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Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

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.

SUBMITTER: Chen KL

PROVIDER: S-EPMC8092377 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

Chen Kuan-Lin KL Lai Chen-Yu CY Pham Mai-Truc MT Chein Rong-Jie RJ Tang Yi Y Lin Hsiao-Ching HC

Organic letters 20200403 8

(-)-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 characterizatio ...[more]

PMID: 32243182

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