(+)-Lactacystin

CAS: 133343-34-7

Ref. TR-L101000

Product Information

• Name: (+)-Lactacystin
• Synonyms: N-Acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-D-prolyl]-L-cysteine, (2R,3S,4R)-3-Hydroxy-2-[(1S)-1-Hydroxy-2-Methylpropyl]-4-Methyl-5-Oxo-2-Pyrrolidinecarboxy-N-Acetyl-L-Cysteine Thioester, 3S-Hydroxy-2R-(1-Hydroxy-2-Methylpropyl)-4R-Methyl-5-Oxo-2-Pyrrolidinecarboxylate-N-Acetyl-L-Cysteine, <span class="text-smallcaps">L</smallcap>-Cysteine, N-acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-<smallcap>D</span>-prolyl]-, <span class="text-smallcaps">L</span>-Cysteine, N-acetyl-, (2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinecarboxylate (ester), <span class="text-smallcaps">L</span>-Cysteine, N-acetyl-, 3-hydroxy-2-(1-hydroxy-2-methylpropyl)-4-methyl-5-oxo-2-pyrrolidinecarboxylate (ester), [2R-[2α,2(S*),3α,4α]]-, Lactacystin (Native), Lactacystin, Streptomyces Sp, Lactacystin, Synthetic, N-Acetyl-S-[(2R,3S,4R)-3-Hydroxy-2-[(1S)-1-Hydroxy-2-Methylpropyl]-4-Methyl-5-Oxo-2-Pyrrolidinecarbonyl]-L-Cysteine, N-Acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-<span class="text-smallcaps">D</smallcap>-prolyl]-<smallcap>L</span>-cysteine, N-acetyl-S-({(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidin-2-yl}carbonyl)-L-cysteine, N-acetyl-S-({(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-4-methyl-5-oxopyrrolidin-2-yl}carbonyl)-L-cysteine, N-acetyl-S-({(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidin-2-yl}carbonyl)-L-cysteine
• CAS: 133343-34-7

Description

Applications A selective and potent inhibitor of proteasome-mediated degradation of ubiquitin-tagged proteins. A Streptomyces metabolite that acts as a highly specific inhibitor of the 20S proteasome (MCP: multicatalytic proteinase complex).
References Fenteany, G., et al.: Science, 268, 726 (1995), Fenteany, G., et al.: Proc. Natl. Acad. Sci. USA, 91, 3358 (1994),

• Brand: TRC

Chemical properties

• Molecular weight: 376.43
• Formula: C₁₅H₂₄N₂O₇S
• Color/Form: White to Pale Brown Solid
• 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/s1
• InChI key: InChIKey=DAQAKHDKYAWHCG-IDRMDIHUSA-N
• SMILES: CC(=O)N[C@@H](CSC(=O)C1([C@H](O)C(C)C)NC(=O)[C@H](C)[C@@H]1O)C(=O)O