868539-99-5

Basic information

• Product Name: (alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate)
• Synonyms: (alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate);(S)-Methyl-2-((S)-2-((S)-2-aMino-4-phenylbutanaMido)-4-Methyl;(S)-Methyl 2-((S)-2-((S)-2-aMino-4-phenylbutanaMido)-4-MethylpentanaMido)-3-phenylpropanoate trifluoroacetic acid;(αS)-α-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine Methyl Ester Mono(trifluoroacetate);L-Phenylalanine, (αS)-α-aminobenzenebutanoyl-L-leucyl-, methyl ester (2,2,2-trifluoroacetate);(S)-Methyl 2-((S)-2-((S)-2-amino-4-phenylbutanamido)-4-methylpentanamido)-3-phenylpropanoate 2,2,2-trifluoroacetate
• CAS NO: 868539-99-5
• Molecular Formula: C₂HF₃O₂*C₂₆H₃₅N₃O₄
• Molecular Weight: 551.5977496
• Mol File: 868539-99-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate)(CAS DataBase Reference)
• NIST Chemistry Reference: (alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate)(868539-99-5)
• EPA Substance Registry System: (alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate)(868539-99-5)

Safety Data

• Hazardous Substances Data: 868539-99-5(Hazardous Substances Data)

Usage

Description

(alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate) is a chemical compound that serves as an intermediate in the synthesis of Carfilzomib (C183460), a second-generation proteasome inhibitor. (alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate) plays a crucial role in the development of pharmaceuticals targeting specific protein degradation pathways.
Used in Pharmaceutical Industry:
(alphaS)-alpha-Aminobenzenebutanoyl-L-leucyl-L-phenylalanine methyl ester mono(trifluoroacetate) is used as an intermediate compound for the synthesis of Carfilzomib, a second-generation proteasome inhibitor. It is utilized in the development of treatments for relapsed and refractory multiple myeloma, a type of blood cancer, due to its ability to inhibit the activity of the proteasome, a cellular enzyme complex responsible for the degradation of proteins. This inhibition leads to the accumulation of proteins within cancer cells, ultimately resulting in their death.

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 15136-32-0 (N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 868539-96-2 (S)-methyl 2-((S)-2-tert.butoxycarbonyIamino-4-phenylbutanamido-4-methylpentanamido)-3-phenylpropanoate 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 868539-97-3 C₃₅H₄₃N₃O₆ 
• 868540-08-3 C₂₈H₃₆ClN₃O₅ 
• 1140908-89-9 C₃₂H₄₄N₄O₆ 
• 868540-16-3 (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid 

Relevant articles and documents

Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors

A series of novel tetrapeptidyl epoxyketone inhibitors of 20S proteasome was designed and synthesized. To fully understand the SAR, various groups at R1, R2, R3, R4 and R5 positions, including aromatic and aliphatic substituents were designed, synthesized and biologically assayed. Based on the enzymatic results, seven compounds were selected to evaluate their cellular activities and soluble compound 36 showed strong potency against human multiple myeloma (MM) cell lines. Microsomal stability results indicated that compound 36 was more stable in mice, rat and human microsomes than marketed carfilzomib. The in vivo activities of this compound were evaluated with the xenograft mice models of MM cell lines ARH77 and RPMI-8226 with luciferase expression and the T/C value of the two models were 49.5% and 37.6%, respectively. To evaluate the potential cardiovascular toxicity, inhibition of hERG ion channel in HEK293 cells by compound 36 and carfilzomib was carried out. The results indicated that 36 had no binding affinity for the hERG ion channel while carfilzomib could bind it with IC50 of 92.1 μM.