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首页> 外文期刊>Proceedings of the National Academy of Sciences of the United States of America >Dichlorination of a pyrrolyl-S-carrier protein by FADH(2)-dependent halogenase PltA during pyoluteorin biosynthesis
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Dichlorination of a pyrrolyl-S-carrier protein by FADH(2)-dependent halogenase PltA during pyoluteorin biosynthesis

机译：pyoluteorin生物合成过程中由FADH（2）依赖性卤化酶PltA对吡咯基-S载体蛋白进行二氯化。

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摘要

The antifungal natural product pyoluteorin contains a 4,5-dichloropyrrole moiety. The timing of dichlorination in the heteroaromatic ring is now shown to occur after proline is tethered by thioester linkage to the carrier protein PltL and enzymatically desaturated to the pyrrolyl-S-PItL. Surprisingly, the FADH(2)-dependent halogenase PltA catalyzes chlorination at both positions of the ring, generating the 5-chloropyrrolyl-S-PItL intermediate and then the 4,5-dichloropyrrolyi-S-PltL product. PltA activity strictly depends on a heterologous flavin reductase that uses NAD(P)H to produce FADH(2). Electrospray ionization-Fourier transform MS detected five covalent intermediates attached to the 11-kDa carrier protein PltL. Tandem MS localized the site of covalent modification on the carrier protein scaffold. HPLC analysis of the hydrolyzed products was consistent with the regiospecific chlorination at position 5 and then position 4 of the heteroaromatic ring. A mechanism for dichlorination is proposed involving formation of a FAD-4a-OCI intermediate for capture by the electron-rich C4 and C5 of the heteroaromatic pyrrole moiety.
机译：抗真菌天然产物焦黄素含有4，5-二氯吡咯部分。现在表明，在脯氨酸通过硫酯键连接到载体蛋白PltL并被酶促去饱和到吡咯基-S-PItL之后，杂芳环中的二氯化时间发生。出人意料的是，依赖FADH（2）的卤化酶PltA在环的两个位置催化氯化，生成5-氯吡咯基-S-PItL中间体，然后生成4,5-二氯吡咯基-S-PltL产物。 PltA活性严格取决于使用NAD（P）H产生FADH（2）的异源黄素还原酶。电喷雾电离-傅立叶变换质谱仪检测到5个共价中间体连接到11 kDa载体蛋白PltL。串联MS将共价修饰位点定位在载体蛋白支架上。水解产物的HPLC分析与在杂芳环的位置5然后在位置4的区域特异性氯化反应一致。提出了二氯化的机理，涉及形成FAD-4a-OCI中间体，以被杂芳族吡咯部分的富电子C4和C5捕获。

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