154226-60-5

Basic information

• Product Name: CLASTO-LACTACYSTIN BETA-LACTONE
• Synonyms: OMURALIDE;LACTACYSTIN, CLASTO-, BETA-LACTONE;BETA-CLASTOLACTACYSTIN;CLASTO-LACTACYSTIN BETA-LACTONE;1R-[1S-1HYDROXY-2-METHYLPROPYL]-4R-METHYL-6-OXA-2-AZABICYCLO[3.2.0]HEPTANE-3,7-DIONE;clasto-lactacystin β-lactone;Clasto-lactacystin (OMuralide);(1R,4R,5S)-1-[(1S)-1-Hydroxy-2-Methylpropyl]-4-Methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• CAS NO: 154226-60-5
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.23
• Product Categories: Calpain and Proteasome InhibitorsProteasome, Calpain and Lysosomal Proteases;InhibitorsProtease Inhibitors;Proteasome inhibitor;Proteasome inhibitorEnzyme Inhibitors by Enzyme;Intracellular Protein Degradation;Nitric Oxide and Cell Stress;P to;Protease Inhibitor Specificity Index;Proteasomes;Inhibitors;ProteasomeInhibitors
• Mol File: 154226-60-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 186-187°C
• Appearance: /
• Storage Temp.: −20°C
• Solubility: DMF, Ethanol, Hot Ethyl Acetate, Methanol, Pyridine
• CAS DataBase Reference: CLASTO-LACTACYSTIN BETA-LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: CLASTO-LACTACYSTIN BETA-LACTONE(154226-60-5)
• EPA Substance Registry System: CLASTO-LACTACYSTIN BETA-LACTONE(154226-60-5)

Safety Data

• Hazard Codes: T
• Statements: 20/21/22-37/38-41-36/37/38-25
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 154226-60-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 154226-60-5 differently. You can refer to the following data:
1. A cell permeable, irreversible proteasome inhibitor. It is 20-fold more potent than Lactacystin. Lactacytstin spontaneously converts to clasto-lactacystin in biological systems. Clasto-lactacystin is the only cell permeable form of lactacystin. Induces neurite growth and inhibits cell cycle progression similar to lactacytin.
2. Clasto-Lactacystin β-lactone has been used as a proteasomal inhibitor.
3. clasto-Lactacystin beta-lactone is a 20S proteasome and cathepsin A inhibitor.

Biological Activity

cell-permeable. a highly specific, potent and irreversible proteasome inhibitor. lactacystin (cat. no. 1709-200) acts as a precursor for clasto-lactacystin β-lactone and the latter compound is at least 10 times more active than the parent lactacystin

Biochem/physiol Actions

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 It also inhibits 20S proteasome activity in Haloferax volcanii?by acting in the N-threonine residue of the? β -type subunits.

Upstream product

• 292615-59-9 (+)-(2R,5S)-2-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one 

Downstream Products

• 155975-72-7 (1R,4R,5S)-1-((R)-1-Hydroxy-2-methyl-propyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione 
• 133343-34-7 Lactacystin 

Relevant articles and documents

Total Synthesis of Proteasome Inhibitor (-)-Omuralide through Asymmetric Ketene [2 + 2]-Cycloaddition

The total synthesis of (-)-omuralide, a potent specific proteasome inhibitor, has been achieved through an unprecedented route. The C3 and C4 chiral centers of the natural product have been selectively installed by an asymmetric [2 + 2]-cycloaddition betw

Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin

Omuralide, a transformation product of the microbial metabolite lactacystin, was the first molecule discovered as a specific inhibitor of the proteasome and is unique in that it specifically inhibits the proteolytic activity of the 20S subunit of the prot

Stereogenic evolution of clasto-lactacystin β-lactone from L-serine

Reported herein is a novel synthesis of clasto-lactacystin β-lactone. The γ-lactam core was selectively prepared by an intramolecular C-H insertion to establish the stereocenter, C(6). The ensuing construction of the quaternary C(5) and carbinol C(9) cent