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Merck
CN

L7035

clasto-Lactacystin β-lactone

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

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
UNSPSC Code:
12352200
PubChem Substance ID:
24896450
NACRES:
NA.77
MDL number:
MFCD01076526

Key Documents

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Product Name

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

100

Related Categories

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

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM4358
MKCK0558
MKCG7816
MKBX4006V
MKBT7113V

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Zvi Granot et al.
Molecular and cellular endocrinology, 265-266, 51-58 (2007-01-16)
Steroidogenic acute regulatory protein (StAR) is a mitochondrial protein essential for massive synthesis of steroid hormones in the adrenal and the gonads. Our studies suggest that once synthesized on free polyribosomes, StAR preprotein either associates with the outer mitochondrial membrane
Jonathan L C Lee
Nature neuroscience, 11(11), 1264-1266 (2008-10-14)
Memories are dynamic, rather than static, in nature. The reactivation of a memory through re-exposure to salient training stimuli results in its destabilization, necessitating a restabilization process known as reconsolidation, a disruption of which leads to amnesia. I found that
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
A Craiu et al.
The Journal of biological chemistry, 272(20), 13437-13445 (1997-05-16)
The antibiotic lactacystin was reported to covalently modify beta-subunit X of the mammalian 20 S proteasome and inhibit several of its peptidase activities. However, we demonstrate that [3H]lactacystin treatment modifies all the proteasome's catalytic beta-subunits. Lactacystin and its more potent
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