Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives.
Fungal cytochrome P450s catalyzing hydroxylation of substituted toluenes to form their hydroxymethyl derivatives.
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DOI：
10.1111/j.1574-6968.2004.tb09541.x
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发表时间：
2004-05
影响因子：
2.1
通讯作者：
H. Teramoto;Hiroo Tanaka;H. Wariishi
中科院分区：
文献类型：
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作者：
H. Teramoto;Hiroo Tanaka;H. Wariishi
研究了木质素降解菌黄孢原毛革菌对一系列硝基芳香化合物的降解。从4-硝基甲苯（4-NT），几个代谢中间体被确定。最初，4-NT转化为4-硝基苯甲醇（4-NBA），随后氧化反应形成4-硝基苯甲醛和4-硝基苯甲酸，尽管缓慢。外源添加的4-硝基苯甲醛和4-硝基苯甲酸主要被还原为4-NBA。4-NBA的真菌形成被细胞色素P450抑制剂胡椒基丁醚抑制，表明细胞色素P450参与甲基的羟基化。类似地，2-和3-硝基甲苯和4-氯甲苯被P. chrysosporium转化为相应的芳基醇。另一方面，甲苯和4-甲氧基甲苯没有转化。因此，黄孢原毛平革菌对被强吸电子基团取代的芳香族化合物具有烷基羟基化活性。
The degradation of a series of nitroaromatic compounds by the lignin-degrading fungus Phanerochaete chrysosporium was examined. From 4-nitrotoluene (4-NT), several metabolic intermediates were identified. Initially, 4-NT was converted to 4-nitrobenzyl alcohol (4-NBA), followed by the oxidation reactions to form 4-nitrobenzaldehyde and 4-nitrobenzoic acid, albeit slowly. Exogenously added 4-nitrobenzaldehyde and 4-nitrobenzoic acid were predominantly reduced to 4-NBA. The fungal formation of 4-NBA was inhibited by piperonyl butoxide, a cytochrome P450 inhibitor, suggesting the involvement of cytochrome P450 in the hydroxylation of the methyl group. Similarly, 2-, and 3-nitrotoluenes and 4-chlorotoluene were converted to the corresponding arylalcohols by P. chrysosporium. On the other hand, toluene and 4-methoxytoluene were not converted. Thus, P. chrysosporium possesses an alkyl hydroxylation activity against aromatic compounds substituted with a strong electron-withdrawing group.