Lactacystin

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Lactacystin
IUPAC name	(2R)-2-(acetylamino)-3-[({(2R,3S,4R)-3-hydroxy-2-[(1S)- 1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidin-2-yl} carbonyl)sulfanyl]propanoic acid
Identifiers
CAS number	[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
Properties
Molecular formula	C15H24N2O7S
Molar mass	376.43 g mol-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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]

[edit] 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.