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Updated: Dec 25, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis
Kuan-Lin Chen1, Chen-Yu Lai1, Mai-Truc Pham1,2,3
1Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan R.O.C.
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.
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