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. Chemistry 24, 11319-11324. PubMed

ILRS Authors

René Benndorf Daniel Leichnitz

Projects

Investigation of secondary metabolites from insect-associated microbes and their contribution to insect homeostasis and defense
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Exploitation and total synthesis of new microbial sphingolipid-type signaling molecules
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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.

Identifier

doi: 10.1002/chem.201802066 PMID: 29846024

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