Comparison of a series of laccase mediators in the electro-oxidation reactions of non-phenolic lignin model compounds

化学 阿布茨 漆酶 产量(工程) 烷氧基 木质素 选择性 有机化学 乙醚 药物化学 烷基 抗氧化剂 催化作用 材料科学 DPPH 冶金
作者
Takumi Shiraishi,Yumi Sannami,Hiroshi Kamitakahara,Toshiyuki Takano
出处
期刊:Electrochimica Acta [Elsevier]
卷期号:106: 440-446 被引量:39
标识
DOI:10.1016/j.electacta.2013.05.112
摘要

The electro-oxidations of non-phenolic lignin model compounds in an electrolytic mediator system (EMS) have been investigated with several laccase mediators, including N-hydroxyphthalimide (NHPI), 1-hydroxybenzotriazole (HBT), violuric acid (VLA), 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS), under the same reaction conditions. In the bulk electrolyses of the monomeric model compound [1-(4′-ethoxy-3′-methoxyphenyl)ethanol (1G)], oxidation with NHPI gave the corresponding CαO product (2G) in high yield, whereas the oxidations with HBT, VLA, and TEMPO afforded 2G in moderate yields. The highest reaction selectivity for the guaiacyl-units was found in the oxidation conducted in the presence of ABTS, although the yield was low. In the bulk electrolyses of the dimeric model compound [4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether (3G)], the oxidation with NHPI gave the corresponding CαO product (4G) in high yield, whereas the oxidations with HBT, VLA, and TEMPO gave 4G in low yields. In contrast, the oxidation with ABTS gave a Cα–Cβ cleavage product (5G) in 5.5% yield. The selectivity of the mediators in the EMS reaction effectively reflected the mechanisms of their reactions, as reported for the laccase mediator system. NHPI was confirmed to be the best mediator in the present system for the selective Cα-carbonylation of the non-phenolic β-O-4 structures in lignin.
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