Total synthesis of the potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology. Other Scholarly Work

Sin, N, Kim, KB, Elofsson, M et al. (1999). Total synthesis of the potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology. . BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 9(15), 2283-2288. 10.1016/s0960-894x(99)00376-5

cited authors

  • Sin, N; Kim, KB; Elofsson, M; Meng, L; Auth, H; Kwok, BH; Crews, CM

authors

abstract

  • Epoxomicin (1), a peptide alpha',beta'-epoxyketone isolated from the actinomycete strain No.Q996-17, possesses potent in vivo anti-tumor and anti-inflammatory activities. In this paper, we report the first syntheses of epoxomicin, [3H]-epoxomicin, and a biotinylated epoxomicin analog as well as the absolute configuration of the epoxide stereocenter. The natural product and derivatives have permitted the first identification of the proteasome as the specific cellular target of epoxomicin.

publication date

  • August 1, 1999

keywords

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antibiotics, Antineoplastic
  • Biotinylation
  • Cysteine Endopeptidases
  • Enzyme Inhibitors
  • Mice
  • Multienzyme Complexes
  • Oligopeptides
  • Proteasome Endopeptidase Complex
  • Receptors, Drug
  • Tumor Cells, Cultured

Digital Object Identifier (DOI)

Medium

  • Print

start page

  • 2283

end page

  • 2288

volume

  • 9

issue

  • 15