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L7035

Sigma-Aldrich

clasto-Lactacystin β-lactone

Synonyme(s) :

(1R,4R,5S)-1-[(1S)-1-Hydroxy-2-Methylpropyl]-4-Methyl-6-Oxa-2-Azabicyclo[3.2.0]Heptane-3,7-Dione, Omuralide

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About This Item

Formule empirique (notation de Hill):
C10H15NO4
Numéro CAS:
154226-60-5
Poids moléculaire :
213.23
Numéro MDL:
MFCD01076526
Code UNSPSC :
12352200
ID de substance PubChem :
24896450
Nomenclature NACRES :
NA.77

Essai

≥95% (HPLC)

Niveau de qualité

100

Forme

film

Solubilité

DMSO: soluble 25 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

FWPWHHUJACGNMZ-NBBQQVJHSA-N

Application

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

Actions biochimiques/physiologiques

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
MKCM4358
MKCK0558
MKCG7816
MKBX4006V
MKBT7113V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Sue-Hyun Lee et al.
Science (New York, N.Y.), 319(5867), 1253-1256 (2008-02-09)
Reactivated memory undergoes a rebuilding process that depends on de novo protein synthesis. This suggests that retrieval is dynamic and serves to incorporate new information into preexisting memories. However, little is known about whether or not protein degradation is involved
Timothy J Jarome et al.
PloS one, 6(9), e24349-e24349 (2011-10-01)
Protein degradation through the ubiquitin-proteasome system [UPS] plays a critical role in some forms of synaptic plasticity. However, its role in memory formation in the amygdala, a site critical for the formation of fear memories, currently remains unknown. Here we
L R Dick et al.
The Journal of biological chemistry, 272(1), 182-188 (1997-01-03)
The natural product lactacystin exerts its cellular antiproliferative effects through a mechanism involving acylation and inhibition of the proteasome, a cytosolic proteinase complex that is an essential component of the ubiquitin-proteasome pathway for intracellular protein degradation. In vitro, lactacystin does
Coordinated regulation of dendrite arborization by epigenetic factors CDYL and EZH2
Qi C, et al.
The Journal of Neuroscience, 34(13), 4494-4508 (2014)
Florian Vogel et al.
Traffic (Copenhagen, Denmark), 8(9), 1205-1214 (2007-07-17)
Intracellular trafficking of viral movement proteins (MPs) in plants has mainly been studied using Tobacco mosaic virus MP30 (TMV MP30) as a model system. Because of the limitations of TMV MP30 expression in Arabidopsis thaliana, these studies have mostly been
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