Enzymatic Synthesis and Characterization of Biodegradable Poly(ω-pentadecalactone-co-ε-caprolactone) Copolymers

Ulker, Cansu; Güvenilir, Yüksel

doi:10.7569/jrm.2017.634189

Cited by 7 publications

(6 citation statements)

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“…13 C NMR spectra of Gl and PGl are compared in Figure S3 (in Supplementary Materials) indicating that the isomeric ratio present in the macrolactone was retained in the copolyesters generated by eROP. Nevertheless, a random distribution of the two comonomers is assumed to be present in these copolymers according to what should be expected from the well-known indiscriminate transesterase activity of lipases [26], and also in agreement with the microstructure generated in the eROP of a diversity of PDL-based copolyesters that have been previously reported [10,11,13,14]. a Subscripts x and y indicate the %-mole composition of the copolymer in globalide (Gl) and pentadecalactone (PDL) units, respectively; b %-mole composition of the feed and the copolymer determined by 1 H NMR; and c number-average molecular weight of the copolymer as determined by end-group 1 H NMR analysis.…”

Section: Pgl-r-pdl Copolyesterssupporting

confidence: 61%

“…The possibilities of PDL as monomer has been widely explored along the last two decades for the synthesis of aliphatic polyesters and copolyesters with high potential as biodegradable and bioresorbable medical materials, whereas such interest for Gl has been moderate. Copolymerization by ROP of PDL with other lactones constitutes the major approach applied for the design of highly hydrophobic polyesters with adjusted thermal and mechanical properties [8][9][10][11][12][13][14][15][16]. A substantial limitation of the polyesters made of PDL is, however, their lack of chemical functionality other than that associated to chain ends.…”

Section: Introductionmentioning

confidence: 99%

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Copolymacrolactones Grafted with l-Glutamic Acid: Synthesis, Structure, and Nanocarrier Properties

2020

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The enzymatic ring-opening copolymerization (eROP) of globalide (Gl) and pentadecalactone (PDL) was performed in solution from mixtures of the two macrolactones at ratios covering the whole range of comonomeric compositions. The resulting P(Glx-r-PDLy) random copolyesters were aminofunctionalized by thiol-ene reaction with aminoethanethiol. ROP of γ-benzyl-l-glutamate N-carboxyanhydride initiated by P(Glx-r-PDLy)-NH2 provided neutral poly(γ-benzyl-l-glutamate)-grafted copolyesters, which were converted by hydrolysis into negatively charged hybrid copolymers. Both water-soluble and nonsoluble copolymers were produced depending on copolymer charge and their grafting degree, and their capacity for self-assembling in nano-objects were comparatively examined. The emulsion solvent-evaporation technique applied to the chloroform-soluble copolymers grafted with benzyl glutamate rendered well-delineated spherical nanoparticles with an average diameter of 200–300 nm. Conversely, micellar solutions in water were produced from copolyesters bearing grafted chains composed of at least 10 units of glutamic acid in the free form. The copolymer micelles were shown to be able to load doxorubicin (DOX) efficiently through electrostatic interactions and also to release the drug at a rate that was markedly pH dependent.

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Section: Pgl-r-pdl Copolyesterssupporting

confidence: 61%

Section: Introductionmentioning

confidence: 99%

Copolymacrolactones Grafted with l-Glutamic Acid: Synthesis, Structure, and Nanocarrier Properties

2020

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“…where ΔH°f PVL = 181.8 J/g [17]. Thermal Gravimetric Analysis (TGA) was applied on a Perkin Elmer apparatus for thermal characterization of the samples.…”

Section: Instrumental Methodsmentioning

confidence: 99%

Performance Comparison of Commercial and Home-Made Lipases for Synthesis of Poly(δ-valerolactone) Homopolymers

Ulker¹,

Gok²,

Güvenilir³

2019

Journal of Renewable Materials

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Novozyme 435, which is the commercially available immobilized form of Candida antarctica lipase B, has been successfully conducted ring opening polymerization of lactones in organic solvents. In this paper, it was aimed to introduce an alternative biocatalyst for Novozyme 435. Candida antarctica lipase B immobilized onto rice husk ashes via physical adsorption (with a specific activity of 4.4 U/mg) was prepared in previous studies and used as a biocatalyst for poly(δ-valerolactone) synthesis in the present work. Polymerization reactions were proceeded at various reaction temperatures and periods via both two immobilized enzyme preparations. The resulting products were characterized spectroscopically and thermally. The highest molecular weight (Mn = 9010 g/mol) was obtained via Novozyme 435 catalysis at 40℃ and 24 hours. The performance of home-made lipase, which resulted in a molecular weight of 8040 g/mol, was close to commercial one.

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“…Among recent works on the enzymatic production of polyesters, one can highlight the production of biodegradable conjugates of proteins and poly-ε-caprolactone using ring-opening polymerization of ε-caprolactone catalyzed by lipase B from Candida antarctica [ 77 ], the production of polyesters from macrolactones, for example, ω-pentadecalactone, and its unsaturated derivatives, using Novozym 435 with a yield of 80-90% and a molecular weight of up to 130 kDa [ 78 , 174 ], as well as copolymers based on ε-caprolactone and ω-pentadecalactone [ 79 ], ε-caprolactone and 5-hydroxymethyl-2-furancarboxylic acid [ 80 ]. Polycondensation methods have been successfully used in the preparation of polyesters based on aromatic and aliphatic diols and dicarboxylic acids obtained from renewable raw materials using lipase B from Candida antarctica (CALB) [ 81 , 82 , 83 ], as well as in the preparation of polyesters containing, in addition to methylene fragments, simple thioether groups [ 84 ].…”

Section: Enzymes and Polymers Produced With Themmentioning

confidence: 99%

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

Nikulin

Švedas

2021

Molecules

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Trends in the dynamically developing application of biocatalysis for the synthesis and modification of polymers over the past 5 years are considered, with an emphasis on the production of biodegradable, biocompatible and functional polymeric materials oriented to medical applications. The possibilities of using enzymes not only as catalysts for polymerization but also for the preparation of monomers for polymerization or oligomers for block copolymerization are considered. Special attention is paid to the prospects and existing limitations of biocatalytic production of new synthetic biopolymers based on natural compounds and monomers from biomass, which can lead to a huge variety of functional biomaterials. The existing experience and perspectives for the integration of bio- and chemocatalysis in this area are discussed.

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Enzymatic Synthesis and Characterization of Biodegradable Poly(ω-pentadecalactone-co-ε-caprolactone) Copolymers

Cited by 7 publications

References 0 publications

Copolymacrolactones Grafted with l-Glutamic Acid: Synthesis, Structure, and Nanocarrier Properties

Copolymacrolactones Grafted with l-Glutamic Acid: Synthesis, Structure, and Nanocarrier Properties

Performance Comparison of Commercial and Home-Made Lipases for Synthesis of Poly(δ-valerolactone) Homopolymers

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

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