Lactacystin

Base Information

• Chemical Name: Lactacystin
• CAS No.: 133343-34-7
• Molecular Formula: C₁₅H₂₄N₂O₇S
• Molecular Weight: 376.431
• DSSTox Substance ID: DTXSID50897422
• Nikkaji Number: J363.724G
• Wikipedia: Lactacystin
• Wikidata: Q6468907
• Pharos Ligand ID: 9S9LJGX8H5G9
• Metabolomics Workbench ID: 58362
• ChEMBL ID: CHEMBL374308
• Mol file: 133343-34-7.mol

Synonyms:lactacystin

Chemical Property of Lactacystin

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.31E-23mmHg at 25°C
• Melting Point: 233-235 ºC
• Refractive Index: 1.559
• Boiling Point: 714.875 °C at 760 mmHg
• PKA: 3.11±0.10(Predicted)
• Flash Point: 386.143 °C
• PSA: 178.33000
• Density: 1.367 g/cm³
• LogP: -0.56230
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 20 mg/ml), in Water (up to 10 mg/ml), or in Ethanol (up to 1 mg/ml).
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 376.13042228
• Heavy Atom Count: 25
• Complexity: 568

Purity/Quality:

98%,99%, ^*data from raw suppliers

Lactacystin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(NC1=O)(C(C(C)C)O)C(=O)SCC(C(=O)O)NC(=O)C)O
• Isomeric SMILES: C[C@@H]1[C@@H]([C@](NC1=O)([C@H](C(C)C)O)C(=O)SC[C@@H](C(=O)O)NC(=O)C)O
• Description: Lactacystin is a microbial metabolite isolated from Streptomyces that is now widely used as a selective inhibitor of the 20S proteasome. Lactacystin was first characterized by its ability to induce differentiation and inhibit cell cycle progression in several tumor cell lines. At concentrations from 2 to 10 μM, lactacystin induces the outgrowth of neurites in the neuroblastoma cell line Neuro2a. Lactacystin irreversibly alkylates subunit X of the 20S proteasome. The concomitant inhibition of proteasome peptidase activity results in the accumulation of a variety of ubiquitinated proteins which would normally undergo rapid degradation. Thus, the effects of lactacystin are pleiotropic and depend substantially on the expression pattern of signalling proteins within the treated cell.
• Uses: 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) Lactacystin has been used:as a proteasome inhibitor to inhibit protein degradationto inhibit proteasomal activity of cells for live cell imagingto block proteasomal proteolysis in human monocyte-derived dendritic cells (MoDCs) for 24 hto provide unilateral injection to animals to induce nigrostriatal lesions

Technology Process of Lactacystin

There total 171 articles about Lactacystin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-acetylcystein (616-91-1,7696-05-1) + omuralide (154226-60-5,186833-31-8,155975-72-7) → Lactacystin (133343-34-7)

Guidance literature:

With triethylamine; In dichloromethane; at 23 ℃; for 4h;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Reference yield: 88.0%

lactacystin allyl ester (145451-98-5) → Lactacystin (133343-34-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triethylamine; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00084a062

Reference yield: 81.0%

N-acetyl-L-cystein allyl ester (145452-04-6) → Lactacystin (133343-34-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triethylamine; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1021/ja9541544

upstream raw materials:

lactacystin allyl ester

N-acetylcystein

omuralide

N-acetyl-L-cystein allyl ester

Refernces

• 1、 Corey, E. J.,Reichard, Gregory A.. "SYNTHESIS OF (6R,7S)-LACTACYSTIN AND 6-DEOXYLACTACYSTIN FROM A COMMON INTERMEDIATE". . p. 6973 - 6976. Retrieved 1993.
• 2、 Gu, Wenxin,Silverman, Richard B.. "Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin". experimental part. p. 8287 - 8293. Retrieved 2012/04/10.
• 3、 Fukuda, Nobuhisa,Sasaki, Kazuki,Sastry,Kanai, Motomu,Shibasaki, Masakatsu. "Catalytic asymmetric total synthesis of (+)-lactacystin". . p. 1220 - 1225. Retrieved 2007/10/03.