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L7035

clasto-Lactacystin β-lactone

Name: clasto-Lactacystin &#946;-lactone
Brand: SIGMA

≥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

Assay:

≥95% (HPLC)

Form:

film

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Properties

Product Name

clasto-Lactacystin β-lactone,

assay

≥95% (HPLC)

Quality Segment

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

Description

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.