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

Chemistry : a European Journal
Huijuan GuoChristine Beemelmanns

Abstract

We characterized two key biosynthetic intermediates of the intriguing rubterolone family (tropolone alkaloids) that contain a highly reactive pyran moiety (in equilibrium with the hydrolyzed 1,5-dione form) 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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Citations

Dec 18, 2018·Natural Product Reports·Huijuan GuoChristine Beemelmanns
Aug 27, 2019·Frontiers in Microbiology·Jonathan L KlassenKi Hyun Kim
Aug 28, 2020·International Journal of Systematic and Evolutionary Microbiology·René BenndorfChristine Beemelmanns
May 10, 2019·Journal of Natural Products·Linli LiLinzhuan Wu

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