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Oxepin Formation in Fungi Implies Specific and Stereoselective Ring Expansion

Liujuan Zheng, Haowen Wang, Lena Ludwig-Radtke, Shu‐Ming Li

2021Organic Letters10 citationsDOI

Abstract

Oxepinamides are fungal oxepine–pyrimidinone–ketopiperazine derivatives. In this study, we elucidated the biosynthetic pathway of oxepinamide D in Aspergillus ustus by gene deletion, heterologous expression, feeding experiments, and enzyme assays. We demonstrated that the cytochrome P450 enzymes catalyzed highly specific and stereoselective oxepin ring formation.

Topics & Concepts

StereoselectivityChemistryEnzymeRing (chemistry)Heterologous expressionStereochemistryHeterologousCytochrome P450GeneBiochemistryCatalysisOrganic chemistryRecombinant DNAMicrobial Natural Products and BiosynthesisFungal Biology and ApplicationsAlkaloids: synthesis and pharmacology
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