Institute of Environmental Biotechnology, Graz University of Technology, Petersgasse 12, A-8010 Graz, Austria.
Bioresour Technol. 2010 Apr;101(8):2793-9. doi: 10.1016/j.biortech.2009.12.002. Epub 2009 Dec 30.
This work presents for the first time the mechanistic evidence of a laccase-catalyzed method of covalently grafting hydrophobicity enhancing fluorophenols onto Fagus sylvatica veneers. Coupling of fluorophenols onto complex lignin model compounds guaiacylglycerol beta-guaiacyl ether and syringylglycerol beta-guaiacyl ether was demonstrated by LC-MS and NMR. Laccase-mediated coupling increased binding of 4-[4-(trifluoromethyl)phenoxy]phenol (4,4-F3MPP) and 4-(trifluoromethoxy)phenol (4-F3MP) to veneers by 77.1% and 39.2%, respectively. XPS studies showed that laccase-catalyzed grafting of fluorophenols resulted in a fluorine content of 6.39% for 4,4-F3MPP, 3.01% for 4-F3MP and 0.26% for 4-fluoro-2-methylphenol (4,2-FMP). Grafting of the fluorophenols 4,2-FMP, 4-F3MP and 4,4-F3MPP led to a 9.6%, 28.6% and 65.5% increase in hydrophobicity, respectively, when compared to treatments with the respective fluorophenols in the absence of laccase, in good agreement with XPS data.
本研究首次提出了漆酶催化的方法，用于将疏水性增强的氟苯酚共价接枝到欧洲山毛榉单板上。通过 LC-MS 和 NMR 证明了氟苯酚与复杂木质素模型化合物愈创木基甘油-β-愈创木基醚和丁香基甘油-β-愈创木基醚的偶联。漆酶介导的偶联使 4-[4-(三氟甲基)苯氧基]苯酚（4,4-F3MPP）和 4-（三氟甲氧基）苯酚（4-F3MP）与单板的结合分别增加了 77.1%和 39.2%。XPS 研究表明，漆酶催化的氟苯酚接枝导致 4,4-F3MPP 的氟含量为 6.39%，4-F3MP 为 3.01%，4-氟-2-甲基苯酚（4,2-FMP）为 0.26%。与没有漆酶存在时的相应氟苯酚处理相比，氟苯酚 4,2-FMP、4-F3MP 和 4,4-F3MPP 的接枝分别使疏水性增加了 9.6%、28.6%和 65.5%，与 XPS 数据吻合较好。
