Biosynthesis of the Polycyclic System in the Antifungal HSAF and Analogues from Lysobacter enzymogenes,Angewandte Chemie International Edition

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Biosynthesis of the Polycyclic System in the Antifungal HSAF and Analogues from Lysobacter enzymogenes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-04-25 , DOI: 10.1002/anie.201802488
Yaoyao Li ₁ , Haoxin Wang ₁ , Yan Liu ₁ , Yujie Jiao ₁ , Shanren Li ₂ , Yuemao Shen ₁ , Liangcheng Du ₂

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The biocontrol agent Lysobacter enzymogenes produces polycyclic tetramate macrolactams (PoTeMs), including the antifungal HSAF. To elucidate the biosynthesis of the cyclic systems, we identified eleven HSAF precursors/analogues with zero, one, two, or three rings through heterologous expression of the HSAF gene cluster. A series of combinatorial gene expression and deletion experiments showed that OX3 is the “gatekeeper” responsible for the formation of the first 5‐membered ring from lysobacterene A, OX1 and OX2 are responsible for formation of the second ring but with different selectivity, and OX4 is responsible for formation of the 6‐membered ring. In vitro experiments showed that OX4 is an NADPH‐dependent enzyme that catalyzes the reductive cyclization of 3‐dehydroxy alteramide C to form 3‐dehydroxy HSAF. Thus, the multiplicity of OX genes is the basis for the structural diversity of the HSAF family, which is the only characterized PoTeM cluster that involves four redox enzymes in the formation of the cyclic system.

中文翻译：

抗真菌HSAF中多环系统的生物合成和溶菌酶基因的类似物。

生物防治剂溶菌酶基因生产多环四酸酯大内酰胺（PoTeM），包括抗真菌HSAF。为了阐明循环系统的生物合成，我们通过异源表达HSAF基因簇鉴定了11个具有零，一，二或三环的HSAF前体/类似物。一系列组合基因表达和缺失实验表明，OX3是负责从溶菌菌素A形成第一个5元环的“守门人”，OX1和OX2负责形成第二个环，但选择性不同，而OX4负责六元环的形成。体外实验表明，OX4是NADPH依赖性酶，可催化3-脱羟基交替酰胺C的还原环化反应，形成3-脱羟基HSAF。因此，

更新日期：2018-04-25

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