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

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

  • Huijuan Guo
  • René Benndorf
  • Stefanie König
  • Daniel Leichnitz
  • Christiane Weigel
  • Gundela Peschel
  • Patrick Berthel
  • Marcel Kaiser
  • Christoph Steinbeck
  • Oliver Werz
  • Poulsen, Michael
  • Christine Beemelmanns

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.

OriginalsprogEngelsk
TidsskriftChemistry - A European Journal
Vol/bind24
Udgave nummer44
Sider (fra-til)11319-11324
ISSN0947-6539
DOI
StatusUdgivet - 2018

ID: 201188776