Expanding the Rubterolone Family - Intrinsic Reactivity and Directed Diversification of PKS-derived Pyrans.
(2018) Expanding the Rubterolone Family - Intrinsic Reactivity and Directed Diversification of PKS-derived Pyrans. Chemistry 24, 11319-11324.
Investigation of secondary metabolites from insect-associated microbes and their contribution to insect homeostasis and defense
Exploitation and total synthesis of new microbial sphingolipid-type signaling molecules
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.
doi: 10.1002/chem.201802066 PMID: 29846024