D-Ala-Lys-AMCA is a known proton-coupled oligopeptide transporter 1 (PEPT1) substrate, which emits blue fluorescence. Based on fluorescence analysis, D-Ala-Lys-AMCA can be transported to liver cancer cells and Caco-2 cells.
CAT No: 10-101-273
CAS No:375822-19-8
Synonyms/Alias:D-Ala-Lys-AMCA;375822-19-8;EX-A7121;AKOS040744055;DA-72540;HY-111956;CS-0094515;(2S)-6-[[2-(7-amino-4-methyl-2-oxochromen-3-yl)acetyl]amino]-2-[[(2R)-2-aminopropanoyl]amino]hexanoic acid;
D-Ala-Lys-AMCA is a synthetic peptide conjugate featuring the dipeptide sequence D-alanine-lysine covalently linked to the fluorogenic dye 7-amino-4-methylcoumarin-3-acetic acid (AMCA). As a fluorescently labeled peptide, it combines the biochemical specificity of a defined peptide substrate with the robust spectral properties of AMCA, making it a versatile tool in enzymology, cell biology, and analytical biochemistry. The presence of the D-alanine residue confers resistance to certain proteolytic enzymes, while the lysine side chain offers a site for conjugation, and the AMCA moiety enables sensitive detection through fluorescence-based methods. This reagent is particularly valuable for studies requiring precise monitoring of peptide processing, enzyme activity, or peptide localization in complex biological systems.
Enzyme substrate assays: D-Ala-Lys-AMCA serves as an effective substrate for protease activity assays, especially those targeting lysine-specific or dipeptidyl peptidases. Upon enzymatic cleavage, the AMCA fluorophore is released or its fluorescence properties are altered, allowing real-time quantification of enzymatic activity through fluorescence measurement. This enables sensitive detection and kinetic analysis of protease function in purified systems, cell lysates, or more complex biological samples, supporting both fundamental research and inhibitor screening campaigns.
Peptidase specificity profiling: The unique sequence and stereochemistry of this peptide conjugate make it suitable for mapping the substrate specificity of various peptidases, including those with preferences for D-amino acid-containing motifs. By monitoring fluorescence changes upon incubation with different enzymes, researchers can delineate substrate scope, characterize novel proteolytic activities, and compare enzyme selectivity under varying conditions. This approach facilitates the rational design of selective inhibitors or optimized substrates for biochemical assays.
Cellular uptake and trafficking studies: The fluorescent labeling of D-Ala-Lys-AMCA allows it to be tracked within cellular environments, providing a means to investigate peptide uptake, intracellular trafficking, and compartmentalization. Its resistance to rapid degradation by common proteases, due to the D-alanine residue, enables prolonged observation in live cell assays. Researchers can use fluorescence microscopy or flow cytometry to visualize and quantify peptide internalization, distribution, and export, yielding insights into peptide transport mechanisms and cellular permeability.
Fluorescence-based detection and quantification: The AMCA tag on this peptide offers strong blue fluorescence with high photostability, making it ideal for sensitive detection in fluorescence-based analytical techniques such as HPLC with fluorescence detection, capillary electrophoresis, or fluorescence polarization assays. The robust spectral properties of AMCA facilitate multiplexing with other fluorophores in multi-analyte assays, supporting high-throughput screening, bioanalytical quantification, and complex sample analysis.
Peptide-protein interaction studies: As a defined, labeled peptide, D-Ala-Lys-AMCA can be employed to probe interactions with peptide-binding proteins, including receptors, transporters, or antibodies. By monitoring changes in fluorescence upon binding or displacement, researchers can characterize binding affinities, map interaction sites, and assess competition with other ligands. These studies provide valuable information for elucidating molecular recognition events and support the development of peptide-based probes or affinity reagents for research applications.
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