868540-15-2

Basic information

• Product Name: benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate
• Synonyms: benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate;(alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine phenylmethyl ester;(6S,9S,12S)-benzyl 12-benzyl-9-isobutyl-2,2-dimethyl-4,7,10-trioxo-6-phenethyl-3-oxa-5,8,11-triazatridecan-13-oate;L-Phenylalanine, (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-, phenylmethyl ester;EOS-60551;Carfilzomib INT;868540-15-2
• CAS NO: 868540-15-2
• Molecular Formula: C₃₇H₄₇N₃O₆
• Molecular Weight: 629.78558
• Mol File: 868540-15-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 818.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.137±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicat
• PKA: 11.22±0.46(Predicted)
• CAS DataBase Reference: benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate(868540-15-2)
• EPA Substance Registry System: benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate(868540-15-2)

Safety Data

• Hazardous Substances Data: 868540-15-2(Hazardous Substances Data)

Usage

Uses

(αS)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-phenylmethyl Ester L-Phenylalanine is used as a reagent in the preparation of peptides for inhibition of enzymes.

Upstream product

• 140834-91-9 (S)-benzyl 2-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanamido)-3-phenylpropanoate 
• 82732-07-8 Boc-L-homophenylalanine 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 70637-28-4 (S)-benzyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate TFA salt 

Downstream Products

• 868540-17-4 carfilzomib 
• 875309-92-5 (S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido) pentanamido)-3-phenylpropanoate 
• 868540-16-3 (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid 
• 875309-83-4 C₂HF₃O₂*C₃₂H₃₉N₃O₄ 

Relevant articles and documents

Development of Novel Epoxyketone-Based Proteasome Inhibitors as a Strategy to Overcome Cancer Resistance to Carfilzomib and Bortezomib

Over the past 15 years, proteasome inhibitors (PIs), namely bortezomib, carfilzomib (Cfz) and ixazomib, have significantly improved the overall survival and quality-of-life for multiple myeloma (MM) patients. However, a significant portion of MM patients do not respond to PI therapies. Drug resistance is present either de novo or acquired after prolonged therapy through mechanisms that remain poorly defined. The lack of a clear understanding of clinical PI resistance has hampered the development of next-generation PI drugs to treat MM patients who no longer respond to currently available therapies. Here, we designed and synthesized novel epoxyketone-based PIs by structural modifications at the P1′ site. We show that a Cfz analog, 9, harboring a hydroxyl substituent at its P1′ position was highly cytotoxic against cancer cell lines displaying de novo or acquired resistance to Cfz. These results suggest that peptide epoxyketones incorporating P1′-targeting moieties may have the potential to bypass resistance mechanisms associated with Cfz and to provide additional clinical options for patients resistant to Cfz.

Compounds for enzyme inhibition

Peptide-based compounds including heteroatom-containing, three-membered rings efficiently and selectively inhibit specific activities of N-terminal nucleophile (Ntn) hydrolases. The activities of those Ntn having multiple activities can be differentially inhibited by the compounds described. For example, the chymotrypsin-like activity of the 20S proteasome may be selectively inhibited with the inventive compounds. The peptide-based compounds include at least three peptide units, an epoxide or aziridine, and functionalization at the N-terminus. Among other therapeutic utilities, the peptide-based compounds are expected to display anti-inflammatory properties and inhibition of cell proliferation.