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C6706

Sigma-Aldrich

Z-Leu-Leu-Norvalinal

≥90% (HPLC), powder

Synonym(s):

MG115, Z-LLnV

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About This Item

Empirical Formula (Hill Notation):
C25H39N3O5
CAS Number:
133407-86-0
Molecular Weight:
461.59
UNSPSC Code:
12352209
PubChem Substance ID:
329775129
NACRES:
NA.32

Quality Level

100

Assay

≥90% (HPLC)

form

powder

color

white

solubility

DMSO: soluble

storage temp.

−20°C

SMILES string

CCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)C=O

InChI

1S/C25H39N3O5/c1-6-10-20(15-29)26-23(30)21(13-17(2)3)27-24(31)22(14-18(4)5)28-25(32)33-16-19-11-8-7-9-12-19/h7-9,11-12,15,17-18,20-22H,6,10,13-14,16H2,1-5H3,(H,26,30)(H,27,31)(H,28,32)/t20-,21-,22-/m0/s1

InChI key

QEJRGURBLQWEOU-FKBYEOEOSA-N

Gene Information

human ... PSMA1(5682) , PSMC1(5700)
mouse ... PSMA1(26440) , PSMC1(19179)
rat ... PSMA1(29668) , PSMC1(117263)

Amino Acid Sequence

Z-Leu-Leu-Nva

Biochem/physiol Actions

Potent inhibitor of the 20S proteasome (Ki = 21 nM) and 26S proteasome (Ki = 35 nM). Cells treated with 54 μM N-CBZ-Leu-Leu-Norvalinal showed complete block of the G1/S and metaphase transitions and delayed passage through S-phase. Induces apoptosis in Rat-1 and PC12 cells, perhaps by accumulation of stabilized p53.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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U G Lopes et al.
The Journal of biological chemistry, 272(20), 12893-12896 (1997-05-16)
Proteolysis by the ubiquitin/proteasome pathway controls the intracellular levels of a number of proteins that regulate cell proliferation and cell cycle progression. To determine whether this pathway of protein turnover was also linked to apoptosis, we treated Rat-1 and PC12
Gangwei Ou et al.
PloS one, 4(11), e7806-e7806 (2009-11-13)
Vibrio cholerae is the causal intestinal pathogen of the diarrheal disease cholera. It secretes the protease PrtV, which protects the bacterium from invertebrate predators but reduces the ability of Vibrio-secreted factor(s) to induce interleukin-8 (IL-8) production by human intestinal epithelial
Brooke A Jude et al.
Journal of bacteriology, 191(22), 6911-6917 (2009-09-08)
Vibrio cholerae is the etiologic agent of cholera in humans. Intestinal colonization occurs in a stepwise fashion, initiating with attachment to the small intestinal epithelium. This attachment is followed by expression of the toxin-coregulated pilus, microcolony formation, and cholera toxin
Raquel M Martinez et al.
Journal of bacteriology, 191(18), 5669-5679 (2009-07-14)
Vibrio cholerae is highly motile by the action of a single polar flagellum. The loss of motility reduces the infectivity of V. cholerae, demonstrating that motility is an important virulence factor. FlrC is the sigma-54-dependent positive regulator of flagellar genes.
Takahiko Ishikawa et al.
PloS one, 4(8), e6734-e6734 (2009-08-25)
The type VI secretion system (T6SS) has emerged as a protein secretion system important to several gram-negative bacterial species. One of the common components of the system is Hcp, initially described as a hemolysin co-regulated protein in a serotype O17
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