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Key Documents

M8699

Sigma-Aldrich

(R)-MG132

Synonym(s):

Z-L-Leu-D-Leu-L-Leu-al

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About This Item

Empirical Formula (Hill Notation):
C26H41N3O5
CAS Number:
Molecular Weight:
475.62
UNSPSC Code:
12352200
NACRES:
NA.32

Assay

≥98%

Quality Level

solubility

DMSO or DMF: 25 mg/mL

storage temp.

−20°C

SMILES string

CC(C)C[C@@H](C(N[C@H](C(N[C@H](C=O)CC(C)C)=O)CC(C)C)=O)NC(OCC1=CC=CC=C1)=O

InChI

1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1

InChI key

TZYWCYJVHRLUCT-VABKMULXSA-N

Application

(R)-MG132 has been used in ubiquitination assay and is used as a proteasome inhibitor.

Biochem/physiol Actions

MG132 (carbobenzoxy-Leu-Leu-leucinal) is a tri-peptide aldehyde. It possesses antitumor activity and boosts cytostatic/cytotoxic effects of chemo- and radiotherapy. (R)-MG132 is a potent, membrane-permeable proteasome inhibitor. It can inhibit proteasome activity in lysates of J558L multiple myeloma cells and EMT6 breast cancer cells. The (R)-MG132 stereoisomer is a more effective inhibitor of chymotrypsin-like (ChTL), trypsin-like (TL), and peptidylglutamyl peptide hydrolyzing proteasome (PGPH) activities than the (S)-MG132.

Physical form

crystalline solid or supercooled liquid

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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