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Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis

Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis

Org Lett. 2020 Apr 17;22(8):3302-3306. Epub 2020 Apr 3.
doi: 10.1021/acs.orglett.0c01132

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Abstract

(-)-Aurantioclavine (1), which contains a characteristic seven-membered ring fused to an indole ring, belongs to the azepinoindole class of fungal clavine alkaloids. Here we show that starting from a 4-dimethylallyl-l-tryptophan precursor, a flavin adenine dinucleotide (FAD)-binding oxidase and a catalase-like heme-containing protein are involved in the biosynthesis of 1. The function of these two enzymes was characterized by heterologous expression, in vitro characterization, and deuterium labeling experiments.