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Biosynthetic Gene Cluster for Asperterpenols A and B and the Cyclization Mechanism of Asperterpenol A Synthase

Zhiyang Quan, Jeroen S. Dickschat

2020Organic Letters47 citationsDOI

Abstract

The biosynthetic gene cluster for the sesterterpenoids asperterpenols A and B from Aspergillus calidoustus CBS121601 is described. The cluster contains two genes, acldAS for a chimeric sesterterpene synthase and acldA-P450 for a cytochrome P450 monooxygenase. The cyclization mechanism of the asperterpenol A synthase, catalyzing the formation of a unique sesterterpene with a 6/6/8/5 tetracyclic ring system, was studied using isotopically labeled terpene precursors.

Topics & Concepts

ChemistryGene clusterATP synthaseTerpeneStereochemistryMonooxygenaseCytochrome P450Ring (chemistry)CytochromeEnzymeGeneMechanism (biology)BiochemistryOrganic chemistryEpistemologyPhilosophyPlant biochemistry and biosynthesisMicrobial Natural Products and BiosynthesisNatural product bioactivities and synthesis
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