Z-Leu-leu-leu-al

Base Information

• Chemical Name: Z-Leu-leu-leu-al
• CAS No.: 133407-82-6
• Molecular Formula: C₂₆H₄₁N₃O₅
• Molecular Weight: 475.629
• Hs Code.: 29242990
• European Community (EC) Number: 849-040-8
• UNII: RF1P63GW3K
• DSSTox Substance ID: DTXSID3042639
• Nikkaji Number: J785.331I
• Wikipedia: MG132
• Wikidata: Q3272916
• NCI Thesaurus Code: C128633
• Pharos Ligand ID: UR9MATC512U9
• ChEMBL ID: CHEMBL64925
• Mol file: 133407-82-6.mol

Synonyms:benzyloxycarbonyl-Leu-Leu-Leu-aldehyde;benzyloxycarbonyl-leucyl-leucyl-leucinal;benzyloxycarbonylleucyl-leucyl-leucine aldehyde;carbobenzoxy-leucyl-leucyl-leucinal;carbobenzoxyl-leucinyl-leucinyl-leucinal-H;carbobenzyloxy-leucinyl-leucinyl-leucinal;LLL cpd;MG 132;MG-132;MG132;Z-Leu-Leu-Leu-al;Z-Leu-Leu-leucinal;Z-LLL;ZLLL-CHO;ZLLLal

Chemical Property of Z-Leu-leu-leu-al

Chemical Property:

• Appearance/Colour: solid film
• Vapor Pressure: 1.86E-18mmHg at 25°C
• Melting Point: 80-84℃ (DEC.)
• Refractive Index: 1.506
• Boiling Point: 682 °C at 760 mmHg
• PKA: 11.14±0.46(Predicted)
• Flash Point: 366.3 °C
• PSA: 113.60000
• Density: 1.073 g/cm³
• LogP: 4.76090
• Storage Temp.: −20°C
• Solubility.: methanol: 1 mg/mL
• Water Solubility.: Soluble in ethanol, chloroform, methanol, water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 15
• Exact Mass: 475.30462142
• Heavy Atom Count: 34
• Complexity: 644

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-Leu-Leu-Leu-CHO ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C=O)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1
• Description: MG-132 (133407-82-6) is a specific inhibitor of the chymotrypsin-like activity of the 20S proteasome (IC50=100 nM with Z-LLL-AMC as substrate).1 Also inhibits calpain (IC50=1.25 μM).1 Suppresses gastric cancer cell proliferation and induces macro-autophagy.2 Activates stress kinases and induces Hsp72.3 Induces neurite outgrowth.1 MG-132 blocks NFκB activation by blocking IκB proteolysis (IC50=3 μM).4 Cell permeable.
• Uses: A proteasome and NF-κB inhibitor. MG 132 is a potent, membrane-permeable proteasome inhibitor. It induces neurite outgrowth in PC12 cells. Neuroprotective product.

Technology Process of Z-Leu-leu-leu-al

There total 17 articles about Z-Leu-leu-leu-al which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

((S)-1-(((S)-1-(((S)-1-hydroxy-4-methylpentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamic acid benzyl ester (1211877-22-3) → N-(benzyloxycarbonyl)-leucinylleucinylleucinal (133407-82-6)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 20h;

DOI:10.1002/anie.201308984

Reference yield: 88.0%

{1-[1-(1-hydroxymethyl-3-methylbutylcarbamoyl)-3-methylbutylcarbamoyl]-3-methylbutyl}carbamic acid benzyl ester (1161015-91-3) → {1-[1-(1-formyl-3-methylbutylcarbamoyl)-3-methylbutylcarbamoyl]-3-methylbutyl}carbamic acid benzyl ester (1161015-92-4,133407-82-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h; chemoselective reaction;

DOI:10.1016/j.tet.2009.03.018

Reference yield: 63.0%

C26H43N3O5 (1211877-30-3) → (R)-MG-132 (1211877-36-9,133407-82-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jm901619n

upstream raw materials:

Z-L-leucine-L-leucine-L-leucine N,O-dimethylhydroxylamide

((S)-1-(((S)-1-(((S)-1-hydroxy-4-methylpentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamic acid benzyl ester

Boc-L-leucine-L-leucinol

C₂HF₃O₂*C₁₂H₂₆N₂O₂

Refernces

• 1、 An, Jing,Chen, Yiling,Ciechanover, Aaron,Fuk-Woo Chan, Jasper,Huang, Lina S.,Huang, Ziwei,Liang, Boqiang,Nie, Linlin,Wang, Juan,Warshel, Arieh,Wu, Meixian,Wu, Yi,Xu, Yan,Ye, Hui,Yuan, Shuofeng,Yuen, Kwok-Yung,Zhou, Jiao. "A new class of α-ketoamide derivatives with potent anticancer and anti-SARS-CoV-2 activities". . . Retrieved 2021/02/27.
• 2、 Voss, Constantin,Scholz, Christoph,Knorr, Sabine,Beck, Philipp,Stein, Martin L.,Zall, Andrea,Kuckelkorn, Ulrike,Kloetzel, Peter-Michael,Groll, Michael,Hamacher, Kay,Schmidt, Boris. "α-Keto Phenylamides as P1′-Extended Proteasome Inhibitors". . p. 2557 - 2564. Retrieved 2015/08/24.