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L7035

Sigma-Aldrich

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

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About This Item

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

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

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
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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