Soluble polyphenol

Oguchi, Takahisa; Tawaki, Shin-ichiro; Uyama, Hiroshi; Kobayashi, Shiro

doi:10.1002/(sici)1521-3927(19990701)20:7<401::aid-marc401>3.0.co;2-6

Cited by 114 publications

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“…In the case of poly(1-naphthol) and poly(2-naphthol), there was a 40–50°C increase in decomposition temperature when they were synthesized in 70% (v/v) BMPy(BF 4 ) which presumably was due to the higher molecular weight compared to poly(naphthols) synthesized in aqueous buffer and possibly structural changes of the polyphenols in the RTIL as compared to aqueous buffer. With respect to the latter, recent studies have shown that polyphenols obtained by peroxidase catalyzed polymerization reactions in aqueous-organic solvent mixtures, are structurally composed of a mixture of phenylene and oxyphenylene units, which are formed by C–C and C–O couplings of phenols, respectively [18, 41]. The regioselectivity of phenol polymerization is mainly affected by the solvent composition and the nature of the phenol [42].…”

Section: Resultsmentioning

confidence: 99%

“…The mild reaction conditions coupled with the highly reactive and stable peroxidase family of oxidative enzymes is also ideal for synthetic applications. In particular, soybean peroxidase (SBP) and horseradish peroxidase (HRP) have been used to synthesize phenolic polymers and copolymers from a wide range of phenols, including p -cresol, p -phenylphenol, various naphthols, and phenol itself, along with related anilines [16–18]. Both SBP and HRP yield similar polymeric products, which appear to be representative of the majority of plant peroxidases [19].…”

Section: Introductionmentioning

confidence: 99%

“…Water-miscible cosolvents have been used to support higher molecular weight polyphenolic synthesis. In addition to 1,4-dioxane-water mixtures, Oguchi et al performed enzymatic oxidative polymerization of phenol in aqueous methanol solutions using HRP yielding number average molecular weights up to 5200 Da [18]. …”

Section: Introductionmentioning

confidence: 99%

“…While highly polar aprotic solvents such as DMF and DMSO are able to solubilize high molecular weight fractions of polyphenols, primarily at very high solvent percentages [18, 20, 27], enzyme activity in these solvents is low [20, 23, 27]. RTILs, however, may provide the advantages of a nonaqueous environment that enables high solubility of phenols and their polymerized counterparts, while maintaining sufficient enzyme activity to allow efficient polymerization, all while providing “green” alternatives to volatile organic solvents.…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic polymerization of phenols in room-temperature ionic liquids

Eker

Zagorevski

Zhu

et al. 2009

Journal of Molecular Catalysis B: Enzymatic

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Soybean peroxidase (SBP) was used to catalyze the polymerization of phenols in room-temperature ionic liquids (RTILs). Phenolic polymers with number average molecular weights ranging from 1200 to 4100 D were obtained depending on the composition of the reaction medium and the nature of the phenol. Specifically, SBP was highly active in methylimidazolium-containing RTILs, including 1-butyl-3-methylimidazolium tetrafluoroborate (BMIM(BF 4 )), and 1-butyl-3-methylpyridinium tetrafluoroborate (BMPy(BF 4 )) with the ionic liquid content as high as 90% (v/v); the balance being aqueous buffer. Gel permeation chromatography and MALDI-TOF analysis indicated that higher molecular weight polymers can be synthesized in the presence of higher RTIL concentrations, with selective control over polymer size achieved by varying the RTIL concentration. The resulting polyphenols exhibited high thermostability and possessed thermosetting properties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Enzymatic polymerization of phenols in room-temperature ionic liquids

Eker

Zagorevski

Zhu

et al. 2009

Journal of Molecular Catalysis B: Enzymatic

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“…It has also been polymerized by a laccase derived from Myceliophthore (ML) in a mixture of acetone-buffer pH 5 rendering an 8,000 Da polymer [129]. In this case, as in other phenol polymerizations [100], the organic solvent/buffer ratio greatly affected the solubility of the synthesized polymer. The antioxidant properties of catechins and ECGC, not only remained, but increased in a concentration dependent manner in poly(catechin) and poly(ECGC) synthesized by HRP and ML [129,130].…”

Section: Enzymes In the Bulk Chemistry Industrymentioning

confidence: 99%

Biocatalysis for Biobased Chemicals

Regil¹,

Sandoval²

2013

Biomolecules

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The design and development of greener processes that are safe and friendly is an irreversible trend that is driven by sustainable and economic issues. The use of Biocatalysis as part of a manufacturing process fits well in this trend as enzymes are themselves biodegradable, require mild conditions to work and are highly specific and well suited to carry out complex reactions in a simple way. The growth of computational capabilities in the last decades has allowed Biocatalysis to develop sophisticated tools to understand better enzymatic phenomena and to have the power to control not only process conditions but also the enzyme’s own nature. Nowadays, Biocatalysis is behind some important products in the pharmaceutical, cosmetic, food and bulk chemicals industry. In this review we want to present some of the most representative examples of industrial chemicals produced in vitro through enzymatic catalysis.

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Enzymatic Polymerization

Kobayashi¹,

Uyama²

2001

Encyclopedia of Polymer Science and Technology

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This article deals with recent advances in enzymatic polymerizations, defined as chemical polymer synthesis in vitro (in test tubes) via nonbiosynthetic pathways catalyzed by an isolated enzyme. The principal target macromolecules via the enzymatic polymerization are polysaccharides, poly(amino acid)s, polyesters, polycarbonates, polyaromatics, and vinyl polymers. For synthesis of polysaccharides, poly(amino acid)s, polyesters, and polycarbonates, hydrolases are used as catalyst; hydrolases, enzymes catalyzing a bond‐cleavage reaction by water, induce the reverse reaction of hydrolysis, leading to polymer production by a bond‐forming reaction. Specific enzyme catalysis provides a novel synthetic route for not only natural biopolymers such as cellulose, xylan, and chitin, but also unnatural polysaccharides, polyesters, poly(amino acid)s, and polycarbonates, many of which are difficult to be synthesized by conventional methodologies. Oxidoreductases act as catalyst for oxidative polymerization of phenol, aniline, and their derivatives, for polymer modification via oxidative coupling, and for production of vinyl polymers. A new class of phenolic polymers are synthesized without use of toxic formaldehyde under mild reaction conditions. Enzyme‐model complexes also catalyze the synthesis of new phenolic polymer materials.

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Soluble polyphenol

Cited by 114 publications

References 0 publications

Enzymatic polymerization of phenols in room-temperature ionic liquids

Enzymatic polymerization of phenols in room-temperature ionic liquids

Biocatalysis for Biobased Chemicals

Enzymatic Polymerization

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