The Single-Component Flavin Reductase/Flavin-Dependent Halogenase AetF is a Versatile Catalyst for Selective Bromination and Iodination of Arenes and Olefins.
The Single-Component Flavin Reductase/Flavin-Dependent Halogenase AetF is a Versatile Catalyst for Selective Bromination and Iodination of Arenes and Olefins.
复制标题
DOI：
10.1002/anie.202214610
复制
发表时间：
2022-12-19
影响因子：
16.6
通讯作者：
Lewis, Jared C.
中科院分区：
文献类型：
--
作者：
Jiang, Yuhua;Snodgrass, Harrison M.;Zubi, Yasmine S.;Roof, Caitlin V.;Guan, Yanfei;Mondal, Dibyendu;Honeycutt, Nicholas H.;Lee, Johnny W.;Lewis, Russell D.;Martinez, Carlos A.;Lewis, Jared C.
黄素依赖性卤化酶（FDH）天然催化富电子芳香族和烯醇基团的选择性卤化。迄今为止报道的几乎所有 FDH 都需要单独的黄素还原酶来为其提供 FADH2，这使生物催化应用变得复杂。在这项研究中，我们确定单组分黄素还原酶/黄素依赖性卤化酶 AetF 使用市售的葡萄糖脱氢酶来催化多种底物的卤化，以驱动其卤化酶活性。证明了高位点选择性、对相对未活化的底物的活性以及对体选择性溴化和溴内酯化的高对映选择性。使用 AetF 也可以进行位点选择性碘化和对映选择性环碘醚化。 AetF的底物和反应范围表明它有可能大大提高生物催化卤化的效用。单组分黄素还原酶/黄素依赖性卤化酶 AetF 催化多种底物的卤化。证明了高位点选择性、对相对未活化的底物的活性以及对体选择性溴化和溴内酯化的高对映选择性。使用 AetF 也可以进行位点选择性碘化和对映选择性环碘醚化。
Flavin‐dependent halogenases (FDHs) natively catalyze selective halogenation of electron rich aromatic and enolate groups. Nearly all FDHs reported to date require a separate flavin reductase to supply them with FADH2, which complicates biocatalysis applications. In this study, we establish that the single component flavin reductase/flavin dependent halogenase AetF catalyzes halogenation of a diverse set of substrates using a commercially available glucose dehydrogenase to drive its halogenase activity. High site selectivity, activity on relatively unactivated substrates, and high enantioselectivity for atroposelective bromination and bromolactonization was demonstrated. Site‐selective iodination and enantioselective cycloiodoetherification was also possible using AetF. The substrate and reaction scope of AetF suggest that it has the potential to greatly improve the utility of biocatalytic halogenation. The single component flavin reductase/flavin dependent halogenase AetF catalyzes halogenation of a diverse set of substrates. High site selectivity, activity on relatively unactivated substrates, and high enantioselectivity for atroposelective bromination and bromolactonization was demonstrated. Site‐selective iodination and enantioselective cycloiodoetherification was also possible using AetF.
登录
查看更多内容
影响因子：
16.6
作者：
Flecks, Silvana;Patallo, Eugenio R.;Zhu, Xiaofeng;Ernyei, Aliz J.;Seifert, Gotthard;Schneider, Alexander;Dong, Changjiang;Naismith, Janies H.;van Pee, Karl-Heinz
通讯作者：
van Pee, Karl-Heinz
DOI：
10.1002/cbic.201700391
发表时间：
2017-11-02
期刊：
Chembiochem : a European journal of chemical biology
影响因子：
--
作者：
Andorfer MC;Belsare KD;Girlich AM;Lewis JC
通讯作者：
Lewis JC
影响因子：
64.8
作者：
Jumper J;Evans R;Pritzel A;Green T;Figurnov M;Ronneberger O;Tunyasuvunakool K;Bates R;Žídek A;Potapenko A;Bridgland A;Meyer C;Kohl SAA;Ballard AJ;Cowie A;Romera-Paredes B;Nikolov S;Jain R;Adler J;Back T;Petersen S;Reiman D;Clancy E;Zielinski M;Steinegger M;Pacholska M;Berghammer T;Bodenstein S;Silver D;Vinyals O;Senior AW;Kavukcuoglu K;Kohli P;Hassabis D
通讯作者：
Hassabis D
影响因子：
3.7
作者：
Neubauer PR;Widmann C;Wibberg D;Schröder L;Frese M;Kottke T;Kalinowski J;Niemann HH;Sewald N
通讯作者：
Sewald N
影响因子：
2.9
作者：
Bitto, Eduard;Huang, Yu;Phillips, George N., Jr.
通讯作者：
Phillips, George N., Jr.