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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.

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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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
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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.
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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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