Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin is a fluorogenic peptide substrate incorporating a coumarin reporter for sensitive protease monitoring. The tripeptide core enhances recognition of arginine-specific catalytic sites. Researchers use it in kinetic assays, inhibitor studies, and structural-functional mapping. Its Boc protection improves synthetic robustness.
CAT No: R2303
CAS No:113866-20-9
Synonyms/Alias:Boc-Gln-Ala-Arg-Mca;Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin;Boc-Gln-Ala-Arg-AMC;113866-20-9;Boc-Gln-Ala-Arg-7-amido-4-methylcoumarin;tert-butyl N-[(2S)-5-amino-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamate;Boc-Gln-Ala-Arg-AMCA;SCHEMBL2143298;CHEBI:84832;Boc-Gln-Ala-Arg-methylcoumarin amide;Boc-Gln-Ala-Arg-4-methylcoumaryl-7-amide;Boc-Gln-Ala-Arg-4-methyl-coumaryl-7-amide;Q27158101;N(2)-(tert-butoxycarbonyl)-L-glutaminyl-L-alanyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-argininamide;N2-[(1,1-Dimethylethoxy)carbonyl]-L-glutaminyl-L-alanyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-argininamide;tert-butyl (S)-5-amino-1-((S)-1-((S)-5-guanidino-1-(4-methyl-2-oxo-2H-chromen-7-ylamino)-1-oxopentan-2-ylamino)-1-oxopropan-2-ylamino)-1,5-dioxopentan-2-ylcarbamate;
Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin is a synthetic peptide substrate widely recognized for its utility in biochemical and molecular biology research. Characterized by the incorporation of a 7-amino-4-methylcoumarin (AMC) fluorophore, this compound enables sensitive detection of proteolytic activity through fluorescence emission. The sequence Boc-Gln-Ala-Arg is specifically designed to be a target for certain proteases, and upon enzymatic cleavage, the AMC moiety is liberated, resulting in a measurable fluorescent signal. This feature makes the substrate highly valuable for real-time monitoring and quantitative analysis of enzymatic reactions. Researchers appreciate its stability, ease of handling, and compatibility with various assay platforms, which together facilitate high-throughput screening and kinetic studies. Its versatility and specificity have made it a preferred choice in diverse fields, ranging from enzymology to drug discovery.
Protease activity assays: Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin serves as a sensitive and specific substrate for the detection and quantification of protease activity, particularly those enzymes that recognize and cleave the Gln-Ala-Arg sequence. When introduced into enzymatic reactions, the substrate is cleaved by the target protease, releasing the AMC group, which emits fluorescence upon excitation. This property allows researchers to monitor enzyme kinetics in real time, providing insights into catalytic efficiency, substrate specificity, and potential inhibitors. The fluorogenic nature of the substrate also enables the development of continuous assays, which are crucial for high-throughput screening of protease modulators in pharmaceutical research.
Enzyme inhibitor screening: The peptide-AMC substrate is extensively utilized in the identification and characterization of protease inhibitors. By incorporating it into in vitro assays, scientists can assess the efficacy of candidate compounds in modulating protease activity. The decrease in fluorescence upon addition of an inhibitor directly correlates with its potency, allowing for rapid and quantitative assessment. This approach streamlines the drug discovery process by enabling the screening of large compound libraries for potential therapeutic leads targeting specific proteases implicated in various pathological conditions.
Kinetic studies of enzymatic reactions: The use of Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin in kinetic analyses provides detailed information about enzyme-substrate interactions, turnover rates, and catalytic mechanisms. The continuous generation of a fluorescent signal upon substrate cleavage allows researchers to collect real-time data, facilitating the construction of Michaelis-Menten curves and the calculation of kinetic parameters such as Km and Vmax. These studies are essential for understanding enzyme functionality, optimizing assay conditions, and elucidating the molecular basis of enzyme regulation.
Biochemical pathway elucidation: In the context of pathway mapping, the substrate's specificity enables the investigation of protease involvement in complex biological processes. By introducing the compound into cell lysates or purified protein systems, researchers can pinpoint the activity of particular proteases within signaling cascades or metabolic networks. The resulting fluorescence provides a convenient readout for tracing enzymatic events, helping to unravel the roles of proteases in physiological and pathological states.
Cell-based assays: Boc-Gln-Ala-Arg-7-Amino-4-Methylcoumarin is also adaptable for use in live cell experiments, where it can be employed to monitor intracellular protease activity. Upon cellular uptake, the substrate is cleaved by endogenous enzymes, leading to fluorescence that can be detected using microscopy or plate readers. This application enables the study of protease dynamics in their native cellular environment, offering valuable insights into enzyme localization, activation, and regulation under various experimental conditions. Collectively, these application directions underscore the compound's significance as a powerful tool for advancing protease research, facilitating drug discovery, and deepening our understanding of enzymatic processes in biology.
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