various advantageous characteristics. Lipase is robust and compatible with other chemical catalysts, which allows novel chemo-enzymatic processes. New syntheses of a variety of functional polyesters and a plausible reaction mechanism of lipase catalysis are mentioned. The polymerization characteristics are of green nature currently demanded for sustainable society, and hence, desirable for conducting ‘green polymer chemistry’.

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Section: Ring-opening Polymerization Of Cyclic Ester (Lactone) Monomersmentioning

confidence: 99%

Lipase-catalyzed polyester synthesis - A green polymer chemistry

Kobayashi

2010

Proc. Jpn. Acad., Ser. B

163

110

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“…Lewatit VP OC 1206, Lewatit VP OC K2629, and Amberlyst 15 were obtained from Sigma-Aldrich. Yarrowia lipolytica lipase (YLL) was obtained according to the procedure described in the literature [12]. Polyester samples in this study were prepared by ring-opening polymerization of ε-caprolactone in the presence of diols, using biocatalysis by Yarrowia lipolytica lipase (YYL) [6] (see Table 1).…”

Section: Methodsmentioning

confidence: 99%

“…In the present paper, we report on a series of 43 samples of PCL diols (see Table 1) that were prepared using Yarrowia lipolytica lipase biocatalysis in the presence of different initiators [12], and characterized using gel permeation chromatography with multi-angle light scattering (GPC-MALS). Although some studies have been reported on the solution behavior of PCL, they have all used commercial samples with conventional macromolecular architecture, with low to medium molecular weights.…”

Section: Introductionmentioning

confidence: 99%

Characterization of chain dimensions of poly(ε-caprolactone) diols in THF by size-exclusion chromatography coupled with multi-angle light scattering (SEC-MALS)

et al. 2015

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In this work, we studied the chain dimensions, shape, and thermodynamic characteristics of poly(ε-caprolactone) diols (HO-PCL-OH) in solution. PCL diol samples of different molecular weights and architectures were synthesized using immobilized Yarrowia lipolytica lipase as catalyst. Gel permeation chromatography (GPC) with online right-angle laser-light scattering (RALLS), differential viscometer (DV), and interferometric refractometer IRS detectors offered a proper way to obtain information on thermodynamic characteristics and chain flexibility. The weight-average molecular weights of the PCL diol samples (M w ) ranged from 2, 750 to 13,120 uma. The z-average radius of hydrodynamic volume ( z 1/2 ) vs. z-average molecular weight curve (M z ) could be satisfactorily fitted to a power-law equation. Mark-Houwink-Sakurada parameters (K=2.74×10 −3 dL/g and a=0.64) were derived from the plots of [η] w against M w . The overall results clearly suggest that a flexible geometry is present in tetrahydrofuran (THF) solution of PCL at 33°C. Unlike other PCL systems, PCL diols are more hydrophilic and expected to form associated species. They behave differently from common hydrophobic polymers and do not strictly conform to thermodynamic relationships generally used in Polymer Science. A more compact geometry is present for M n lower than 4,000 Da. For higher molecular weights, the chain expands and become more elongated. Plots of ln [η] w against ln M w (MHS equation) and of log R hz against log M z suggest that PCL diols behave as flexible chains in a good solvent.

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“…The decreased monomer conversion in concentrated monomer solutions is probably due to the poorer partitioning of PCL between toluene and the lipase, which could lead to enzyme inhibition by the reaction product and/or slow diffusion of monomer to the enzyme active site. Barrera‐Rivera et al evaluated a new lipase from Yarrowia lipolytica in the ROP of ϵ‐caprolactone in n ‐heptane at 50–70 °C, producing PCL with the highest M n of 977 g mol ‐1 at 55 °C for 360 h along with a complete monomer conversion.…”

Section: Enzymatic Rop In Organic Solventsmentioning

confidence: 99%

Enzymatic ring‐opening polymerization (ROP) of polylactones: roles of non‐aqueous solvents

Zhao

2017

J of Chemical Tech & Biotech

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Aliphatic polyesters such as polylactides (PLAs) and other polylactones are thermoplastic, biodegradable and biocompatible polymers with the potential to replace petro-chemical-based synthetic polymers. A benign route for synthesizing these polyesters is through the enzyme-catalyzed ring-opening polymerization (ROP) reaction; this type of enzymatic process is very sensitive to reaction conditions such as solvents, water content and temperature. This review systematically evaluates the crucial roles of different solvents (such as solvent-free/in bulk, organic solvents, supercritical fluids, ionic liquids, and aqueous biphasic systems) on the degree of polymerization and polydispersity. In general, many studies suggest that hydrophobic organic solvents with minimum water contents lead to efficient enzymatic polymerization and subsequently high molecular weights of polyesters; the selection of solvents is also limited by the reaction temperature, e.g. the ROP of lactide is often conducted at above 100 ∘ C, therefore, the solvent typically needs to have its boiling point above this temperature. The use of supercritical fluids could be limited by its scaling-up potential, while ionic liquids have exhibited many advantages including their low-volatility, high thermal stability, controllable enzyme-compatibility, and a wide range of choices. However, the fundamental and mechanistic understanding of the specific roles of ionic liquids in enzymatic ROP reactions is still lacking. Furthermore, the lipase specificity towards L-and D-lactide is also surveyed, followed by the discussion of engineered lipases with improved enantioselectivity and thermal stability. In addition, the preparation of polyester-derived materials such as polyester-grafted cellulose by the enzymatic ROP method is briefly reviewed.

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Enzymatic ring‐opening polymerization of ε‐caprolactone by a new lipase from Yarrowia lipolytica

Cited by 38 publications

References 27 publications

Lipase-catalyzed polyester synthesis - A green polymer chemistry

Lipase-catalyzed polyester synthesis - A green polymer chemistry

Characterization of chain dimensions of poly(ε-caprolactone) diols in THF by size-exclusion chromatography coupled with multi-angle light scattering (SEC-MALS)

Enzymatic ring‐opening polymerization (ROP) of polylactones: roles of non‐aqueous solvents

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