吲哚试验
化学
劈理(地质)
单加氧酶
戒指(化学)
催化作用
立体化学
酶
生物化学
生物
有机化学
细胞色素P450
古生物学
断裂(地质)
作者
Ling‐Hong Meng,Takayoshi Awakawa,Xiaoming Li,Zhiyang Quan,Sui-Qun Yang,Bin‐Gui Wang,Ikuro Abe
标识
DOI:10.1002/ange.202403963
摘要
(±)‐Penindolenes A–D (1–4), the first representatives of indole terpenoids featuring a γ‐lactam skeleton, were isolated from the mangrove‐derived endophytic fungus Penicillium brocae MA‐231. Our bioactivity tests revealed their potent antimicrobial and acetylcholinesterase inhibitory activities. The biosynthetic reactions by the five enzymes PbaABCDE leading to γ‐lactam ring formation were identified with heterologous expression and in vitro enzymatic assays. Remarkably, the cytochrome P450 monooxygenase PbaB and its homolog in Aspergillus oryzae catalyzed the 2,3‐cleavage of the indole ring to generate two keto groups in 1, in different manners from well‐known tryptophan dioxygenases. This is the first example of the oxidative cleavage of indole by a P450 monooxygenase. In addition, rare secondary amide bond formation by the glutamine synthetase‐like enzyme PbaD was reported. These findings will contribute to the engineered biosynthesis of unnatural, bioactive indole terpenoids.
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