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L7035

Sigma-Aldrich

clasto-Lactacystin β-lactone

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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
Empirical Formula (Hill Notation):
C10H15NO4
CAS Number:
Molecular Weight:
213.23
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥95% (HPLC)

Quality Level

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

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This Item
SML0041SML0358B6309
vibrant-m

L7035

clasto-Lactacystin β-lactone

vibrant-m

SML0041

Batimastat

vibrant-m

SML0358

AA74-1

vibrant-m

B6309

(R)-Butaprost

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

film

form

powder

form

film

form

oil

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: soluble 25 mg/mL

solubility

DMSO: ≥15 mg/mL

solubility

DMSO: >15 mg/mL

solubility

DMSO: freely soluble, ethanol: freely soluble

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Customers Also Viewed

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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
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
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
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
A K Ho et al.
Endocrinology, 148(2), 743-751 (2006-11-04)
In this study, we investigated the role of two inducible repressor proteins, inducible cAMP early repressor (ICER) and Fos-related antigen 2 (Fra-2) in the adrenergic induction of MAPK phosphatase-1 (MKP-1) as compared with their roles in the induction of arylalkylamine-N-acetyltransferase

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