D-Ala-Lys-AMCA hydrochloride is a fluorescent dipeptide featuring a D-alanine residue and an AMCA label for monitoring enzymatic cleavage. The charged lysine side chain enhances solubility and interaction with catalytic pockets. Researchers use it in kinetic studies and mapping substrate specificity. Its hydrochloride form provides stable aqueous behavior.
CAT No: R2203
CAS No:2703746-41-0
Synonyms/Alias:D-Ala-Lys-AMCA hydrochloride;D-Ala-Lys-AMCA (hydrochloride);2703746-41-0;(2S)-6-[[2-(7-amino-4-methyl-2-oxochromen-3-yl)acetyl]amino]-2-[[(2R)-2-aminopropanoyl]amino]hexanoic acid;hydrochloride;AKOS040744053;HY-111956B;N2-(D-Alanyl)-N6-(2-(7-amino-4-methyl-2-oxo-2H-chromen-3-yl)acetyl)-L-lysine hydrochloride;MS-28667;PD126278;CS-0107380;G17093;
D-Ala-Lys-AMCA hydrochloride is a specialized fluorescently labeled dipeptide designed for advanced biochemical and molecular biology research. Featuring the AMCA (7-amino-4-methylcoumarin-3-acetic acid) fluorophore conjugated to a D-alanine and lysine backbone, this compound offers unique advantages for studies requiring sensitive detection and precise molecular tracking. Its blue fluorescence emission, high photostability, and compatibility with a wide range of biological systems make it a valuable tool for visualization and quantification in complex experimental environments. The hydrochloride salt form further enhances its solubility and stability, facilitating integration into aqueous biological assays and minimizing background interference.
Protease Activity Assays: D-Ala-Lys-AMCA hydrochloride is widely utilized as a fluorogenic substrate in the assessment of protease activity. Upon enzymatic cleavage of the peptide bond, the AMCA label is released or altered in its fluorescence properties, allowing for real-time monitoring of proteolytic processes. This enables researchers to quantify enzyme kinetics, evaluate inhibitor efficacy, and study substrate specificity in a highly sensitive and non-radioactive manner. The distinct emission spectrum of the AMCA fluorophore also permits multiplexing with other fluorescent substrates, broadening the scope of simultaneous enzyme analyses in complex biological samples.
Peptide Transport Studies: The unique structure of this AMCA-labeled dipeptide makes it an ideal probe for investigating peptide transporter mechanisms in cellular and membrane systems. By tracking the uptake and intracellular localization of D-Ala-Lys-AMCA hydrochloride, scientists can elucidate the dynamics and specificity of peptide transporters such as those found in bacterial, mammalian, or plant cells. The fluorescent signal enables both qualitative imaging and quantitative analysis, offering insights into transporter affinity, capacity, and regulatory factors that influence peptide absorption and distribution.
Cellular Imaging and Localization: The blue fluorescence of the AMCA moiety provides a powerful tool for visualizing peptide localization within cells and tissues. Researchers employ D-Ala-Lys-AMCA hydrochloride in live-cell imaging or fixed specimen studies to monitor the intracellular trafficking, compartmentalization, and processing of peptides. Its compatibility with standard fluorescence microscopy techniques facilitates high-resolution imaging alongside other fluorophores, supporting multi-channel analyses and co-localization studies in diverse biological contexts.
Enzyme Substrate Specificity Profiling: With its well-defined peptide sequence and fluorescent tag, this compound serves as a model substrate for profiling the specificity of various peptidases and proteolytic enzymes. By systematically varying experimental conditions or enzyme sources, investigators can map cleavage preferences, identify novel enzyme activities, and characterize substrate-enzyme interactions in vitro. The sensitive fluorescence readout accelerates assay throughput and data acquisition, supporting both fundamental enzymology research and applied screening platforms.
Drug Discovery and Screening: D-Ala-Lys-AMCA hydrochloride is increasingly incorporated into high-throughput screening assays for the identification of enzyme modulators, such as inhibitors or activators. Its robust fluorescent response to enzymatic modification enables rapid, automated detection of compound activity in large chemical libraries. This application is particularly valuable in early-stage drug discovery, where efficient and reliable screening methods are essential for identifying promising therapeutic candidates targeting proteolytic pathways.
Bioconjugation and Labeling Studies: The AMCA-labeled peptide also finds utility in the development and validation of new bioconjugation strategies. Researchers leverage its defined structure and fluorescence properties to optimize coupling chemistries, assess labeling efficiencies, and evaluate the stability of peptide conjugates under various conditions. These studies contribute to the advancement of peptide-based probes, sensors, and diagnostic reagents, expanding the toolkit for molecular biology, analytical chemistry, and biotechnology research.
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