Leucylleucine methyl ester offers a hydrophobic dipeptide with terminal ester functionality ideal for hydrolysis and cleavage studies. The structure supports modeling of early folding and enzyme recognition. Researchers assess its stability and solvent interactions. Uses include peptide synthesis improvement, stereochemical analysis, and substrate evaluation.
CAT No: R2454
CAS No:13022-42-9
Synonyms/Alias:13022-42-9;Leucylleucine methyl ester;Leu-leu-ome;Leucyl-leucine-methyl ester;l-leucyl-l-leucine methyl ester;L-Leucine, L-leucyl-, methyl ester;L-Leucine, N-L-leucyl-, methyl ester;Methyl L-leucyl-L-leucinate;74SY3EEM9R;methyl (2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoate;AJMOLNFDYWTVQW-QWRGUYRKSA-N;N-L-Leucyl-L-leucine methyl ester;starbld0037349;leucylleucine-methyl-ester;UNII-74SY3EEM9R;METHYL LEUCYLLEUCINATE;SCHEMBL56187;CHEBI:184067;AKOS028112805;PD062609;HY-165398;BRD-K81136890-003-01-6;
Leucylleucine methyl ester is a synthetic dipeptide derivative comprised of two leucine residues linked via a peptide bond, with the C-terminal carboxyl group esterified as a methyl ester. As a peptide-based compound, it serves as a versatile tool in biochemical research, particularly in studies focused on peptide transport, metabolism, and enzymatic specificity. Its structure, mimicking short peptide sequences with a protected carboxyl terminus, makes it highly relevant for exploring peptide uptake mechanisms, enzyme-substrate interactions, and protease activity. The compound's unique properties enable researchers to probe various aspects of peptide chemistry, cellular transport, and metabolic processing, establishing it as a valuable reagent in the study of peptide function and dynamics.
Peptide Transport Studies: Leucylleucine methyl ester is widely utilized in investigations of peptide transport systems across cellular membranes. Due to its dipeptide structure and esterified terminus, it can serve as a model substrate for oligopeptide transporters, such as those in the SLC15 family. These transporters play crucial roles in nutrient uptake and drug delivery, and the compound's uptake and hydrolysis patterns provide insights into transporter specificity, kinetics, and substrate preference. By tracking its cellular localization and metabolic fate, researchers can elucidate mechanisms underlying peptide absorption and intracellular processing.
Enzyme Substrate Profiling: As a synthetic dipeptide ester, this compound is frequently employed to characterize the specificity and catalytic efficiency of peptidases and esterases. Its dual peptide bonds and esterified carboxyl group make it an informative substrate for distinguishing between proteolytic and esterolytic activity in enzymatic preparations. By monitoring the hydrolysis of the methyl ester or the peptide bond, researchers can dissect the selectivity and mechanistic features of various proteases, supporting the development of enzyme assays and inhibitor screening protocols.
Peptide Synthesis Validation: In peptide chemistry, leucylleucine methyl ester functions as a key intermediate or reference standard in solid-phase peptide synthesis and solution-phase coupling reactions. Its protected carboxyl group aids in controlling reaction specificity and minimizing side reactions during peptide chain elongation. Analytical studies using this compound help validate coupling efficiency, optimize deprotection protocols, and ensure the fidelity of synthetic strategies, thereby enhancing the reliability of peptide production workflows.
Cellular Uptake and Metabolism: The compound's dipeptide nature and esterified terminus make it a useful probe for studying cellular uptake pathways and intracellular metabolism of small peptides. Researchers utilize it to assess the involvement of specific transporters, peptidases, and esterases in the processing of exogenous peptides. The resulting data inform understanding of peptide bioavailability, metabolic stability, and the impact of chemical modifications on cellular handling, which are critical parameters for peptide-based drug design and delivery research.
Analytical Method Development: Leucylleucine methyl ester also finds application as a calibration standard or test analyte in the development and validation of analytical techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry. Its physicochemical properties and well-defined structure make it suitable for method optimization, system suitability testing, and quantitation of peptide derivatives. By serving as a benchmark compound, it supports the accuracy and reproducibility of analytical workflows in peptide research and quality control environments.
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5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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