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Organocatalyzed ring-opening copolymerization of ?-bromo-?-butyrolactone with ?-caprolactone for the synthesis of functional aliphatic polyesters - pre-polymers for graft copolymerization.

ABSTRACT: Diphenyl phosphate (DPP) was exploited as an organocatalyst to synthesize copolymers by ring-opening polymerization with ?-bromo-?-butyrolactone (?Br?BL) and ?-caprolactone (?CL) as monomers and polyethylene glycol (PEG) as initiator. The conversion rates of monomers and molecular weights of copolymers synthesized under different conditions were determined by ¹H-NMR. The ¹H-NMR results showed that the copolymers of ?Br?BL and ?CL initiated by PEG (PEGCB) were successfully synthesized and the conversions of ?CL were relatively high (?70%), while the conversions of ?Br?BL were relatively low (?26%). The highest molar ratio of ?Br?BL to ?CL units in these copolymers is 0.17, when the copolymerization was carried out at 100? for 17h. The bromine atoms hanged on the chain of the copolymers PEGCB provide a good opportunity to construct graft copolymers via atom transfer radical polymerization (ATRP). The subsequent grafting of 2-(dimethylamino)ethyl methacrylate (DMAEMA) was conducted by using PEGCB3 as macroinitiator, CuBr/N,N',N',N",N"- pentamethyldiethylenetriamine (PMDETA) as catalysts and toluene/anisole as solvents via ATRP. According to the analysis of ¹H-NMR, the grafting efficiency, grafting ratio and grafting frequency were 22.4%, 160.7% and 1133.8, respectively.

SUBMITTER: Gao C

PROVIDER: S-EPMC6282472 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Organocatalyzed ring-opening copolymerization of α-bromo-γ-butyrolactone with ε-caprolactone for the synthesis of functional aliphatic polyesters - pre-polymers for graft copolymerization.

Gao Chen C Tsou Chi-Hui CH Zeng Chun-Yan CY Yuan Li L Peng Rui R Zhang Xue-Mei XM

Designed monomers and polymers 20181129 1

Diphenyl phosphate (DPP) was exploited as an organocatalyst to synthesize copolymers by ring-opening polymerization with α-bromo-γ-butyrolactone (αBrγBL) and ε-caprolactone (εCL) as monomers and polyethylene glycol (PEG) as initiator. The conversion rates of monomers and molecular weights of copolymers synthesized under different conditions were determined by <sup>1</sup>H-NMR. The <sup>1</sup>H-NMR results showed that the copolymers of αBrγBL and εCL initiated by PEG (PEGCB) were successfully s ...[more]

PMID: 30532666

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Project description:Polyethylene terephthalate (PET) is one of the most widely used synthetic plastics in the packaging industry, and consequently has become one of the main components of plastic waste found in the environment. However, several microorganisms have been described to encode enzymes that catalyze the depolymerization of PET. While most known PET hydrolases are thermophilic and require reaction temperatures between 60°C and 70°C for an efficient hydrolysis of PET, a partial hydrolysis of amorphous PET at lower temperatures by the polyester hydrolase IsPETase from the mesophilic bacterium Ideonella sakaiensis has also been reported. We show that polyester hydrolases from the Antarctic bacteria Moraxella sp. strain TA144 (Mors1) and Oleispira antarctica RB-8 (OaCut) were able to hydrolyze the aliphatic polyester polycaprolactone as well as the aromatic polyester PET at a reaction temperature of 25°C. Mors1 caused a weight loss of amorphous PET films and thus constitutes a PET-degrading psychrophilic enzyme. Comparative modeling of Mors1 showed that the amino acid composition of its active site resembled both thermophilic and mesophilic PET hydrolases. Lastly, bioinformatic analysis of Antarctic metagenomic samples demonstrated that members of the Moraxellaceae family carry candidate genes coding for further potential psychrophilic PET hydrolases. IMPORTANCE A myriad of consumer products contains polyethylene terephthalate (PET), a plastic that has accumulated as waste in the environment due to its long-term stability and poor waste management. One promising solution is the enzymatic biodegradation of PET, with most known enzymes only catalyzing this process at high temperatures. Here, we bioinformatically identified and biochemically characterized an enzyme from an Antarctic organism that degrades PET at 25°C with similar efficiency to the few PET-degrading enzymes active at moderate temperatures. Reasoning that Antarctica harbors other PET-degrading enzymes, we analyzed available data from Antarctic metagenomic samples and successfully identified other potential enzymes. Our findings contribute to increasing the repertoire of known PET-degrading enzymes that are currently being considered as biocatalysts for the biological recycling of plastic waste.

Dataset Information

Organocatalyzed ring-opening copolymerization of ?-bromo-?-butyrolactone with ?-caprolactone for the synthesis of functional aliphatic polyesters - pre-polymers for graft copolymerization.

Publications

Organocatalyzed ring-opening copolymerization of α-bromo-γ-butyrolactone with ε-caprolactone for the synthesis of functional aliphatic polyesters - pre-polymers for graft copolymerization.

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