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A Desaturase‐Like Enzyme Catalyzes Oxazole Formation in Pseudomonas Indolyloxazole Alkaloids
Ist Teil von
Angewandte Chemie (International ed.), 2021-04, Vol.60 (16), p.8781-8785
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2021
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Indolyloxazole alkaloids occur in diverse micro‐ and macroorganisms and exhibit a wide range of pharmacological activities. Despite their ubiquitous occurrence and simple structures, the biosynthetic pathway remained unknown. Here, we used transposon mutagenesis in the labradorin producer Pseudomonas entomophila to identify a cryptic biosynthetic locus encoding an N‐acyltransferase and a non‐heme diiron desaturase‐like enzyme. Heterologous expression in E. coli demonstrates that both enzymes are sufficient to produce indolyloxazoles. Probing their function in stable‐isotope feeding experiments, we provide evidence for an unusual desaturase mechanism that generates the oxazole by decarboxylative cyclization.
Indolyloxazole alkaloids are widespread natural products with diverse bioactivities but previously unknown biosynthesis. Transposon mutagenesis, heterologous pathway expression, and labeling experiments provide evidence for a Pseudomonas pathway involving oxazole formation by cyclization as a new reaction type catalyzed by a desaturase‐like enzyme.