Cyclodextrins in Polymer Chemistry:  Enzymatically Catalyzed Oxidative Polymerization of Para-Functionalized Phenol Derivatives in Aqueous Medium by Use of Horseradish Peroxidase

Pang, Yanjie; Ritter, Helmut; Tabatabai, Monir

doi:10.1021/ma021678x

Cited by 30 publications

(19 citation statements)

References 21 publications

(38 reference statements)

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“…The alternative route of enzymatic synthesis of phenolic resin has advantages such as mild reaction conditions and without the use of toxic formaldehyde. So far, many new useful phenolic polymers have been prepared by enzymatic catalysis, most of which cannot be obtained by conventional chemical methods …”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of soluble phenol polymer in water using anionic surfactant as additive

Zhang

Xue

et al. 2012

Polym. Int.

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In phosphate–citric acid buffer (pH = 8.0) containing sodium dodecylbenzenesulfonate (SDBS) as a surfactant, enzymatic polymerization of phenol catalyzed by horseradish peroxidase (HRP) is efficiently performed. The as‐synthesized phenol polymer is completely soluble in organic solvents such as dimethylfomamide, dimethylsulfoxide, acetone and tetrahydrofuran. The aqueous micelle system provides a new environmentally friendly method for HRP‐catalyzed phenol polymerization. The effects of the dosage of SDBS and reaction temperature on the yield of the target phenol polymer are investigated. The soluble phenol polymer is composed of phenylene and oxyphenylene units as determined using infrared and 1 H NMR spectral analyses. The number‐average molecular weight calculated from gel permeation chromatography (GPC) is in the range 900–1500 g mol−1 and the dispersity in the range 3.4–6.3. In all cases, the values of weight‐average molecular weight characterized using GPC–static light scattering are tens of thousands. It is concluded that a branched structure is produced in the aqueous micelle system. The phenol polymer prepared possesses good thermal stability for it is completely decomposed at a temperature as high as 628 °C in air.

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Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of soluble phenol polymer in water using anionic surfactant as additive

Zhang

Xue

et al. 2012

Polym. Int.

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“…Implementing such transformations in a heterogeneous phase reaction can overcome solubility issues, but such diffusion-controlled processes are inherently slower than those in a homogeneous phase. By using CDs, the apparent water solubility of the substrate can be increased, thereby allowing for an efficient biocatalytic conversion of poorly water-soluble organic molecules [ 41 ]. CDs can also mitigate the inhibitory effect of the substrate, or the product in certain enzymatic reactions, by the complexation of the interfering component, thus keeping its concentration low [ 42 ].…”

Section: Introductionmentioning

confidence: 99%

Nanofibrous Formulation of Cyclodextrin Stabilized Lipases for Efficient Pancreatin Replacement Therapies

et al. 2021

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Enzyme replacement therapies (ERT) have been of great help over the past 30 years in the treatment of various lysosomal storage disorders, including chronic pancreatitis and its common complication, exocrine pancreatic insufficiency. Research shows that difficulties in designing such drugs can be overcome by using appropriate additives and various enzyme immobilization techniques. Cyclodextrins (CDs) can be considered as a promising additive for enzyme replacement therapies, as they are known to enhance the activity of enzymes in a complex process due to their specific binding. In this study, we investigated the formulation of lipases (from Aspergillus oryzae and Burkholderia cepacia) paired with different cyclodextrins in poly(vinyl alcohol) (PVA) nanofibers by electrospinning technique. We examined the effect of the presence of cyclodextrins and nanoformulation on the lipase activity. The rheological and morphological characterizations of precursors and nanofibers were also performed using a viscometer as well as electron and Raman microscope. We found that by selecting the appropriate CD:lipase ratio, the activity of the investigated enzyme could be multiplied, and cyclodextrins can support the homogeneous dispersion of lipases inside the solid formula. In addition, the entrapment of lipases in PVA nanofibers led to a significant increase in activity compared to the preformulated precursor. In this way, the nanofibrous formulation of lipases combining CDs as additives can provide an efficient and sustainable possibility for designing novel solid medicines in ERT.

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“…The hydrophobic cavity of CDs binds suitable organics by hydrophobic interactions and/or H-bonds, while the hydrophilic outer shell provides the water solubility. Ritter et al successfully polymerized various hydrophobic monomers, such as styrene [33][34][35][36][37][38], (meth)acrylates [33,34,[39][40][41][42][43][44], phenol derivatives [45,46], fumarates [47,48], dienes [49,50], halo-olefins [51][52][53], and other non-commercial ones [54][55][56][57][58][59][60][61] in water, solubilized by CD, via free radical polymerization methods. During the polymerization, the CD, every time, slips off from the last monomeric unit of the polymer, and the product precipitates, resulting in a pure product, or simple purification.…”

Section: Introductionmentioning

confidence: 99%

New, Aqueous Radical (Co)Polymerization of Olefins at Low Temperature and Pressure

Hero

Kali

2020

Processes

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In this communication, we describe our preliminary results for the development of a new method of ethylene and propene (co)polymerization at low pressure at room temperature, using cyclodextrin-assisted aqueous radical polymerization for the first time. For polypropylene homopolymerization, the cyclodextrin was entirely removed, and the partially soluble polymer was characterized. The purification of polyethylene was not complete, since the threaded cyclodextrins remained on the polymer chain, enhancing its solubility and enable to analyze the sample. With this environmentally benign method, polyolefines could be produced, for the first time. The estimated yield was low, and therefore the conditions should be further tuned for industrial application. This straightforward approach could also be applied to synthesize poly(ethylene-co-vinyl acetate) copolymer with an ethylene content of 20 mol% and enhanced yield. Although the procedure in this stage of research has some limitations, the theory behind can later be applied to develop new, energy-efficient, and versatile industrial processes for olefin copolymerizations for a wide range of comonomers.

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Cyclodextrins in Polymer Chemistry: Enzymatically Catalyzed Oxidative Polymerization of Para-Functionalized Phenol Derivatives in Aqueous Medium by Use of Horseradish Peroxidase

Cited by 30 publications

References 21 publications

Enzymatic synthesis of soluble phenol polymer in water using anionic surfactant as additive

Enzymatic synthesis of soluble phenol polymer in water using anionic surfactant as additive

Nanofibrous Formulation of Cyclodextrin Stabilized Lipases for Efficient Pancreatin Replacement Therapies

New, Aqueous Radical (Co)Polymerization of Olefins at Low Temperature and Pressure

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