Lactacystin

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File:Lactacystin.png
Chemical structure of lactacystin.

Lactacystin is an organic compound naturally synthesized by bacteria of the genus Streptomyces first described in 1991.[1] The first total synthesis of lactacystin was developed by Elias Corey in 1992.[2] The molecule is most commonly used as in biochemistry and cell biology laboratories as a selective inhibitor of the proteasome.[3] The molecule is a lactam, or cyclic amide. A number of syntheses of this molecule have been published and there are no less than 300 references to this natural product in the literature. .[4]


References

  1. Omura S, Fujimoto T, Otoguro K, Matsuzaki K, Moriguchi R, Tanaka H, Sasaki Y. (1991). Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells: S. Omura, et al. J. Antibiot. 44(1):113-6.
  2. "Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
  3. Orlowski RZ. (1999). The role of the ubiquitin-proteasome pathway in apoptosis. Cell Death Differ 6: 303-313.
  4. Christopher J. Brennan, Gerald Pattenden, Gwenaella Rescourio . (2003). Formal Synthesis of (+)-Lactacystin Based on a Novel Radical Cyclization of an -Ethynyl-Substituted Serine: C Brennan et al. Tetrahedron Lett 44 (2003) 49, 8757-8760.



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