70637-28-4

Basic information

• Product Name: L-Phenylalanine, L-leucyl-, phenylmethyl ester (monotrifluoroacetate)
• Synonyms: L-Phenylalanine, L-leucyl-, phenylmethyl ester (monotrifluoroacetate);Benzyl L-leucyl-L-phenylalaninate trifluoroacetate (1:1);(S)-benzyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate 2,2,2-trifluoroacetate
• CAS NO: 70637-28-4
• Molecular Formula: C₂HF₃O₂*C₂₂H₂₈N₂O₃
• Molecular Weight: 482.4926696
• Mol File: 70637-28-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Phenylalanine, L-leucyl-, phenylmethyl ester (monotrifluoroacetate)(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, L-leucyl-, phenylmethyl ester (monotrifluoroacetate)(70637-28-4)
• EPA Substance Registry System: L-Phenylalanine, L-leucyl-, phenylmethyl ester (monotrifluoroacetate)(70637-28-4)

Safety Data

• Hazardous Substances Data: 70637-28-4(Hazardous Substances Data)

Upstream product

• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 
• 140834-91-9 (S)-benzyl 2-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanamido)-3-phenylpropanoate 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 868540-16-3 (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid 
• 868540-15-2 (S)-benzyl 2-((S)-2-((S)-2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-4-methylpentanamido)-3-phenylpropanoate 

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.

The greening of peptide synthesis

The synthesis of peptides by amide bond formation between suitably protected amino acids is a fundamental part of the drug discovery process. However, the required coupling and deprotection reactions are routinely carried out in dichloromethane and DMF, b