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首页> 外文期刊>RSC Advances >The efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4
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The efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4

机译：通过细胞色素P450单氧化酶，CYP199A4的高分子蛋白肉桂酸衍生物的高效和选择性催化氧化氧化剂，CYP199A4

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The cytochrome P450 enzyme, CYP199A4, demethylated 4-methoxybenzoic acid, but not 4-methoxyphenylacetic acid, with high product formation activity. The oxidative demethylation of 3-(4-methoxyphenyl)propionic acid was 8-fold more active than 4-methoxyphenylacetic acid and 4-methoxycinnamic acid was efficiently oxidised at a product formation rate of 180 nmol nmol-P450 ~(?1) min ~(?1) . Accordingly the oxidation of cinnamic acid derivatives was investigated in order to determine the potential of CYP199A4 to act as a biocatalyst for this important class of biological molecules. 4-Methoxy- and 4-methyl-cinnamic acids bound tightly to CYP199A4 and were better substrates for CYP199A4 than cinnamic acid itself. The oxidations of both 4-methoxy- and 4-methyl-cinnamic acids was 100% selective for attack at the para substituent. Certain dimethoxy substituted cinnamic acids were demethylated more efficiently than 4-methoxycinnamic acid and retained the selectivity for the para -methoxy substituent. Only very low product turnover was observed with 3,5-dimethoxycinnamic acid. 4-Isopropylcinnamic acid was hydroxylated and desaturated by CYP199A4 at the isopropyl group. Cinnamic acids with a para -substituted alkyl- and alkyloxy–cinnamic acid framework were a good fit for the active site of the CYP199A4 enzyme and as a consequence were efficiently and selectively oxidised. Whole-cell oxidations resulted in high yields of product and CYP199A4 could be developed for applications in the biocatalytic oxidation of cinnamic acid derivatives and related phenylpropanoids.
机译：细胞色素P450酶，CYP199A4，去甲基化4-甲氧基苯甲酸，但不是4-甲氧基苯基乙酸，具有高产物形成活性。 3-（4-甲氧基苯基）丙酸的氧化去甲基化比4-甲氧基苯基乙酸和4-甲氧基氨基酸在180nmol Nmol-P450〜（α1）分钟的产物形成速率上有效氧化4-甲氧基氨基酸。 （？1）。因此，研究了肉桂酸衍生物的氧化，以确定CYP199A4的潜力作为这种重要的生物分子的生物催化剂。 4-甲氧基和4-甲基肉桂酸紧密到CYP199A4，并且对于CYP199A4的底物比肉桂酸本身更好。 4-甲氧基 - 和4-甲基 - 肉桂酸的氧化是在对帕拉取代基的攻击中得到100％的选择性。某些二甲氧基取代的肉桂酸比4-甲氧基氨基酸更有效地脱溶，并保留了对 - 甲氧基取代基的选择性。用3,5-二甲氧基氨基酸只观察到唯一非常低的产品转换。在异丙基的CYP199A4中，4-异丙基氨基酸羟基化和去饱和。具有Para-取代的烷基和烷基氧基 - 肉桂酸框架的肉桂酸是CYP199A4酶的活性位点的良好适合，结果有效且选择性地氧化。可以为肉桂酸衍生物和相关苯丙醇的生物催化氧化中的应用产生高产量的产物和CYP199A4的全细胞氧化。

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