Department of Chemistry, Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8602, Japan.
Core Research for Evolutional Science and Technology (Japan), Science and Technology Agency, 5 Sanbancho, Chiyoda-ku, Tokyo, 102-0075, Japan.
Angew Chem Int Ed Engl. 2017 Aug 21;56(35):10324-10329. doi: 10.1002/anie.201703461. Epub 2017 Jun 8.
The selective hydroxylation of benzene to phenol, without the formation of side products resulting from overoxidation, is catalyzed by cytochrome P450BM3 with the assistance of amino acid derivatives as decoy molecules. The catalytic turnover rate and the total turnover number reached 259 min P450BM3 and 40 200 P450BM3 when N-heptyl-l-proline modified with l-phenylalanine (C7-l-Pro-l-Phe) was used as the decoy molecule. This work shows that amino acid derivatives with a totally different structure from fatty acids can be used as decoy molecules for aromatic hydroxylation by wild-type P450BM3. This method for non-native substrate hydroxylation by wild-type P450BM3 has the potential to expand the utility of P450BM3 for biotransformations.
在氨基酸衍生物作为诱饵分子的辅助下，细胞色素 P450BM3 可以实现苯的选择性羟化，而不会产生过度氧化导致的副产物。当使用 N-庚基-l-脯氨酸修饰的 l-苯丙氨酸（C7-l-Pro-l-Phe）作为诱饵分子时，催化周转率和总周转率数分别达到 259 min P450BM3 和 40200 P450BM3。这项工作表明，与脂肪酸完全不同结构的氨基酸衍生物可用作野生型 P450BM3 芳香族羟化的诱饵分子。这种通过野生型 P450BM3 对非天然底物进行羟化的方法有可能扩大 P450BM3 在生物转化中的应用。
