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Concise Biosynthesis of Phenylfuropyridones in Fungi.
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-08-10 , DOI: 10.1002/anie.202008321
Zhuan Zhang 1, 2 , Tianzhang Qiao 1 , Kenji Watanabe 3 , Yi Tang 1, 2
Affiliation  

Phenylfuropyridone natural products from fungi exhibit a range of antibacterial and cytotoxicity activities, and can potentiate azole antifungal compounds. We elucidated the biosynthetic pathway of compounds in the citridone family through heterologous reconstitution of the pfp pathway. We demonstrate that multiple members of this family can be accessed from a reactive ortho‐quinone methide (o‐QM) intermediate through electrocyclization, cycloisomerization, or conjugate addition. Formation of the quaternary carbon center in citridone B is catalyzed by an epoxide‐forming P450 enzyme, followed by carbon skeletal rearrangement. Our results showcase how nature harvests the reactivities of an o‐QM intermediate to biosynthesize complex natural products.

中文翻译:

真菌中苯并呋喃啶酮的简明生物合成。

来自真菌的苯并呋喃啶酮天然产物显示出一系列的抗菌和细胞毒性活性,并且可以增强唑类抗真菌化合物。我们阐明了通过pfp途径的异源重组,在西地酮家族中化合物的生物合成途径。我们证明该家族的多个成员可以通过电环化,环异构化或共轭加成从反应性邻苯二甲酸甲酯(o- QM)中间体中获得。环戊烯B中季碳中心的形成是由环氧化物形成的P450酶催化,然后碳骨架重排。我们的结果展示了大自然如何收获o的反应性‐ QM生物合成复杂天然产物的中间体。
更新日期:2020-08-10
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