Lajkiewicz, Neil J.Cognetta, Armand B.Niphakis, Micah J.Cravatt, Benjamin F.Porco, John A.2018-01-252018-01-252014-02-12Neil J Lajkiewicz, Armand B Cognetta, Micah J Niphakis, Benjamin F Cravatt, John A Porco. 2014. "Remodeling natural products: chemistry and serine hydrolase activity of a rocaglate-derived β-lactone.." J Am Chem Soc, Volume 136, Issue 6, pp. 2659 - 2664.1520-5126https://hdl.handle.net/2144/26428Flavaglines are a class of natural products with potent insecticidal and anticancer activities. β-Lactones are a privileged structural motif found in both therapeutic agents and chemical probes. Herein, we report the synthesis, unexpected light-driven di-epimerization, and activity-based protein profiling of a novel rocaglate-derived β-lactone. In addition to in vitro inhibition of the serine hydrolases ABHD10 and ACOT1/2, the most potent β-lactone enantiomer was also found to inhibit these enzymes, as well as the serine peptidases CTSA and SCPEP1, in PC3 cells.p. 2659 - 2664© 2014 American Chemical SocietyChemistryEnantioselective photocycloadditionStreptomyces toxytriciniEukaryotic translationProteasome inhibitorAglaia elliptifoliaComplex proteomesPancreatic lipasePotent anticancerOrganic synthesisBenzofuransBiological productsCyclizationHydrolasesLactonesMolecular structureSerineStereoisomerismArticle10.1021/ja412431g25213353