Volume 200, Issue 9 pp. 1998-2002
Research Article

Chemoenzymatic synthesis of a poly(hydroquinone)

Hiroyuki Tonami

Hiroyuki Tonami

Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606–8501, Japan

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Hiroshi Uyama

Hiroshi Uyama

Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606–8501, Japan

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Shiro KobayashiKarsten Rettig

Karsten Rettig

Institut für Organische Chemie, Johannes-Gutenberg-Universität, 55099 Mainz, Germany

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Helmut Ritter

Helmut Ritter

Institut für Organische Chemie, Johannes-Gutenberg-Universität, 55099 Mainz, Germany

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Abstract

Chemoenzymatic synthesis of a poly(hydroquinone) was achieved by enzymatic oxidative polymerization of 4-hydroxyphenyl benzoate, followed by alkaline hydrolysis of the resulting polymer. The polymerization of 4-hydroxyphenyl benzoate was performed using a peroxidase and hydrogen peroxide as catalyst and oxidizing agent, respectively, in an aqueous organic solvent. Soybean peroxidase afforded the polymer in good yields. IR analysis of the polymer showed the formation of the polymer consisting of a mixture of phenylene and oxyphenylene units. By alkaline hydrolysis of the resulting polymer, benzoate moiety was completely removed to give poly(hydroquinone).

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