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Lactacystin

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Lactacystin
Names
IUPAC names (2R)-2-(acetylamino)-3--4-methyl-5-oxopyrrolidin-2-yl}
carbonyl)sulfanyl]propanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10-,11+,15-/m1/s1Key: DAQAKHDKYAWHCG-WBMULXAQSA-N
  • InChI=1/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10-,11+,15-/m1/s1Key: DAQAKHDKYAWHCG-WBMULXAQBF
SMILES
  • CC(=O)N(CSC(=O)1((O)C(C)C)NC(=O)(C)1O)C(=O)O
  • O1(C)C(=O)N1(C(=O)SC(NC(C)=O)C(O)=O)(O)(C)C
Properties
Chemical formula C15H24N2O7S
Molar mass 376.42 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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. Fenteany G, Standaert RF, Lane WS, Choi S, Corey EJ, Schreiber SL. (1995) Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin. Science 268:726-731.
  4. Orlowski RZ. (1999). The role of the ubiquitin-proteasome pathway in apoptosis. Cell Death Differ 6: 303-313.
  5. 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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