Expanding the Rubterolone Family: Intrinsic Reactivity and Directed Diversification of PKS‐derived Pyrans.

Guo H, Benndorf R, König S, Leichnitz D, Weigel C, Peschel G, Berthel P, Kaiser M, Steinbeck C, Werz O, Poulsen M, Beemelmanns C (2018) Expanding the Rubterolone Family: Intrinsic Reactivity and Directed Diversification of PKS‐derived Pyrans. Chem Eur J 24(44), 11319-11324. PubMed

Abstract

We characterized three key biosynthetic intermediates of the intriguing rubterolone familiy (tropolone alkaloids) that contain a highly reactive pyran moiety (1,5-dione) and undergo spontaneous pyridine formation in the presence of primary amines. We exploited the intrinsic reactivity of the pyran moiety and isolated several new rubterolone derivatives, two of which contain a unique thiazolidine moiety. Three rubterolone derivatives were chemically modified with fluorescence and biotin tags using peptide coupling and click reaction. Overall, eight derivatives were fully characterized by HRMS/MS and 1D and 2D NMR spectroscopy and their antimicrobial, cytotoxic, anti-inflammatory and antiparasitic activities evaluated.

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Involved Units and Groups

Molecular and Applied Microbiology Chemical Biology of Microbe-Host Interactions Bio Pilot Plant Jena Microbial Resource Collection

HKI-Authors

Christiane Weigel Dr. Christine Beemelmanns René Benndorf Dr. Huijuan Guo Dr. Gundela Peschel Patrick Berthel Daniel Leichnitz

Identifier

doi: 10.1002/chem.201802066 PMID: 29846024