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Remodeling natural products: chemistry and serine hydrolase activity of a rocaglate-derived beta-lactone

Academic Article
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Overview

related to degree

  • Cognetta III, Armand B, Ph.D. in Chemical Biology, Scripps Research 2013 - 2018

authors

  • Lajkiewicz, N. J.
  • Cognetta III, Armand B
  • Niphakis, M. J.
  • Cravatt, Benjamin
  • Porco Jr., J. A.

publication date

  • February 2014

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Flavaglines 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.

subject areas

  • Benzofurans
  • Biological Products
  • Cyclization
  • Hydrolases
  • Lactones
  • Molecular Structure
  • Serine
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC3978386

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja412431g

PubMed ID

  • 24447064
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Additional Document Info

start page

  • 2659

end page

  • 2664

volume

  • 136

issue

  • 6

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