Identification by Synthesis: Imidacins, Urocanate-Derived Alkaloids from the Myxobacterium Stigmatella aurantiaca

Innovative discovery approaches such as genome-mining and metabolomics-inspired methods have reshaped the natural product research field, complementing traditional bioactivity-based screens and allowing hitherto unseen compounds to be uncovered from previously investigated producers. In line with th...

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Bibliographic Details
Published in:Organic letters 2024-08, Vol.26 (30), p.6359-6363
Main Authors: Kostka, Michael, Krug, Daniel, Herrmann, Jennifer, Dickschat, Jeroen S., Meyer, Julia, Müller, Rolf, Schulz, Stefan
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - pharmacology
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Cyclopropanes - pharmacology
Letter
Molecular Structure
Myxococcales - chemistry
Stigmatella aurantiaca - chemistry
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Summary:Innovative discovery approaches such as genome-mining and metabolomics-inspired methods have reshaped the natural product research field, complementing traditional bioactivity-based screens and allowing hitherto unseen compounds to be uncovered from previously investigated producers. In line with these trends, we report here imidacins, a novel class of secondary metabolites specific to the myxobacterial genus Stigmatella. A combination of secondary metabolome analysis, genome-mining techniques, spectroscopic analysis, and finally total synthesis was used to allow structure elucidation. Imidacins are urocanate-derived aliphatic acids with an adjacent cyclopropane moiety, structural features unprecedented in natural products to date.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02036