Enzymatic Polymerization to Polyesters

Kobayashi, Shiro; Uyama, Hiroshi

doi:10.1002/3527600035.bpol3a14

Cited by 11 publications

(11 citation statements)

References 141 publications

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“…Characteristic nature of enzymatic catalysis was fully used for controlling the stereochemistry, chemoselectivity, and regioselectivity for the ester products, which are often needed in the total synthesis of complicated structured natural products or in the preparation of pharmacologically active compounds. In polymer chemistry field, synthesis of polyesters by using enzymes as catalyst has been developed almost concurrently, and short or comprehensive review papers on this field have been published from time to time . It is to be noted here that enzymatic polyester synthesis involves several characteristic features of “green polymer chemistry”, which we often pointed out in our previous publications .…”

Section: Introductionmentioning

confidence: 88%

“…These results initiated to actively study enzyme‐catalyzed polyester synthesis. Thereafter, various lactones of different ring‐size, unsubstituted and substituted, have been polymerized or copolymerized, catalyzed by lipases of different origin . Unsubstituted 4‐ to 17‐membered lactone monomers are given in Scheme .…”

Section: Ring‐opening Polymerization Of Lactonesmentioning

confidence: 99%

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Enzymatic ring‐opening polymerization and polycondensation for the green synthesis of polyesters

Kobayashi

2015

Polymers for Advanced Techs

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Enzyme-catalyzed polyester synthesis has been briefly reviewed with focusing on the studies achieved mainly by our group. This article describes the polyester synthesis based on the reaction mode catalyzed by enzyme with using lipase in major and protease in minor. First, ring-opening polymerization of cyclic esters (lactones), where the macrolide monomers showed a higher polymerizability by lipase catalyst than smaller ring-sized lactones. This tendency is the reverse with the anionic and metal (Zn) catalyzed polymerizations, which was explained from the specific mechanism of the enzymatic reaction. Chemoselective and enantioselective as well as end-functionalizing polymerizations were mentioned. Second, condensation polymerization (polycondensation), where two modes of reactions using oxyacid or its ester as monomer and carboxylic acid or its ester and diol as monomers were shown. Third, ring-opening addition-condensation polymerization, where carboxylic anhydride and diol monomers were reacted involving dehydration. Finally, advantageous aspects of enzymatic polyester synthesis are described in terms of conducting green polymer chemistry. Scheme 1. Main reaction modes of lipase-catalyzed polyester synthesis.Scheme 2. Lipase-catalyzed ROP of CL (a), and ROCP between CL and VL (b).Scheme 3. Unsubstituted lactone monomers for lipase-catalyzed ROP.

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Section: Introductionmentioning

confidence: 88%

Section: Ring‐opening Polymerization Of Lactonesmentioning

confidence: 99%

Enzymatic ring‐opening polymerization and polycondensation for the green synthesis of polyesters

Kobayashi

2015

Polymers for Advanced Techs

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“…Enzyme catalysis has provided a new synthetic strategy for a variety of useful biomaterials, most of which would to be difficult to produce using conventional chemical catalysts [48,49,50,51,52,53,54]. For example, tin(II) 2-ethylhexanoate Sn(Oct) 2 , probably the most often used catalyst in the polymerization of cyclic esters, has been approved by FDA as a food additive.…”

Section: Biocatalytic Synthesis Of Polymers For Biomedical Applicamentioning

confidence: 99%

Enzymatic Polymerization of Cyclic Monomers in Ionic Liquids as a Prospective Synthesis Method for Polyesters Used in Drug Delivery Systems

Piotrowska

Sobczak

2014

Molecules

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Biodegradable or bioresorbable polymers are commonly used in various pharmaceutical fields (e.g., as drug delivery systems, therapeutic systems or macromolecular drug conjugates). Polyesters are an important class of polymers widely utilized in pharmacy due to their biodegradability and biocompatibility features. In recent years, there has been increased interest in enzyme-catalyzed ring-opening polymerization (e-ROP) of cyclic esters as an alternative method of preparation of biodegradable or bioresorbable polymers. Ionic liquids (ILs) have been presented as green solvents in enzymatic ring-opening polymerization. The activity, stability, selectivity of enzymes in ILs and the ability to catalyze polyester synthesis under these conditions are discussed. Overall, the review demonstrates that e-ROP of lactones or lactides could be an effective method for the synthesis of useful biomedical polymers.

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“…Horseradish peroxidase (HRP), an oxidation-catalyzing enzyme with high stability and activity, can catalyze gelation via radical coupling of phenol and aniline derivatives in the presence of exogenous hydrogen peroxide (H 2 O 2 ). 20 Such reactions offer the ability to tune the gelation rate and final gel properties (e.g., stiffness). Notably, Groll et al reported HRP-catalyzed redox-sensitive disulfide crosslinked hydrogels in basic pH conditions (pH 8.5) and without H 2 O 2 but with slow (>110 min) reaction times.…”

Section: Introductionmentioning

confidence: 99%

Rheological Analysis of the Gelation Kinetics of an Enzyme Cross-linked PEG Hydrogel

et al. 2019

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The diverse requirements of hydrogels for tissue engineering motivate the development of crosslinking reactions to fabricate hydrogel networks with specific features, particularly those amenable to the activity of biological materials (e.g., cells, proteins) that do not require exposure to UV light. We describe gelation kinetics for a library of thiolated poly(ethylene glycol) sulfhydryl hydrogels undergoing enzymatic cross-linking via horseradish peroxidase, a catalyst-driven reaction activated by hydrogen peroxide. We report the use of small-amplitude oscillatory shear (SAOS) to quantify gelation kinetics as a function of reaction conditions (hydrogen peroxide and polymer concentrations). We employ a novel approach to monitor the change of viscoelastic properties of hydrogels over the course of gelation (Δt gel) via the time derivative of the storage modulus (dG′/dt). This approach, fundamentally distinct from traditional methods for defining a gel point, quantifies the time interval over which gelation events occur. We report that gelation depends on peroxide and polymer concentrations as well as system temperature, where the effects of hydrogen peroxide tend to saturate over a critical concentration. Further, this cross-linking reaction can be reversed using L-cysteine for rapid cell isolation, and the rate of hydrogel dissolution can be monitored using SAOS.

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Enzymatic Polymerization to Polyesters

Abstract: Introduction Historical Outline Ring‐opening Polymerization of Cyclic Monomers Polymerization of Lactones Polymerization of Other Cyclic Monomers Copolymerization of Cyclic Monomers Single‐step Synthesis of End‐functionalized Polyesters Polymerization o… Show more

Cited by 11 publications

References 141 publications

Enzymatic ring‐opening polymerization and polycondensation for the green synthesis of polyesters

Enzymatic ring‐opening polymerization and polycondensation for the green synthesis of polyesters

Enzymatic Polymerization of Cyclic Monomers in Ionic Liquids as a Prospective Synthesis Method for Polyesters Used in Drug Delivery Systems

Rheological Analysis of the Gelation Kinetics of an Enzyme Cross-linked PEG Hydrogel

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