Lactacystin

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IUPACName=(2"R")-2-(acetylamino)-3- [({(2"R",3"S",4"R")-3-hydroxy-2- [(1"S")-
1-hydroxy-2-methylpropyl] -4-methyl-5-oxopyrrolidin-2-yl}
carbonyl)sulfanyl] propanoic acid
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Section1= Chembox Identifiers
CASNo=133343-34-7
PubChem=6610292
SMILES=CC1C(C(NC1=O)(C(C(C)C)O)C(=O)SCC(C(=O)O)NC(=O)C)O
Section2= Chembox Properties
C=15|H=24|N=2|O=7|S=1
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Section3= Chembox Hazards
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Lactacystin is an organic compound naturally synthesized by bacteria of the genus "Streptomyces" first described in 1991.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.] The first total synthesis of lactacystin was developed by Elias Corey in 1992."Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. "J. Am. Chem. Soc." 1992, "114", 10677.] The molecule is most commonly used as in biochemistry and cell biology laboratories as a selective inhibitor of the proteasome.Orlowski RZ. (1999). The role of the ubiquitin-proteasome pathway in apoptosis. "Cell Death Differ" 6: 303-313.] 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.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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