CAS 133343-34-7

Lactacystin

Description:

Lactacystin is a naturally occurring compound that is primarily known for its role as a proteasome inhibitor. It is derived from the bacterium *Streptomyces* and has garnered interest in the field of biochemistry and pharmacology due to its ability to selectively inhibit the proteasome, a cellular complex responsible for degrading ubiquitinated proteins. This inhibition can lead to the accumulation of regulatory proteins, thereby affecting various cellular processes, including cell cycle regulation and apoptosis. Lactacystin is often utilized in research to study the proteasome's role in cellular functions and its implications in diseases such as cancer and neurodegenerative disorders. The compound is characterized by its specific structure, which includes a lactone ring, contributing to its biological activity. While it has potential therapeutic applications, the use of lactacystin in clinical settings is limited due to its toxicity and the need for further research to understand its effects and mechanisms fully.

Formula: C₁₅H₂₄N₂O₇S

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-RWTHQLGUSA-N

SMILES: C(SC[C@H](NC(C)=O)C(O)=O)(=O)[C@@]1([C@H](C(C)C)O)[C@@H](O)[C@@H](C)C(=O)N1

Synonyms:

• (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
• N-Acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-D-prolyl]-L-cysteine
• L-Cysteine, N-acetyl-, 3-hydroxy-2-(1-hydroxy-2-methylpropyl)-4-methyl-5-oxo-2-pyrrolidinecarboxylate (ester), [2R-[2α,2(S*),3α,4α]]-
• (+)-LACTACYSTIN
• L-Cysteine, N-acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-D-prolyl]-
• L-Cysteine, N-acetyl-, (2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinecarboxylate (ester)

Lactacystin

CAS: 133343-34-7

Formula: C₁₅H₂₄N₂O₇S

Color and Shape: Solid

Molecular weight: 376.4253

Ref: IN-DA0014PU

Lactacystin

CAS: 133343-34-7

Lactacystin is a natural non-peptide proteasome inhibitor and anticancer that controls the UPS of cellular protein turnover,, induces neurite outgrowth.

Formula: C₁₅H₂₄N₂O₇S

Purity: 98%

Color and Shape: White To Off-White Powder

Molecular weight: 376.43

Ref: TM-T15702

Lactacystin

CAS: 133343-34-7

Formula: C₁₅H₂₄N₂O₇S

Purity: ≥ 95.0%

Color and Shape: White solid or powder

Molecular weight: 376.43

Ref: 7W-GK3911

Lactacystin

CAS: 133343-34-7

Lactacystin

Purity: ≥95%

Molecular weight: 376.43g/mol

Ref: 54-BUP21500

Lactacystin

CAS: 133343-34-7

Formula: C₁₅H₂₄N₂O₇S

Purity: 95%~99%

Color and Shape: Powder

Molecular weight: 376.424

Ref: BP-BPC0121

(+)-Lactacystin

Controlled Product

CAS: 133343-34-7

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),

Formula: C₁₅H₂₄N₂O₇S

Color and Shape: Neat

Molecular weight: 376.43

Ref: TR-L101000

Lactacystin

CAS: 133343-34-7

Lactacystin is a peptide that acts as an activator of ion channels. It binds to the receptor and activates the ligand-gated ion channel, which then opens the ion channel. This leads to increased influx of ions into the cell and an increase in intracellular calcium concentration. Lactacystin has been used as a research tool for studies on protein interactions, such as antibody-antigen interactions and receptor-ligand interactions. Lactacystin is also used for pharmacological purposes, such as for pain relief or for treatment of epilepsy.

Formula: C₁₅H₂₄N₂O₇S

Purity: Min. 95%

Molecular weight: 376.43 g/mol

Ref: 3D-ILC-4368-V

Lactacystin

CAS: 133343-34-7

Formula: C₁₅H₂₄N₂O₇S

Purity: >95%

Molecular weight: 376.42

Ref: 10-M02066