Biosynthesis of Biscognienyne B Involving a Cytochrome P450-Dependent Alkynylation.,Angewandte Chemie International Edition

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Biosynthesis of Biscognienyne B Involving a Cytochrome P450-Dependent Alkynylation.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-05-04 , DOI: 10.1002/anie.202004364
Jian-Ming Lv _{1,

2} , Yao-Hui Gao ₁ , Huan Zhao ₃ , Takayoshi Awakawa ₄ , Ling Liu ₅ , Guo-Dong Chen ₁ , Xin-Sheng Yao ₁ , Dan Hu ₁ , Ikuro Abe ₄ , Hao Gao ₁

Affiliation

The alkyne is a biologically significant moiety found in many natural products and a versatile functional group widely used in modern chemistry. Recent studies have revealed the biosynthesis of acetylenic bonds in fatty acids and amino acids. However, the molecular basis for the alkynyl moiety in acetylenic prenyl chains occurring in a number of meroterpenoids remains obscure. Here, we identify the biosynthetic gene cluster and characterize the biosynthetic pathway of an acetylenic meroterpenoid biscognienyne B based on heterologous expression, feeding experiments, and in vitro assay. This work shows that the alkyne moiety is constructed by an unprecedented cytochrome P450 enzyme BisI, which shows promiscuous activity towards C5 and C15 prenyl chains. This finding provides an opportunity for discovery of new compounds, featuring acetylenic prenyl chains, through genome mining, and it also expands the enzyme inventory for de novo biosynthesis of alkynes.

中文翻译：

Biscognienyne B的生物合成涉及细胞色素P450依赖的炔基化作用。

炔烃是在许多天然产物中发现的生物学上重要的部分，也是现代化学中广泛使用的多功能官能团。最近的研究已经揭示了脂肪酸和氨基酸中炔键的生物合成。然而，在许多类萜中出现的炔基异戊二烯基链中的炔基部分的分子基础仍然不清楚。在这里，我们基于异源表达，饲喂实验和体外试验，鉴定了生物合成基因簇，并表征了乙炔类金属萜类双缩乙炔B的生物合成途径。这项工作表明，炔烃部分是由空前的细胞色素P450酶BisI构建的，该酶对C5和C15异戊二烯基链具有混杂活性。这一发现为发现新化合物提供了机会，

更新日期：2020-05-04

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