L7035

clasto-Lactacystin β-lactone

• Synonym(s): (1R,4R,5S)-1-[(1S)-1-Hydroxy-2-Methylpropyl]-4-Methyl-6-Oxa-2-Azabicyclo[3.2.0]Heptane-3,7-Dione, Omuralide
• Empirical Formula (Hill Notation): C₁₀H₁₅NO₄
• CAS Number: 154226-60-5
• Molecular Weight: 213.23
• MDL number: MFCD01076526
• UNSPSC Code: 12352200
• PubChem Substance ID: 24896450
• NACRES: NA.77

Properties

• Assay: ≥95% (HPLC)
• Quality Level: 100
• form: film
• solubility: DMSO: soluble 25 mg/mL
• storage temp.: −20°C
• SMILES string: [H][C@@]12OC(=O)[C@@]1(NC(=O)[C@@H]2C)[C@@H](O)C(C)C
• InChI: 1S/C10H15NO4/c1-4(2)6(12)10-7(15-9(10)14)5(3)8(13)11-10/h4-7,12H,1-3H3,(H,11,13)/t5-,6+,7+,10-/m1/s1
• InChI key: FWPWHHUJACGNMZ-NBBQQVJHSA-N

Description

Application

Clasto-Lactacystin β-lactone has been used as a proteasomal inhibitor.[1][2]

Clasto-Lactacystin β-lactone has been used as a protein degradation inhibitor to test its effect on memory improvements in mice.[3] It has also been used as a proteasome inhibitor in human ovarian surface epithelium (HOSE) cells[4] and dendritic cells (DCs).[5]

Biochem/physiol Actions

Cell-permeable and irreversible proteasome inhibitor. Lactacystin acts as a precursor for clasto-lactacystin β-lactone.

Clasto-Lactacystin β-lactone (cLβL) is synthesized from lactacystin. It is cell-permeable and cLβL acts on the N-terminal threonine of subunit proteasome β -subunit X[6] It also inhibits 20S proteasome activity in Haloferax volcanii by acting in the N-threonine residue of the  β -type subunits.[7]

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H319
• Precautionary Statements: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable