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首页> 外文期刊>Applied Microbiology >RedH and PigC Catalyze the Biosynthesis of Hybrubins via Phosphorylation of 4′-Methoxy-2,2′-Bipyrrole-5′-Carbaldehyde
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RedH and PigC Catalyze the Biosynthesis of Hybrubins via Phosphorylation of 4′-Methoxy-2,2′-Bipyrrole-5′-Carbaldehyde

机译：Redh和Pigc通过4'-甲氧基-2,2,2'-BiPyrol-5'-Carbaldehyde的磷酸化催化杂交的生物合成

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Hybrubins are “unnatural” alkaloids with the same 4′-methoxy-2,2′-bipyrrole-5′-methine moiety found in prodiginines and a different ring derived from tetramic acids. Here, we demonstrated that RedH, a homologue of prodigiosin synthetase PigC, was responsible for the biosynthesis of hybrubins A and B in Streptomyces lividans . In vitro reactions indicated that RedH and PigC catalyzed the intermolecular condensation between 4′-methoxy-2,2′-bipyrrole-5′-carbaldehyde (MBC) and ( Z )-5-ethylidenetetramic acid (ETA) to produce hybrubin B. Moreover, we demonstrated that RedH and PigC activated MBC via phosphorylation of the aldehyde group to form an intermediate P_(i)-MBC and that the subsequent condensation between P_(i)-MBC and ( Z )-5-ethylidenetetramic acid occurs in a nonenzymatic way.IMPORTANCE Hybrubins are an emerging class of prodiginines possessing a new C ring derived from 5′-substituted tetramic acids and the methylene bridge connecting the C ring at a different position. We have supposed that condensation between 4′-methoxy-2,2′-bipyrrole-5′-carbaldehyde (MBC) and 5-ethylidenetetramic acid (ETA) yields the hybrid natural products hybrubins, which was proposed to be catalyzed by the undecylprodigiosin synthetase RedH. However, it is doubted whether RedH is able to catalyze another type of condensation between MBC and tetramic acids. In this study, we have demonstrated that the MBC-ETA condensation proceeds through RedH/PigC-catalyzed enzymatic activation of MBC via phosphorylation and a nonenzymatic condensation of P_(i)-MBC with ETA. Since MBC analogues have been shown to be accepted by PigC, more hybrubin analogues might be produced by using combinations of MBC analogues and other tetramic acids in future studies.
机译：杂交是“不自然”的生物碱，其具有相同的4'-甲氧基-2,2'-甲基 - 甲基 - 5'-甲基部分，其在生物素线中发现和衍生自四酸的不同环。在这里，我们证明了Prodigiosin合成酶Pigc的一种同源物，该猪的同源物负责杂菌菌和B中的杂菌素A和B中的生物合成。在体外反应表明REDH和PIGC催化了4'-甲氧基-2,2'-双溴硼-5'-碳醛（MBC）和（Z）-5-乙基乙酰丁酰胺酸（ETA）之间的分子间缩合以产生杂肠蛋白B.此外，我们证明，REDH和PIGC通过醛基的磷酸化形成MBC以形成中间体P_（I）-MBC，并且在非酶的情况下发生P_（I）-MBC和（Z）-5-亚乙酰苯甲酰酰胺酸之间的随后的缩合方式。分析杂交是一种具有来自5'-取代的四酸的新的C环和将C环连接到不同位置的新的C环的新出现类别。我们假设4'-甲氧基-2,2'-双溴罗醛（MBC）和5-亚乙基乙酰酸（ETA）之间的缩合产生杂交天然产物杂交杂蛋白，其被提出通过未索甲基蛋白合成酶催化redh。然而，怀疑REDH是否能够在MBC和四酸之间催化另一种类型的凝结。在这项研究中，我们已经证明了MBC-ETA缩合通过磷酸化的RedH / PIGC催化的MBC酶活化和P_（i）-MBC的非酶缩合进行。由于MBC类似物已被仔猪接受，因此可以通过使用未来研究中的MBC类似物和其他四酸的组合来产生更多的杂蛋白类似物。

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