6491-83-4

Basic information

• Product Name: ((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride
• CAS NO: 6491-83-4
• Molecular Weight: 294.822
• Mol File: 6491-83-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 177-181°C
• CAS DataBase Reference: ((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: ((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride(6491-83-4)
• EPA Substance Registry System: ((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride(6491-83-4)

Safety Data

• Hazardous Substances Data: 6491-83-4(Hazardous Substances Data)

Usage

Description

L-Leucyl-L-Leucine methyl ester (LLME) is a lysosomal condensation product that has been reported to be cytotoxic towards natural killer cells and CD4+ and CD8+ T lymphocytes without affecting helper T cells and B cells. It has also been shown to induce death of monocytes, polymorphonuclear leukocytes, and myeloid tumor cells. Upon entry into cells via receptor-mediated endocytosis, LLME undergoes a condensation process catalyzed by dipeptidyl peptidase I (DPPI) in lysosomes. This condensation leads to lysosomal rupture and DNA fragmentation in DPPI-expressing immune cells such as cytotoxic T cells and natural killer cells.

Uses

H-Leu-leu-OMe HCl

Upstream product

• 67-56-1 methanol 
• 3303-31-9 L-leucyl-L-leucine 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 15136-13-7 N-tert-butoxycarbonyl-L-leucyl-L-leucine methyl ester 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 

Downstream Products

• 1252575-05-5 C₂₃H₃₈N₃O₇P 
• 98695-41-1 N-carbobenzoxy-L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucine methyl ester 
• 106561-18-6 N-(benzyloxycarbonyl)-L-leucyl-L-leucyl-L-leucine methyl ester 
• 952-43-2 (3S,6S)-3,6-diisobutylpiperazine-2,5-dione 

Relevant articles and documents

Additivity or cooperativity: Which model can predict the influence of simultaneous incorporation of two or more functionalities in a ligand molecule?

Predicting how binding affinity responds to ligand structural modifications in structure-activity relationship studies (SAR) is a major challenge in medicinal chemistry. This is particularly true when two or more of these modifications are carried out simultaneously. In this study, we present binding affinity data from several series of thermolysin inhibitors in which simultaneous structural modifications were investigated to determine whether they are cooperative or additive. Data revealed that, while additivity is at work in some cases, cooperativity is more commonly demonstrated. Cooperativity and additivity were then correlated with ligand descriptors, such as the spacing and the topological features of the modified groups, in a manner that may provide guidance as to when each model should be utilized. Cooperativity was particularly associated with contiguous groups and small unbranched hydrophobic side chain. Additivity, on the other hand, was associated with moderately distant hydrophobic group combinations and side chain branching. Such correlations can improve the predictability of SAR studies and can provide a starting point for additional investigations that may lead to further significant enhancements in the current scoring functions.

Dissecting the hydrophobic effect on the molecular level: The role of water, enthalpy, and entropy in ligand binding to thermolysin

The hydrophobic effect is associated with the successive replacement of water molecules in the binding site of a protein by hydrophobic groups of the ligand. Although the hydrophobic effect is assumed to be entropy-driven, large changes in enthalpy and entropy are observed with the model system thermolysin. Structural changes in the binding features of the water molecules ultimately determine the thermodynamics of the hydrophobic effect. Copyright

Syntheses of [12]aneN3-oligopeptide conjugates as effective DNA condensation agents

With the aim to develop effective and low toxicity DNA condensation agents, a series of oligopeptide derived macrocyclic polyamine [12]aneN3 conjugates 7a-h·3HCl have been designed and synthesized through multi-step amidation reactions. Structu