Molecular structure of clasto-Lactacystin β-Lactone, CAS Number: 154226-60-5
clasto-Lactacystin β-Lactone (CAS 154226-60-5)
See product citations (3)
Alternate Names:
Omuralide
Application:
clasto-Lactacystin β-Lactone is an active species of lactacystin proteasome inhibition
CAS Number:
154226-60-5
Purity:
≥95%
Molecular Weight:
213.23
Molecular Formula:
C10H15NO4
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Clasto-Lactacystin beta-Lactone is the beta-lactone active form of the Streptomyces antibiotic lactacystin, a widely employed inhibitor of the 20S proteasome. Hydrolysis of lactacystin releases N-acetyl-L-cysteine and reveals the inactive clasto-Lactacystin dihydroxy carboxylic acid, which then cyclizes to form the active beta-lactone species. Clasto-Lactacystin beta-Lactone is thought to be the primary compound that interacts with the proteasome, as conditions stabilizing to lactacystin that prevent accumulation of the beta-lactone also display diminished inhibition of the proteasome. Clasto-Lactacystin β-Lactone is an inhibitor of cathepsin A.
clasto-Lactacystin β-Lactone (CAS 154226-60-5) References
- Simple enantiospecific syntheses of the C(2)-diastereomers of omuralide and 3-methylomuralide. | Reddy, LR., et al. 2005. Org Lett. 7: 2703-5. PMID: 15957926
- Proteasome inhibition by a totally synthetic beta-lactam related to salinosporamide A and omuralide. | Hogan, PC. and Corey, EJ. 2005. J Am Chem Soc. 127: 15386-7. PMID: 16262399
- Proteasome-independent down-regulation of estrogen receptor-alpha (ERalpha) in breast cancer cells treated with 4,4'-dihydroxy-trans-stilbene. | Balan, KV., et al. 2006. Biochem Pharmacol. 72: 573-81. PMID: 16822479
- Prediction of the mechanism of action of omuralide (clasto-lactacystin beta-lactone) on human cathepsin A based on a structural model of the yeast proteasome beta5/PRE2-subunit/omuralide complex. | Aikawa, S., et al. 2006. Biochim Biophys Acta. 1764: 1372-80. PMID: 16870514
- New entry to convertible isocyanides for the Ugi reaction and its application to the stereocontrolled formal total synthesis of the proteasome inhibitor omuralide. | Gilley, CB., et al. 2007. Org Lett. 9: 3631-4. PMID: 17672474
- Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin. | Hayes, CJ., et al. 2008. J Org Chem. 73: 2041-51. PMID: 18288868
- The proteasome inhibitor lactacystin attenuates growth and migration of vascular smooth muscle cells and limits the response to arterial injury. | Barringhaus, KG. and Matsumura, ME. 2007. Exp Clin Cardiol. 12: 119-24. PMID: 18650992
- Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin. | Gu, W. and Silverman, RB. 2011. J Org Chem. 76: 8287-93. PMID: 21916437
- Omuralide and vibralactone: differences in the proteasome- β-lactone-γ-lactam binding scaffold alter target preferences. | List, A., et al. 2014. Angew Chem Int Ed Engl. 53: 571-4. PMID: 24285701
- Total Synthesis of Proteasome Inhibitor (-)-Omuralide through Asymmetric Ketene [2 + 2]-Cycloaddition. | Rullière, P., et al. 2018. Org Lett. 20: 4558-4561. PMID: 30011218
- Mechanistic studies on the inactivation of the proteasome by lactacystin: a central role for clasto-lactacystin beta-lactone. | Dick, LR., et al. 1996. J Biol Chem. 271: 7273-6. PMID: 8631740
- Lactacystin and clasto-lactacystin beta-lactone modify multiple proteasome beta-subunits and inhibit intracellular protein degradation and major histocompatibility complex class I antigen presentation. | Craiu, A., et al. 1997. J Biol Chem. 272: 13437-45. PMID: 9148969
- Total synthesis and biological activity of lactacystin, omuralide and analogs. | Corey, EJ. and Li, WD. 1999. Chem Pharm Bull (Tokyo). 47: 1-10. PMID: 9987821
Inhibitor of:
20S Proteasome, cathepsin A, and Protease.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
clasto-Lactacystin β-Lactone, 100 µg | sc-202105 | 100 µg | $225.00 |