Synthesis of functional polymers from lignin and its related compounds by using enzymes from wood-rotting basidiomycetes.

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Synthesis of polymers using the one electron oxidation mechanism of manganese peroxidase (MnP) produced by lignin-degrading basidiomycete, Bjerkandera adujsta, and horseradish peroxidase (HRP) was examined.First, polyguaiacol was synthesized from guaiacol by using both enzymes in 50 % aqueous solution of organic solvents. The reaction in dioxane, acetone and acetonitrile resulted in the production of DMF-insoluble products with over 60 % yield based on guaiacol added. Weight average molecular weight of the polymer, polyguaiacol, was about 1700. ^<13>C-NMR and IR spectra indicated the presence of C-C and C-O bonds and quinone structure in the polymer. MnP also gave polyguaiacol which was richer in quinine structure than HRP. Thermal analysis showed the absence of crystalline structure in the polymer. HRP polymerize phenol, ο-methoxyphenol, ο- and m-methylphenol to give their polymers.Arbutin, a glucoside substituted by hydroquinone at C1, was polymerized by MnP at the position of quinine moiety. About 35 % of arbutin added was converted to methanol-insoluble polymer. ^<13>C-NMR indicated arbutin was combined at hydroquinone moiety to give polymer whose molecular weight was estimated to be 1200. Addition of ρ-cresol to arbutin resulted in the production of the co-polymer which contained both moieties. HRP also produce this co-polymer, whereas polymerization of arbutin itself did not occur.Thus, MnP has the possibility to produce various types of polymers which can be used as functional polymers other than engineering polymers.