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Merck

L7035

clasto-Lactacystin β-lactone

≥95% (HPLC), irreversible proteasome inhibitor, film

Sinónimos:

(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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Acerca de este artículo

Fórmula empírica (notación de Hill):
C10H15NO4
Número CAS:
Peso molecular:
213.23
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Nombre del producto

clasto-Lactacystin β-lactone,

SMILES string

[H][C@@]12OC(=O)[C@@]1(NC(=O)[C@@H]2C)[C@@H](O)C(C)C

InChI key

FWPWHHUJACGNMZ-NBBQQVJHSA-N

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

assay

≥95% (HPLC)

form

film

solubility

DMSO: soluble 25 mg/mL

storage temp.

−20°C

Quality Level

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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).

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

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Coordinated regulation of dendrite arborization by epigenetic factors CDYL and EZH2
Qi C, et al.
The Journal of Neuroscience, 34(13), 4494-4508 (2014)
Kristen Willeumier et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 26(44), 11333-11341 (2006-11-03)
The ubiquitin proteasome system, generally known for its function in protein degradation, also appears to play an important role in regulating membrane trafficking. A role for the proteasome in regulating presynaptic release and vesicle trafficking has been proposed for invertebrates
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
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
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

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