Enzymatic oxidative polymerization of 4-hydroxybenzoic acid derivatives to poly(phenylene oxide)s

Ikeda, Rinsei; Sugihara, Junji; Uyama, Hiroshi; Kobayashi, Shiro

doi:10.1002/(sici)1097-0126(199811)47:3<295::aid-pi7>3.3.co;2-n

Cited by 30 publications

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“…10. The findings that the polymer is composed of oxyphenylene units is consistent with literature results on the enzymatic polymerization of phenolic monomers (Aktas et al, 2003;Ikeda et al, 1998;Marjasvaara et al, 2006). In consequence of the C-O-C coupling, the synthetic polymer can not be regarded as a fully conjugated system.…”

Section: Methylene and Carboxylic Groupssupporting

confidence: 90%

Structural characterization of allomelanin from black oat

et al. 2016

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The brown to black coloration found in plants is due to the melanins, which have been relatively poorly investigated among the plant pigments. The aim of this work was to study the dark pigment extracted from the black oat hull with respect to composition and structure. Ultraviolet-visible (UV-Vis) spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, matrix-assisted laser desorption/ionization-time of flight mass spectrometry (MALDI-TOF MS) and Fourier transform infrared (FT-IR) spectroscopy were applied for the characterization of the pigment. UV-Vis spectroscopy revealed that the extracted material displayed the absorption profile typical of melanins. MALDI-TOF MS measurements demonstrated that oat melanin is a homopolymer built up from p-coumaric acid and consists mainly of low molecular weight (500-900 Da) oligomers of between 3 and 9 monomer units. The tetramer oligomer proved to be dominant. The results of the FT-IR analysis indicated that oat melanin is a fully conjugated aromatic system containing tetrasubstituted aromatic rings linked by C-C coupling. The in vitro preparation of melanin from p-coumaric acid by horseradish peroxidase was performed for comparison. The resulting polymer consisted of oligomers of 4 to 9 monomer units similarly to those in oat melanin. However the building blocks proved to be connected to each other via C-O-C linkages in contrast with the C-C linkages in oat melanin. This is the first demonstration of the structure of melanin originating from plants.

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Section: Methylene and Carboxylic Groupssupporting

confidence: 90%

Structural characterization of allomelanin from black oat

et al. 2016

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“…Another interesting example is the polymerization of p-hydroxy benzoic acid (derivates), which proceeds highly regioselectively producing oxyphenylene connections exclusively (Figure 14) [95]. Polymerization of catechols and hydroquinones can be tedious due to facile oxidation to the corresponding quinones.…”

Section: Substrate Engineeringmentioning

confidence: 99%

Enzyme Initiated Radical Polymerizations

2012

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“…4 Recently, it has been found that oxidoreductases (HRP, SBP, and laccases) induce the oxidation polymerization of 4-hydroxybenzoic acid derivatives in an aqueous organic solvent at room temperature under air to give a PPO in good yields (Scheme 16). 80 or laccase/O 2 system, liberating carbon dioxide during the reaction. Monomer a did not polymerize.…”

Section: Synthesis Of Poly(phenylene Oxide)smentioning

confidence: 99%

Enzymatic polymerization: A new method of polymer synthesis

Kobayashi

1999

J. Polym. Sci. A Polym. Chem.

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248

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Enzymatic polymerization denotes an in vitro polymerization via nonbiosynthetic pathways catalyzed by an isolated enzyme. This article describes the recent progress of this polymerization technique, developed mainly during this decade. The polymerization utilizes enzymes of hydrolases and oxidoreductases as catalysts. This new method of polymer synthesis provided natural polysaccharides like cellulose, amylose, xylan, and chitin, and unnatural polysaccharides catalyzed by a glycosidase from well‐designed monomers, various functionalized polyesters catalyzed by lipase from a variety of monomers, and polyaromatics materials catalyzed by an oxidoreductase and an enzyme model complex from phenols and anilines. An oxidoreductase also initiated vinyl polymerizations. Characteristic features of enzymatic polymerizations are discussed, including the importance of the combination of substrate monomer and enzyme. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3041–3056, 1999

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Enzymatic oxidative polymerization of 4-hydroxybenzoic acid derivatives to poly(phenylene oxide)s

Cited by 30 publications

References 0 publications

Structural characterization of allomelanin from black oat

Structural characterization of allomelanin from black oat

Enzyme Initiated Radical Polymerizations

Enzymatic polymerization: A new method of polymer synthesis

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